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Jake Sullivan:

Welcome to our Mailbag segment for subscribers. We’re happy to have you here, and we’re going to do a couple of questions today. The first question has just come in an email from Carla in Connecticut, who asks, “What do you make of CIA director John Ratcliffe’s unannounced trip to Moscow this week? What do you thi…

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Jon Finer:

The World War II analogies are just completely overblown. There’s no more necessary existential conflict the United States has ever faced than World War II. This war has been the opposite of that; unnecessary. Second, we didn’t announce D-Day before we acted.

Jake Sullivan:

The larger strategic point is that the Canadian public has just had it with the United States of America. They are vibrating with intense rage at what they regard as aggression and betrayal that transcends any particular trade negotiation. And frankly, I think the Canadian public didn’t want Mark Carney doing any deal.

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Jake Sullivan: Welcome back to The Long Game. I’m Jake Sullivan.

Jon Finer:

And I’m Jon Finer. Just the two of us today for a late August edition that is shaping up almost as something of an economic warfare edition of The Long Game, or maybe warfare by other means. We’re going to talk about what President Trump has called THE MOST CRUSHING ECONOMIC OPERATION EVER TAKEN AGAINST ANY COUNTRY. That was in all caps, by the way. His new steps to try to pressure his way out of the Iran war.

We’ll then get into the escalating trade dispute between the United States and Canada, which Canadian Prime Minister Mark Carney has likened to a war. And we’ll conclude with a Red Team, Blue Team debate over President Trump’s new EO, new executive order licensing private companies to conduct cyber attacks against foreign criminal cyber actors. A controversial step. A lot to say about that. So that’s the episode. But first, Jake, there was some news overnight that may be a bit off brand for us, but something that struck, I think, both of us as worthy of a bit of a discussion before we get going with the harder news.

Jake Sullivan:

Yes. The passing of an absolute American legend, Dolly Parton. And it’s been really fascinating to see not just the outpouring of emotion from so many different people from so many different walks of life who she touched in one way or another over the course of her life and career, but also to just hear so many interesting stories about her. This is a person who truly has the quintessential American story. She’s born the fourth of 12 children in a one room cabin in the foothills of the Great Smoky Mountains. Her father can’t read or write. She makes it. Makes a career in music and then becomes this incredible philanthropist.

And a couple of the things that stood out to me, which I knew about but didn’t have at the front of mind with respect to Dolly Parton, one is her Imagination Library, which mails a free book, specially selected every month, directly to register children from birth until their fifth birthday, regardless of household income. And friends of ours have signed up for this and had their kids get these books. And she did this because her father, Robert Lee Parton, grew up without the opportunity to learn how to read or write. She started it just as a local project in her home county in Tennessee. Now it operates across the US, Canada, the UK, Australia, Ireland. Millions of free books every month to young leaders. And then the second thing that’s totally wild, I had completely forgotten this: She played a direct role in funding the Moderna COVID-19 vaccine by giving a donation to Vanderbilt University Medical Center.

And oftentimes when celebrities get credited with things like this, it ain’t very real. But in this case she was actually cited by the New England Journal of Medicine for having done this. So beyond her music, which is remarkable and which played as kind of the background music of my upbringing in my family, her contribution as a humanitarian and philanthropist has just been incredible. And as somebody who came from humble circumstances, to leave this kind of mark on the world, wow, you’ve got to say, makes you proud to be from a country where that’s possible.

Jon Finer:

It’s hard to imagine, especially if your main frame of reference is Washington like, for better or worse, ours is, someone more universally admired and mourned with no real detractors. None of the kind of on-the-other-hand takes that you sometimes see when a world historic figure dies. For me, hers was the first concert I remember my parents telling me they went to in 1979 at a hockey rink in Hanover, New Hampshire. Not a lot of big music acts come through Hanover, New Hampshire, as you well know now that you have ties to that part of the country. But she did, and it made an impression on them.

She also, kind of famously, hated politics. And I was interested to read that, although she really did tend to stay out of politics, let alone geopolitics, at the March 2022 Academy of Country Music Awards in Vegas, which came, as you’ll know, just after Russia invaded Ukraine, she actually opened the show by saying, “I don’t want to be political, and this is not. I’d rather pass a kidney stone than do that. I want us to send our love and hope to our brothers and sisters in Ukraine. Why don’t we just dedicate this entire show to them and pray for peace around this crazy world?” Which got a huge standing ovation, one of countless numbers of standing ovations she got throughout her career and continues to get. But interesting to me that she took a moment to recognize that particular time in geopolitical turbulence in spite of largely staying out of politics throughout her career. So remarkable person. Good to spend a few minutes remembering her.

Jake Sullivan:

All right. So I think we should dig into the main events for this week. As you said, Iran, Canada, and then this new presidential memo on cyber operations. But before we do, just a little bit of housekeeping. We took the last two weeks off, which was nice. Reset, and coming with fresh eyes to all of these challenges this week. We will be taking next week off and then we will be back with a great guest the week after Labor Day. So tune back in then after you listen to this episode. And then the other thing is I have learned over the last couple of weeks that we have to ask our listeners to go on wherever you listen to your podcasts, Apple or Spotify or YouTube, and subscribe. Give us a review.

Any of you who listen to this regularly and haven’t given us a review, please do. We’d prefer if it was a good review, but we’ll take it regardless because that really helps the podcast continue to grow. And it’s been really cool to see, over the past many months, the audience that we’ve been able to build. But this is the first time that we’re actually doing the normal podcaster thing of saying, “Hey. Please subscribe, like, give a review, et cetera.” But we are asking our listeners to do that. And I’m doing that dirty work for you, Jon, so that you don’t have to.

Jon Finer:

Better you than me. No, I agree with everything Jake said. We can use all the help we can get. And it’s been a lot of fun, to watch the community grow, and even more fun when we get to interact with people who send things in online. So thanks very much.

Jake Sullivan:

Okay. So do you want to set the table for where we are with respect to Iran?

Jon Finer:

Sure. We have talked quite a lot over the last few months about the Trump administration’s launching of an unnecessary and pretty reckless, ultimately, war against Iran, and its flailing around in recent weeks and months to try to get out of that war. The “agreement,” in air quotes, of an MOU with Iran that ultimately probably did not represent a meeting of the minds between the two countries. The unraveling of that MOU. The return to, maybe, a lower grade version of conflict. And now, over the last week or so, the launching of what the administration is calling a new phase of the war.

And I read the description from President Trump at the outset of this episode: Unprecedented. Harder economic consequences than any country’s ever faced. Scott Bessent had a different way of describing what the administration is trying to do.

Scott Bessent:

In the Second World War, D-Day marked the historic beginning of a campaign with our allies to target and drive the enemy from its positions, including those in third countries. Today, in that same spirit, we are launching an economic onslaught against Iran’s financial connections around the globe. Around the globe.

Jon Finer:

Secretary of Treasury Bessent said that, “President Donald Trump and the overwhelming might of our Military have significantly dismantled Iran’s military capabilities and weakened its nuclear program.” (We can debate a lot of that). But continuing on with Secretary Bessent: “Now we are entering the end game,” he says, “At dawn begins an economic D-Day: The single greatest financial offensive ever marshaled against an adversary.” So the rhetoric here is spicy. I’m not sure the analogy is particularly well-chosen, particularly given what they’ve actually done. But maybe you can give us your reaction to this shift in strategy. What you think of it, where you think it’s headed.

Jake Sullivan:

Yeah. First I think it’s important to put this in context and then to zero in on the puts and takes of this new economic strategy. So taking a step back, we’ve been off for the last couple of weeks and, just in that time, a lot has happened and nothing has changed, basically because the current status quo with respect to the Strait of Hormuz, with respect to Iran’s position in the region, with respect to the United States’ inability to achieve its objectives. All of that remains as true today as it did two weeks ago, two months ago, and heading all the way back to the start of the war. They are calling this particular operation, this economic operation, Operation Economic Outcast, but I think you could call this entire thing Operation Kitchen Sink, because this is just the latest in a long line of different strategies they’ve pursued to try to shake things loose.

So going back to February first, it was an effort at regime change by taking out the supreme leader. Now we’ve basically given up on that. Second, it was a focus on complete surrender of the nuclear program through a bombing campaign where they used this rhetoric about the largest bombing campaign in the history of the world, et cetera. Similar to what they’re doing now. We’ve given up on that. Third, it was going to be to forcibly open the Strait through sending multiple American Naval vessels in something called Operation Project Freedom. That was short-lived, like 48 hours. Fourth, it was do this memorandum of understanding with Iran and hope it sticks. That broke down after just a couple of weeks. Fifth, it was, we’re just going to blockade Iran into submission, and the blockade will work and strangle them. That’s been underway now for some time, but we’ve gotten impatient with that. So now here we are on economic D-Day. And the assertion is this is the end game. This will do it.

And A, I think the administration is not well-known for its humility, but maybe should take a little bit of a cue from all of these other efforts that started with huge rhetoric and ended with very little to show for them, and take that into account when they start making these very puffed up assertions about what this will do. Economic D-Day. Let’s talk about what the initiative actually does. It adds some sanctions in sectors of Iran’s economy. Shipping, aviation, gold, technology, cryptocurrency. Okay. That looks a lot like many, many rounds of sanctions against Iran in years past.

It hits 60 entities, individuals, and vessels globally that help fund Iran, evade sanctions, or handle military procurement. 60 is a, I think, totally pedestrian number. A standard package even in the Biden administration, let alone back to when we were doing significant economic pressure before the Iran nuclear deal. We would’ve done a lot more than 60 entities in one fell swoop globally. And then it threatens secondary sanctions. Bessent has warned international banks, foreign companies anywhere in the world doing business with Iran that they could lose access to the US financial system.

But here’s where the thing starts to putter, sputter out a bit: Bessent was asked, okay, what’s the deadline? When are you going to start imposing these sanctions? He didn’t really answer. He said, “How quickly do you expect countries to comply?” He said, “I’m not going to set timelines. We don’t have infinite patience here.” And then he was asked about China, because China is 90% of Iran’s oil exports right now. Somewhere in that neighborhood, between 80% and 90%. So he got asked about whether he’ll sanction China, especially Chinese banks. He says, “No one is above the reach of US sanctions,” but did not address China specifically.

And with President Xi coming to meet with President Trump, at least on the schedule in a month’s time, less than a month’s time, it’s really hard to see us coming down hard on China. So this all, to me, feels more like show than reality. Not shocking. That’s been a lot of what we’ve seen out of the administration when it comes to trying to figure out a way forward with respect to Iran. But fundamentally, it is hard to take very seriously the idea that this is going to be the game-changer that the administration asserts that it is. One last point: Iran is hurting economically. There is no doubt about that. The Iranian rial has cratered, inflation has spiked, a hard currency is in short supply, there’s a shortage of critical goods. People are feeling it, and I think they will feel it more as we add incremental economic pressure. But whether that converts into Iran throwing up its hands and saying, “Okay. You got us.” There, I think history does not tell a particularly good story for the Trump administration, particularly if they try to maintain a set of demands that are maximalist.

So one can’t say, “Economic pressure is just a silly idea.” We have been part of two administrations that pursued it. But the notion that it’s going to be a silver bullet to solve this particular crisis and end this particular war, I think that basically defies common sense and the history that we have seen so far. And I think the Trump administration is going to come to learn that here over time. But what do you think?

Jon Finer:

I was struck by a few things here, some of them very similar to what you just described. The first is just on a basic trade craft of government. They have a funny habit of raising expectations for every policy move they take kind of sky-high, and then underperforming. The normal approach, which is hard to execute in the best of times, is to try to manage expectations and then exceed them, or at least meet them if you can. But when you set the standard of economic D-Day, greatest this, most Draconian that, you’re expecting and raising the expectation of pretty significant results. But this is so far from a step that is that consequential. First of all, the World War II analogies are just completely overblown. There’s no more necessary existential conflict the United States has ever faced than World War II. This war has been the opposite of that: Unnecessary.

Second, we didn’t announce D-Day before we acted. We certainly didn’t announce D-Day and then launch a phase of negotiations to determine whether the countries on the other side of the table might take steps that we were hoping they might take rather than actually acting. So terrible analogy there. And then, third, when we acted, to your point, it was severe and decisive. And the most significant thing that Scott Bessent said was that we would push countries, essentially, to try to take steps to cut off Iran, the way the Emirates has announced they would do but I think in practice is going to have a hard time actually executing on.

So just as a matter of basic function of government, not a good practice to raise expectations and fail to meet them. And I think that’s likely where this is headed. Second, the China example that you raised is the whole game in some sense. Oil is the number one revenue source for the Iranian regime. China is by far and away the largest driver of that revenue. So is China going to take actions on their own to reduce their purchases of Iranian oil? Seems very unlikely. It was very hard for administrations we worked in to get China to take such actions. And at that time China was actually working with us in the construct of the P5+1. One of the countries that was involved in the Iran negotiations had voted for sanctions in the United Nations and basically was an ambivalent but partner, in some ways, in that effort. Often undermining it, often working alongside us. Always had to stay on top of them.

Now I think China basically has reached its wits’ end with the US approach to the Middle East, and so the last thing they’re going to do is do the Trump administration the favor of taking steps on their own, which puts the administration in the very awkward position of having, potentially, to consider sanctions against China at a time when we have myriad other higher stakes issues with the Chinese, from rare earths to tech competition to Taiwan to everything else that’s going to be at issue when Xi Jinping shows up in Washington.

And hard to imagine that Trump, who has been very unlikely to risk the positive feeling around his meetings with Xi Jinping or the relationship overall, is going to take a step that infuriates the Chinese over the next month and, to be honest, probably even after that. So if we can’t hit China, which we probably won’t in a significant way, unlikely this is going to have a significant impact.

And then to your point about Iran’s economy being severely damaged, I fully agree with that, but the example I always come back to when I think about, how much economic pressure can move a country’s decision-making calculus, it can always be a part of changing a country’s mind. Certainly economic sanctions were a part of what got Iran to agree to massive nuclear constraints during the JCPOA era. But I always think about Syria which, between 2011 when the civil war there began and a bunch of sanctions were imposed on the Assad regime, and the end of the Obama administration where we were working in 2016, Syria lost as much as two thirds of its GDP during that time. And the Assad regime did not change course, did not make concessions because they believed they were facing an existential struggle and they prioritized that above everything else including, certainly, the entire economic wellbeing of their country.

So the notion that the Iranian regime is going to make the sorts of compromises that Trump is expecting I think is very unlikely to say the least, just given that precedent, which is a similar sort of authoritarian government. Last thing I’ll say. Sorry to go on so long. To make this work would require aggressive enforcement of these sanctions. Closing loopholes, updating target lists with new designations, working with other countries to shut down illicit operations inside their borders. One thing this administration has really not demonstrated the capacity for is that kind of detailed diplomatic follow-through to actually make the sanctions real and effective. And if they can’t do that, I think this is kind of over before it started. But we’ll see.

Jake Sullivan:

Okay. So I think we have a similar kind of meta reaction to what’s happened with this, “Economic D-Day,” but let me try to play out a possibly optimistic scenario. And I want you to tell me where this just doesn’t work. So the administration goes out. Says, “We’re in the end game. We’re going to crush their economy. Most decisive economic pressure campaign in human history.” At the same time, we get reports that President Trump has spoken with the Pakistani head of the army, Munir. That Munir has actually gone to Iran to talk to the Iranians. That Iran and Oman are back to negotiating some kind of temporary arrangement to open the Strait. And that what Trump is trying to do is kind of set up a way for him to accept a bad deal and then claim basically, “Ha-ha, it was what I did on the economic front that got us to that deal.” So in a sense that this is theater to try to generate an off-ramp to produce an agreement that gets the Strait open and, frankly, gets Trump out of the mess that he’s made in Iran.

Do you think that’s possibly what’s happening here? And then on the Iranian side, is it plausible that they could end up making an offer that Trump could accept? Or by virtue of the fact that Trump and Bessent have gone out and said, “We’re going to crush these people. We’re going to grind them down to nothing,” that the Iranians, in a sense, have been backed into a corner and can’t do a deal because it will look like they’re negotiating under pressure? Any chance of this more optimistic scenario coming to pass, Jon?

Jon Finer:

I think there is a chance. I think it’s a version of another play the administration has tried to run on the military side, where they said, “All right. We’re going to escalate massively over an extended period of time and bring Iran to its knees and get them to fold.” And then they do a sort of nominal military escalation; hit a bunch of additional targets, but nothing, really, that is categorically different from what they’ve been already doing. On the theory, basically, that they can then say, “We escalated. Now Iran is coming to us, saying they want to negotiate,” which is another classic Trump claim: “The Iranians keep contacting us because they want to negotiate, but we’re not sure we’re ready,” when in reality it’s almost certainly the other way around.

So yes, I think this could, in some sense, be an artifice to justify a deal. But what I think is not likely to be the case, almost guaranteed not to be the case, is that whatever Iran ultimately offers or is willing to agree to is somehow better than what was on the table for the administration two months ago, three months ago, three weeks ago. I think, if anything, Iran is maybe willing to agree to roughly the same terms that were in the MOU, or a version thereof the MOU that Trump agreed to and then that unraveled. But very unlikely that they’re going to give the Trump administration more than they’ve already put on the table because of this economic pressure. Best reason for that, best evidence for that is that Iran’s negotiating position has not really changed throughout the course of this entire conflict. So not clear why we would believe it would change now.

Jake Sullivan:

If anything, going back to February 28th when this thing kicked off, the deal for the United States has gotten progressively worse with each passing month. And the best we can hope for now is essentially a deal that we could’ve had a couple months ago, and it may end up worse. That is a through line of this conflict that is both maddening and quite remarkable to watch. And speaking of things to watch, I think in the midst of all the zigging and zagging, in the midst of all the different kitchen sink plays the administration is running, in the midst of all the stories about what is and is not happening in the Strait, I think it’s important for us to try to give our listeners and viewers a sense of what things to really zero in on to see how this is likely to unfold.

And I basically have a list of three things. The first is to watch the number of ships going through the Strait of Hormuz. There’s been a number of different reports about that number creeping up as Iran’s capacity to fully shut, particularly that southern Oman route, has been challenged to a certain extent. So will we actually see more ships getting through than, maybe, we expected? And that’s something for us to watch. And then of course, how does Iran respond to that?

The second is, do the sanctions actually end up biting more than we expect? We have to hold open the possibility that in fact the administration does something more dramatic with these secondary sanctions, including against China, than you and I are predicting. I don’t think that’s likely, but that’s really the thing to watch. Will they actually hit third countries with sanctions? Or will China, without getting hit with sanctions, choose to give something to the Trump administration by dramatically reducing its economic intercourse with Iran?

That’s the second thing to watch. And of course, how does Iran respond to that? And Iran could, to either a growing number of ships through the strait or a growing feeling of economic pressure, respond by escalating. By hitting Gulf countries, by hitting oil infrastructure, by doing things that it has to date been more restrained in terms of its posture than it might be if it feels like it’s under greater pressure or greater threat. And then the third thing is really the debate within Iran. I think some of the smart Iran experts you and I talk to are increasingly of the view that there is a robust debate between hardliners who basically just want to keep embarrassing the United States and are prepared to let this play out indefinitely, and pragmatists who think that they can get a good deal now and they should take it now because the situation may get worse over time.

I do believe Trump will accept something like the memorandum of understanding. He’ll accept making large payments to Iran. He’ll accept a degree of Iranian control of the Strait. He’ll accept that he’s getting little movement on the nuclear program. Iran just has to offer it. So right now I think the main focus is, how does this debate within Iran play out? And do the pragmatists win out and Iran come and put something on the table? And that, I think, right now is very much up in the air. So that’s on my list of what to watch before we round out this section. Jon, what’s on yours?

Jon Finer:

Two very strange governments that are doing this dance. Ours, unfortunately, and the Iranian government. On the Iranian side, I think the big near term question they’re going to face if there is any meaningful impact of this sanctions campaign, and particularly if countries in their region involve themselves in enforcement, is the one you put on the table, whether they re-escalate. I think there is the possibility, if not the probability, that if countries like the UAE, certainly like Qatar or Saudi Arabia actually decide to participate in sanctions enforcement in a way that hurts Iran, that Iran will not focus its retaliation as much on the United States as it will on its neighbors the way it has throughout the course of this conflict. So that’s one thing I think that’s important to watch. By the way, I’m not sure those countries will involve themselves as much as the Trump administration would like, but if they do, they will probably face a degree of retaliation.

The second is the Trump administration’s ability. Ability I say somewhat tongue in cheek, to just shift course without any real explanation, and discard previous approaches without feeling the need to justify that. Remember that, just before the MOU was reached, President Trump threatened to destroy Iran’s entire civilization. Didn’t stick with that line of policy attack for very long and, ultimately, reached a deal. It is entirely possible that this, as you said, economic D-Day will lead pretty shortly to a pivot towards direct negotiations. But again, I think the most important point, which both of us have made during the course of this conversation, is those negotiations are not going to lead to a better deal than was on the table during the MOU, at the beginning of this war and, frankly, as we’ve said in previous podcasts, before this war was even conducted, when the US was also negotiating with Iran on terms pretty similar to what is being discussed now and what was in that MOU. So the lack of necessity of all of this cannot be said enough times and can’t be overstated. And we’ll see where it goes.

Jake Sullivan:

That we will. And some things to watch. We’ll continue, obviously, to monitor the situation. And obviously we will be coming back to this topic sooner rather than later. Should we move on to another type of war closer to home?

Jon Finer:

Yeah. Or another type of economic war closer to home. So maybe just briefly, to review the bidding on the US-Canada trade conflict, last week Canadian-American and American negotiators seemed to be getting closer to a deal. President Trump hinted as much at least twice in public comments, including hours before, spoiler alert, the whole thing fell apart. On Friday, just last Friday, Canadian Prime Minister Mark Carney pulled out of the negotiations, claiming the United States had made last minute unacceptable demands and that Trump’s signature was, “Written in pencil.” Very good phrase, I think, that represents a lot of how this administration negotiates.

Jake Sullivan:

That’s like Canadian shit talk, right?

Jon Finer:

Yeah, it is. Written in pencil. Absolutely.

Jake Sullivan:

Yeah, yeah. Yeah, I get it.

Jon Finer:

On Saturday, Carney gave a speech to the Canadian people saying that this was a bad deal for Canada, that the US had sort of fundamentally changed its character. That we, “cannot accept what they offered, and we cannot give them what they asked.” And that, “We were not prepared to compromise Canada’s sovereignty or undermine our key industries.” He also said, “You’re at war when you get attacked, and we got attacked.” So more or less telling Canadians that they are now at war, or a version of war, with the United States. President Trump then announced 50% tariffs on as much as $20 billion in imports from Canada.

By the way, the overall trade relationship between US and Canada is approaching $400 billion, and this is on $20 billion. And Carney then came out and announced, more or less, a parallel set of tariffs on about $28 billion Canadian dollars worth of US goods that are imported by the Canadians. And we’re sort of off to the races. So that’s the tail of the tape when it comes to the facts. Maybe your reaction to, one, how we seem to have stumbled our way into this situation. Why the United States is going down this path and whether the Canadians can stick to what right now is a pretty hard line that very few countries have taken with President Trump, which is basically just to say, “No,” and punch him back.

Jake Sullivan:

I think there’s a policy element to this and I think there’s a personnel element to this. The policy element is that the Trump administration feels that it has been able to steamroll trade partners, especially friends and allies, in these negotiations, and that it can always ask for a little bit more, and it can always ask for a little bit more especially right at the end. It’s a classic Trump administration negotiating tactic. You have a hard fought negotiation. Then you say, “Here’s three more things we need.” And I think they did that here. And they did it in particular on some issues that we can come back to that go to the heart of Canadian sensitivities about sovereignty and dignity.

I think there’s also a personnel aspect to this, which is that you’ve had this two-headed monster of Jamieson Greer, the US trade representative, and Howard Lutnick, the secretary of commerce, working these negotiations. And Greer, by all accounts, has actually been constructive and tried to get to yes with Canada. Lutnick, who owns some of the tariffs, particularly with respect to steel and autos, has been, I would say, much more pugilistic, much more escalatory, and much more dismissive of Canadian concerns. And I think he came in and basically said, “I want to stick it to these guys.” And the seams between what Greer was trying to land and what Lutnick was demanding I think started to widen as we came down the home stretch. And the result, basically, was the Canadians, the Canadian Prime Minister Mark Carney throwing up his hands and saying, “We’re done.”

Now, briefly on the issues, because I think this is important. One, the Americans negotiated in the US-Canada-Mexico trade agreement, the USMCA, the ability basically to have a veto over trade deals of any of the parties with China on the notion that American and North American supply chains would be impacted by any such deal, so they’d have to get sign-off from all three countries. What they were trying to do here was get Canada to agree that the US would get a form of veto over any deal it does with any country, including market economies.

And for Canada that was just absolutely a bridge too far. The second thing that the Trump administration wanted to accomplish was weakening Canadian French language packaging and digital streaming quotas. Basically rules they have in their system to preserve and protect the French language. And obviously this is a third rail in Canadian politics, and the Canadians pushed back hard on that. And then, finally, there were issues associated with heavy trucks being assembled in Ontario. Essentially, Carney said, “You’re going to make our vehicle manufacturing structurally uneconomic if we agree to this. We just simply can’t do it.” And I think this was a Lutnick push in the end.

I make those specific points because I think it’s important to recognize that there is actual substance here that is being fought over. This isn’t all just purely posturing. But the larger strategic point is that the Canadian public has just had it with the United States of America. They are vibrating with intense rage at what they regard as aggression and betrayal that transcends any particular trade negotiation.

And frankly, I think the Canadian public didn’t want Mark Carney doing any deal, even a deal that didn’t implicate some of these things I just walked through, because the Canadian public wants their prime minister to stand up to the United States and essentially push back hard on behalf of Canadian sovereignty. More than three quarters of Canadians, 76% of Canadians said the country was right in refusing the terms being offered and ending negotiations without an agreement. And that’s despite the fact that 66% of Canadians believe the trade war will negatively affect their profits.

They’re basically saying, “We’re ready to pay some degree of economic price to stand up to the United States of America.” And this larger point I think is really fundamental because it’s not just about the Trump administration. It is about the larger relationship, it’s about the future, and it’s about the direction that Canada will want to go and the degree of loss of trust, structural loss of trust in one of our closest allies, our immediate neighbor. And I find that exceedingly distressing, and the larger story that’s at play here well-beyond the back and forth over the tariffs.

Jon Finer:

We are both from Canada border states, and it is clear that this has touched something deep inside Canadian identity. Over history, Canada has been willing to tolerate, has benefited from, in many ways, this sometimes big brother, little brother relationship that it’s had with the United States because the two countries have largely been like-minded. Have been good neighbors, have had this symbiotic, mutually beneficial relationship. Sometimes, obviously, there have been periods where we’ve been at odds, but nothing grave has ever really divided politically the United States and Canada. Certainly nothing on this order of magnitude. And I think you’re absolutely right.

And not only has the Canadian public rallied behind Carney in spite of the fact that not only do they believe that this will hurt them. A majority of Canadians believe it is at least possible, strongly agree or somewhat agree that this could lead to military conflict, this trade dispute between the United States and Canada.

So they’re not Pollyannish about where all this could go, and still are strongly in support of what Carney has done. I thought this statement, by the way, from Pierre Poilievre, who’s Carney’s election opponent and, at one point, a sort of quasi-Canadian MAGA, if you will. His statement in response to this most recent flare-up: Conservatives, his party is, the Conservative Party, are disappointed that the United States has chosen to impose further unjustified tariffs on Canada. Canadians must stand united to defend our country against these unfair attacks on our jobs and businesses. Canada cannot accept one-sided tariffs that will de-industrialize our country. If that’s the opposition to Carney, he’s on pretty strong ground, standing firm against Trump.

Last thing I’ll say just as a flag, although I don’t expect this to really be a change in the course of the overall situation: There is a referendum taking place in Canada on October 19th that is not unrelated to this standoff. On October 19th in the province of Alberta voters will take up a question, which is whether the province should remain in Canada. This is probably the most conservative province in Canada. Also one of the wealthiest provinces in Canada, if not the wealthiest. It’s an energy-rich province. Whether Alberta should remain in Canada or the government should begin the legal process to hold a binding vote on actual separation, independence from Canada.

The numbers in the polls of who would support taking that action are starting to creep up. Now, they’re still well-below majority in the most recent polls. And if anything, my bet would be that this standoff is not actually going to help the people who want that referendum to succeed. It’s probably going to hurt them. The Pierre Poilievre comments would suggest that. But that is maybe a data point to keep an eye on. If that referendum goes against the unity of the Canadian government, that could recalibrate. One of the few things, perhaps, that could recalibrate Mark Carney’s stance. I don’t expect that to happen. And I expect this not to stay as it is this week for much longer, given the factors I just described.

Jake Sullivan:

By the way, just on that last point, massive shades of Brexit here. You have the premiere of Alberta coming out and saying, “I do not support independence or separation, but I believe Albertans should have a democratic opportunity to express their views.” That’s pretty much exactly what David Cameron, the prime minister of the United Kingdom, said when he put the Brexit referendum on the books for the British people to vote on. He did not support it but he’s like, “Well, people should get the chance to speak.” Privately, he told everyone he didn’t think it was going to pass, and then of course it passed.

Here, when you look at the polling and everything else, it doesn’t seem likely but, man, Brexit came as a surprise to a lot of people, and now there’s a lot of buyer’s remorse for that in the UK. I’ll be very curious to see how this referendum on October 19th plays out. And by the way, the MAGA movement in the United States is pretty heavily-involved in stoking and stirring a lot of this up. And watching that unfold, the kind of reverse foreign election interference coming from the United States into Canada, I think will be a feature of the run-up to that referendum on October 19th.

For me the key bottom line is less about the immediate trade dispute and how that gets resolved, and if it gets resolved, and more about the future of the US-Canada relationship. I’ve been up to Canada a couple times in the last few months, and I do worry that a new president, even a president that wants from the start to build a strong, vibrant partnership with Canada is going to face a huge amount of headwinds and is going to have to overcome a lot of skepticism, understandably.

And yet, I also believe, structurally, that the United States and Canada, our destinies are bound up and we have to find a way forward. So I think this is a very significant strategic matter for the United States, that we, over time, come up with a way to get beyond what has been, to use a Carney term, a rupture in this relationship that goes way beyond just this particular trade dispute.

Jon Finer:

America’s word being written in pencil in addition to America’s actions being coercive and bullying is, I think, language that will not soon be forgotten and will bedevil and challenge a new administration every bit as much as it’s challenging this administration right now. People are just going to be disinclined to believe that we can stick to things we say and agree to because this administration has demonstrated such an unwillingness or inability to stand by its word or the word of previous US administrations. So that is not something that’s going to change anytime soon.

Jake Sullivan:

So we’re moving on to a Red Team, Blue Team exercise. The topic is a new presidential memo that creates a program allowing vetted US private companies to conduct offensive cyber operations against foreign cyber criminal organizations. So the targets are supposed to be foreign cyber-enabled criminal organizations, not foreign governments, but the memo says, “Groups are presumed not to be government-controlled unless there is clear evidence or intelligence showing otherwise.”

Now, this is not a blanket authorization for companies to hack back on their own. Participating firms would basically operate under contracts with the Justice Department or the Department of Homeland Security, and they would operate under federal oversight and federal legal authority. And this memo, which has gone into effect, explicitly authorizes two categories of activity: Cyber surveillance operations, basically getting onto foreign criminal networks to collect intelligence, and then cyber effects operations, operations that disrupt, deny, degrade, destroy information systems, networks, or infrastructure. Basically offensive cyber ops that aren’t just aimed to collect intel but to cause effects against those systems.

The administration basically has said the rationale is the private sector has cyber capabilities that the government has underutilized. And the White House has said that, basically, they’re trying to take advantage of the private sector’s scale, speed, and capacity. Some have compared this to privateering, basically having private ships go and attack foreign enemy vessels back in the 1800s, 1700s. That this is the modern version of that.

Now, this has gone into effect, but what we’re going to do for the Red Team, Blue Team today is take us back in time to before this was signed and put into effect. And we are going to have a debate in the room in front of President Trump with one of us arguing that he should go ahead and sign this memo and one of us arguing that he should not go ahead and sign this memo.

And we will simulate and play out the debate as we think maybe it didn’t unfold but should have unfolded in the course of deciding to reach this rather remarkable development in US cyber doctrine. So Jon, you drew the straw to make the case for this memo, for this new approach. So do you want to go first, and then I will make the case against it?

Jon Finer:

Happily. All right. Mr. President, the United States has for a long time been subject to relentless cyber attacks from criminals around the world and, in the vast majority of cases, we have done nothing about it. Your predecessors have done nothing about it. There are various rankings of cyber targets around the world. By number, by financial impact, by various metrics. And the United States is nearly always at the top of that list, the biggest victim.

The direct cost of this is in the tens of billions of dollars, and the macro costs when you consider second-order effects on the economy could be in the high hundreds of billions of dollars by some estimates. What do we do about this? Well, historically, we charge, criminally, a few stray organizations or individuals through our Justice Department. Often they have a big press conference with a lot of fanfare, though rarely do they bring any of these people to justice, because we can’t get extradition from the places where these people actually live.

Sometimes we recover some money from a crypto wallet. Also then issue a big press release to make the victims whole. But in the vast majority of these cases, as I’ve said, the money is not recovered and none of this amounts, as is very clear, to a meaningful defense or deterrence. These activities only increase over time. We are also playing a bit of a sucker’s game, Mr. President, when it comes to the main country perpetrators.

And I say, “Country perpetrators,” because the countries involved, and you know the list, China, Russia, Iran, North Korea, they say they aren’t responsible for what private criminal enterprises do, even though they are, at best, indifferent to these criminals. And more accurately, they encourage and create conditions for these predators to thrive. For some countries like Russia and China, they are clearly becoming tools of foreign policy. Just a reminder that we are not helpless here. We have incredible national resources when it comes to cyber at the Cyber Command, at the NSA, at the CIA, among others.

But as a well-known cyber official, nonpartisan person who served in many previous administrations, Anne Neuberger, has pointed out, those capabilities are a finite resource and are mostly taken up dealing with nation state actors like the ones I mentioned. And that tends to leave comparatively little capacity to deal with the criminals, who are also perpetrating these crimes, which is one reason why they’re left to law enforcement after the fact, which has been so ineffective.

We are also relatively vulnerable, Mr. President, since so much of our critical infrastructure, from healthcare to our electrical grid to our water supply, is held in private hands. And we struggle to make those companies adhere to higher standards and protect themselves. We lack the legal authority to make them, and many of them just simply do not act responsibly on their own. By the way, Mr. President, we are also on the cusp of a massive increase in AI-driven cyber attacks.

We’ve seen these capabilities with Mythos, which you smartly, wisely have withheld from broader public release. While the US government is, for now, doing the right thing and withholding access to these models, there are open source models available to anyone, the best of which come from China, that are catching up fast. And criminals are going to have capabilities like this before too much longer. We are fighting all of this with one big hand tied behind our backs.

Our private sector has extraordinary cyber capabilities. To establish a measure of deterrence the criminals need to know that if they stick their heads up and conduct attacks, they will get hit hard. Not just maybe face criminal charges down the road that they will never likely have to see a courtroom and address. There’s a history of this, as my colleague mentioned. Letters of mark and reprisal are mentioned in Article I, Clause 11 of the US Constitution.

And the US has actually deputized, authorized private actors to take analogous actions like this before. Okay. It’s been a while. The American Revolution is the best example. The US government issued 1,700 of these letters of mark and 800 commissioned privateers destroyed 600 British ships during that period. The Confederate Army tried a similar tactic in the Civil War, thankfully with less success. Now, lawyerly sticklers like my colleague may argue that the Constitution grants this power to Congress, which might be true, but Congress no longer really enforces its prerogatives anyway, as you’ve seen in many other contexts. And there is currently pending in Congress a cyber letters of mark bill that would authorize exactly what the executive order before your desk would have you do. And we want to thank Senator Mike Lee for putting that bill forward.

Obviously this has to be carefully overseen. I suspect my colleague will say that implementation is going to be challenging. Target selection may produce errors. Companies who conduct such attacks will likely face retaliation and may have trouble defending themselves. All of those are legitimate concerns. The biggest concern, as with many things our administration takes on because we are so bold and so brave and so daring, is going to be implementation.

But I’m telling you, Mr. President, we are up to this task. Ultimately, a worthy goal in addition to deterrence is going to be establishing an enforceable, broadly agreed set of standards for the rest of the world to follow in cyber, like we have when it comes to weapons of mass destruction. This will have to be negotiated, including with our adversaries, people you have developed a relationship of trust with who we can bring to the table. But for us to get them to do things they don’t want to do, we will have to embark on this diplomacy backed by a meaningful threat of force. And this action empowering our private sector will give us that meaningful, credible threat of force. We need deterrence, Mr. President.

Jake Sullivan:

My colleague has made a reasonable case but, unfortunately, Mr. President, this approach makes absolutely no sense. Let me start with the fact that we are essentially putting the power in the hands of private actors to drag us into open cyber conflict, cyber war, and maybe even full scale war with the likes of China, Russia, North Korea, and other countries. My colleague just admitted that these countries’ foreign criminal organizations or non-state organizations that do cyber activity are deeply intertwined with their military and intelligence agencies.

So let’s say we give a letter of mark, an authorization to some private actor in the United States to go hit a system in one of these countries, and they screw up. And instead of hitting a foreign criminal organization, they hit a Chinese intelligence agency, a Russian military agency, a North Korean government server. And those countries say, “Hey, we’re going to hit back.” And then we’re off to the races all because some private actor who we, at the end of the day, don’t have a whole lot of control over, has just been empowered to go do that.

And we’ve announced to the world, “Hey, we’re backing these companies when they go do these things.” This makes no sense. It is massive escalation and retaliation risk we’re courting without a really clear way of being able to manage that risk, because we are mortgaging, we are outsourcing this capability to the private sector. And by the way, it’s not a small thing that it’s the private sector that is the one that we’re saying, “Hey, go do this.” They’ve got seriously perverse incentives.

When we ask a military cyber unit to conduct cyber operations, they operate under strict strategic calculus. The cost-benefit analysis is strategic. It’s not about profit. Private contractors are incentivized to demorate constant op tempo to justify their contract renewals, and this increases the likelihood of aggressive, high-risk actions, because they’re being driven by a profit motive. That makes no sense. That is putting the entire American security at risk so some cyber CEO can meet his bottom line or get his bonus.

There’s also a problem with precedent risk here. Yeah, these other countries are doing all kinds of things in cyberspace, but we go out publicly and announce that we’re opening all these new fronts of cyber offense. You don’t think that our adversaries are going to respond by thinking that they’re empowered and emboldened to do more as well? I certainly think they will. And while the United States, historically, has been the most protected geography in the world, we have these two oceans and Canada and Mexico, we are the least-protected in cyberspace. We are the most wide open, the most vulnerable in sector after sector because we still don’t have basic mandatory cybersecurity requirements in our critical infrastructure. So we’re going to escalate the cyber game at a time when we are more vulnerable than our adversaries.

Next point: execution risk. These private companies have no visibility into what US intelligence, military, or allied cyber operations look like. And they could be going against the exact same target set that the NSA is going against, or CyberCom is going against, or an allied cyber actor is going against, and everyone could just end up bumping into each other. And also keep in mind that criminal actors rarely host operations on their own physical hardware. They use innocent people’s hardware; hijack servers or commercial cloud providers or hospitals or universities.

So we’re going to unleash a bunch of private actors to go start taking down third-party systems that criminals are using just as transit nodes? That also is going to wreak havoc and I think end up costing us a lot more than the ransomware challenges that we’re facing right now. My colleague says that the history shows that letters of mark have really worked. Yeah. They weren’t too bad in the American Revolutionary War. Back when we didn’t really have a navy this was the only thing we could do. As it turns out, now we actually have an NSA, a CyberCom, a Cybersecurity and Infrastructure Security Administration, CISA. Why don’t we use those? I’ll come back to that in a minute.

But there’s also a reason the practice fell out of favor, that we stopped doing this after we built our own navy. And it’s because, over time, privateering ended up competing with our navy for sailors and resources. You had really high attrition because privateers acted recklessly and many of them were captured or sunk. And the whole thing became much more of a pain to deal with than it was a benefit. I think we can learn, from the fact that privateers basically went out of business, to not bring them back into business in the 21st century.

I know we believe in unfettered presidential power in this administration, but I actually feel duty-bound to know what our critics will say, which is that Article I, Section Eight clause in the Constitution does give Congress the power to grant letters of mark, not the administration. Okay. I’m not going to dwell on that because we don’t really want to buy into that stuff. Let me close with a better option: Don’t fire people. Don’t can 30% of CISA. Don’t can the top leadership, uniform military leadership, of the NSA. Don’t erode and hollow out our own government capabilities to conduct cyber operations. Build them up. We don’t need to rely on the private sector if we were to build up our own capabilities within the government, where we have command and control, we have aligned incentives, we have the capacity to manage how things actually end up playing out. So there is an answer to this, and it ain’t outsourcing this to the private sector.

It’s actually reversing the cuts that we’ve made and enhancing the overall muscle we have in the US government to conduct these kinds of operations. So I would just say, “Let’s not do this.” It makes no sense and I think we’re going to live to regret it.

Jon Finer:

Sounds like a fireable offense, firing-worthy offense by a Biden administration holdover to me.

Jake Sullivan:

A deep-stater.

Jon Finer:

Deep-stater.

Jake Sullivan:

Exactly.

Jon Finer:

So in hearing this, and even before hearing this, I think this is pretty crazy, honestly. I do think, though, the current situation is untenable. We just take it, take it, take it, take it. And so I do have some sympathy for them wanting to try something big and bold and creative. Unfortunately... And many of the points you made I think, in the hands of a different administration, would still be valid but would be at least diminished.

The coordination challenges and the execution challenges, I think a more competent set of actors could manage their way through while mitigating the risk. But the risk of this is enormous. And to me it’s less, actually, like privateering as the framework and the analogy, which is the line that everybody’s drawn, and more, almost, like mercenary work or private contracting work in a military context, in which you ask people who will have less accountability, more vulnerability, who will not adhere to the same standards that the US government will adhere to do things that are basically quasi-governmental or quasi-military.

And we’ve seen the consequences of that sort of thing in Iraq and Afghanistan, and elsewhere and sort of walked back a bit from it as a result of that. I think, probably, we’re going to be chastened by this experience, too, if it ends up being authorized to the extent that they are suggesting it will. Remember, as you’ve said, as I said, it’s not like companies can just go out and start hitting a bunch of targets. They have to get approval target by target, company by company. So it’s possible that they’re going to be quite conservative and judicious in implementing this, although conservative and judicious does not tend to be their MO.

Jake Sullivan:

I think that’s well said. I do actually think this is a closer call than, certainly, I laid out with my bill of particulars, because I do think we want to leverage the enormous capacity of the private sector. And I do think that there are ways to think about public-private partnerships in this space in targeted and specific areas that could make sense. I’m very concerned about it being in this administration’s hands, in part because they could end up attacking allies more than they attack North Korea, Iran, or China.

And in part because when you declare it that the target’s foreign criminal organizations, think about who they think of as criminal. It includes a wide swath of political opponents who are not ransomware actors operating out of Russia. So I’m particularly concerned about it with this administration. But on balance, I’d probably say, “Let’s build the muscle within the government and maybe come up with creative ways to second or bring into the US government on details, talent and capacity from the private sector but that’s operating entirely under the command and control of the US Military and intelligence enterprise.” That would probably be how I would play things out.

Jon Finer:

Also cannot rule out a corruption motive in some or any of this. Attacks against business competitors of friends and family, that sort of thing. There’s just so much that they do not get the benefit of the doubt on given how they’ve conducted themselves. But anyway, I think we’ve said our piece.

Jake Sullivan:

All right. So it will be interesting to watch how this plays out. We will be able to revisit it here over the coming months. But for today, I think we’ve covered economic D-Day, trade war US-Canada, and now cyber war launched by cyber privateers. I think a good through line for this episode, as you laid out at the top. And we’ll have next week off and be back the week after Labor Day with our regular cadence, our regular weekly episodes through the fall.

Jon Finer:

Thanks everybody. Well, that’s all for today. We’ll be back in two weeks with a new episode of The Long Game.

Jake Sullivan:

Subscribe to our YouTube channel and follow the audio feed so you never miss an episode.

Jon Finer:

For additional content, episode transcripts, and exclusive podcast segments, subscribe to The Long Game on Substack or join The Long Game Plus on Apple Podcasts.

Jake Sullivan:

This week, why was CIA Director John Ratcliffe in Moscow? The fact that it was a very brief meeting, only a couple of hours, suggests to me this was not some larger negotiation about the war. That it was about delivering a message. So I think this is a distinct possibility. It’s also possible, there’s been some reporting that this was more about Iran. That it’s about trying to get the Russians to help with respect to the Strait of Hormuz and other things. That would be more consistent with this administration thinking Russia is a friend of the United States and, hey, we can go work with them on these issues.

Jon Finer:

Head to thelonggame.substack.com, or subscribe to The Long Game Plus on Apple Podcasts. The links are in the show notes. That’s it for this episode of The Long Game.

Jake Sullivan:

If you like the show, please follow, share with friends, and leave a review. It really helps listeners find us. The Long Game is a Vox Media Podcast Network production.

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In this exclusive Listener Mailbag segment for paid subscribers, Jake Sullivan and Jon Finer consider several possibilities. Then, they answer a question about surviving the physical and mental toll of senior government service.

If you’re a paid subscriber, thank you for supporting the show. Watch the segment and share your thoughts and questions by commenting below or email Jake and Jon at longgame@voxmedia.com.

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A NOTE FROM THE PRODUCER

Tamara Sepper is the Executive Producer of The Long Game

Treasury Secretary Scott Bessent announced this week what he called an economic D-Day against Iran: “the single greatest financial offensive ever marshalled against an adversary.” Days earlier, U.S.–Canada trade talks collapsed, and Prime Minister Mark Carney told Canadians the American signature was “written in pencil.” This week, it’s just Jake and Jon, for what Jon sets up as an economic warfare edition of the show. Or warfare by other means.

Also in this episode: a red team–blue team debate over President Trump’s memo allowing private companies to run offensive cyber operations against foreign criminal networks, with Jon arguing for the cyber “privateers” and Jake against; and, at the top, a few minutes on Dolly Parton.

We love hearing your thoughts. Please comment below or email Jake & Jon at longgame@voxmedia.com.

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REFERENCES & SUPPLEMENTAL MATERIALS:

Scott Bessent: an economic D-Day is coming for Iran, The Financial Times, 8/23/26

Remarks by Secretary Scott Bessent Announcing Operation Economic Outcast, YouTube, 8/24/26

“Prime Minister Carney delivers remarks on Canada-U.S. trade negotiations,” Office of the Prime Minister of Canada, 8/22/26

“Expanding Capabilities to Combat Transnational Cyber-Enabled Crime,” The White House, 8/12/26

“Lee Bill Authorizes American Hackers to Fight Foreign Cyber Attacks” (S. 5000, the Cyber Letters of Marque and Reprisal Act), Office of Sen. Mike Lee, 7/15/26

Photo by ANDREJ IVANOV / AFP via Getty Images

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If you haven’t yet listened to the conversation, check it out now.

They also shared a few books worth adding to your summer reading list. Here are their recommendations:

Jon’s Summer Reading List

Absurdistan by Gary Shteyngart

Country People by Daniel Mason

Hub fans bid Kid adieu by John Updike

Transcription by Ben Lerner

Jake’s Summer Reading List

Chokepoints by Edward Fishman

Spies, Lies, and Algorithms: The History and Future of American Intelligence by Amy Zegart

Technology and the Rise of Great Powers: How Diffusion Shapes Economic Competition by Jeffrey Ding

Don’t miss the video for paying subscribers, where they examine how Trump-era impunity and outrage fatigue can normalize corruption.

Which books are you reading this summer? Let us know in the comments below.

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is the Executive Producer of The Long Game.

Investigative journalist Patrick Radden Keefe has spent two decades exposing corruption. The traditional syllogism of his profession is simple: corruption happens, the press exposes it, someone steps in and stops it.

He no longer believes step three is reliable. Sometimes the reporting lands, everyone shrugs, and the thing keeps going.

In this exclusive segment for paid subscribers, Keefe, Jake Sullivan, and Jon Finer discuss how the Lance Armstrong logic (everybody else is cheating, so only a fool doesn’t) spreads beyond politics.

If you’re a paid subscriber, thank you for supporting the show. Watch the segment and share your thoughts and questions by commenting below or email Jake and Jon at longgame@voxmedia.com.

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COLD OPEN

Patrick Radden Keefe:

There’s an old saw in Hollywood among Hollywood screenwriters that if you’re writing a villain for your movie, your villain shouldn’t know that he’s the villain. Outside of a comic book, most villains don’t think that they’re the villain in the movie, they think they’re the hero of the movie. They’re watching a different movie than you are.

Jon Finer:

Welcome back to The Long Game. I’m Jon Finer.

Jake Sullivan:

And I’m Jake Sullivan. Today we’re joined by one of the premier investigative storytellers of our time, Patrick Radden Keefe. Patrick is a staff writer at The New Yorker who spent the last two decades illuminating the above ground and underground institutions, the financial networks, the colorful characters, and the moral compromises that shape the modern world. For The Long Game audience, Patrick’s work is indispensable because he excels at taking a specific story, a single disappearance, a single corporate dynasty, a single mysterious death, and using it to diagnose broader trends in state capacity, social decay, crime and conflict, and even the map of global power. You can see this across his entire body of work, including his most recent book, London Falling, which came out earlier this year. I’ve read it. It’s a gripping investigation into the mysterious death of a London teenager who impersonated an oligarch son. And Patrick uses that tragedy to reveal how decades of deregulation, and frankly, a culture of willful blindness turn London into a sanctuary for anonymous, often illicit foreign capital.

He also wrote one of my favorite books, which we’ll also talk about on this podcast, Say Nothing, back in 2018, a book about Northern Ireland’s troubles. Framed around the 1972 disappearance of a mother of 10 children, which examines political violence, codes of silence, and the moral trade-offs that come along with peace negotiations. Then there’s Empire of Pain, which is just a brutal accounting of the Sackler family and Purdue Pharma that was behind much of the American opioid epidemic. And his earlier work included Chatter, which was an ahead of its time look into Western electronic surveillance networks and post 9/11 signals intelligence. Patrick also conceived and hosted an addictive eight-part podcast, Winds of Change, which investigated whether the CIA secretly authored the Scorpion’s Cold War hit song as part of the covert influence operation. So we’re excited to talk to him about all of that, about how he does his work, what it means for the world around us.

And with that, Patrick Radden-Keefe, welcome to The Long Game.

Patrick Radden Keefe:

So good to be with you guys.

Jon Finer:

It’s great to have you. And Patrick, we’ll just dive right in. In London Falling, your most recent book, which Jake just referenced, you zoom out from the tragic death of a teenager to a larger story about London and Britain, and really, the wider world. For listeners coming to this story fresh, can you just give a bit of background of who was Zac Brettler, what happened on the night he died, and what did it reveal?

Patrick Radden Keefe:

Yeah, absolutely. In some ways, the easiest way to tell you, to set up the book is to tell you how it came to me. In the summer of 2023, I was living in London for the summer, producing a TV drama based on the book Say Nothing, that Jake just mentioned. And I was on the set one day and there was a guy who was a guest of the director of that episode, and he came and he just sat down next to me. We were killing time between setups on the show, and we started chatting. And I told him what I do, that I write for The New Yorker, that I write these investigative narrative pieces. And he said, “I might have a story for you.” And what he told me was, there was a family here in London, the Brettlers, who I’m very close with, and they had a son named Zac, a 19-year-old who died in the summer of 2019.

So this is summer 2023 when I’m talking to him. And he died in mysterious circumstances. He went off the balcony of a luxury apartment building overlooking the Thames. And after he died, his parents, Matthew and Rachelle, made this astonishing discovery, which is that unbeknownst to them, he had been leading this secret double life. And he had been moving around adult London as a teenager, pretending that he was the son of a Russian oligarch. And so you had a mystery in the forefront of just how did this kid die? How did he end up on the foreshore of the Thames? Was it a suicide? Was he pushed? Did he fall? And then you had this deeper question, which is, why would, in this case, an upper middle class, nice Jewish boy from West London, Zac Brettler, from this loving family... What is it about London today that would make that kid aspire to be the son of a Russian oligarch?

Jon Finer:

So Patrick, can you just talk a little more about, one, hearing the pitch, I guess, which may not have even been a formal pitch that you got. What made you think that’s more than just an interesting story to tell somebody in a bar, but something that’s worth 10,000, 15,000 words in The New Yorker? And then, what makes that 10 to 15,000 word story actually worth going even deeper into and treating it in full book form? What are the different hurdles that you overcome in your own mind to take those steps?

Patrick Radden Keefe:

I have always, since my first book really, and my early days in journalism 20 years ago, I’ve always gravitated to narrative as a delivery device for complex information. I tend to find that people are much more amenable to following you down whatever your chosen path is if they feel as though they’re following characters in a story, if they feel as though there’s some sort of drama that you’re inviting them into rather than just a complex treatise on the origins of the opioid crisis, say, or the troubles in Northern Ireland. There always has to be some sort of frame story for me. And I should say that was initially a matter of just my own proclivities as a reader and as a writer. It’s always been that way in my career. But I think particularly over the last 10 or 12 years, it feels in some ways more urgent than ever to do that because I read less attentively.

I don’t read as well as I used to. My phone has broken my brain. I think this is true for a lot of people. And it doesn’t mean that I think we should all give up and just make videos or do podcasts. But it does mean, I think, that there’s a real premium on figuring out how to engage people and pull them into something. So I had already written an essay in The New Yorker, a short essay after Russia’s invasion of Ukraine, about the awkward place in which the British establishment found itself, where suddenly it was as if they belatedly woke up to the fact that London had provided this pretty commodious sanctuary for a bunch of fairly dodgy Putin-connected cronies. And they, very late in the game, were getting around to sanctioning people in a more aggressive way.

And there was a a sense of embarrassment, honestly, I think, at fairly high levels of British society over this state of affairs. So I’d written a short essay on that, but it wasn’t the thing that I could sustain in a longer piece of writing unless I had some sort of narrative frame. And so in that respect, it was a gift to meet this guy because he told me this story. And in an instant, I knew this is a a family story, it’s a mystery, it’s quite an intimate story, and yet it’s a way to continue to explore these questions about the way in which foreign money has corrupted London that I was intrigued by. So I wrote the piece. It was a long piece. I think it was about 15,000 words. Most of the time when I finished a long piece for The New Yorker, I think readers probably feel the same way, you get to the end and you feel like, “I never need to hear anything about this again. I’ve done it.”

This was one of four occasions in my career where I got to the end and I felt as though there was much more. And we can get into it, but I was very interested in the backstories of... There ended up being three people in that apartment that night when Zac goes off the balcony. There’s actually two, and it’s him and this other guy and then there’s another person who’s there just before and just after. And their family histories were really interesting. And I was thinking about how cities change. And it’s also a book about parenting and adolescence and how people change and transform. And all of that felt, in a very purely literary way, just rich and novelistic in terms of the material. And I felt as though I could squint and I could see how there would be a basis, not just for stretching the piece out, but a basis for building something much bigger and more ambitious.

Jon Finer:

So you said a lot of interesting things there, but the one that really struck me maybe is the smallest thing you said, but the most relatable to me, which is that even you, as somebody who is just steeped in this tradition of long-form journalism, a writer’s writer of non-fiction, finds that your attention span, your ability to digest long-form material has been impacted by technology.

Patrick Radden Keefe:

Totally. Not completely wrecked, but I still read probably more than most people, but I can’t explain to you the nostalgia that I have. I look back, it wasn’t even that long ago, but it has been years since I did what I used to do just routinely through much of my life, which is lie down on the couch on a Saturday afternoon and read uninterrupted for two or three hours. Maybe get up to get a coffee or go to the bathroom, but other than that, just be completely absorbed by a book. And that doesn’t happen anymore. I’m constantly reading, but I’m also checking my phone every 15 minutes. And I think, for me, it’s mostly been destructive. I think there was a time when I thought, “Oh, isn’t this convenient? Look at all the things I can do.” And I think now I’m beginning to, I have a real sense of what I’ve lost.

Jon Finer:

I think Jake probably felt the same way, but particularly I’ve found, coming out of government where you’re digesting everything in such short bursts, getting back the ability to even sit down and read a long article takes time. So anyway, gratifying to hear that you’re wrestling with the same phenomenon.

Jake Sullivan:

Just to come in here, because now that we’re all bearing our souls on this topic, I think is a really important one. When Jon and I were in government, our phones were in a box for most of the day, sometimes all the day. We’d go morning till night and maybe check our phone once. And actually, it didn’t take too long to lock into just a different type of attention span, a different type of focus. And so I found two competing impulses coming out of government. One is, I have more time to go in depth to read, to digest, to reflect. And on the other hand, I have the phone in my hand and I’m just constantly checking it. I can’t watch a movie straight, like a two-hour movie without maybe not even just looking at my phone, but doing something on my phone. And I just find that my nostalgia is about that. It’s about the feature film having disappeared from my life as a relevant pastime. So yeah, it’s been interesting.

Patrick Radden Keefe:

I can walk out about this stuff all day, but I think about increments of narrative time and how long it takes to tell a certain story. And there is a thing that I often come up against, which is these people who sort of want the TLDR version. They want the sort of what are the bullet points? What’s the takeaway? And it’s funny, because for me, that’s completely antithetical to what I do. What I’m thinking about is the seductions, the narrative pleasures that you can get out of absorbing something that is told in a leisurely way. And I guess, without getting into too many specifics, if you’ve read London Falling, there are big reveals that come in the last third of that book about some of the characters, which, if it was a series of tweets or if it was a 2000 word article, just wouldn’t land with you in the same way because they actually...

I think about this stuff all the time, and I think about my own most profound reading experiences have often been these ones where you’re so immersed in something and you become emotionally involved over time that when the twist comes, it just hits you like a ton of bricks. It takes your breath away. And in a world in which none of us are capable of absorbing a longer narrative in the heedless way that we used to, that becomes more elusive, those kinds of pleasures. And again, I think there’s something lost there. Now listen, as I say this, people are buying the book and they’re reading the book. I don’t know how much comfort I can take in being one of the last of the dinosaurs, but people are still engaging with this thing. But I think the bar is very, very high to getting them to do so.

Jon Finer:

The change that you’ve just described has really happened during the course of your career. It was not present to the same extent when you started. It is obviously omnipresent now. I think another change in the milieu in which you operate, the context, is that people are just less trusting of what they read even at a place, maybe even especially at a place like The New Yorker than they once were. By the way, they’re less trusting of what they hear from their government too, sometimes with very good reason. But how has that contested nature of truth impacted your work? And do you find that when you put out something like London Falling that took just an almost infinite amount of reportage and interviews and research... I’ve seen you quoted as saying only roughly 3% of what you report ends up in the final product. So obviously a ton of rigor behind this. Do you find that some people, at least more people than maybe used to be the case, question the veracity even of something as rigorous as that?

Patrick Radden Keefe:

There’s a thing that I think I have benefited from to some extent, which, broadly speaking, I think is a lamentable trend, people don’t trust mastheads anymore in the way that they used to. They don’t trust institutions in the way that they used to. They do weirdly trust individuals. And I think you see this... Pushing away from my own personal experience, if you look at The New York Times, clearly there has been a institutional decision at The New York Times to promote certain individual writers as individual brands. I don’t entirely understand the push to vertical video. I don’t know why. I love listening to the Ezra Klein podcast, I don’t need to watch it. Part of the beauty of a podcast is that you can do the dishes or drive your kids to school while you listen to it. So I don’t-

Jake Sullivan:

Is this the time that I should tell our listeners to subscribe to our YouTube channel?

Patrick Radden Keefe:

There you go. Absolutely.

Jake Sullivan:

Yeah.

Patrick Radden Keefe:

Yeah. Okay. Keep it on in the background. It’s a comforting... It’s like having the TV on in the corner. You see what I’m saying? That there is a sense in which I think people increasingly identify with individuals and there’s a whole weird parasocial thing that goes on there. So I’ve benefited from that to some extent, because there are people who’ve read my other books, and I have a very open kitchen, show my work approach with the books where you can go to the end notes and you can see how everything got there. So with the book, it hasn’t been an issue, honestly.

There’s a separate issue, which is when you’re writing for The New Yorker or any other outlet along those lines, yeah, there’s a huge amount of distrust. And you experience that both when you put a piece out there in the world, that you can spend months and months investigating something and put out a big story, and there’s a bunch of people who just shrug and say, “Fake news,” or, “Liberal New York media,” or whatever it is. You also experience it when you’re reporting. I’ve had, when I’m sitting here at my desk making outgoing calls to various parts of the country to work on various types of stories, there are now some people who just won’t get on the phone at all because they’re making some a judgment about where they think I’m coming from. And it’s hard.

I’d be interested to hear your views on this. I personally have a little bit of an optimistic scenario here, which is that I think as you get more and more uncanny AI slop, as we’re exposed to more and more junk on our phones, strangely, I think some legacy media might make a comeback. Because I think that there is going to have to be a sense of, you need some port in the storm. You need something you can trust. And I think it’ll be a smaller number of outlets than it used to be, but I do think that there may be a sense in which the much derided legacy media ends up being one of the few places where you can believe what you see. Not just in the sense that there’s... I’m not talking about agendas here, I just mean you believe what you see in front of your eyes.

Jake Sullivan:

Jon, as a former legacy media journalist yourself, how does that strike you? You think that optimistic case could bear out?

Jon Finer:

I hope so. I guess what I would say though is I think even more likely than that is that people do have outlets, individuals outlets that they trust, but that they tend to be segmented into certain geographies or certain subsets of society, and anything that is not of their corner of the country and of the universe, they just put in a different category, and either don’t digest it at all or assume that it’s false. That’s what I worry about. The ability to just... And in the government context, I think it manifests itself as, if you work on certain issues, development, anti-corruption, you are in some ways stating a partisan affiliation, because one side of the partisan divide actually cares about those issues and the other has said explicitly in some sense they’re not important. And so crossing that divide is increasingly challenging. And I think there’s a similar thing going on when it comes to media consumption, but I hope Patrick’s right.

Patrick Radden Keefe:

But what do you think, and I don’t mean to go too off course here, but I’m curious what you think about the... One of the challenges that I think a lot of those of us who do investigative journalism have in the Trump era is that the sort of traditional syllogism in which corruption happens, the press exposes the corruption, and then somehow this is remedied. Some referee steps in and puts an end to the corruption. And that you can still have the first two steps, and then what happens is that in some cases you spend months and months exposing something and everybody just shrugs, and it’s sort of priced in and keeps going.

Jon Finer:

But I think it’s a little different from that. My own view is that it requires the actors whose bad acts are being exposed to actually feel shame about that or care about that on some level and then change course. And if you have leaders, officials whose revelations do not bother them in the least, and in fact in some ways they celebrate them in some ways, then you’re not going to get the same impact because they’re not going to alter course, they’re just going to proceed. That’s what I worry about in-

Jake Sullivan:

It has been striking how much just this element of shame has been central to that syllogism you laid out, Patrick. A key ingredient of investigative journalism holding leaders accountable is that once this misdeed or corruption is exposed, the leader feels some sense of shame. And if you have a completely shameless leader, a lot of the power of that revelation is removed. And then second, if you have behind that shameless leader a political movement or a political party that’s basically willing to close ranks and say, “We’re not going to keep our own house in order,” that makes things worse. And then finally, I think the other issue on corruption is that so many people in this country across the political spectrum see the entire system is fundamentally corrupt in some way because of campaign finance and other things. So there’s a little bit of a pox on all their houses, which has reduced the exposure of any particular act of corruption or any particular deeply corrupt individual, because so many people shrug because they say they’re all doing it. And I don’t know quite how you handle that.

One thing that I thought was quite striking was watching the election in Hungary play out. And Peter Magyar, who won that election, was able not just to say this guy, Orban, is corrupt, but to connect that corruption directly to people’s daily lives.

Well, this is a good time to actually shift to this larger macro point about what happened in the UK that you tell in the book, London Falling, but frankly, that also is present in the US. You talk about London shifting from this industrial port city to a global capital destination that essentially welcomed all of this anonymous foreign wealth with basically no questions asked, with a number of consequences. And the US has its own sordid history. We’ve had flows of capital from oligarchs and shady foreign billionaires. Up until midway through the Biden administration, you could purchase property in the United States with a shell company without revealing who the true owner was, which allowed people to move billions, tens of billions in ill-gotten gains to be invested in the US real estate market with no transparency or enforcement. The Biden administration changed that by requiring the true owner to be identified, but really implementation is hard. And our system is a wash in illicit cash.

I’m just curious if you could spend a moment talking about both this dynamic as you’ve studied it in London, and then also whether you feel that the Russian invasion of Ukraine woke people up there and whether you think 2026, the story looks a little different than it did in 2019 when Zac Brettler died, or whether this is just a deep feature of these Western capitalist systems.

Patrick Radden Keefe:

Yeah, I’m really glad you put it in that way, because on the one hand, this book is very specifically about London. It’s this extremely specific London story about the history of that city and going back well before the arrival of the oligarchs in the early aughts. On the other hand, it’s a broader story you could tell in a lot of places. I will tell you that when I traveled around the US for three weeks on book tour and talking about this book in Miami, there were a lot of heads nodding in the audience as I talked about scoundrels and supercars and dodgy real estate deals and all the rest of it.

Jon Finer:

Maybe not even judgmental in a place like that always, but sort of a little relatable. It’s funny, our mutual friend, who actually we had in our podcast, Evan Osnos, wrote this book, The Haves and Have-Yachts, about basically the super rich. And one of the story he told is that there are people who came up to him and said, “I’ve got a giant yacht. You never came to talk to me.” The book in some ways was a satire or a scathing critique, but there were some people who felt a little left out not to be included, given their stature.

Patrick Radden Keefe:

It’s funny you should say that because I sent a note to somebody the other day. A lot of people are reading the book in the UK, and I’m getting notes every day from all kinds of people. But there is a sort of funny thing where you’ll have people read the book and then send me a note expressing their appreciation for the book. And in some cases, these are people who, I was just pointing out to a friend, that they feel totally unimplicated when they read the book, that there’s a funny way in which you can get... There’s this super high-end real estate person who really enjoyed and admired the book and has sent me a series of notes. And it’s just funny because I’m thinking, “Wow, you read the whole thing and didn’t feel like you might be one of the bad guys.” Some of this is not new.

At the end of London Falling, I quote The Gilded Age, the novel. And there is also, I think, a sense that you have to acknowledge that when London really started to change in a significant way, some of it was the oligarchs who came in the early aughts. But before the oligarchs, there were the Americans. It was the American bankers who came in with deregulation in the ‘80s, who really came in and said, “We want nice apartments and sports cars and fancy restaurants and all the rest of it.” That go-go atmosphere really started with the... It’s that the Michael Lewis generation. If you remember Michael Lewis’s first book, it’s about how he was one of those bankers who went into London.

In terms of the post-invasion question, Jake, they have taken steps to have more transparency in the housing market, which I think is a flawed system. There are loopholes, there are ways around, but it feels like a positive step. There have been a raft of new sanctions. People like Roman Abramovich had to sell Chelsea Football Club, and symbolically that has, I think, real meaning. But I will say, one of the things that I encountered when I started looking into all of the oligarchs who were selling their mansions because they were worried about sanctions, was I talked to one real estate guy who was like, “Yeah, it’s a huge opportunity for Chinese buyers.” So there’s a sense in which the revolving door keeps turning. I guess the one other thing I would add just quickly is that they’re getting rid of non-dom tax status, which does seem like a really significant thing. And I think that as is often the case in these situations, there was a hysteria sense that the wealthy would flee London, and it doesn’t seem to be happening in practice.

Jake Sullivan:

Can you say a word non-dom tax status for our listeners who aren’t familiar with it?

Patrick Radden Keefe:

Yeah. The idea is that you can be resident in London, but not domiciled there for tax purposes. And it’s got a whole fascinating history actually dating back to the colonial era. But the idea is that money made abroad, you wouldn’t be taxed on in the UK. And what it has meant is that it becomes an extremely attractive second home, and probably second home only on paper, for all kinds of people. And they’re in the process of rolling that back.

Jon Finer:

New York City going through a version of this in a slightly different way right now with the pied-a-terra tax that the mayor has-

Patrick Radden Keefe:

Yeah. And as Mamdani has found, the devil’s in the details. These things are not actually easy once you get in and start sorting it out. But I think there’s a ethos that I describe in the book where, there’s a quote from Boris Johnson when he was the mayor of London, and he said, “London is to the billionaire as the jungles of Sumatra are to the orangutan. We are their natural habitat, and we’re proud of that.” And I think that on the one hand, I understand the sentiment. If you’re the mayor of a city, you want to attract investment. You like the idea of having wealthy people come in. I think Bloomberg’s New York had some element of this as well. On the other hand, these things sometimes have unpredictable consequences.

Jake Sullivan:

By the way, I used to do a pretty good Boris Johnson impersonation, but I’ve lost it.

Patrick Radden Keefe:

Used to? No time like the present.

Jon Finer:

Exactly.

Patrick Radden Keefe:

You want that YouTube channel to-

Jon Finer:

Yeah, there you go. That’s going to be subscriber only material, I think.

Patrick Radden Keefe:

Exactly.

Jon Finer:

Yeah. Patrick, because you’ve mentioned it a few times and I’ve been interested in it, you’re assiduously fair to the people you write about on the page, but I’m actually wondering how you have come to think about them, these “rogues” as you’ve called them. Our listeners probably don’t know that your mom, Jennifer Radden, is known for her philosophical work on identity and the idea that people can be, I love this quote, “Strangers to themselves.” I should have said Radden. How much of the corruption and moral rot that you document do you think is driven by explicit malice versus just this human capacity for self-delusion and rationalization? And how do you come to think about these characters when you are done with them, in terms of writing about them, but obviously they go on in the world, as do you?

Patrick Radden Keefe:

I suppose there are people who are purely evil, but they’re not very interesting to me as a writer. I’m very interested in questions of self-delusion, sometimes individual self-delusion, sometimes collective self-delusion, but the stories we tell ourselves about the decisions we make. Having written about a lot of these types of people over a couple of decades, I’m always struck by how nobody ever gets there overnight. You get these incremental deviations. Those are the gray areas I’m really fascinated by. I’ve always been interested in, what does Chapo Guzman tell himself about the life he is leading? What did the Sackler family tell themselves? There’s a sort of interesting thing. We see it in a lot of the discourse about Trump too, where if you’re somebody who’s very wealthy and successful, you can curate your environment where you don’t actually have a lot of touch points with the real world.

And I’m fascinated by the way in which that can bleed over into an almost... It’s not clinical delusion, but it is this weird situational delusion that you can build. And yeah, those kinds of questions are really fascinating to me. I think there’s an old saw in Hollywood among Hollywood screenwriters that if you’re writing a villain for your movie, your villain shouldn’t know that he’s the villain. Outside of a comic book, most villains don’t think that they’re the villain in the movie. They think they’re the hero of the movie. They’re watching a different movie than you are. And those questions of how the person gets from here to there are always very intriguing to me.

Jon Finer:

Are you surprised that people who could end up the villains of your stories are still in many cases willing to talk to you?

Patrick Radden Keefe:

Yeah, listen, sometimes they’re not, and often they’re not. I think people want to be understood. Listen, even the Sacklers, who didn’t talk to me and threatened to sue me for a couple of years, I think the Sacklers would tell you that they are just terribly misunderstood. I think it’s often the case with some of the people that I’ve talked to, gangsters and ex-IRA people and murderers and gun runners, and what have you, they often have this sense of, “The problem is just that my story hasn’t been told in a good and honest way.” I am surprised sometimes, but I do think that there’s a very natural urge that we have as humans to talk and be understood.

Jake Sullivan:

Patrick, I wrote my master’s thesis on the troubles in Northern Ireland. Nobody has offered yet to turn it into a TV miniseries. I’m still waiting. Maybe I can get some tips from you. But I did want to say to you directly that Say Nothing was honestly one of my favorite books ever. I thought it was just absolutely masterful. One thing that I was struck by in reading it is how it really exposes that the Good Friday Agreement, which brought an end to the act of conflict in Northern Ireland, relied on a certain level of collective amnesia, that people had to forget a little bit of the bad stuff that happened so everyone could move forward.

I was wondering if you could talk a little bit about that, both generally and taking your cue that it’s always best to answer questions in the context of a character. You decided in the book to actually identify the individual that you concluded killed Jean McConville. How did you come about reaching the decision to do that? And how did that fit into this larger question about accountability, about documentation of the truth as balanced against the desire for moving forward for political stability, for sustaining a fragile peace?

Patrick Radden Keefe:

I grew up in Boston, which is a city with a big Irish American population. I came of age during the Clinton administration. You had the Good Friday Agreement, which at the time was really embraced, I think rightly, as a diplomatic miracle. And I think there was probably some slightly triumphalist sense in which there was a sense that this happened because of people like Bill Clinton and George Mitchell, and the sort of American hand was indispensable in getting everybody to the table. And so I grew up with maybe a somewhat rosy picture. And I was startled when I went to Northern Ireland to find that the peace was so cold and that there were so many unresolved issues. And to be clear, I say none of that to diminish the miracle of the Good Friday Agreement. It’s more just that I think that in the American imagination, it was sort of done and dusted. And in fact, the truth is messier than that.

And in this case, what happened was, when they got all the parties to the table, they essentially had to say, “Listen, we are not going to discuss what happened in the past. There’s going to be no question about truth and reconciliation, statutes of limitations. Is there going to be an amnesty process?” All these types of questions basically were tabled because there was a sense, I think a realistic sense that if all that stuff was in play, there would be no Good Friday Agreement. You’d just never get there. And so they had to instead concoct an agreement which was essentially purely forward-looking. So you end up then with this vacuum where there are prosecutions, but it’s all a little piecemeal and there is no established process of historical memory or accountability or any of these types of things. And into that vacuum, Russia’s litigation and journalism and all these less than ideal substitutes.

So I came into a situation in which you had this place, you had this conflict. Everybody in Belfast seemed incredibly haunted by what happened during those three decades of conflict. And I should say, including so-called ceasefire babies, that is kids who were born basically after the ceasefire and had grown up during peace time. There was a sense in which they too were surrounded by the ghosts of things that had happened before they were born. I was looking at this one particular murder. I ended up figuring out who had pulled the trigger. The decision to name that person was probably the most consequential decision I’ve made in my career. I just mean in terms of the moral consequences. It’s a significant thing to accuse somebody who’s never been accused before of this very famous war crime. But I gave it a ton of thought and consulted with a lot of lawyers in four different jurisdictions and ultimately felt it was the right thing to do. And I’ve never had any regrets about that.

I should say, this person has never been prosecuted subsequently, not even questioned by the police. And that was an eventuality that I could have predicted. But I think importantly, the threshold, the evidentiary threshold for a writer is different than it is for the cops or for prosecutors. And so I felt very comfortable and confident with what I did, but I also think that I’m in a different lane.

Jake Sullivan:

One thing that really came through in your book is just how local this conflict is. It had this international patina to it because the whole world had its eyes on Northern Ireland. But we’re talking about neighborhoods and streets. And when you have that close quarters reality and people know the people on the other side, they know the faces and the characters and the gangs and the whole thing, it does make it hard to just say, “Okay, we’re all moving on. We’re just going to look at the macro and not focus on the micro.” I think that’s definitely true in Northern Ireland. On the other hand, Irish people in general like to just shove things down. Beyond just getting the Good Friday Agreement done culturally, it strikes me as a Sullivan that there’s a certain degree of-

Jon Finer:

I was going to say, this is now taking on the era of the local and the personal.

Patrick Radden Keefe:

Jump in anytime, Jon.

Jon Finer:

Yeah, exactly.

Jake Sullivan:

Yeah, please, Jon.

Patrick Radden Keefe:

Yeah. Listen, there’s a moment in the book, which was for me, one of the most chilling things that I encountered in the reporting, which is that the story starts with this woman, Jean McConville, this widowed mother of 10, being taken away from her children at gunpoint in 1972. So you have her kids clinging to her legs and she’s taken away by this gang of intruders and never seen again. The kids are orphaned and they grow up not knowing what happened to their mother. And one of the people that I talked to extensively for the book was this guy, Michael McConville, now a middle-aged man with children of his own, but at the time an 11-year-old boy who was hanging onto his mom’s legs as she was pulled out of this apartment. And Michael told me the story about, as a grown man, being in Belfast and catching a taxi one night, and flagging down this taxi and getting into the back. And they pull away from the curb and he looks in the mirror and he recognizes one of the men who in 1972 took his mother away.

And to this day, it’s unclear whether the taxi driver knew who he was. Michael didn’t say anything. They basically finished the ride and he paid the guy and walked away. But the intimacy of that, the horror of that, that idea that you have these things that nobody’s spoken of that happened decades ago, but then you keep bumping into the people. Again, listen, I think it would be familiar to people who come from Sarajevo or any number of other... Rwanda. These stories are hardly unique to Belfast, but they’re really striking.

Jon Finer:

It’s just a small place in some ways. Patrick, you know this. Jake may not actually, and our listeners certainly don’t, but I actually showed the first episode of Say Nothing to Irish American President of the United States, Joe Biden, on Air Force One on the way back from one of our trips. And he was predictably enthralled by it. Didn’t find it uplifting, maybe enough for his entertainment taste, but was an interesting moment to be able to see how he absorbed this material. Obviously, he’s been intimately familiar with the subject for a long time. But our fan credentials are in good standing, given that.

I want to ask you about Wind of Change as well. That was the first podcast I ever really consumed in full, podcast serial, I guess. It came out at a very opportune moment when everybody was stuck inside their house or able to go on walks and not much else. I listened to it running around Brooklyn Bridge Park in New York. I want to ask you point-blank, after all the interviews, the dead ends, the new leads, the deep dives, what does your gut tell you now, I’m sure you hate this question, as to whether the CIA actually was involved in writing or propagating the Scorpion song Wind of Change.

Patrick Radden Keefe:

Well, I should be asking you guys if you want to make some news here.

Jon Finer:

We spent a ton of time on this, as you can imagine.

Patrick Radden Keefe:

That YouTube channel isn’t going to watch itself. I think that there was something there. I don’t think this... Spoiler alert for your listeners who have not yet consumed the whole podcast. I think there was something there. I think it is very unlikely that the CIA wrote the song Wind of Change. I think it’s unlikely that some songwriter under contract with the CIA in some cutout capacity wrote the song. I think the band probably wrote the song. But at that time, the way in which music traveled in the Soviet Union was through the copying of tapes and this whole underground rock scene. And it wouldn’t surprise me at all if the agency had something to do with that promotion, making the song what it was.

The one thing I know for certain is that there are people inside the agency who have passed this story down. And so I think probably it was a game of telephone, where it starts with, “Oh, we had something to do with that,” and it becomes, “We wrote the song.” Not the first time in rock and roll history where success would have many fathers. But yeah, I think there was something there.

Jon Finer:

You have said previously that part of how this became a podcast is that you had some sense it would be a sort of open-ended ending, and that you think that lends itself better to the podcast as a medium than it does to, say, a magazine article or a book. Maybe because we could use the advice. What else do you think makes podcasts work, or not, that is different from other media, given how much you are interviewed on them and obviously have been a producer of one yourself?

Patrick Radden Keefe:

One of the things that’s so interesting about the podcast business, and on some level this is true of the media business in general now, is just like, everything is constantly in flux. And so podcasting now is totally different than it was when we made Wind of Change six years ago. I’m in the very early stages of a new podcast, and it’s really striking the degree to which... It’s like, I get no credit for any of my hard won experience from six years ago because it’s a completely different industry now. It’s interesting. I think that podcasting has moved in a really dramatic fashion much more toward the conversation we’re having right now, for understandable reasons. I think it’s somewhat lamentable that the heavily produced, heavily reported, long narrative podcast, like Wind of Change, they still do them, but not as much. It’s not really where the business model is at this point.

And I think that’s a shame because I think there are some great ones. I did think that in the case of Wind of Change, there is something about... I think it’s because we all started with serial, if you remember serial, that serial was... Ironically, they subsequently did figure out what happened in that case. But at the time when the podcast was made, it ended in this ambiguous fashion, and that was okay. I think it’s tougher to do that with an article or a book where it’s a mystery story and you don’t solve the mystery, at least to some extent. Another big one for me, honestly, it’s not, I mean, this wouldn’t be relevant for you guys necessarily, but this new podcast I’m doing is about music. And I do think there is something about being able to incorporate music and really fully... And with Wind of Change, that was a big part of it, was being able to play the songs.

Jake Sullivan:

Especially the song, man. I hadn’t heard that song in a while when I started listening to Wind of Change and it was in my head for weeks. What just a great, great song.

Patrick Radden Keefe:

Well, and the thing is, and to be... We went, for the podcast, we saw The Scorpions play Kyiv in 2019. And when that song came on, it was like thousands of people around me were crying. These big, scary looking Ukrainian guys with tears streaking down their faces. When you experience the song with people for whom it had this profound historic importance, I don’t know, it was magic.

Jake Sullivan:

So we’ve kept you for a long time. I want to ask you one other question, then turn it over to Jon to bring us home with a couple of questions. My question is that you actually spent time serving as a policy advisor at the Office of the Secretary of Defense at OSD, and I’m curious whether in your experience there, there was anything you found that national security reporters and journalists actually get wrong about the Pentagon or about how government decisions are made? Anything you’ve learned in that where you said, “Huh, I had a different view, coming from the world of journalism, than I do seeing things from the inside.”?

Patrick Radden Keefe:

Yeah, it was a very profound case of exactly that. Part of the reason I wanted to do it was to sort of... I didn’t have a sense that I would become a public servant in any longer term capacity. I had a fellowship where I came in under the, I think it’s called the Intergovernmental Personnel Act, and I came in for a year. I thought of myself as having a PIF helmet and trying to learn the anthropology of DOD. I was just struck by the magnitude of the bureaucracy and the strange functioning of the bureaucracy at quite a low level. I think I went in expecting Seven Days in May. And when I got there, it felt like The Office to me, in a a strange way.

I was there before the show, Veep, but the thing that Veep captured really brilliantly was the degree to which... On the one hand, there’s the grandeur of the idea that you’re working for the federal government and major matters of national security and what have you. On the other hand, there’s also just office politics the way there are anywhere else. And I was very struck by that and struck by the degree. There would be little pet projects and things that were funded because there’s one guy on The Hill and the appropriation keeps coming through. And then you have this whole little office of people who are working and everybody else around them is wondering, “Why are they doing that?” But they have this, just all those types of being able to see the map and understand a little bit better.

It’s funny, it’s a thing Jon has talked about in the past, but just the idea of being a reporter in Iraq and being downrange and seeing the consequences of decisions that are made over the horizon back in Washington. And I was working at a low level. I wasn’t much help to anyone, honestly, but I learned an enormous amount just by being there. And I have to be candid with you, it wasn’t hugely reassuring to me as a citizen.

Jon Finer:

There’s a cliche about TV shows about Washington, probably a cliche because it’s largely true, that The West Wing is what people want to believe Washington is like. House of Cards is what people actually believe Washington is like, and then Veep is the most accurate depiction of life in Washington. I think there’s some truth to that. Patrick, last couple questions, and thank you again for giving us so much of your time. The first is one that we’ve been asking many, if not most of our guests. And then the last is particular to this episode, which will function effectively as our August summer reading edition, to the extent you can have that on a podcast. But the first one is, I’d like you to give us one opinion you hold, on any subject, it can be related to your work, it can be related to anything else, that is unpopular, that you’re willing to confess on this show.

Patrick Radden Keefe:

Well, this is going to be a cheat because it’s hard for me to gauge the popularity of this, but if you want to know the thing that has occupied an enormous amount of my psychic energies lately, I’ve been traveling a lot. It is people in public places and on public transportation who listen to stuff on their phones without headphones. And I think that this should be a federal crime. This may secretly be a popular-

Jon Finer:

I think it pulled pretty well.

Patrick Radden Keefe:

But let me tell you, it is often. I’ve just been traveling a lot-

Jon Finer:

A lot of people do it.

Patrick Radden Keefe:

... and I am always wanting to engage the person. And I will say, “Do you have headphones?” Sometimes I’ll come over and be like, “What are we watching?” And my poor children are mortified that I would do this. But I truly think it is hard for me to envision a sanction too severe for this behavior, and it’s gotten out of control.

Jake Sullivan:

It’s good.

Patrick Radden Keefe:

So that’s my subway take.

Jon Finer:

You heard it here first. And then, what are you reading right now? And what would you recommend, either that you haven’t read yet or that you’d like to recommend for our audience?

Patrick Radden Keefe:

Oh, boy. So I’m always reading a lot. I just recently quit blurbing, but until recently, a lot of books coming in to blurb. There’s a book by-

Jon Finer:

Do you always read every book that you blurb, start to finish?

Patrick Radden Keefe:

Well, so this is part of the problem is that it just starts to seem insane if I’m just blurbing books that I haven’t read, and so I do try and read them. And there’s no good system. I don’t want to just log roll for friends. Anyway, this is why I quit. But yes, I mostly do read most of the book, at least, if I’m going to blurb it. There’s a book by Pam Colloff, has a new book called Catch the Devil. Really incredible non-fiction book. She’s an amazing reporter. It’s a page turner, but it’s also a story of a really remarkably bad guy who realizes that he can essentially be a a witness for law enforcement and put other people in prison by lying, and stay out of prison himself. And so it’s a very scary upside down picture of the American justice system and where it can go wrong.

There’s a new book I just finished called The Castle, by Jon Ronson, a very funny English writer, which gets into a lot of the weirdness of the present moment. It’s a non-fiction book. Very funny, very strange. I read the Ben Lerner novel, Transcription, which I though was-

Jon Finer:

I did too.

Patrick Radden Keefe:

It’s hardly original, but did you like it?

Jon Finer:

I thought it was excellent. Yeah.

Patrick Radden Keefe:

Yeah, I did too.

Jon Finer:

And short, mercifully short. I think more books should be short.

Patrick Radden Keefe:

Short is good. Well, and then on the other side, I’m listening to East of Eden, which I haven’t read since I was in the ninth grade. And it is great. It’s great. Boy, it holds up.

Jake Sullivan:

I haven’t read that since the ninth grade either. I’m excited to go back.

Patrick Radden Keefe:

It’s great. It’s really good. Oh, and one last one, a nonfiction book, which really knocked me out. There’s a book by a young guy, young Spanish journalist who’s now with The New York Times. His name is Carlos Barragan. And he has a book called Yahoo Boys, which is... I’ll set it up for you. It’s incredible. It’s nonfiction. His mother fell for a Nigerian romance scam. And he went to Nigeria to try and track down the scammer. Didn’t find the guy or woman who tricked his mother, but did fall in with these young guys who were engaged in that business. And earns their trust and figures out this whole economy of Nigerian romance scams. But then it gets into the psychology of why do, essentially lonely Americans who get these messages out of the blue and know that it’s not real, but then are sending money. And it’s an extraordinary piece of reporting. It’s called Yahoo Boys.

Jake Sullivan:

Good list. Excellent.

Jon Finer:

Yeah. Patrick, an honor and a privilege. And thank you.

Patrick Radden Keefe:

Thanks, guys.

Jon Finer:

And great to see you.

Patrick Radden Keefe:

Thanks for having me.

Jake Sullivan:

Thanks, Patrick. Real appreciate it.

Patrick Radden Keefe:

Fun to talk with you.

Jake Sullivan:

That was good fun.

Patrick Radden Keefe:

Known Patrick a long time. I think I first met him when we were grad students overseas. And it’s been fascinating to watch his career, because he did not begin his professional life as a journalist. He went to law school, he sort of wrestled with wanting to become a writer and then just has absolutely become one of the most successful nonfiction writers in America, if not the world. So remarkable to see his trajectory. And while we got a few recommendations from Patrick as to what’s been on his mind, what he’s reading, what he thinks our audience would benefit from, we figured we should probably offer some of those thoughts ourselves. So Jake, do you want to start off by sharing some reading recommendations for people as we head into August? Maybe the month the most reading takes place, in the United States at least.

Jake Sullivan:

Okay. Since you’re the more lyrical and literary among us, I assume you’re going to have a good diverse list. I’m more of the nerdy, technocratic type. So I’m going to recommend a few books in our area, national security and technology in particular. But the first book I want to recommend is from a former colleague of ours, Eddie Fishman, called Chokepoints, which is a book about the use of economic statecraft and economic tools to advance political ends. And he argues basically, these tools, whether it’s sanctions or the swift banking system or export controls, have become impactful and powerful in the way that only really military force used to be. And the book does just a fantastic job of explicating this in a way that is not boring or wonky at all. It’s really quite compelling. So that’s the first one.

The second one is a book by a guy named Jeffrey Ding that’s called Technology and the Rise of Great Powers. And boiled down to its essence, what Ding is arguing is that invention is not enough. The way that great powers succeed is by being able to diffuse technology through their economies, their societies, their militaries. And that it was really the United States’ ability to diffuse technology even more than invent it that led to the US winning the Cold War. And he puts that in the context of the current US-China technology competition. And I think that’s just an awesome book for people to read.

And then the third is a book by Amy Zegart who’s out at Stanford, called Spies, Lies and Algorithms. I recommend it just on the title alone. The subtitle is The History and Future of American Intelligence. It’s now a few years old, it’s from 2022, but it just really stands up well for people trying to understand the role of technology, AI, cybersecurity in the intelligence enterprise today. So I know that’s all books in the same vein, but I thought I would have a thematic basket for people to consider from different perspectives on somewhat different elements in national security.

Jon Finer:

Despite your description, I reject the label that I’m in any way literary or lyrical, but I will share some books that I’ve been looking at recently that I think are fantastic. One, and I won’t dwell on it because Patrick recommended it, is this book Transcription by Ben Lerner. Which, to give just the one sentence synopsis, is about a young academic who goes to interview his mentor at the end of his life and has a technological failure of some kind that prevents a transcript of this interview from being created, and then much flows from that. The second is a book I recently reread, but that I think is quite illuminating about our current moment. It’s another novel. It’s called Absurdistan by Gary Shteyngart. Which, if you haven’t read it and you are someone who has traveled to particular parts of the world... And what’s interesting about this book is it’s not about any one part of the world, it is about a fictional country called Absurdistan, essentially. Parts of the world that are in the east that cause so much geopolitical trouble and turmoil and embroil themselves in our politics.

It’s a hilarious sendup of all that, from the perspective of someone who has become American, didn’t start that way, and I think is as good as any nonfiction book can be as an introduction to many of the places that are sources of geopolitical instability today. Third one, also fiction, is a book called Country People by a guy named Daniel Mason, who is a friend of mine from college, who I’ve probably not seen in 25 years. He is a doctor, a psychiatrist who is also one of America’s greatest novelists. He wrote a book called The Piano Tuner, which was his first novel, which was a sensation. He wrote another book that came out a couple years ago called North Woods, which was about a house in Massachusetts and its various occupants over more than 200 years of history. This one is close to my heart, not just because it was written by a friend, but because it’s about Vermont, about an academic couple that moves to Vermont to take a job.

And I will confess, I’m only halfway through this book, but it is fantastic. And look forward to finding the time to finish this very soon. Another one I would recommend. Last book, the only nonfiction one I will put on my list is a baseball book, because for me, summer has always been baseball related and baseball themed. And it is a book that is short and actually really is basically a book length version of an article that was written in The New Yorker in 1960. And it’s by John Updike. It’s called, Hub Fans Bid Kid Adieu. And it is the story of John Updike, who was 28 years old at the time, a student in Boston, going to Fenway Park to watch Ted Williams play his last baseball game. It is very short. It will take you less than an afternoon to read. And it’s the beginning of literary sports writing in America, and of just a fantastic read. So I will stop there.

Jake Sullivan:

I will second that as a... I read the article. I didn’t actually realize it was turned into a book.

Jon Finer:

Yeah, they published it in a little short length book version, which is great.

Jake Sullivan:

It’s just awesome. You put me to shame in a couple of respects. First, you managed to get a Vermont book plugin. Maggie’s going to kill me that I didn’t get a New Hampshire themed book on my list. Sorry, Maggie. And second, a book that involves Ted Williams, who Maggie actually met as a kid, got to know Ted Williams a bit. So I’m going to have-

Jon Finer:

Friend of her grandfather’s.

Jake Sullivan:

Yeah, exactly. Something like that. So I’m going to have some-

Jon Finer:

Well, you did Eddie Fishman’s book, who worked for me at Policy Planning and is a buddy in New York.

Jake Sullivan:

So it’s okay, good.

Jon Finer:

Eddie’s the best. Good choice. Well, that’s all for today. We’ll be back next week with a new episode of The Long Game.

Jake Sullivan:

Subscribe to our YouTube channel and follow the audio feed so you never miss an episode.

Jon Finer:

For additional content, episode transcripts, and exclusive podcast segments, subscribe to The Long Game on Substack or join The Long Game Plus on Apple Podcasts.

Patrick Radden Keefe:

I always go back to Lance Armstrong on this for some reason, but that sort of Lance Armstrong notion that, “Listen, I’m the best biker who ever lived. And I wanted to play by the rules, but we live in a system that is so corrupt, that everybody else is cheating and so the only way for me to get a level playing field is to cheat as well. And I don’t want to be the fool who doesn’t cheat when everybody else is cheating and I actually deserve to win.” I think that that quite Trumpian sense of the world is dangerous.

Jon Finer:

Head to thelongame.substack.com or subscribe to The Long Game Plus on Apple Podcasts. The links are in the show notes. That’s it for this episode of The Long Game.

Jake Sullivan:

If you like the show, please follow, share with friends, and leave a review. It really helps listeners find us. The Long Game is a Vox Media Podcast Network production.

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You can listen to this episode on Spotify, Apple Podcasts, and other listening apps.

Watch episodes of The Long Game on YouTube.

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A NOTE FROM THE PRODUCER

is the Executive Producer of The Long Game.

Investigative reporter Patrick Radden Keefe is known for entering hidden worlds and revealing how power actually works. From the Sackler dynasty and the IRA to oligarch money in London, he investigates not only what powerful people have done, but also how they justify it. As Patrick puts it, “Nobody ever gets there overnight.” Corruption begins with “incremental deviations.”

Nobody thinks they are the villain. Gangsters, corporate dynasties, and political leaders alike tend to believe they’ve simply been misunderstood. “Most villains don’t think that they’re the villain in the movie,” Patrick says. “They think they’re the hero.” In a shameless age, that self-delusion becomes dangerous: “Everybody just kinda shrugs and it's sort of priced in and it keeps going.”

Patrick joined Jake Sullivan and Jon Finer on the show this week to discuss what happens when that mindset spreads from individuals to an entire culture.

They also discuss the mysterious death at the center of Patrick’s new book, London Falling, and how oligarch wealth transformed the city; the 1972 murder he investigated in Say Nothing and the truths left buried by the Good Friday Agreement; and whether the CIA helped turn the Scorpions’ “Wind of Change” into a Cold War anthem.

At the end of the episode, Patrick, Jake, and Jon share their summer reading recommendations.

We love hearing your thoughts. Please comment below or email Jake and Jon at longgame@voxmedia.com.

Transcripts here.

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REFERENCES & SUPPLEMENTAL MATERIALS

• Patrick Radden Keefe, London Falling, Doubleday, April 7, 2026.

• Patrick Radden Keefe, Say Nothing, Vintage, February 25, 2020.

• Patrick Radden Keefe, Empire of Pain, Vintage, October 18, 2022.

• Patrick Radden Keefe, Chatter, Random House, July 11, 2006.

• Evan Osnos, The Haves and Have-Yachts, Scribner, June 3, 2025.

• Mark Twain and Charles Dudley Warner, The Gilded Age, Penguin Classics, September 1, 2001.

• Pamela Colloff, Catch the Devil, Knopf, July 14, 2026.

• Jon Ronson, The Castle, Riverhead Books, September 1, 2026.

• Ben Lerner, Transcription, Farrar, Straus and Giroux, April 7, 2026.

• John Steinbeck, East of Eden, Penguin Classics, October 18, 2016.

• Carlos Barragán, The Yahoo Boys, Farrar, Straus and Giroux, June 9, 2026.

• Edward Fishman, Chokepoints, Portfolio, February 25, 2025.

• Jeffrey Ding, Technology and the Rise of Great Powers, Princeton University Press, August 20, 2024.

• Amy B. Zegart, Spies, Lies, and Algorithms, Princeton University Press, February 1, 2022.

• Gary Shteyngart, Absurdistan, Random House Trade Paperbacks, April 3, 2007.

• Daniel Mason, Country People, Random House, July 7, 2026.

• Daniel Mason, The Piano Tuner, Vintage, August 19, 2003.

• Daniel Mason, North Woods, Random House Trade Paperbacks, October 1, 2024.

• John Updike, Hub Fans Bid Kid Adieu, Library of America, April 29, 2010.

• Photo by Albert Llop/NurPhoto via Getty Images

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Radosław Sikorski:

I don’t think Russia could prosecute the war and I don’t think she could survive as a state without trade with China. So this would be a credible threat. So China, unlike us, actually could force Russia to end the war. But my guess is that the war suits China just fine. Russia is selling them gold. Russia with every year becomes more dependent. And what’s not to like about that?

Jake Sullivan:

Welcome back to The Long Game. I’m Jake Sullivan.

Jon Finer:

And I’m Jon Finer. We’ve spent a lot of time on this podcast discussing the state of America’s relations with various countries around the world, especially our allies. But today we have our first opportunity to do that with someone who is sitting at the table managing those relationships from across the Atlantic. Radosław Sikorski, who goes by Radek, is Poland’s deputy prime minister and foreign minister. He’s been in and out of Polish politics for a long time with previous stints as foreign minister and his defense minister. He is also a longtime advocate for the transatlantic relationship, so much so in fact that he married into one. His wife is the acclaimed American journalist and historian Anne Applebaum. He’s the author of seven books on international affairs himself and of particular interest to me. He began his career as a war correspondent during the Soviet War in Afghanistan and later in Angola.

No one has a keener eye when it comes to NATO, to European security, to great power competition and the transatlantic relationship, and we’re very much looking forward to this conversation. So Radek Sikorski, welcome to The Long Game.

Radosław Sikorski:

Hello, and thank you for the generous introduction.

Jake Sullivan:

We really appreciate you taking the time today because I think our listeners getting your perspective will be really enriching. So let’s get right into it. Europe is simultaneously facing a Russian invasion that has produced the bloodiest conflict on the continent since the Second World War. Chinese industrial overcapacity that threatens to hollow out the manufacturing sector across Europe, and a US administration that seems to put it charitably less than fully interested in working with their European allies and sometimes downright hostile, though usually not to Poland. Since the end of the Cold War, Radek, has there been a more challenging time for Europe? How do you see the picture today?

Radosław Sikorski:

It is challenging, but give us credit for not starting wars of choice that we can’t win.

Jake Sullivan:

Credit given. We’re credit given.

Radosław Sikorski:

We do. And of course I was speaking about the Russians.

Jake Sullivan:

Right, right, of course.

Radosław Sikorski:

We are doing something about unfair Chinese practices. We’ve just introduced, partly inspired, I have to say, by the United States, a charge on small postal packages that we’re pouring in at the rate of 13 million per day. And since the 1st of July, the volume has decreased because of the EU charge at our customs barrier. Look, we in Central and Eastern Europe knew that the window of a history in which Russia was cooperative wouldn’t last forever. And we have been spending 2% of GDP on defense since 20 years ago at a time when 2% seemed like a lot. We’re now spending 4.8% on defense on hard defense and 7% if you count dual use stuff. And we are re-industrializing in the area of defense from our national budget and also from EU funds. The EU has passed safe mechanism, soft loans, 150 billion euros in total almost, of which Poland is getting about a third.

So yes, there are many challenges, but I wouldn’t count Europe out. We are still a very big single market. We are a confederation. We don’t have the unity of command that you have in the United States. We are slower. It takes time for us to synchronize, but it also means we can’t do anything rash. And that of course has its advantages too.

Jake Sullivan:

It surely does. So I am interested in the optimism, the tempered but real optimism in your answer, and wanted to just zoom out for a minute to something that you wrote last year. You wrote about being asked what keeps you up at night? And you said the answer, and this is a quote, is the fear that the post-war international order shaped by memories of World War II and the trauma of the Holocaust and built on the foundation of political compromise, respect for other countries, sovereignty, free markets, civil liberties, and the protection of minorities may collapse. How do you assess the state of the international order today? What’s your diagnosis? And then what’s your prescription for what collectively those of us who want to stand for the principles that you wrote about what we should be doing?

Radosław Sikorski:

I still have those fears both internationally and internally. Internationally because the wars in Eastern Europe, Russian aggression against Ukraine and in the Middle East seem to be widening. Russia is getting help from Iran, North Korea, and some significant support from China. And as you know, an Iranian ship was hit in the Caspian Sea for, I think, legitimate reasons. Iran was sending military support to Ukraine, but nevertheless, that’s a link between the two theaters. And we now have a problem not only in the Strait of Hormuz, but also with access to the Red Sea. So the international situation is not getting better. It is actually getting more concerning. And internally, it seems to me that with the passage of time, people are forgetting how fragile both peace and democracy are. And there is popularity on both sides of the Atlantic of purelist forces that are fueled by nostalgia and by a sense that nothing bad can happen.

We can have everything that we want without paying a price. And we want it now and we don’t have to compromise. And that worries me. It means that we have constitutional and political challenges inside our own countries.

Jon Finer:

Let’s talk a bit about the United States. You know us better than most for a range of reasons. We have a president who sometimes seems to prefer the company of authoritarians to that of democratic leaders. We may or may not be involved in our own war of choice that’s unwinnable, as I think you hinted at, even if you were really speaking about Russia. How do you rate the current health of the transatlantic relationship? This is the first US conflict in recent memory, if ever, that none of our transatlantic allies participated in a meaningful way. And then as an official from a country that is flirted with its own illiberal turn in recent years, what about the state of American democracy?

Radosław Sikorski:

Well, we don’t interfere in the internal affairs of our great allies. And of course we expect the same in return and we don’t always get it. But we have different institutions. So for example, when I speak to Americans and I was just on the West Coast, made a speech at the Reagan Library, visited Stanford and so on. In the United States, people no longer seem to realize how unique the role of big money in politics is in the United States. When I tell people in the US that I was elected to be a member of the European Parliament for five years and my electoral budget was $30,000, they don’t believe me.

Jake Sullivan:

Wow. What was your opponent? Was that standard?

Radosław Sikorski:

It’s the legal limit.

Jake Sullivan:

Legal limit. Wow.

Radosław Sikorski:

And you know what? It’s enough. You can do social media advertising and if it applies to everyone, it’s sufficient. So this is a big difference. And in Poland we say, well, if someone gives you $1,000, that means they like you. If they give you a million, they expect a return. Here we are different. But the larger picture is this, and I ended one of my speeches in the US on this. Ronald Reagan used to say, and I know how beloved he was of Democrats-

Jake Sullivan:

Well, he’s become better yet, in retrospect.

Radosław Sikorski:

He sure does. I know, I know, but it’s not what they said at the time, was it? He said that if someone agrees with you 80%, that means he’s an 80% friend, not a 20% traitor. And we sometimes have the impression that there is a fashion for doing down Europe. And I also think there is something wrong with the comparative statistics. You have these amazing companies in AI and tech and so on, but we also have our achievements. We live longer on average. We spend about half of our GDP on health on average on what you spend, and we cover all our people. And you don’t. That’s not nothing. In Poland, guess how many school shootings we’ve had over the last three decades? Zero. And so on. So what I’m saying is that we have things that we can learn from each other, and the tone of superiority either way is unjustified.

Jon Finer:

So let’s turn to the security partnership a bit. The US formally launched a strategic Europe posture review of its military presence on the continent. Wondering what you expect to come of that. And do you anticipate a significant drawdown of US forces during the course of the rest of this Trump administration?

Radosław Sikorski:

I think this was inevitable. Successive US presidents asked us to spend more. We have to give President Trump credit where credit is due. He got us to spend more. Of course, Putin helped too. And we should now be capable of deterring Putin mainly on our own with some over-the-hill help from the United States. So I think this is under US pressure, of course, but the US has global responsibilities and we are a rich continent. So we will provide most of the conventional capabilities with the US providing some strategic enablers, and that should be plenty to deter Putin by the end of the decade. Putin has proven incapable of conquering Donbas over 13 years. So let’s not be too panicky about him. His intent is worse than some people thought, but his capability, thank God, is less.

Jon Finer:

So let’s maybe drill down a little bit on that over-the-hill help as you described it. By the end of the decade, things may be in a better place. Right now, I think much more of an open question. And you’ve described Russia already waging-

Radosław Sikorski:

You know what? I think Putin would be nuts to attack a NATO even now.

Jon Finer:

So that’s what I was going to ask about. You’ve described Russia as waging what you call a hybrid war against the West for the last decade or so. You said we have arson, we have interference in politics, we have disinformation, espionage, but we also have some [inaudible 00:12:45] facts-

Radosław Sikorski:

Well, we have death squads and assassinations and we have state terrorism. They tried to blow up a moving train in Poland.

Jon Finer:

Exactly.

Radosław Sikorski:

No one was killed, only thanks to their incompetence.

Jon Finer:

And it sometimes feels like it’s only a matter of time before Russia, either intentionally or not, crosses a line that triggers a real conversation about NATO Article Five. The provision, as you well know, that is an attack.

Radosław Sikorski:

We will fight back. I mean, NATO or no NATO. In Poland, we’ve been resisting Russia for 500 years and we are not about to stop.

Jon Finer:

So you’ve claimed famously to be a loyal US ally, but also not a sucker, I think was the phrase that you used. How confident are you of the American commitment in the current moment to that Article 5 principle?

Radosław Sikorski:

Of course, it’ll be a political judgment in the light of events and in the light of what else is happening in the world. If the US is involved in a confrontation with China, then that’ll consume all of US bandwidth and capabilities. But if not, then it’s more likely. The main thing is that Putin doesn’t know what we will do or what the United States will do. But we have some prepositioning of equipment in Norway, in Poland, in Romania. We have one permanent US base in Poland already, the missile defense base, the agreement I signed with Condi Rice, which is now operational. We are negotiating a second base, a sort of heavy brigade type of presence. We have personnel on a rotational basis plus US Air Force personnel. And the US, we are paying for the war for Ukraine’s defense, but the US is still helping with targeting data and sells us Europeans the equipment, the PAC3 effectors that we supply to Ukraine. And I hope that the Lindsey Graham Bill passes and that the US imposes tougher sanctions on Russia.

Jake Sullivan:

The Lindsey Graham Bill, as you just mentioned, is a bill that actually received very wide bipartisan support in the Senate just in the last 24 hours to move forward, which gives the president the authority to impose very tough sanctions, but also tariffs on countries that potentially purchase Russian oil. So we will see what happens with that bill, especially in light of the tragic passing of Lindsey Graham. Radek, I’m struck by the comment that you made a minute ago that you think Putin would be crazy to attack NATO, to attack the West. You’ve at various points warned about the possibility of a Russian false flag operation, basically a staged attack by the Kremlin inside Russia that it would blame on someone else maybe to justify attacking a NATO country. That sounded to me to us like a concern driven not just by speculation, but maybe by something more informed.

Can you talk a little bit about that concern? And if you don’t think Russia will just frontally attack NATO, do you think they’re looking to escalate against NATO in some other way now, or they’re just going to keep doing this pattern of hybrid warfare that you and Jon were just talking about?

Radosław Sikorski:

Well, you were at the White House in the run-up to the invasion of Ukraine. So you know that for Russia to do anything serious in Ukraine, she would need to concentrate forces. And we would immediately see that. You can’t attack NATO with a battalion. You would need many, many divisions. The gathering of forces against Ukraine took them six months, a year. I mean, they would do it the classic way on the pretext of an exercise and all that. But still, we would know well in advance. So he’s not really capable of a running start invasion of nature. What he’s capable is some kind of provocation that in their mind would show East Europeans that NATO is pathetic and would not react. Well, first of all, we would react. And secondly, we know they’re considering it. And here I’d like to give credit to the Biden administration.

As you remember, the Russians were trying to do provocations in the run-up to the war. And you were wise and brave in risking sources by telling the world that they are up to no good. And this deprived them of a credible Casas Bellai, and it was very important. So yes, we know a thing or two, and we are pre-warning Putin that he should drop his provocation plans because it will not be credible.

Jake Sullivan:

When you think about what they have in mind for potential types of provocation, are there scenarios you’re thinking of? Is this something in the Baltics? Is it more of these drones? Is it a wayward cruise missile that they say, “Oops, we didn’t mean to do that?” What do you have in mind for the kind of thing we want to do?

Radosław Sikorski:

We’ve had cruise missiles already. One landed 10K from my house. So in September last year, Poland fought an incursion of 21, I think, drones. Drones. Yeah. And if this was an accident, you would’ve expected a mix of armed drones and decoys. They were all decoys. So the Russians were provoking us without wanting to start a war. And one of the scenarios that’s discussed publicly, not all Ukrainian drones make it to the target, just like some Russian drones fall in Ukraine. So we have to assume that the Russians have got hold of some Ukrainian drones that have landed there. So they could repair them and send them from some border location against themselves to claim that Ukraine attacked them or against the NATO country. Who knows? But remember, strategic false flag and the deception is Russia’s standard operating procedure.

Jake Sullivan:

Absolutely. Now you’ve said, taking this to Ukraine, that we are at the end of the phase of Russian initiative in Russia’s brutal war against Ukraine, that Ukraine now is seizing the initiative. Can you talk for a minute about how you see Ukraine turning that initiative into a victory? How you see the war ending in a way that produces a secure, resilient, democratic Ukraine that ends at least for the time the Russian threat? How does Ukraine get to victory here?

Radosław Sikorski:

Let’s take the long view. If we were having this conversation five years ago when the Russians started gathering forces for Ukraine, if we went through scenarios of Russian invasion, we would not have guessed, neither you nor I, that after more than four years of war, Ukraine would still be not only standing, but having the initiative in some fields. And this is the case. So it’s a draw in the Black Sea. It’s a draw in the air. Both countries can hit each other, but neither can operate over the territory of the other. And it’s a draw on land where the Russians have gained some territory, Ukrainians gain other bits of territory. And the Ukrainians are inflicting losses on the Russian army that are bigger than Putin’s ability to recruit. And all the while, Ukraine being supplied by Europe with financial resources and Russia seriously aching now.

They’re having to sell their gold reserves. They’ve raised taxes. They’re beginning to be quite desperate for funds. Putin still has a couple of cards to play. One is to do mobilization. As you know, he’s still fighting with contract soldiers, but that’s risky for him politically. He must be hoping that having destroyed 80% of Ukraine’s electricity and heat generating capacity, if there is another tough winter, and if we don’t supply Ukraine with the capacity to take down ballistic missiles, then Ukraine might be left with only the nuclear power plant, and that might not be enough to sustain the winter. He must be thinking that. But Ukraine has cards. Ukraine clearly has the advantage in drone war, and Ukraine is clearly more innovative in this war than the Russian side.

Jake Sullivan:

Just briefly, you’ve said recently something that struck me that Donald Trump likes winners and Ukraine and Zelenskyy are impressive in the way they’re taking the fight to the Russians right now. Do you think Trump could actually end up backing Ukraine in a more full-throated way, which would be a really significant shift in posture from him from when he had Zelenskyy in the Oval in 2025 saying, “You don’t have any cards?”

Radosław Sikorski:

Literally just yesterday I had a meeting at the White House, which I’m told went well. And it’s been choppy between President Trump and President Zelenskyy in the past. The relationship seems to be better. And there are rumors that President Trump’s invoice might for the first time visit Kiev. Some of MAGA people have now seen the light and are supporting Ukraine. And as you said, Republicans in both the House and the Senate are supporting tougher sanctions on Russia. So in those terms, maybe the worst is behind Ukraine.

Jon Finer:

Radek, you gave a speech to the Polish Parliament recently in which you described the European Union, not NATO, you were very positive about NATO as well, but the European Union as Poland’s strategic shield, which was notable since the EU is an economic and political organization more at least than it is a defensive one. I’m wondering why you chose to characterize it that way. Can you explain a bit more about how the EU provides this shield?

Radosław Sikorski:

Well, first of all, we now have a defense budget. And at the time when we were creating it, it was meant to pay for some police type election monitoring missions in Africa or Asia. It’s now used to support Ukraine, and it should be increased. I believe that EU and all opinion polls tell us that the peoples of Europe want the EU to be more active in the field of defense, that we shouldn’t beg for help from the United States at every emergency on our periphery. Libya or the Balkans, we should be able to sort the march ourselves. And it’s this financial power. We’ve spent well over 200 billion euros on helping Ukraine. Ukraine is provided for at least two years, and that includes paying for Ukraine’s own defense industry, which still has some spare capacities. So this has a direct strategic consequence.

And of course, Europe is also developing capabilities in space. We have our own surveillance system. We hope by the end of the decade to be able to have our own satellite system and portable internet provision, which I think will be welcomed in the United States because monopoly is never a good thing. Monopolists usually overcharge.

Jon Finer:

You also said there is no free, safe, or prosperous Poland without a strong European Union. I assume you feel the same about NATO in Poland’s prosperity and security. You’re supportive of Ukraine ultimately joining both of those institutions, though I think not yet. How long do you think it will take for Ukraine to join NATO and the EU? And what conditions do you believe they would have to meet for you to say now is the time?

Radosław Sikorski:

I was at the NATO Summit in Bucharest in 2008 when Ukraine’s NATO membership was discussed. And we gave them a sort of half promise that it might happen someday, but we denied them the actual membership action plan.

Jon Finer:

Alongside Georgia at that time.

Radosław Sikorski:

Right. And at the time of the Russian anschluss of Crimea, remember the green men that Putin said were not his? Ukraine was actually constitutionally a neutral country, which shows you how absurd are the Russian claims that they had to invade because Ukraine was joining NATO. So let’s put that aside. But as regards, the EU, Ukraine through its valor, has earned the right to become a candidate country. And we have now opened negotiations on two clusters. Fundamental issues, which is to do with democracy, rule of law, fighting corruption, proving that both the history and the future is democratic and foreign policy where Ukraine has already synchronized its foreign policy with that of the EU.

Joining the EU is much harder than joining NATO because it’s a single market. You have to adopt something like 80,000 pages of EU legislation. You’re becoming a member of the family. It’s not NAFTA. It’s a confederation with, for example, delegating all of your trade policy to the European Commission. And you have to prove in advance that you are going to be a clubbable, loyal member, that you won’t just take from the community, that you’re also prepared for compromises. And that’s not easy. And that you will live by the agreed rules rather than your own, which some countries proved incapable of doing. So it’ll take some time. And for us existing members, membership will be in the long run beneficial. Germany now trades with Poland as much as with France. A Polish GDP has troubled since our economic reforms, and it accelerated after joining the EU. And the old EU of course benefited, but we benefited even more. But there are always some sectoral challenges and everybody has politics.

Jon Finer:

I’ll turn it back to Jake, but I do want to register a bit of concern about this legislation that you mentioned, the Lindsey Graham bill, which I wonder whether you will come to see differently over time. The concern that I’ll just put on the table is that it authorizes a range of new tariffs for the president. It gives him a national security waiver, which would basically allow him to use those tariffs as he chooses, including against US allies, including against EU and NATO members, because of their purchases-

Radosław Sikorski:

I didn’t know about that.

Jon Finer:

... of Russian oil. So I would just take a closer look at it. There have been some concerns expressed. It’s gotten a lot of bipartisan support, but on sanctions authority for new authorities, it’s actually pretty limited. The executive has a lot of those already-

Radosław Sikorski:

Only sanctions on Russia, not on others, not on allies, for Christ’s sake.

Jon Finer:

Take a look at the tariff authorities authorized by the legislation, which could be more extensive than people realize. Anyway, I’ll turn it back to Jake.

Jake Sullivan:

I’ll just say, Radek, that was a good reflection of the difference between Jon and me. I sort of loosely referred to the tariffs and Jon went right to the heart of the matter. It is a matter of some concern because it gives the president pretty broad authority and discretion with respect to the application of tariffs, including potentially against the European Union. So worth looking at. I think a lot of senators haven’t exactly looked closely at that because they’re focused on the kind of underlying message of the bill, which is we have to squeeze Russia harder, we got to pressure them more, which is something that both Jon and I would strongly agree with. But the actual mechanics of this bill are quite interesting because it could present challenges in terms of health.

Radosław Sikorski:

On the other hand, we already have tariffs on allies.

Jake Sullivan:

That is true. That is true. And potentially more coming depending on how the president deals with some of these continuing trade investigations. Okay. So speaking of tariffs and economic coercion and all the rest of it, I’d like to come back to China. You started in this conversation talking about some of the steps that Europe is taking now to deal with the challenge of Chinese goods flooding into the European market. You personally have been one of the European leaders who’s been most clear-eyed about the China challenge writ large. We spent a lot of time during the Biden administration talking to our European allies about that challenge and how we could align on it. Can you just talk a little bit more about how Europe should think about China right now, how Europe is thinking about China right now, and whether we’re at the start of a different kind of policy than we have seen? I would be very interested in your perspective on this dynamic.

Radosław Sikorski:

So the relationship between Europe and China is not like the old Cold War, because with China, it’s far more complex. We are huge customers and trade partners for each other, and we have a one China policy, for example. But we are concerned, just like the United States, at the attempt to limit the access to magnets and to critical minerals. And here, Secretary Rubio did the traditional thing, which is to use America’s convening part. And we had a successful conference in Washington on critical minerals, and I hope this gets a follow-up. I regret that a useful institution devised in previous years between the EU and the United States is not being continued. It was actually inspired consciously by the Reagan administration, by the COCOM. And I’m talking about the US EU Trade and Technology Council, whereby we could at least exchange information and hopefully agree some minimum standards on trade, on ingoing and outgoing investments, and on research and production standards so as to preempt unfair competition. I thought this was mutually useful, and I hope the idea is rediscovered.

Jake Sullivan:

Do you think we can rediscover that idea in light of the degree to which there seems to be bad blood over Greenland, over tariffs, over other things?

Radosław Sikorski:

Well, it’s difficult to do when there are these other issues. And yes, it requires trust.

Jake Sullivan:

And just to keep pressing on that, do you think trust can be rebuilt or a sense of common purpose can be rebuilt? And I’m not just talking about in the next year or two in this administration, just projecting forward, whoever takes the oath of office on January 20th, 2029, can that president turn the page to a certain extent or are we just living in a little bit of a different world when it comes to the transatlantic relationship? How do you assess that?

Radosław Sikorski:

Some losses of trust are probably irreversible, but others can be. Remember a few years ago on your watch, China was doing its wolf warrior diplomacy. And now the United States is going through its phase of wolf warrior diplomacy.

Jake Sullivan:

I’ve not heard someone put it that way before. I like that.

Radosław Sikorski:

And I think the results will be similar. And then after a couple of years, memories fade.

Jake Sullivan:

One more thing about China before turning it back to Jon. You’ve said that China’s one of the few countries that could press Russia to end the war in Ukraine. Do you have any reason to believe they would do so? Is that a viable pathway to get Putin to change course in some way or is that China just [inaudible 00:35:28].

Radosław Sikorski:

So the reason I think they could is if you remember, because it was on your watch, in January ‘22, there was a brief Russian military foray into Kazakhstan to interfere in Kazakhstan’s succession. And I believe that the Chinese told the Russians, “Get out right now or we will sever trade with you.” And the Russians obeyed. I don’t think Russia could prosecute the war, and I don’t think she could survive as a state without trade with China. So this would be a credible threat. So China, unlike us, actually could force Russia to end the war. But my guess is that the war suits China just fine. Russia is selling them gold. Russia with every year becomes more dependent. And what’s not to like about that?

Jon Finer:

I want to ask you a few questions about the future. Russia has reportedly, although I suspect you’d confirm it, moved nuclear weapons into Belarus on Poland’s border. Is the US nuclear Umbrella-

Radosław Sikorski:

Actually quite close to the Russian border, if at all. But yes.

Jon Finer:

Okay. Is the US nuclear umbrella sufficient for European security, for Polish security? And what are the prospects of additional European countries, even Poland, deciding they need their own nuclear deterrent?

Radosław Sikorski:

No, we are a happy member of NPT and we are not thinking about it. But as you know, this is an ancient discussion. During the Cold War, Germans threatened over whether the US would sacrifice New York for Hamburg and so on. So these are similar worries. The main thing is to keep the adversary uncertain as to our intentions and to keep capabilities that they would find unbearable.

Jon Finer:

As you said earlier in this conversation, Poland has been building up militarily in response to the Russia threat even well before the full-scale invasion of Ukraine in 2022. Now Germany and others are more belatedly getting into the act, which probably feels like a strange thing for a Polish official to consider good news, but here we are. Is this happening just in time or are you concerned given the timeline you laid out, end of this decade, that it’s all coming too little and too late at this point?

Radosław Sikorski:

It would’ve been better to have started earlier because when you have to re-arm quickly, you find yourself abutting production schedules. And what’s actually happened is that there is a global shortage of ammunition of equipment and prices have risen. So if some countries had done it in a more measured way, it would’ve been cheaper to do. But look, if we spend what we have pledged to be spending, we meaning the European part of NATO, at the Hague, then by the end of the decade, our joint military budget will be about what the US military budget was last year. So around a billion. It’s a huge military budget. And of course we have to spend it more efficiently and all that, but still that’s a huge military budget.

And remember, all of our military budget is spent on the defense of Europe. Only a very small proportion of your military budget is spent on the defense of Europe. And also remember that for an adversary to attack us, the adversary would need a three to five advantage over us. They don’t have it even today, let alone by the end of the decade when we’ve retooled. So I actually, we should do what we have to do, but there is no reason to be panicky vis-a-vis Putin anymore. It’s Putin who’s in trouble.

Jake Sullivan:

Radek, you said earlier that we kind of collectively overestimated Russia’s capabilities. I would second that and say we got, as our intelligence community and military experts got one big thing very right, which was Putin was going to invade, was going to try to swallow Ukraine. And one big thing not so right, which was that he would take Kyiv in a matter of days or weeks. And to your -

Radosław Sikorski:

We weren’t sure, and we couldn’t be sure whether the Ukrainians would fight. They over-fulfilled expectations. Ukraine has over-fulfilled expectations. Europe has done much more than I would’ve expected five years ago. The US also, and Russia has done much more poorly.

Jake Sullivan:

So on that, one more prediction. You’ve said Putin is pushing Russia off an economic cliff, not unlike Brezhnev during the Cold War. How fragile is the Russian economy? And more fundamentally, how fragile is the Russian state in your view?

Radosław Sikorski:

So I don’t accept the dominant Western paradigm, which is kind of Marxist, but even though couched in market terms, because the fundamental narrative in democracies is that if you get the economy right, politics follows based the term in superstructure. Whereas in Russia, it’s the other way around. And it manifests itself, for example, in these myths in the West about how the oligarchs will come and sort out Putin, put pressure on him to end the war, which is how it would happen in the United States to some extent. In Russia, it’s the other way around and always has been. It’s the political authority who decides who is rich and who isn’t, who gets the business and who gets terminated with extreme prejudice or falls off a window. And Russia has always, under the Tzars, under the Bolsheviks, and now created huge military and diplomatic capacities from a very small economic base.

But of course, there are limits. And just as [inaudible 00:42:08] Germany eventually ran out of resources to continue the war, and Cyrus Russia ran out of resources to continue in World War I. So Putin is running out of resources. I think he probably has enough for another year or so.

Jake Sullivan:

We’ll end with a question that we ask a lot of our guests, which is tell us one unpopular opinion you hold on any subject. It doesn’t have to be related to your work, though of course it can be, but an unpopular Radek Sikorski opinion.

Radosław Sikorski:

All right. So it’s unpopular in some quarters, but quite popular in others. So I think that electorates everywhere in Europe and in the United States are telling us that we need to sort out mass migration and that unless democratic governments do it, they’re ready to hire populists and radicals to do it. So in Poland, we won the election and we are leading in the polls because we outflanked our populists on the right on migration. We have built a big and beautiful fence on our border with Belarus, 440 kilometers. The border is now totally secure. We have passed a law which denies people the right of asylum if they cross the border illegally. And we have sorted out our visa system to be much stricter towards people who come to work in the guise of students or others. And so I think this is the way that democracies fix their problems.

When the establishment neglects something that people feel strongly about, fringe parties take that issue and run with it. And a wise establishment has to fix the reasonable part of the demand, and then equilibrium is restored.

Jake Sullivan:

How do you pair that with things like hosting refugees, like fighting back against racism, xenophobia, what have you? So tough on border security, tough on an orderly process, but holding true to your small L liberal values at the same time. Can you just spend one second on that?

Radosław Sikorski:

So you will not like me after what I’m about to say. And I’m speaking as a former refugee myself. So I think the Biden administration made a major error in lifting some of the Trump won decrees on the southern border, because people understand and they are right that there are too many genuine refugees that countries cannot absorb. And the fault of the left in both the United States and Europe was to couch any discussion about migration as a possible racial issue. People feel that there is room for a civilized non-racist dialogue about the types of migration we want, the rate of migration that is acceptable, the sources of migration that we would prefer, and the control over migration that nation states have the right to exercise.

If you are going to tolerate open borders, then why do we have border guards? Why do we have visas? Why do we have passports and everything else? People understand more than we think, namely that you can have an open border policy in the 19th century in the United States or in Australia when you’re desperate for migrants when there are no social provisions. You come in and make your fortune in the Wild West, but you cannot have high social provisions and open borders at the same time. In Europe, we have the Mediterranean, Northern Africa plus the Middle East. That’s maybe up to a billion people who would rather live here in Europe than where they are. And you can’t blame them. And I’m speaking as a refugee myself. But we cannot have a billion people. Numbers matter.

Jake Sullivan:

Radek, where were you a refugee from?

Radosław Sikorski:

I was a refugee in Britain when-

Jake Sullivan:

You sought asylum [inaudible 00:47:17]-

Radosław Sikorski:

... [inaudible 00:47:18]. martial law. And I got practical asylum, but people act for mixed motives. I had some prospect of some persecution, but also Poland was very poor and people migrate for mixed reasons. Let me remind you what I can’t remember whether it was Mao Zedong or [inaudible 00:47:43] told another Democrat president, Jimmy Carter, who famously stood up for human rights, Helsinki presses, all that. And he is supposed to have told, let’s say Mao Zedong that he should ease up on dissidents and let them travel if need be, get asylum in the West. And Mao Zedong was supposed to have told him, “Mr. President, do you really want all my dissidents in your country? How many do you want? 50 million?”

Jon Finer:

So we should leave this here. I will say we probably disagree with you less than you might think about some of the moves that were made early in the Biden administration. And the project in our party right now is about how to preserve what I think Americans rightly want, which is a secure and orderly border and enforcement of our laws while staying true to the fact that Americans are also basically a pro-immigration country when it’s conducted in an orderly way. How do you do both? And I think that is the challenge.

Radosław Sikorski:

And by the way, the percentage of people born outside either the United States or the U in your case is 15%. A percentage of our population born outside the European Union is 10%. And we are being told that we face civilizational erasure.

Jon Finer:

Not by us.

Jake Sullivan:

A quote from the national security strategy of the United States. Right. Yeah, exactly. Correct. Well, on that, Radek, thank you for taking the time with us today. We really appreciate it.

Jon Finer:

All right. So Jake, what did you think?

Jake Sullivan:

Radek is high value, man. I wish we could have had him for longer because he can speak so fluently across geopolitics, economics, culture, politics, and history. It’s just refreshing to get to hear someone like that opine on a range of subjects with the kind of texture that he was able to do. I know that’s not the most sophisticated reaction, just like I’m impressed, but I was impressed.

Jon Finer:

Like all former journalists. No, but more seriously, I guess I was struck by a couple of things. One is on the question about Article five and NATO, I kind of expected him to give a, “Oh yes, of course the United States would be a credible participant in any Article five situation or some kind of yes, but we have concerns about some of the comments that have been made.” But he kind of just jumped straight to the butt. He didn’t say no, certainly, but he basically seemed to say to me, “We don’t need them that much anymore. Maybe as enablers, maybe with logistics, maybe in extremists. But for the most part, Europe has to take care of these problems increasingly on its own and may sooner than we think be ready to do that.” He almost sounded a bit, and this is a stretch probably that he would reject, but a bit like how we used to hear Emmanuel Macron back in the day talking about strategic autonomy in Europe.

That increasingly seems to be the case that even real strong proponents of the transatlantic relationship are making in light of some of the positions being taken by the Trump administration. I don’t know if you heard that differently.

Jake Sullivan:

I didn’t. And to your point about Macron, it used to be Poland on the other side of that debate, right? Exactly. That Poland saying, “We need the United States at the center of our security.” And France saying, “No, we need more strategic autonomy.” And there does seem to be a greater degree of convergence across Europe, including from great proponents of the transatlantic relationship like Radek Sikorski. I was struck that he basically did not want to go very deep on the question of the nature of the relationship right now. He was very expansive in answer to some questions, and I think very cautious in answer to a few different attempts by us to probat the health of the alliance, the health of the transatlantic relationship. But in how he talked about Europe standing up on its own two feet, he was in a sense giving a very deep substantive answer to the question that the relationship will change in quite fundamental ways and will involve Europe taking much more responsibility and reducing its overall reliance on and counting on the United States in an extreme situation.

The other thing that I though in his answer on the question, would the US come to Europe’s defense if Article five were triggered by some kind of Russian provocation? I thought part of it was a characterization of the US and Europe and their relationship, but part of it was the difficulty of actually discerning when Article five has been triggered. He talked about it’s going to have to be a fact-dependent circumstance because his conception of this is not Russian forces rolling across NATO frontier. His conception is some kind of gray zone activity that’s more upstream than what we’ve seen that leads to a loss of life, potentially a significant loss of life, and then NATO having to figure out what is the nature of our response. He said NATO would respond. He was quite forceful on that, but the nature of the response is complicated. And this is something we contended with when we sat in the job and thought about all these scenarios.

It’s very straightforward what happens if Russia invades the Baltics. Okay, we know how to respond to that. We have war plans for that. But errant missiles that kill some people and the Russians saying, “Oh, we didn’t mean to do it,” or one of these false flag operations that we don’t get ahead of the way we were able to get ahead of it in 2022. Much more unclear exactly what the option said is. And I think that was reflected a bit in the way that he talked about the nature of hybrid warfare.

Jon Finer:

It’s funny, the whole conversation in the back of my mind was a story we’ve told, I think, versions of before, but about the closest we came during our tenure to a real Article Five crisis, which is basically a phone call we got from the intelligence community in the middle of a day in Washington. I was in Washington, you were overseas-

Jake Sullivan:

Middle of the night.

Jon Finer:

In Bali, Indonesia, sound asleep as you should have been, that basically said a missile just landed in Poland and killed a couple people. Killed two people. And the assumption is this could be a Russian attack, the first one on NATO territory during the course of the Ukraine war. And thank God, the more we dug into this, the more it became clear it was actually a kind of errant Ukrainian missile. But there were a couple of hours in there where we had to wake you up, wake the president up, get the polls on the phone, and make sure we got all the facts before we reacted or said too much, God forbid, did anything. And this one turned out to be a sort of a dodged bullet other than the tragedy of the two people whose lives were lost, but the next one might not be.

Jake Sullivan:

Absolutely. Yeah. And not just get the polls on the phone, get the NATO Secretary General on the phone because of the possibility that we’d have to go for Article five in that moment. That was not a moment where we’re all like, “Oh no, this is no big deal.” It was like, “This could be it. This could be-

Jon Finer:

Arguably the most stressful hour or two we had during our time, although there’s other candidates for that.

Jake Sullivan:

There certainly are. Actually, sometime we should just do a top 10 ranking of most stressful moments because there are a lot of candidates for that. Yeah, I think otherwise, hearing his take on China and a view that basically Europe is going to have to figure out how to align its policy tools to deal with this massive economic threat, the potential hollowing out of their industrial base, that was striking to me in that he started off with moves Europe has made just quite recently on this and took a quite robust line on that. I think there’ll be a real debate in Europe about just how hard to push on this, but that is something for us to very much watch closely, even as we are obviously tuned into what exactly happens in the Russia-Ukraine dynamic. This larger strategic and economic question of China’s relationship with Europe, I think is just a massive priority and something that we should continue to return to as a topic here on the podcast.

Jon Finer:

Absolutely. Lot to digest, lot to think through. Hope you all enjoyed listening to it as much as we enjoyed talking to him. He’s a good guest. Well, that’s all for today. We’ll be back next week with a new episode of The Long Game.

Jake Sullivan:

Subscribe to our YouTube channel and follow the audio feed so you never miss an episode.

Jon Finer:

For additional content, episode transcripts, and exclusive podcast segments, subscribe to The Long Game on Substack or join The Long Game Plus on Apple Podcasts.

Jake Sullivan:

This week we discuss the FCC ban on foreign-made humanoid robots.

Jon Finer:

Humanoid robots are a clear possible next step in terms of automated warfare that people have been flagging. So there’s also the potential for these technologies, not just the potential when it comes to drones, but certainly when it comes to humanoid robots to be dual use in a military sense too. And I think whether or not that’s part of the explicit rationale, that is certainly some of the subtext of what’s happening with the writing of this rule. Head to thelonggame.substack.com or subscribe to the Long Game Plus on Apple Podcasts. The links are in the show notes. That’s it for this episode of The Long Game.

Jake Sullivan:

If you like the show, please follow, share with friends, and leave a review. It really helps listeners find us. The Long Game is a Vox Media podcast network production.

A NOTE FROM THE PRODUCER

Tamara Sepper is the Executive Producer of The Long Game.

The Trump administration is banning foreign-made humanoid robots and power inverters from the U.S. market. The rule applies globally, but the real target is China. And the agency behind it is the FCC—better known lately for its fight with Jimmy Kimmel.

The concern: connected foreign technology could collect sensitive data, disrupt critical infrastructure, or be adapted for military use.

In this special segment for paid subscribers, Jake Sullivan and Jon Finer tackle the bigger questions:

• Where is the line? If nearly every device is now a sensor, what separates a humanoid robot from a toaster?

• Do import bans work? Chinese EVs are shut out of the U.S. market but spreading worldwide. Can restrictions buy time without replacing the need to build competitive American industries?

• Who is ahead? What does the rule reveal about the U.S.–China race to apply AI to the physical world?

If you’re a paid subscriber, thank you for supporting the show. Watch the episode and share your thoughts and questions by commenting below or email Jake and Jon at longgame@voxmedia.com.

And if you’re not yet a paid subscriber, now is a great time to join. You’ll get access to exclusive podcast segments like this one, recommendations from Jake and Jon, and other exclusive subscriber-only content.

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You can listen to this episode on Spotify, Apple Podcasts, and other listening apps.

Watch episodes of The Long Game on YouTube.

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A NOTE FROM THE PRODUCER

Tamara Sepper is the Executive Producer of The Long Game.

This week on The Long Game, Jake Sullivan and Jon Finer examine the future of European security with one of the continent’s most experienced—and most candid—foreign-policy voices.

Polish Deputy Prime Minister and Foreign Minister Radosław “Radek” Sikorski joins the show as the Pentagon begins reviewing the future of the US military presence in Europe, Russia intensifies its hybrid campaign against NATO countries, and Ukraine seeks to turn battlefield momentum into lasting strategic gains.

Sikorski’s argument is blunt: Europe should be capable of deterring Vladimir Putin largely on its own. The US will remain essential for intelligence, equipment, logistics, and other strategic support—but Europeans can no longer assume Washington will carry primary responsibility for their conventional defense.

The wide-ranging conversation covers key questions, including:

• Can NATO deter Russia if the U.S. reduces its military presence in Europe?

• Would Washington respond if Russian sabotage or a false-flag attack triggered an Article 5 crisis?

• How could Ukraine translate its current position into a durable victory?

• Is President Trump moving toward stronger support for Ukraine and tougher sanctions on Russia?

• How close is Putin to exhausting the resources needed to sustain the war?

• Does China have any incentive to force Russia to end the war?

• What would Ukraine need to do before joining the European Union?

After the interview, Jake and Jon reflect on what Sikorski did—and did not—say about America’s commitment to NATO. They also recall a tense moment during their time in government, when a missile landed in Poland and killed two people, briefly raising the possibility that Russia had struck NATO territory and the alliance’s collective-defense commitment could be tested.

For paid subscribers, Jake and Jon break down the rationale for FCC’s new restrictions on foreign-made humanoid robots and connected power inverters. We’ll be posting that segment Thursday afternoon.

We love hearing your thoughts. Please comment below or email Jake and Jon at longgame@voxmedia.com.

Transcripts here.

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REFERENCES & SUPPLEMENTAL MATERIALS

• “Never Again,” Again, Radosław Sikorski, Project Syndicate, December 15, 2025.

• “Pentagon launches review that could reshape US military presence in Europe,” John Vandiver, Stars and Stripes, July 28, 2026.

• “Information of the Minister of Foreign Affairs on the Tasks of Polish Foreign Policy in 2026,” Radosław Sikorski, Ministry of Foreign Affairs of the Republic of Poland, February 26, 2026.

• Photo by Wojtek Radwanski/AFP via Getty Images

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Tamara Sepper is the Executive Producer of The Long Game

Kash Patel is reportedly planning an October trip to Russia, a rare journey for an FBI director, and, given the Trump administration’s posture toward the Kremlin, a suspicious one. Across the Atlantic, new UK Prime Minister Andy Burnham enters Downing Street with virtually no foreign policy record, leaving his first cabinet picks to signal Britain’s next direction.

In this special Mailbag episode for paid subscribers, Jake Sullivan and Jon Finer answer listener questions about both developments.

If you’re a paid subscriber, thank you for supporting the show. Watch the episode and share your thoughts and questions by commenting below or email Jake and Jon at longgame@voxmedia.com.

And if you’re not yet a paid subscriber, now is a great time to join. You’ll get access to exclusive podcast segments like this one, recommendations from Jake and Jon, and other exclusive subscriber-only content.

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You can listen to this episode on Spotify, Apple Podcasts, or other listening apps.

Watch episodes of The Long Game on YouTube.

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A NOTE FROM THE PRODUCER

is the Executive Producer of The Long Game

This week, Jake Sullivan and Jon Finer break down Ukraine’s military leadership shakeup, the drone revolution reshaping warfare, and America’s shrinking choices in Iran.

In Ukraine, President Volodymyr Zelensky has dismissed both his defense minister and the commander of the armed forces—an extraordinary reshuffle at a moment when Ukraine has been gaining ground. The personnel fight reflects a larger debate over how the war should be fought: with traditional military tactics or a new model built around drones, autonomous systems, and technological innovation.

“To have both the defense minister and the overall commander of Ukrainian forces fired basically within a week of one another—while the war is going pretty well—that’s a striking thing,” Jake says. The overhaul also raises questions about Zelensky’s management of increasingly popular officials who could someday become political rivals.

Jake and Jon then trace the rise of Ukraine’s drone industry, including the U.S.-backed “technology sprint” they helped launch after the failed 2023 counteroffensive. Jon argues that Ukraine has now “surpassed the United States military, and basically every other military on the planet” in integrating autonomous systems into combat.

Meanwhile, the U.S.-Iran war is intensifying, the Strait of Hormuz remains effectively closed, and more U.S. service members have been killed. Jake and Jon outline President Trump narrowing set of bad choices: escalate, pursue another deal, declare victory and leave, or simply continue exchanging strikes with Iran in the hope that something changes. As Jake puts it: “All of the options are pretty bad, because the choice of getting into this mess in the first place was pretty bad.”

Listen to the episode and share your thoughts and questions. Comment below or email Jake & Jon at longgame@voxmedia.com.

Transcripts here.

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REFERENCES & SUPPLEMENTAL MATERIALS:

YouTube, “2014 Hero of Mariupol Becomes Ukraine’s New Army Chief”

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Transcript: Why Zelensky Fired His War Chiefs & Where Trump’s Iran War Goes Next

The Long Game with Jake Sullivan and Jon Finer

July 23, 2026

TEASER:

Jon Finer:

The Ukrainians have now surpassed the United States military and basically every other military on the planet in terms of doctrine for how to fight and integrate these autonomous systems on the battlefield, and we should be learning from them how they do that.

Welcome back to The Long Game. I’m Jon Finer.

Jake Sullivan:

And I’m Jake Sullivan. And today it’s just me and you, Jon. No guest, just mano a mano.

Jon Finer:

Lonely here out in the internet world, but we’ll make it work.

Jake Sullivan:

So today we’re going to cover developments on two files that we have discussed repeatedly over the course of the Long Game Podcast, one on Ukraine, the other on Iran. On Ukraine, there have been some significant developments in the past few weeks given the firing first of the defense minister and then of the chief of staff of the military. We’ll talk about the implications of that and also what’s going on in the war generally.

And then second, Iran, obviously there are developments every day, new things to talk about. And we thought this would be a moment for us not just to cover what’s happened over the last several days, but also to revisit the options memo that we did a few weeks ago. Because once again, President Trump has got to be turning to his people to say, “What the heck are my options for actually getting out of the mess that I put myself in?” And I will preview by saying all of the options are pretty bad because the choice of getting into this mess in the first place was pretty bad. But Jon and I will go through that and talk to you about how we think this conversation may be unfolding in the White House and at the Pentagon as they try to figure out what comes next.

But before we dive into all that, Jon, I am mourning the end of the World Cup. It is always sad to wake up and not have great soccer on, the great spectacle that we saw for the past month. It’s interesting, the vibes going into the World Cup just weren’t really great. It felt like there was lots of controversy, lots of questions about enthusiasm. But frankly, as soon as the game started, it was like a switch of positivity and the light flipped on. The soccer was great. The scenes from American cities were great. The videos of foreign visitors discovering all kinds of curious and wonderful things about America were great. And man, was it, I think, just a tremendous production and really enjoyable to be a part of. How are you feeling now in the dismal world of no more World Cup soccer?

Jon Finer:

Yeah, so it was a great month. I think we each got to go to some games, which was a lot of fun. I think I watched, God, I don’t even know how many dozen games with friends, with my family, with my dad, my siblings, which was a ton of fun. Didn’t exactly get the results maybe that either of us were looking for. The US team didn’t make it quite as far. I’m a bit of an undercover England fan and was sad that they went down in the semifinals. But now actually for me, you enter this month of August that has a lot of downsides the last month of the summer coming up and no meaningful sports other than Major League Baseball. And the one bright light for me is now the Red Sox are on a 14 game winning streak having started the season in a pretty dismal fashion.

So I’m trying to find the silver lining where I can and that’s it for now.

Jake Sullivan:

I do recall that when we recorded the episode with Franklin Four, who had written an update to his book, How Soccer Explains the World, you and Frank and me each gave our predictions for who would win the World Cup, but I don’t remember who predicted what. Do you remember?

Jon Finer:

I don’t exactly remember either, to be honest. I usually just predict England because I don’t like a misalignment between my desires and the outcome, and it’s just too hard to pick the United States given how far they are from being competitive at that level. So I think I did say England probably.

Jake Sullivan:

You did. And Frank said France. Who did Jake say? Oh, I think it might’ve been Spain.

Jon Finer:

Yeah, it might’ve been Spain, Spain. Might’ve been Spain.

I’ve gotten a lot of predictions wrong on this podcast from the start, but on the most consequential, the most important geopolitical prediction, who wins the World Cup? Well, I got that one right so I have to take at least one second to bask in the globe. They were damn good, Spain, damn good. I mean, they just efficient, team oriented, not the most exciting to watch, but clinical in a way.

You’re not going to lose a World Cup giving up one goal in the entire tournament, that’s for sure.

Jake Sullivan:

Entire tournament. Yeah. All right. Well, since the soccer is over on television and the stadiums, it probably should be over on our podcast for a little while. So we will now move on to talk about the first topic, which is Ukraine and a series of developments there that caught our attention and I think are worth some time reflecting on. So Jon, do you want to set the table on this and give us some of your initial thoughts?

Jon Finer:

Sure. The headline for me in some ways is that Ukraine has politics. Ukraine is a democratic country, a flawed democracy like many others, but a democratic country in which the leadership, even during times of war, faces a series of complicated political decisions. And that’s a bit of what has confronted President Zelenskyy over the last few days and even weeks. At a time when the war is going very well on the battlefield, and we’ve talked about that over a number of episodes, there are internal interpersonal political dimensions to governance there that have grown quite complicated for him. In the starkest case, sort of a standoff between the commander-in-chief of the Ukrainian Army, a guy named Syrskyi who was in that role when we were still in government and the Minister of Defense of the Ukrainian government, a man named Fedorov, who we both have had some exposure to, both of which one or the other one fired.

And ultimately what Zelenskyy decided to do was to relieve both of them of their duties along with Ukraine’s sitting prime minister. So in the context of a pretty significant reshuffle, those three roles are probably the most important that are now under new occupancy. And now we will see how Zelenskyy manages the aftermath of this because at least one of those figures, Mr. Fedorov, has got quite a political following inside Ukraine. And there have been demonstrations in the streets in response to his firing that have led Zelenskyy to reach back out to him, talk to him maybe about a different title, different role somewhere within the national security establishment of Ukraine, although no announcements on that front yet.

But what is happening here that you see sort of driving these decisions? We have seen Zelenskyy relieve significant officials of their duties before during the course of this war, but this is a pretty big set of changes.

Jake Sullivan:

Yeah. To have both the defense minister and the Archyde, what they would call the Archyde, basically the commander, the overall commander of Ukrainian forces, the top uniformed military officer in the Ukrainian army fired basically within a week of one another while the war is going pretty well, that’s a striking thing. I think three things are going on. And I don’t know exactly how to assign the weights among them, but I’ll put them all on the table. The first is kind of what’s above the waterline, which is an open debate between the civilian defense minister and the uniformed chief military officer over exactly how this war should be fought.

Fedorov, the defense minister’s 35, was previously the minister of digital transformation. He’s young, he’s dynamic, and he’s very focused on advanced technology. He is in many ways the architect of the drone program that has been central to a lot of the gains that Ukraine has been making on the battlefield in the last few months. And he believes deeply in evolving the very nature of warfare from the more traditional Soviet style that Ukraine started this war with into more of what it has become here in 2026.

Syrskyi, much more old school, 60 years old, you’ve got a generational difference. Someone who was at the heart of defending Kyiv when this war kicked off. He was the guy who stood there stoutly with his forces to fend off the Russian invaders and save the capital. He’s been kind of driving this more traditional form of land warfare, defending this long frontline, several hundred miles long frontline trying to hold cities at great human cost. And so you had a real debate between the two of them. And frankly, that debate got untenable because the two really couldn’t work together. So Zelenskyy had to choose. And at first he went by backing Syrskyi, the military guy over Fedorov firing the defense minister.

That brings me to the second thing that I think is going on here, which is a bit below the waterline. And that is President Zelenskyy has been an incredible leader in this war over many years under enormous pressure of all kinds, both domestically and obviously pressure day in, day out from Russia and the pressure of trying to hold together a coalition of countries supporting him. But he has had one kind of consistent issue that I think has undermined his ability to provide the kind of leadership that he has sought to provide over the course of this war. And that is he doesn’t like characters becoming larger than life within the Ukrainian system. Two years ago, he fired the previous commander-in-chief, Zaluzhnyi, moved him out to be the ambassador to London, to the UK because he was concerned that Zaluzhnyi was getting too politically powerful and could potentially challenge him.

He took the head of their intelligence services, Budanov, and actually brought him in to be his chief-of-staff. So bring him in close because he was concerned about how he was gaining political popularity and that made him nervous.

Jon Finer:

After years of rumors that he might be fired, Budanov, he ultimately decided-

Jake Sullivan:

Exactly.

Jon Finer:

... to pull him instead of kick him out.

Jake Sullivan:

Yeah, make him kind of directly in his office and responsive and reporting directly to him. And then Fedorov was gaining this enormous following, this enormous standing both within Ukraine and globally. And I think Zelenskyy looked at that and made him a little nervous. And in fact, when he fired Fedorov, you saw an outpouring massive protests in cities across Ukraine, more than a dozen cities, a serious backlash to the point where I think Zelenskyy had to take two steps that he probably wasn’t expecting to take.

One was saying Fedorov should come back into the government in some form. And the second, that he had to fire Syrskyi. When he originally fired Fedorov, he said, “I had to choose one or the other.” And by the end of this, he’s chosen both to go as opposed to neither and now is trying to coax Fedorov to come back in some role other than being defense minister. Which leads me, and I’m sorry to go on for so long, and then I’ll stop to the third factor here that I think is present and that we should absolutely put a spotlight on, and that is the question of procurement and corruption in the Ukrainian military.

One of the things that Fedorov was really taking aim at in his public comments and some of his actions within the ministry was trying to reduce the level of corruption associated with military contracts. And I think this probably created a set of opponents and enemies throughout that entire defense enterprise. And when you start collecting enemies, you create certain vulnerabilities for yourself. So I don’t know how much to put on that third one, but I think it is a factor for sure. And so when you add those three things up, a big fight over exactly how to fight this war and what role technology should play in it versus traditional tactics, Zelenskyy’s own concern about figures arising with their own independent power bases and then disputes over the nature of military contracting and the constant specter of corruption in Ukraine, that to me is the mix of factors that we should be looking at to understand what is happening here.

And underlying all of it is the point you made at the outset, which is Ukraine’s a democracy. And in democracies you get fights over personnel, you get debates and disputes, you get public backlash and pushback, and that has to have some impact on an elected leader like Zelenskyy.

Jon Finer:

It must have been particularly painful on some level for Zelenskyy to relieve Syrskyi, who was his hand-selected overall commander of the Ukrainian army, replacing Zaluzhnyi with somebody who he had a closer personal relationship with and who I think by most accounts still has his confidence, but he felt like he had to because of all the reasons that you’ve described. And maybe it’s worth just pausing for a minute on the two individuals who are replacing these two key figures in the war because they’re interesting aspects of their careers as well. And one of the things I wondered in reading about them, and I’ll say a board or two about each of them, is whether Zelenskyy runs the risk of just replicating the problem that he had between a kind of a new school and an old school figure in modern warfare between Fedorov and Syrskyi. He’s replaced Fedorov with a man named Khmara who was at one point the commander of probably Ukraine’s most elite special forces unit, or one of them, a unit of the SBU, the Intelligence Service called the Alpha Unit, then ultimately the head overall of the SBU.

And somebody who Zelenskyy himself has described as having unprecedented experience with technological combat operations, an innovator, a pioneer in the use of drones and other autonomous systems. So replacing one innovator, Fedorov with another innovator Khmara. And he has replaced Syrskyi with a man named Drapatyi who is a tank commander. So in some ways one of the most old school forms of combat on the battlefield, a 26-year veteran of the Ukrainian armed forces and somebody whose main claim to fame inside Ukraine, and actually you can look online and find this video on YouTube, is a video of him smashing an armored infantry vehicle through Russian barricades to prevent essentially the Russian encirclement and takeover of Mariupol back in 2014 long before Russia again assaulted that city and ultimately took it over. And it’s quite a shocking video actually when you see it. But very early in the current war, he was already a well-known sort of war hero for that perceived to be very brave action, but an old-school sort of war fighter.

And so who knows what relationship these two have to each other? I certainly don’t have that information, but you do wonder whether Zelenskyy either wisely or hoarding I think the same sort of challenges has paired again a more technologically-oriented modern warfare proponent and an old-school tank warrior in these two key rules.

Jake Sullivan:

Yeah, I do think the question on Drapatyi, and that video is really remarkable, so we’ll make sure that we put it up for people to take a look at. A, has a huge amount of credibility because of that and also because of his continued service from 2014 to today. But, B, is a generational change from Syrskyi as considerably younger. I think he’s in his mid - 40s and so the next generation. And therefore his contemporaries, a lot of the people that he’d be closest with are folks who probably are moving from the old school towards the new school. So maybe he’s not quite at the Syrskyi level of old school, even though he’s steeped in this history of being a tank or armored personnel carrier commander. So it’d be interesting to see how he plays things. And obviously he’s going to have to balance what is within the Ukrainian armed forces, a series of different stakeholders, some of whom were much more aligned with Syrskyi’s view of the world and many, many of whom chafed under Syrskyi’s command because they thought that the fundamental mode of war fighting had to evolve considerably here.

So it will be interesting to see how these two go at it. It will also be interesting to see if Fedorov agrees to come back in. He basically, to Zelenskyy’s first in treaty to return to government said, “I’ll only come back if I’m defense minister.” That doesn’t at the moment look likely because someone else has been given that job. But Zelenskyy’s trying to get him to come back into some larger technology position that could give him a lot of sway over the question of how exactly Ukraine prosecutes this conflict on a going forward basis. So we will have to watch that closely in the period ahead.

But I think Jon, it would be worth us spending a minute just reflecting on this evolution of drone warfare in Ukraine and what it has meant for the changing nature of the battlefield and also for Ukraine’s changing fortunes with respect to their capacity both to resist Russia and to bring the fight to Russia in a way that was more difficult for them in earlier phases of the war. Do you want to reflect on that as somebody who personally put a lot of time and energy into this back before it was headline news that this drone program was central to the way in which Ukraine would defend itself?

Jon Finer:

Yeah, we talked about this a bit with Tim Snyder when he was on, and I think it’s worth fleshing out here just given that this dynamic is now front and center in the personnel decisions Ukraine is making, not just how it’s fighting on the battlefield, but we essentially identified a few potentially fatal problems with Ukraine’s war effort as far back as 2022 and early 2023, which were they were struggling on the battlefield even when they were extremely well resourced with the sort of traditional tools of warfare, significant numbers of armored vehicles, significant numbers of artillery rounds, significant numbers of short and medium-range rockets and other munitions. They were just running into all kinds of problems moving forward against Russian encampments and lines, Russian fortified positions. And the counteroffensive that we planned with them and resourced for them that ultimately was a pretty significant military failure illustrated this in spades.

And so they weren’t making progress on the battlefield and we identified really two fundamental problems that were holding them back. One is they always had a munitions gap with the Russians. The Russians always had more of every significant munition than Ukraine had. So you had two armies that fought basically the same way, one of which had more stuff than the other. And Russia also had more people in its army and to draw from in its population than Ukraine had. So if the two sides were going to fight the same way and one had more stuff and more people over time, Ukraine was just faded to lose this conflict. And so the question was, is there a different way to fight this war? And could we help them develop that different way to fight this war? Because otherwise it was hard to project them being able to hold out much longer against this just larger, more massive foe.

So you should pick this up here because it was really your directive to our government that launched the effort to try to find a solution to these problems.

Jake Sullivan:

Well, as you said, we were playing around with this even as early as 2022 and beginning to put some resources and funding into supporting the buildup of new technologies, including drones for Ukraine to use. But it was really after that failed counteroffensive in 2023 that you and I basically became obsessed with the idea that Ukraine needed a technological edge in order to win the war. So in the fall of ‘23, we actually convened the cabinet in the situation room to kickstart what we called the Ukraine technology sprint. And the purpose of it was to provide Ukraine with funding and components for its own drone and missile development. And we brought industry leaders into the White House and we tasked our team, you’ll remember this, to convene the US government every day on this. That was our concept of the tech sprint. And there were people in our government who pushed back on it.

There were some officials in the Pentagon who didn’t want to spend money on Ukraine’s drone industry. We actually ended up having to put a hold on their Ukraine spending plan overall until they agreed to back the tech sprint. Frankly, there was an active debate inside the Ukrainian government as to whether to prioritize this effort. There were some, as we see playing out today, the debate between the old school and the new school back then there were those who kind of said, “Ah, the drone thing, I don’t know about that. We really want to focus on more traditional capabilities.” And then of course there were real proponents within the Ukrainian government champions who have helped propel this effort forward.

But we kept at it. We sent our teams to Kyiv to meet with Ukraine’s brilliant drone manufacturers directly. We poured in funding and components. We briefed Zelenskyy many times.

And by the end of 24, just before we left office, we’d invested more than a billion and a half dollars into Ukraine’s drone industry. And I think you and I were both astonished by the pace of progress and by what we were able to do to support them. Now, they have done the incredible creativity, entrepreneurship, innovation, testing, deployment, all the things like this is Ukraine’s success. But I think the US government can be proud of the role it played in helping support that as a key supporting actor. And in my view, it’s just vital that the US and Europe keep providing Ukraine with the funding and components that they need to scale their industry even further because this is ultimately how Ukraine can win this war. And so I think you and I both have a bias in favor of the New School here in a big way, a bias that we really gained from watching the traditional methods founder on the fields of the counteroffensive.

And so I hope that Ukraine continues down the track that has brought it a considerable degree of success here. And I guess my question to you, Jon, is reflecting on the experience you’ve seen over the last three years and now looking at this debate and this personnel fight, what’s your level of confidence that we are going to continue to see the refinement and improvement of this particular set of capabilities such that it can lead Ukraine to a victory?

Jon Finer:

Well, it’s working for now. And to be honest, that’s a lot more than we expected to be able to say when this kicked off. I think there was a lot of uncertainty about how successful this would ultimately be and what it would lead to. And as you said, the Ukrainians get a lot of credit for turning this concept and those resources into the reality that we’re now seeing on the battlefield. I think by the way though, it’s also important to point out that this is not some act of charity on the part of the US government. There is hard-nosed self-interest behind this. One, because Ukraine is really the front lines of a Russian onslaught that could ultimately go a lot further than Ukraine, which the Ukrainians are not reluctant to point out, but they’re right about that. But two other reasons I think kind of bolster the argument that not only were we right to invest in this, but we have to keep investing in it.

One is the Ukrainians have now surpassed the United States military and basically every other military on the planet in terms of doctrine for how to fight and integrate these autonomous systems on the battlefield. And we should be learning from them how they do that. We should be bringing over their field commanders to the United States and debriefing them about what works and what doesn’t work against a highly capable adversary. And I worry and I feel a bit that if we had done more of that over the last year, we would’ve been more successful than we’ve ultimately been in the Iran conflict going up against some of the very same capabilities that the Ukrainians have been fighting against. That’s one. And second is more of a forward-looking thing. Ukraine is ultimately going to have one of the largest arms industries on earth.

And I remember there’s a moment I’ll just never forget having gone through a drone factory with one of the entrepreneurs that established one of these companies who we had supported and funded where as we were walking out, he said something to me along the lines of, “When the war is over, do you think there’s going to be a market for this sort of thing?” I remember thinking, “Oh my, I mean, not only is there going to be a market, there’s going to be a massive market and we are going to have a real strong interest in who ultimately gets access to what they’re able to produce and who doesn’t. They’re going to become a massive exporter of this technology. And the closer we are to them, the more we will have some influence over who ultimately can become a buyer of this and who can’t.” And as a country that has a strong military, but that is not very effective at dealing with these capabilities, we have a very keen interest in where this technology gets proliferated. Another reason I think to stay close to the Ukrainians on this stuff.

Jake Sullivan:

What could have said to him when he asked you when the war’s over, will there be a market for this to say no, not when the war’s over while the war’s still going on? There will be a market for this. Because in fact, Ukraine has managed to scale production to such a degree that it actually can be an exporter, a provider of this capability, even while it is defending its sovereignty and territorial integrity and taking the fight to Russia. And the Pentagon has gone to Ukraine just in the last few days to say, we want to work with you on this. We want to procure. Other countries have obviously been very interested in that. And for certain of these capabilities as we saw in the opening weeks of the Iran war, countries in the Gulf are saying, you guys have learned how to defend effectively against these Iranian drones, which were used on the battlefield in Ukraine.

Now we need your help to do so here too. So this isn’t even a question of the future, it’s a question of the present and Ukraine already being not just a security provider by being a bulwark against Russian aggression directly, but also increasingly being a security provider by supplying capabilities and know-how and learning to democracies, including our own, that will make a difference in our ability to fight and deter conflict.

Jon Finer:

So I suspect we will revisit all of this, including by the way, the personnel discussion we had at the beginning, which I don’t think is necessarily over. As you said, Fedorov may come back. There may be some other shoes to drop. One interesting dimension I just wanted to add as we kind of wrap and maybe shift here is Ukraine is fighting this war in a context in which they have not had an election now in many years. Under their constitution, they cannot hold an election during a time of martial law being declared during a time of war. And so they have used that as a valid reason not to conduct a presidential election since the war began. But if you look at recent polls of who the most popular political figures are in Ukraine, the names are very familiar from the discussion that we just held.

At the top of the list of one recent poll that I saw is still Valerie Zaluzhnyi, the initial overall commander at roughly 70%. Fedorov now coming in at 65% approval in the recently dismissed minister of defense, Budanov, who was on the rumor to be on the chopping block and is now Zelenskyy’s effectively chief of staff close advisor at 62% and Zelenskyy at 59%. So below those others, but still quite high by the standards of most democratically elected leaders. And so just in the background of all of these personnel machinations is probably these people all sizing each other up and Zelenskyy sizing up potential opponents in some future election again, God willing, when this war is finally over.

Jake Sullivan:

And certainly both Zaluzhny and Budanov have played footsie with the idea of ultimately running for president. We probably haven’t seen that yet from Fedorov, but the way he’s been operating in the last few days calling these press conferences, taking to social media, he definitely has some political bones in his body. There’s no doubt about it and some genuine political skills. So I think you’re right to point that out and that’s a dynamic worth watching.

We will return to Ukraine to talk about the larger dynamics on the battlefield and what the prospects are for the evolution of this war through the rest of this year into next year and beyond. And we had a great conversation with Michael Kaufman. I think we should find more guests and there is no shortage of good ones on this in the coming weeks.

Now we should turn to Iran.

Jon Finer:

Yes. From one complicated conflict to another that we thought had been winding down and now seems very much not to be. The memorandum of understanding that the United States and Iran seemed to have reached several weeks ago feels effectively all but dead at this point. The war has resumed at a relatively lower grade, but there is still US bombardment of Iran, so Iranian attacks on US Navy and international commercial vessels trying to transit the strait. The strait is effectively closed to virtually all commercial traffic at this point. And President Trump is yet again threatening all manner of escalation against Iran. You add to that mix now we have the Houthis who have been relatively quiet, I think unexpectedly quiet during the course of this conflict now saying they will no longer tolerate Saudi commercial traffic through the Bab Al Mandeb. Having fired Han ships yet, but they have said that the Bab Al Mandeb where Saudi Arabia exports on the order of five million barrels a day of oil throughout this conflict is effectively closed, which could even exacerbate the energy shock that this conflict has produced.

And then you have reports that Iran may have moved some of its nuclear equipment, including advanced centrifuges to a underground facility at Pickax Mountain, which we’ve talked about before on this conflict. So all of this trending in a very bad direction, which you should add your two cents to, and then we should talk a little bit about what is available to the administration at this point to actually do. None of which I expect is going to feel particularly satisfying to people because the problem of continuing a war you should not have entered into in the first place and it did not go well as the options get worse, not better over time.

Jake Sullivan:

I think you laid it out very well in terms of the update since we last covered this in the state of play as we see it now. The only thing I would add is that we’ve had US service members killed in Jordan and in Iraq, three US service members killed in an airstrike by the Iranians against a base in Jordan, which raises questions as we continue to flow personnel and capabilities into the region to keep up this tempo of daily strikes against Iran, whether in fact we can adequately protect them against Iranian strikes, whether Iran is getting better at targeting, whether our ability to mount air defense is getting depleted. Frankly, whether other countries, Russia, maybe even China are supplying intelligence or know - how to Iran to target us in a better way. There’s a lot of questions for me just around the vulnerability of our personnel in the region that have been raised by this strike in Jordan.

And the fact that service members have been killed led President Trump to say we’re going to escalate our response accordingly. And of course he’s also gone back to Truth Social once more to re-raise the possibility of widespread attacks on civilian infrastructure in Iran, which has been a threat he’s periodically deployed and never kind of fully followed through on, but also something for us to watch. So what I think would be worth us spending the time for this episode on is to try to talk our listeners through how it is to sit in the White House or in the national security enterprise of the US government and look at the current situation and say, what are our options? What can we do now? And I’m sure there’s a lot of conversations happening about how to take the situation from where it is today to some kind of more durable resolution.

And you and I a few weeks ago did an options memo exercise on this in which we laid out three options. One was basically just declare victory and go home. One was escalate by either introducing ground troops or expanding the nature and scale of targets in Iran. And the third was basically try to do a deal, negotiate some agreement with Iran as a way out of this. So those are the three options we presented. They went basically down the path of option three. They negotiated an MOU. That MOU fell apart on a real difference of perspective on what Iranian control of the Strait of Hormuz would actually look like. So that MOU has fallen apart. But basically we’re back as I see it, Jon, to these same three options. That memo, how the options look today are different, but the basic categories of options haven’t really changed very much.

Am I right about that or are there other options that could get added to the memo now as the president kind of grapples with the fact that he’s stuck in this situation and needs to find a way out?

Jon Finer:

Yeah, I think often when leaders are presented with options, all of which are pretty unfavorable, they send their teams back to sort of shake the trees and see what else they can come up with. And it’s possible there are more creative minds at work than ours doing this on behalf of the president. And candidly, I actually hope that that is the case. But having looked at this hard, it does strike me that basically the options are the same. The likely outcome of any of them is probably worse than it was a few weeks ago when we first went through them, but that I don’t think there’s anything new under the sun and available to him here unless you’ve got something up your sleeve.

Jake Sullivan:

I guess implied in your comment that the president will look at bad options and say, “Go back and get me more,” is just the almost structural existence of a fourth option, which is just kind of keep doing what we’re doing and hope that it produces a different result. I think someone said something about definition of insanity, but leaving that aside, the fourth option is we’re 11 days of strikes as of the time we’re recording this and counter strikes just keep going, just keep bombing and hope that something gives that changes the nature of the options before the president. And so the default is that we strike, they strike, we strike, they strike. But to actually drive to an outcome, these kind of broad three categories seem to be what’s available to the president.

So then the question is as we talked through it last time, both of us really alighted on the third option. We said, “Negotiate an outcome and get it and then do it. And then that’s your way out of this misadventure, this misbegotten war.” Do you think that option is, you made the point that all the options are a bit worse now than they were a few weeks ago. Do you think that option is really available to the president? Is Iran so dug in its heels that there isn’t really a deal available? That’s question one. Question two is, do you think the option of just declare we’re done and walk away looks better today than it did a few weeks ago? Or is it equally unpalatable for the reasons that we had kind of laid out before?

Jon Finer:

So I guess I always think there is a deal available and the question is on what terms and is it better than essentially what you just described as option four, which is continuing to kind of mull along. I think the difference between the deal available now and the deal available when the president made the MOU is that there was some ambiguity when the MOU was reached actually a fair bit of ambiguity because it’s clear that there was not a meeting of the minds between the two sides over how the strait would be administered going forward. There is currently very little ambiguity about that question. Iran is not, I don’t think, going to reach an agreement in which its control dominance over the strait is not in some way ratified almost explicitly at this point. And that doesn’t mean necessarily that Iran is going to require the US to explicitly agree to a toll or a fee, but it does mean that those questions are going to be left to a later time for Iran to determine.

Maybe Iran in conjunction with Oman, that was the structure that was reached before. And we now know what that’s going to look like, which is Iran essentially treating this formerly internationally traversable waterway as essentially its internal property. And that’s a terrible outcome. I mean that’s a terrible outcome for the United States. It’s a terrible outcome for the rest of the world. I don’t think there is a deal without that outcome unless the United States would like to find some other way to funnel a massive amount of funding to Iran that makes it financially more attractive than monetizing the strait. But I think basically that’s unlikely at this point. Trump does not seem to want to do massive US funding or sanctions relief under the current circumstances with Iran. And so the deal probably looks something like the MOU with a lot more clarity that Iran is going to be in control of the strait for the foreseeable future.

And that’s a tough pill for the administration to swallow unless I’m missing something.

Jake Sullivan:

So I guess if I were sitting in the situation room listening to that presentation of what the MOU would be, I would at least want to offer the devil’s advocate position and say, “Well, Mr. President, if you’re essentially going to negotiate a document where you have ratified that Iran has unambiguous control over the strait, isn’t that a worse outcome than basically just walking away? Because you’re also going to get that de facto, but you won’t have ratified it, which preserves you some options in the future. And you certainly don’t have to pay for it as with sanctions relief and other things as you would under any negotiated solution. So in just presenting the option of declare victory and go home, I guess the argument would be we can hit Pickax Mountain. And by the way, it’s interesting the president has been raising the possibility of doing that.

Try to render it inaccessible to the Iranians and then basically say, look, we’ve set their nuclear program back years and we’ve shown we can hold it at risk. So we have in a way put it in the box. So you’d say that. Then you’d say, as long as Iran’s letting ships through the strait, what do we care what exactly happens in terms of insurance or fees or this kind of thing? The flow of oil will happen. That’s the rest of the world’s problem. As far as we’re concerned, the strait’s going to be open. You get Iran to pull the Houthis back, so you kind of resolve that issue if that’s possible. And you essentially say, we’re going to now reduce our overall presence in the Middle East because we don’t have to be there as much. And it’s a kind of story of saying we’re turning the page on this whole thing.

I see immediate problems with this argument, but you have to imagine some people inside the Trump administration are making this to the president and that the arguments they have to Marshall comparing this option to the MOU option given where we are now, those arguments may be a bit stronger. They still may not outweigh a negotiated deal. The deal may still be the best option. But you could see how in the dynamic of this conversation, the rationale I just laid out could get some heads nodding around the table. I’m just trying to picture how this conversation would actually go. And I’d be interested in your reaction to that. And then also you’re going to have someone at the table who’s saying, let me play devil’s advocate. It’s time to ratchet this thing up. It’s time for you to finally follow through on those true social posts and really bring the pain.

And you got to think that there’s at least a voice in that system that is putting that option before the president. And certainly in his mind, he considers it an option since he keeps floating it publicly. So that’s kind of how I see this dynamic unfolding in the room, but curious whether you have any reaction to or any difference of view on those first two options now as compared to when we last looked at them and said they both seem pretty unpalatable.

Jon Finer:

Yeah. Look, I think it’s a much closer call now between doing the best deal available, which is what I think we both basically said he should do the last time and what he ultimately I think did. Yeah, exactly. And walking away. In some ways, those two options have converged in the sense that even the best deal available ultimately seems to leave Iran in control of the strait. And I think you could make an argument that walking away at least doesn’t have the United States paying

For the outcome in which Iran continues to control the strait. The argument in part for doing the deal the last time was maybe you get to a next phase where you’re dealing with the nuclear problem. It’s now pretty clear that that next phase of Iran making a bunch of nuclear concessions is not going to happen. Basically, the best deal available at this point is something very narrow, focused to some extent on getting the two sides to stop shooting at each other, more or less a ceasefire with some happy talk around reopening the strait, but reopening it under new management or under current management. It’s not clear to me anymore that is meaningfully better than declare victory and step away because our ability to extract anything additional from Iran in a negotiation and agreement is pretty limited. And because at least the walkaway option doesn’t have the United States on top of all of this offering additional sanctions relief or financial incentives to Iran.

Am I wrong about that?

Jake Sullivan:

First of all, I agree with everything you just laid out and that’s kind of where I land too. But then of course, what you and I would do is say, okay, what are we missing? So what premise could we have wrong? And the main premise upon which we’ve built this analysis in this options memo is that Iran’s not going to fold on the strait. They’re not going to say, okay, actually it’s international waters again. Could that be wrong? The only way that could be wrong is if there was a pathway to increased American military pressure on Iran that had them say, okay, now we got to quit. I want to at least just state that because we got to essentially red team our own options memo here. That does not seem very plausible to me given what’s going on, but is it possible we’re missing something on that?

Could Iran be under more pressure than we are perceiving right now and might cut a better deal than we would anticipate? My answer to that question coming into this was no. I think going out will be no, but for purposes of rigor in this exercise, I think it’s important to face the question square.

Jon Finer:

So we’ve had guests on this podcast who I think would be on opposite sides of this question. I think someone like H.R. McMaster would say, not to put words in his mouth, but he basically did say this when he came in, that more pressure is ultimately going to lead at some point to regime collapse or capitulation. We’ve also had on this podcast Danny Senchinowicz, who continues to be more right than wrong in his analysis in public, but continues to make the argument that they’re not going to make meaningful concessions to the United States. I come down closer to Danny than to H.R. As I think is not a surprise to you or anyone else, but we have heard versions of those two arguments. To my mind, the best way ultimately to get to an outcome in which the strait is as close to open as possible may actually involve something that would be more likely to occur in a walkaway scenario, which is that a consortium of other countries negotiates with Iran on a more open strait in the future.

Just remove the United States where there’s too much antagonism, too much ill will, too much conflict from the equation and allow a group of European countries, maybe some Gulf countries, maybe some of the Asian customers of Gulf hydrocarbons products to basically reach an arrangement that is going to involve probably trade incentives and investment in Iran and all lot of things that people that want to isolate Iran, and we’ve been in this category, don’t want to see. But ultimately that to me is the path to reopening or re-normalizing flow of traffic through the strait, a negotiation that involves other countries that are more willing to offer Iran incentives and more able to politically than the United States is. And maybe us taking a bit of a step back having declared “victory” is the best path to reaching that. So maybe another argument for the walkaway, not one that’ll be palatable to the current administration.

Jake Sullivan:

I see you moving on this question in the options memo, which is why we do the exercise in the first place because as you play through it, you can see the puts and takes for each of the different options. So it’ll be worth watching. I think this question of whether there are indicators that our assumptions about Iranian staying power are off in some way, we can look for that, but I think you and I both come down closer to Danny than to the view that this regime’s going to capitulate or collapse anytime soon.

So I think that we can bring this to a close and both of these issues, Ukraine and Iran obviously are hardy perennials on this podcast and we’ll be back to both of them among many other issues as we go forward. But unless you’ve got anything further to add, Jon, that brings us to a close for today.

Jon Finer:

Well, that’s all for today. We’ll be back next week with a new episode of The Long Game.

Jake Sullivan:

Subscribe to our YouTube channel and follow the audio feed so you never miss an episode. For additional content, episode transcripts, and exclusive podcast segments, subscribe to The Long Game on Substack or join The Long Game Plus on Apple Podcasts. Head to thelonggame.substack.com or subscribe to the Long Game Plus on Apple Podcasts. You will find the links in the show notes.

Jon Finer:

That’s it for this episode of The Long Game.

Jake Sullivan:

If you like the show, please follow, share with friends and leave a review. It really helps listeners find us. The Long Game is a Vox Media podcast network production.

You can listen to this episode on Spotify, Apple Podcasts, or other listening apps.

Watch episodes of The Long Game on YouTube.

A NOTE FROM THE PRODUCER

is the Executive Producer of The Long Game

This week on The Long Game, Jake Sullivan and Jon Finer take on a threat that is both foreign and domestic: the security of American elections.

Just as President Trump prepares to deliver a Thursday primetime address expected to focus in part on “election integrity,” Michigan Secretary of State Jocelyn Benson joins the show.

Benson is one of the country’s leading election officials and a frontline target of President Trump’s repeated claims about voter fraud and election rigging. In the episode, she offers a clear bottom line about the 2026 midterms: despite growing threats from disinformation, foreign interference, and sustained federal pressure on state election systems, the election will be free, fair, and secure.

The most dangerous form of election interference, she warns, may not come from “hacking of voting machines,” but what she calls the “hacking of the mind”: efforts to flood the public square with fear and confusion so voters either stay home or stop trusting the result.

In the discussion, they address several key issues, including:

• What would happen if federal agents were sent to polling places

• Whether evidence supports claims about widespread noncitizen voting

• The SAVE Act and how it could make voting harder for eligible citizens

• Trump’s efforts to access voter rolls and pressure state election officials

• The dismantling of federal election security support

Then, Jake and Jon turn abroad for a Red Team / Blue Team debate on Russia, Ukraine, and NATO. They take on the opposing roles of advisers to President Vladimir Putin, arguing for and against Russia escalating against NATO member countries as Ukraine gains more and more territorial ground.

We’d love to hear your thoughts and questions. Please comment below or email Jake & Jon at longgame@voxmedia.com.

Earlier this week, Jake and Jon did a special segment for paid subscribers breaking down the big strategic questions raised by the latest Iran news, including the unraveling ceasefire and President Trump’s decision to reimpose a blockade on Iran’s ports and cargo. You can find it here.

Subscribe now

REFERENCES & SUPPLEMENTAL MATERIALS:

Photo credit: Bill Clark/CQ-Roll Call, Inc via Getty Images

Episode transcript is here.

Jon Finer, “The World Is Cutting Ties With America. It’s Already Costing Us,” NYT, 7/21/26

Marc Caputo, “Trump plans ‘potpourri’ prime-time speech Thursday,” Axios, 7/14/26

“Appeals court upholds dismissal of Trump’s demand for Michigan voter rolls,” Detroit Free Press, 6/24/26

U.S. Court of Appeals for the Sixth Circuit, “United States v. Benson, No. 26-1225,” Justia, June 24, 2026 (Court decision related to the Trump administration’s effort to obtain Michigan voter data from Jocelyn Benson)

William J. Clinton, “Inaugural Address,” The American Presidency Project, January 20, 1993 (Source for the Clinton line Jocelyn Benson paraphrases: “There is nothing wrong with America that cannot be cured by what is right with America.”)

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Transcript: Trump’s Election Playbook, Explained by Jocelyn Benson

The Long Game with Jake Sullivan and Jon Finer

July 15, 2026

TEASER:

Jocelyn Benson:

We know that domestic interference can be just as problematic and possible as international efforts to undermine our elections. So with that in mind, we have to look at everything that the president and his Justice Department and others and his allies do. Not just in terms of what will he do, but what will he say he’ll do but not do anything, but of course inspire copycats or others to actually try on their own.

Subscribe now

Jon Finer:

Welcome back to The Long Game. I’m Jon Finer.

Jake Sullivan:

And I’m Jake Sullivan. And we are recording this on Tuesday, July 14th. And as it happens, we have an amazing guest for this week. We actually recorded our interview with her yesterday, Monday, July 13th. It is Jocelyn Benson, the Secretary of State from the State of Michigan, who is also the Democratic candidate for governor. And as Secretary of State, she is responsible for administering the elections in Michigan and has been on the front lines of election integrity, election protection. And dealing frankly, directly with challenges and threats to the election, including from this current administration.

So we will have that whole interview. But shortly after we finished it, we got news that President Trump is planning on giving a primetime speech on Thursday night among other things to discuss threats to the election, election integrity, quote unquote, from his perspective. And so it makes this episode all the more timely. We knew this was something we wanted to cover, even though we tend to focus on the kind of core of geopolitics and national security. Doesn’t get too much more core to national security than the fundamental integrity of our democracy. So we knew we wanted to talk to Jocelyn. We just didn’t realize quite how newsy it would end up being because of the context of the speech that President Trump will give Thursday evening just shortly after we post this episode.

So with that, Jon, I don’t know if there’s anything you want to lay out to set all this up before we get into the interview with Jocelyn. And then the second half of the episode, we will come on to Russia-Ukraine and in particular the choice facing Vladimir Putin as to whether he wants to escalate directly against NATO beyond the hybrid warfare and gray zone activities he’s already been conducting for some time. But Finer, let me turn it over to you.

Jon Finer:

The only thing I’d add is that every profession, every job has occupational hazards. It feels like the main occupational hazard of podcasting is this gap between when you record and when the podcast actually airs so people can listen to it. And we just found that out again this week, we found that out in the past. Particularly with this administration where the velocity of news is such that nobody could possibly keep up with it even if you were just live tweeting everything that came out of the White House. And we don’t know exactly what the president will say on Thursday night. I would bet it’s entirely possible he doesn’t know exactly what he’s going to say on this topic and others.

But one thing I am confident about is this interview with Jocelyn, which lays out the stakes of the upcoming election, the threats to the upcoming election, how people who are trying to protect the integrity and the security of the upcoming election will go about doing their jobs. And what voters need to know as they prepare to participate in the upcoming election is going to be extremely relevant. And I suspect validated by many of the things that come out of the president’s own mouth either on Thursday or subsequently. So I think well worth a listen and appreciate all of you being with us.

Jake Sullivan:

Jon, you know how when you’re a diehard sports fan for a particular team and you think if you sit in a certain way or you cross your fingers or you leave the room that a play will go in your favor as opposed to against you. But somewhere deep down you know that’s not actually the case. I feel like with this podcast, when we choose topics, sometimes it ends up causing the news. Even though I know that’s not true, I tend to think it may end up being true. So maybe for the next few episodes we should just do things that are super positive and we can manifest them into existence.

Jon Finer:

Something like about England winning the World Cup. Oh, sorry, maybe that’s just positive for me. Less so for others.

Jake Sullivan:

That’s just you. That’s just you.

Jon Finer:

And with that, here’s our conversation with Jocelyn Benson.

So Jocelyn, welcome to The Long Game.

Jocelyn Benson:

Thanks for having me and thanks for all your great service, both of you to our country and in this moment helping us stay all informed on all things domestic and international.

Jake Sullivan:

Well, we’re very excited to have you. Jocelyn, we’ve only got about a half hour with you and probably hours worth of material that we’d love to get your views on. So we’re going to prioritize as best we can and dive right in.

In the national security world, we have something called the BLUF, the Bottom Line Up Front. Our country has a midterm election coming up in less than four months. Can you give us your bottom line? Do you think that election will be free and fair? And what’s top of mind for you in terms of your concerns?

Jocelyn Benson:

I love that, the BLUF, and here it is. Yes, our elections will be free and fair. They will be held on schedule, on time. And when they are, they’ll be secure and the results will be an accurate reflection of the will of the people. We know that because in the vast majority, over 90% of our elections in this country are conducted with paper ballots that are auditable after the fact if there are ever any questions. And we have multiple layers of security to ensure that every valid vote and only valid votes are counted.

But of course, a lot of the chatter around elections, changes to election laws, potential observers/interference from the federal government in cities like Detroit and elsewhere around the nation. A lot of that is designed not to actually interfere with our elections because we have provisions in place and laws to protect against that.

It’s actually designed to cause us fear, to create the sense of confusion and chaos and worry that can ultimately lead people to either stay home on election day or worse, give up on democracy altogether. That’s the real tactic here. And that’s what keeps me up at night. That’s where state and local election officials are critical to providing that clarity and that certainty and that confidence.

But it’s also where we all can play a role in protecting our fellow citizens against what we, in the election community, refer to as the hacking of the mind. The efforts to confuse or interfere with our understanding of our elections. We all can play a role in helping to cut through those lies and share the truth. And that’s really, I think, the goal for us in the next three and a half months as we approach the midterms.

Jake Sullivan:

It’s so important to emphasize this point about the hacking of the mind as opposed to the hacking of a voting machine and trying to cast out, as you’ve said, on the sanctity of our election system. Or to make people feel like their vote doesn’t count so they won’t go vote.

One of the things, Jocelyn, that we’ve seen over the course of the past several years is particularly foreign governments. Russia comes to mind seeking to interfere in our elections in large part for that reason. To undermine faith in American democracy and to cast out on the results. And we saw that in 2016. We saw it again in 2020. We’ve seen it in other instances as well.

Something that is coming into focus this year that’s a little different from years past is whether the president himself is trying to take steps to interfere with the elections. Politico recently wrote that Senate Democrats have been war gaming a whole range of election related scenarios, including the president doing things like ordering the National Guard or another federal force to seize ballots or to interfere with voting. How do you think about the role of the federal government right now and particularly this administration? And do any of these kinds of scenarios that have been floated in the press give you cause for concern? Do you think the president may try something coming down the stretch here in the closing months before the midterms beyond what he’s already tried to do?

Jocelyn Benson:

Yes. I think yes to all of the above. Essentially in our work, we say we always hope for the best but prepare for every contingency. And that’s exactly what is required and what has enabled us frankly to go through not one, not two, but three election cycles in 2020, ‘22 and 2024 with these very same threats. With this multinational potential threat to our democracy, not just in actuality, but in our minds. And it’s come certainly, particularly in presidential years, that threat has been amplified by foreign governments we’ve seen. But we know that domestic interference can be just as problematic and possible as international efforts to undermine our elections.

So with that in mind, we actually scenario plan and we have been doing this since 2020. Where we partner at the local level with local clerks, law enforcement, first responders to go through every possible scenario. Not just what if the president sends in federal troops, but what if someone just shows up claiming that they are? That’s the other piece of this. We have to look at everything that the president and his Justice Department and others and his allies do. Not just in terms of what will he do, but what will he say he’ll do but not do anything, but of course inspire copycats or others to actually try on their own. So we have to plan for all of that in the fact that we have 1,500 local jurisdictions in 83 counties in Michigan alone. So that also provides multiple points of entry, multiple vulnerabilities, multiple challenges, and we scenario plan through all of them.

We also have three ways of voting in Michigan. You can vote from home through returning your ballot through the mail or in a drop box or at your clerk’s office. You can vote early prior to election day in person for the week prior, or you could vote on election day itself in your local precincts. That also provides multiple potential entry points for anyone to try to disrupt our elections processes or interfere with any means. So we prepare for all of those things and we’ve been doing that well.

And then on election day itself, we actually have not just a war room, but people throughout our state within five minutes of every polling location. So that if anything does occur or if there’s any chatter online of anything potentially happening, we can have eyes on the ground within five minutes of any precinct or voting location to actually assess what’s actually happening and then respond appropriately. So we’re ready. We continue to be ready.

It’s one of the things that’s also happened alongside of these escalation of threats over the last six years. We’ve become more wiser and seasoned as well in dealing with the threats. Doesn’t make it any easier, but it does make us more prepared for every contingency.

Jon Finer:

Jocelyn, I think it was at the end of the Obama administration where the United States first declared election systems to be critical infrastructure. I think it was very early 2017. The Trump administration has now dismantled at least some of the apparatus that was built up after that declaration over time, including a lot of the election security function at DHS’s cybersecurity and infrastructure security agency.

How concerned are you and how concerned should voters be about the loss of that apparatus? And particularly when it comes to threats to elections from countries overseas, Russia, China, Iran and others come to mind.

Jocelyn Benson:

Yeah. In 2020 in particular, we were really fortunate to have the support ... And certainly in 2024. By a web of networks at the federal level of security provisions and data collection and support, frankly, in coordination with other states. That’s completely been dismantled. And what we’ve done since then, though the structures at the federal level may have been defunded and dismantled, the expertise is not gone.

And so what many states have done, particularly the critical battleground states like ours, Arizona and Pennsylvania, we’ve hired internally a lot of these national security folks to help us and coordinate with each other, prepare and continue to prepare for all the potential threats. It is nowhere near the level of security that we had in 2024, and that’s unfortunate. Especially while the president talks out of one side saying election security, this and that. And then on the other side, dismantles all efforts to protect the security of our elections that actually work.

But we’ve tried to do what we can at the state level to rebuild a lot of those networks, a lot of that information sharing, a lot of that security apparatus. And my hope is that’ll be sufficient at least for ‘26. But of course, ‘28 is a whole new ballgame. And I’m deeply concerned about that because it opens up significant vulnerabilities and frankly, the president knows that.

And so I think you’ll continue to see other structures emerge to help us protect the security of our elections in partnership with state and local officials. And all of it really underscores that in the absence of any type of protections or real leadership at the federal level in this front, states are left to themselves and state leaders are responsible for filling in the gaps, building out a patchwork of security and response. And we’ve worked to do that to the best that we can and we’re going to continue doing that. And again, it’s one of the reasons why governors and secretaries of state and local clerks are so critical right now.

Jon Finer:

It’s interesting. You haven’t mentioned it, and I think I know why, but the threat that the Trump administration seems far more focused on is voting by people who came to this country illegally and therefore are not eligible to vote. You’ve investigated this extensively in Michigan, so I’d love to hear a bit more about evidence, not just allegations. Let’s just put it on the table. How big a problem is this really? And why do you believe that Trump and his team are so heavily focused on it and so much less focused on these other threats?

Jocelyn Benson:

Well, it certainly feeds into the othering, the messaging that there’s this sort of other force that’s coming to interfere with our country. And those folks come from countries like Mexico or other places and they’re taking over our country and our elections. You hear this rhetoric, it’s getting more and more fever pitched as we get closer to the midterms. What that manifests itself as is the sense that though there is no evidence and though we have looked for that evidence, not just in Michigan, but in Georgia and other states. There is no evidence that any type of ineligible citizens or ineligible residents are voting in significant numbers in any election.

If there was any evidence of that, we would have found it. Instead, we find sporadic examples in which case we are able to prosecute and hold people accountable. That’s how the system works and should work to protect the security of the process. But yet you still have ... Because it is a very palatable and scary proposition to say that this is actually happening in widespread numbers to create, again, fear and distress in the process. And also feed into the sense that there’s a group of Americans, there’s a group of residents that “don’t belong here.” And to add to that fuel, they’re mythically participating in or trying to quote unquote rig our elections. Again, no evidence to any of that, but it feeds into this fear and this sense of insecurity. Not just around our elections, but around America writ large.

So our challenge is to respond as always with the truth and to simply say, “We’ve looked at that. We hear you. Welcome to ask questions about the process and let us answer them.” But when we answer them and when we say definitively as we have in Michigan, that there’s no widespread evidence of either voter fraud or ineligible individuals voting in our elections, then we have to close the book on that so that we can move forward with the work. Which is ensuring every eligible citizen can vote in our elections.

Jake Sullivan:

As you’ve alluded to a couple of times, it’s a facet of our system, of our constitution that states largely control the conduct of elections. But the Trump administration is trying to use legislation and also lawsuits to muscle through changes.

The president seems particularly obsessed with passing the SAVE Act to the point of holding up appointments and other bills, including a housing bill to try to force it through the Congress. He’s even threatened to withhold federal funding for counter-terrorism from states that don’t make the changes that he’s demanding. He’s claiming, the administration is claiming that this is a common sense effort to require voters to provide evidence that they’re citizens consistent with federal law. Can you explain what’s actually going on with the SAVE Act? What concerns you and what should concern our listeners?

Jocelyn Benson:

Yeah. The SAVE Act is not what Trump, believe it or not, says it is. It’s actually an act to make it more difficult for citizens to vote in our elections. It’s an act that creates barriers upon barriers among many communities, including married women, including overseas voters and voters serving in the military. It’s an effort to essentially not just interfere at the federal level with how states oversee and manage our elections, but do so in a way that will make it more expensive, more difficult and more challenging for citizens to vote.

And that’s the bottom line that not only is it a solution in search of a problem, it is a solution that creates a lot more problems. Particularly for millions of eligible voters here in Michigan, two million married women alone. So we’re trying to help respond with that with the truth.

And the thing for us to find optimism in, frankly, on this is that two things. One, the law is on our side, even if the SAVE Act were to be enacted. I highly suspect there would be an immediate effort to seek an injunction in federal court that would protect it from going into effect, especially this year. But again, that doesn’t stop the narrative from being out there that somehow our elections are not secure even though they are.

The second piece of it is that it obscures the facts of all that we’re actually doing in states like Michigan to ensure that only eligible citizens are voting. We do verify people’s ID before they vote, either through a photo ID, which is the vast majority, or through a signature, which is then matched to the signature on the voter file, which is just as effective at identifying someone’s identity.

In addition to that, we have layers upon layers of verifications, opportunities for people to challenge the possibility of someone’s eligibility. All of which are designed to ensure we have checks on the process and ensure only eligible citizens are voting without policies like the SAVE Act that would not just be duplicative, but would ultimately make it more difficult for eligible citizens to vote. It’s important that we talk about all this because it’s our best way to counter the narrative and the misinformation the president’s getting out there. But it should alarm us all that he is so willing to shut down government, hold back necessary reforms to reduce the cost of housing and other things to address the economy that he’s created that’s driving up costs for just about everyone.

Jake Sullivan:

He’s also sued you and other secretaries of state, as John was alluding to. And used other tactics like sending the former director of National Intelligence, Tulsi Gabbard, and hundreds of FBI agents to Georgia to try to get access to state voter roles. What’s really going on here? Why does he want this information so badly? What’s he looking for in trying to get this access to voter databases, voter roles, and other voter information?

Jocelyn Benson:

I think it’s two things. One, it keeps the story alive. Every time there’s a false allegation or a false evidence-less investigation or baseless investigations, it keeps sowing the seeds of doubt that something’s wrong with our elections, even though these investigations often go nowhere.

You’re right, when the president tried to pressure me to contrary to protections under the law, turn over the private data of our citizens. I said no, and I’ll see you in court, and I won. And it’s important to note as well the laws on our side when it comes to not just protecting the private information of our citizens, but protecting our election system against the overreach of the president and the Justice Department who are trying to use every tool in their toolbox to not just undermine our elections, not just cast doubt on the processes. But also gum up the system so much that it becomes difficult or impossible for us to just do the work of administering elections. Not only that creating a lot of fear for just about everyone involved because no one likes to be the subject of federal investigations, even if they are baseless. It creates a lot of challenges in people’s lives.

So all that to say is this is part of the multi-year coordinated effort to dismantle elections and democracy in this nation at a time where again, the president is increasingly unpopular and does not want to be held accountable at the ballot box. So I think we need to see all of that as interconnected. But that doesn’t take away from the real toll that these types of threats, pressures, lawsuits, sham, legislative hearings, everything takes on ourselves, our families as professionals just trying to do a job here.

Jon Finer:

We currently have Bill Pulte, a political operative, totally loyal to President Trump, serving in an acting capacity as the nation’s top intelligence official. The guy responsible for telling the president and the country about the threats we all face.

So let’s say just before the election, he issues some sort of a statement that the United States has detected a credible threat to attack or interfere with the election, maybe from a foreign actor, maybe a plot by a collection of ineligible voters, people who came to this country illegally as they want to be concerned about in large numbers to try to swing the election. And in response to this supposed threat, President Trump or maybe the DHS Secretary Markwayne Mullin announced that in order to protect the integrity of the election, federal agents, ICE, CBP, FBI, whoever, will be deployed to polling places of greatest concern, which oh, by the way, maybe also happen to be urban precincts with high Democratic Party turnout. Mullin I think has already said during his confirmation hearing that he’d deploy federal agents if there were a specific threat to polling places.

Is this plausible and what can be done before, during, and maybe even after the election to prevent this sort of nightmare from playing out?

Jocelyn Benson:

Yeah. I think it’s important for us to recognize this is plausible. The less evidence there is, and there likely won’t be any, the less plausible it becomes. Because ultimately even if there were, let’s say, a declaration, the role I would hope of local officials, investigative journalists, and others would be to quickly uncover the fact that it’s baseless and then go to court to try to stop it. That’s sort of one avenue.

The second avenue is to recognize even without that declaration, there could still be an effort to send federal troops. Or in this case, we already know federal observers will be deployed. And that is quite typical to have federal observers in the Justice Department overseeing or watching elections. There’s nothing unusual about that. But no matter who it is deployed or sent by the federal government, if they disrupt our elections, if they interfere with the process, if they try to intimidate voters or election officials, we will be there to stop them from doing so. Because the law does not permit that, allow that, and we will immediately go to court to stop it.

This is why we’re doing scenario planning with local law enforcement who respond to the state, not the federal government. And ensure that they’re there to protect state laws from being followed and protect voters from being blocked from the polls. So we have a number of pathways and protections in place to stop federal interference of our elections. What it’s important for every American citizen to know, however, is that the goal is to stop them from showing up at all. And so the number one thing every American citizen needs to be prepared to do this fall is vote.

Jon Finer:

I guess one of the things I’m worried about or I would be worried about if I were responsible for elections is that all of this happens in kind of a crescendo right at the end, right in the days leading up to the elections. And yes, there’s court action and maybe the court action is correctly decided and rules out some of these extreme actions. But it happens in an environment of a lot of confusion without a lot of time for people to process.

The only analogous situation I can think of, and Jake may have another in mind, that we dealt with when we were in government is when we got sort of advanced warning that Russia was going to invade Ukraine through our intelligence community. And what we decided to do, and it was a bit controversial at the time, and I give Jake a lot of credit for driving this, is to go out publicly and tell people what we thought was going to happen and to go to our friends, partners, allies around the world so that they could be prepared. And it took a lot of convincing. And it took a lot of convincing, I think, for the public to believe that something this crazy could transpire.

But the public dimension of this I think was quite important in not allowing, in this case, the adversary to set the narrative and basically come up with a false pretext for why it had to go to war. It does feel like information in advance for the voting public is going to be quite important here. So what would you say is the most important thing that people need to know in the coming months as all this may play out?

Jocelyn Benson:

I can’t underscore enough how critical it is that we all be critical consumers of information right now. That the press and the media also do their job of asking tough questions and uncovering fallacies and challenging falsehoods. And it’s never been more important, frankly, for us as citizens to not take our eye off the ball and to see exactly what’s going on. To be not just critical consumers of information, but engaged voters determined to ensure that no matter how we vote or cast our ballot, that our voice is heard.

And then also to do so strategically. Meaning here in Michigan, as I mentioned, we have options on how to vote. You do not have to wait until election day to vote in the vast majority of states in this country. Including in Michigan where you could vote in person prior to election day, or you could vote by mail up to several weeks, 45 days before election day or at a local drop box.

So we encourage citizens who have any concerns that something might happen on election day to get it out of the way and vote early. That also reduces the potential for long waits on election day and gives people the peace of mind that their ballot is counted and in the bag before anything potentially goes awry.

We’ve succeeded in Michigan in ensuring ... Well, not ensuring. But through successfully administering these options to vote, two thirds of voters in Michigan actually participate prior to election day. And that also minimizes the potential for interference on election day to be as effective as it might otherwise be if everyone was voting in that window on a Tuesday. So use your options to vote if you’ve got them. Vote early if you can. That’s one of the best things you can do to stay engaged.

And then be that critical consumer of information. Encourage others to do the same. One of the things that we found in our work in Michigan to not just secure the vote, but help promote a narrative of facts and security is how important it is to have multiple voices talking about trusted and accurate information on our elections. And anyone can be that trusted voice for elections. We also work with faith leaders and business leaders and nonprofit leaders and teachers and others who can be equipped with truth about our elections and share that with people in their worlds and spheres of influence.

Jake Sullivan:

Jocelyn, first, that is a great place to end. Second, Jon and I have both been subject to interviewers who kept us way over the time we agreed because we had busy jobs just like you do. We are not going to be those interviewers. So we are going to let you go, get back to all that you’re doing, both to protect this election as well as your campaign. And we’re just really grateful for you to come onto The Long Game because I think this is an enriching conversation for the two of us and for our listeners.

Jocelyn Benson:

Thank you. I appreciate the work you guys are doing and have done to protect our democracy and our country. And the one thing history teaches us is that we’re all in this together and democracy can prevail when the people of America determine that it does.

I think a lot about ... I think it was Clinton who said there’s nothing that’s wrong with our country that can’t be solved, but what’s right and best about our country. I think about that every day because it really reinforces to me that the way out of this dark time, the light out of this dark time are the American citizens who believe in who we are and believe in the best of us. And that’s going to be ultimately how we get through this.

Jake Sullivan:

Amen.

Jon Finer:

So Jake, I have to say I said this to Jocelyn as well. I was a bit pleasantly surprised by the degree to which she was optimistic about the fact that we will have free, fair elections in which the outcome will match the votes that are cast. And there’s so much speculation at this point about all manner of interference, certainly foreign actors and that’s been with us for a while. But as you pointed out in the episode for the first time really from the federal government itself. And she is not pollyannaish about all of that, but does seem to think the system is equipped to manage it.

Jake Sullivan:

It’s interesting. I was empathizing with her throughout the conversation because you and I have both been in the position of having to stand before the press or speak to the public and try to manage the tension. And the tension is on the one hand being real and true and straight about the threats. And in fact making sure that people are educated about those threats. And on the other hand, trying to convey a sense of reassurance, stability, and calm.

And striking that balance is never easy. And I think she was trying really to do that, not just in this conversation, but that’s basically her job. She has to tell people, “Your vote will count. The system will work.” Because as she pointed out, a lot of the impetus behind either foreign interference or Trump interference in the elections is about trying to discourage people, trying to make them stay home or trying to make them disbelieve the results of the election. So she has to reinforce that they will fail. The election will go off and it will go off successfully and your vote will count.

But she also at the same time, and she did this throughout the interview, has to say there are efforts by a lot of bad actors out there. Right now, including within our own country, within our own government, federal government who are seeking to undermine the legitimacy of the election and perhaps even directly interfere in its proper conduct. And I thought it was really interesting watching her walk that line, I thought extremely effectively as she has done. And she obviously has a lot of practice added after multiple election cycles.

But I think her BLUF, her Bottom Line Up Front is basically right that there is a resilience and robustness to our election system in part because it’s so damn decentralized. She threw out some stats just about Michigan alone. When you map that onto the whole country, there’s so many polling places, so many local officials, so many state officials. That even for a president with all the tools at his disposal to effectively change the outcome of an election is a tall order. That being said, we have seen plenty of evidence that President Trump may nonetheless try and that is something that requires us to speak out about. And it’s why we did this episode in the first place. And your analogy to Russia-Ukraine, I think is very apt.

Jon Finer:

Should we shift to another topic that is a recurring challenge for us that we’ve been at for quite some time on this podcast and before?

Jake Sullivan:

We should.

Jon Finer:

All right. So we spoke with Michael Kaufman a few weeks back. I think some people remember the military analyst who we had on to talk about the war in Ukraine, about how much better Ukraine is doing on the battlefield recently.

The good news is that’s continued. The bad news, as we also discussed with Michael, is that Russia doesn’t seem to be responding to this pressure by seeking negotiations to end the war. Instead, they seem to be trying to do the opposite and actually escalate the conflict against the Ukrainian people as we talked about, but also against our allies in Europe. So maybe you can tee up the conversation that we’re about to have along these lines.

Jake Sullivan:

Yeah. So one thing that has been a constant presence in Russia’s brutal war against Ukraine has been Russia also rattling the cages of engaging in what’s called hybrid warfare against countries in Europe, against NATO by conducting a range of different destabilizing activities. And those have included everything from sabotage to attempted assassinations to arson of public officials’ houses to drone incursions in multiple countries. Up to and including a drone in Romania not too long ago that hit an apartment building and actually caused casualties. To things like removing navigation buoys from the river that separates the border between Russia and Estonia to kind of shake confidence in Estonia that Russia would have recognized that border going forward.

So a wide range of activities to escalate not just in Ukraine, but against the country supporting Ukraine, against European countries and through that against NATO itself. And the question has always been, will Russia take that to another level? Will it escalate its direct challenge to Article 5 to a point that goes beyond this set of what is kind of broadly categorized as gray zone activities. To include things like a more direct conventional strike against or incursion into NATO territory. To include a dramatic increase in the use of drones, to hit targets in NATO territory. Or to include just a systematic escalation of sabotage activities and other things that actually cause loss of life and damage at a scale that far exceeds what they have done so far.

And Jon, as you know, because you’ve been in Europe frequently in the last few months as have I, there is growing concern that Russia may choose to test NATO, to test Article 5, to press further, to move up the escalation ladder as part of its response to the pressure it’s under in the war in Ukraine because of Ukraine’s success. Both directly on the battlefield and in terms of its strike campaign against targets inside Russia.

So the question for Russia is, do they want to do this? Do they want to take steps further up the escalation ladder? And I think they are grappling with the pros and cons of doing that. And NATO countries and the United States have to think through what the possible scenarios are. Have I fairly described that or is there anything you would add or subtract or amend?

Jon Finer:

You have and it’s not merely a hypothetical as you indicated. We now know through reporting in The Daily Telegraph and in the Polish Press that American officials are now warning European allies and in particular Poland about exactly the sort of provocation playing out on their territory to test NATO’s resolve that you just described.

Drone or missile attacks on critical infrastructure, even Russian troops potentially crossing the border. Claiming some sort of mistake, perhaps, and then negotiating their withdrawal in exchange for concessions like cutting off support for Ukraine. So this is becoming quite real and quite concrete.

And we thought one way to sort of tease out the stakes and how this could play out that would be a bit different for us would be to do a red team blue team discussion, debate. But not from the perspective of either the United States or our European allies. But actually from the perspective of Russian President Vladimir Putin and the people who are advising him one way or the other, escalate or do not. And I think I drew either the short straw or the long straw and agreed to make the case that Russia should escalate against NATO. So unless there’s any other preamble that you want to add here, maybe I’ll just launch in and then you can explain exactly why this would be a very bad idea.

Jake Sullivan:

So you are a senior Russian official making the case to President Putin that he should in fact escalate against NATO. And I’ll be a senior Russian official making the case that he should not. And that is our red team, blue team for today. And fire away.

Jon Finer:

This is going to be one of those great statements that if clipped properly is going to make me seem like a truly insane person, but we’ve put all the disclaimers upfront. All right.

Mr. President, Vladimir Vladimirovich, I’m going to tell you something that your military is sometimes too reluctant to say. We are losing the war, excuse me, the special military action in Ukraine. And when I say that, I don’t just mean that we are losing soldiers. You and I both know they’re expendable and we can probably keep avoiding unrest by paying off their families when they are killed. What I mean is we are now losing territory. And for the first time in years, our economic team is telling us that there is real pain coming if something doesn’t change soon.

Obviously none of this is your fault. This war was a brilliant strategic master stroke that has been badly executed by others and they should pay a price. But that doesn’t change the basic predicament and the need for a new approach which only you, the world’s greatest strategist, can deliver. And the question is, what do you do? You will hear lots of soft willed and frankly un-Russian arguments from others about the risk of escalation and maybe even the need for negotiation. Which I believe translates in English as defeat.

But to beat our enemies and make no mistake, as you’ve said all along, the brotherly Ukrainian people are not our enemy, nor could they possibly defeat us on their own. Our enemy is America and it’s in feebled little brother, Europe. To beat our enemies, we have to understand them. And so I’m proposing an idea that comes from American strategic doctrine and some of its greatest generals, Dwight Eisenhower comes to mind. He once said, “Whenever I run into a problem I can’t solve, I always make it bigger. I can never solve it by trying to make it smaller. But if I make it big enough, I can begin to see the outlines of a solution.”

Mr. President, I urge you to make the Ukraine problem bigger so that we can reach the outlines of a solution that works for Russia. In this war, NATO has been able to hurt us for free, or at least at very low cost. If we are to win, that cannot continue. They must pay a price or they will never ever stop funneling money and arms that Ukraine can use to kill our people. And ultimately, and I say this with the greatest possible respect, even to try to topple you as Russia’s leader. That’s where they want this to go.

You will hear from others about the risk of escalation. Is there a risk? Yes, of course. Is there any gain in this world without such risk? No. And I think this risk is manageable. And the reward for this may not just be victory over Ukraine, but a much larger prize, breaking NATO once and for all. For one thing, those countries are small and soft. Do you really think nations that have never really fought and barely fund their armies will accept real pain of a war with Russia? The entire active duty British army can fit in Wembley Stadium. And they might be the best of all of them.

But the other thing to keep in mind is these countries are slowly waking up. They’re spending more on defense. They’re recognizing how vulnerable they are. And in a few years, it won’t be as easy to intimidate them as it is now. Particularly Germany, which is spending the most and has a martial history I don’t need to recount to you or any other Russian.

But there’s another reason they’re vulnerable. Some may pipe up with, what about America? Which spends more on defense than the next six countries in the world combined. But there has never been a better time to prove that at the end of the day and for all the rhetoric about all for one and one for all, America will not trade its security and prosperity for countries its citizens can’t find on a map with names they can barely pronounce.

President Trump has mocked NATO from the moment he first ran for president. This term, he has threatened NATO territory himself. Let him have Greenland. In fact, we should be encouraging him to take it. And since the failed US war in Iran, he seems much more angry at and openly willing to tell Europe that they did not help him when he asked and not to bother asking him for help in their hour of need. We need to call that question.

So what do we do? We do more of what we’re doing already. Assassinations when warranted. Sabotage when we can find useful idiots to carry it out. Drones to make life more threatening and uncertain. But also now we must do more. Show that NATO is a paper tiger, a lie. That we will need to draw real blood and take territory to do that. We can do it in a way that gives you deniability if you want, munitions that went off course, soldiers whose GPSs led them astray. And when NATO fails to respond or fails to respond adequately, as I think is likely, all of the allies will know that they are actually alone. And they will negotiate on our terms, not theirs. And not just over Ukraine, but over the rest of our demands in Europe.

This is the only way we can begin the process slowly but surely of reversing what you rightly described as history’s greatest tragedy, the disintegration of the Soviet Union without any real shots being fired.

Jake Sullivan:

Well, Mr. President, you are a former KGB officer who has been trained through your entire career in psychological warfare. And what you just heard was a version of psychological warfare from your very own advisor who thought he could just flatter you, so transparently, frankly. We all know who you are and what you represent to our country. We don’t need these type of cheap tricks that we just heard from your other advisor to try to bring you down a course that will lead Russia into Fali. You have very wisely chosen not to directly attack NATO, either with missiles or with troops crossing the border. You have very wisely chosen to undermine NATO’s sense of confidence and sense of cohesion through an active gray zone campaign that I believe you should continue.

And going down the road of a more direct challenge, I think creates far more risk than reward. Let’s start with President Trump, who you know as well as anyone. President Trump doesn’t like Ukraine, doesn’t really want to support them, is sympathetic to you and to Russia and to your arguments. But he also really doesn’t like to be a loser. And right now in Iran, he is losing badly. Iran is making him out to look like frankly, a bit of a clown. Because they have been able to show they can open and close the Strait of Hormuz essentially at will that they control it and America can’t do anything about it.

And when you have someone who thinks they look like a loser in one place and you push them in another place, they are more likely to lash out in a dramatic and unpredictable way. And I think that’s what President Trump would do if we decided to test Article 5 right now. He cannot accept looking weak and feckless in the face of a Russian attack on NATO territory of one sort or another. He would have to show some degree of strength because he is already in such a weak position when it comes to the Persian Gulf. So I think President Trump would in fact respond even though his natural impulses, his natural sympathies are not with NATO. He would feel he had to given the current circumstance he finds himself in.

Second, there has been a lot floated in the American press right now about steps President Trump is thinking about taking that we don’t want him to take. One is this tariffs bill where he would impose tariffs on Russian oil being sent around the world, but particularly to our major purchasers like China and India. This would in fact make it harder if this bill went through for us to be able to get the money that we need to continue to fund this war.

And you just heard from your advisor that we are facing some economic challenges through a combination of mismanagement of some of your weak underlings, not through any of the choices that you’ve made. And from the fact that we already are facing some pressure for our oil sales overseas. If in fact we attack NATO territory, I believe that the United States Congress would prevail upon the president to finally move this bill into law and we would face a much more significant economic hit as a result.

Second, President Trump has been thinking about turning on Starlink for Ukraine in Russia, making it easier for them to strike critical infrastructure targets right here in Moscow and in other places across our country. Again, in response to an attack on NATO territory, there would be a huge upswell, a huge push to do this and I think the Americans probably would do it.

And frankly, we can’t rule out much crazier responses. Remember, it was President Trump when Wagner forces, Russian mercenary forces crossed that boundary in Syria in 2018 that allowed his military to kill hundreds of them without a second thought because he felt he was being tested, his manhood was being tested. If we test his manhood in a very direct way like we did back then, he may choose to directly strike and kill Russian forces. And then what would your next move be? I would ask the advisor to answer that question.

The third point that I would make is right now the threat of more direct action I think is having some effect. You see the American media and the Western media full of concern that you might do this. That’s good. We want them concerned. Have them keep thinking we may do it and it could have some deterrent effect. In fact, send messages that say if they go too far on tariffs or Starlink or other things, we may have no choice, but hold back on actually doing it. Because the threat of it may actually have a greater impact than following through, which could cause them to react in ways that put us at a disadvantage.

And this relates to a larger point, the fourth point that I want to make. Right now, the underlying trends in terms of NATO are running in our direction. There was a brilliant analyst in America, former government official named Jon Finer, who wrote an article in The New York Times just a few days ago saying that Europe has completely lost faith in America. That they’re trying to go their own way as are many other countries around the world. Let that continue.

President Trump just last week said he’s thinking about cutting American troops in Europe by a third, tens of thousands of troops coming out of Europe. Let that play out. You go attack right now and the odds are you only extend the long term American deployment of troops in Europe for the foreseeable future. And you only push NATO closer together, not drive them further apart.

And then finally, and I hate to even raise this because we know that you are the senior partner when it comes to the Moscow-Beijing relationship. But Beijing, we still need as a core economic partner and strategic ally. And a direct attack on NATO is going to lead Beijing, I believe, to recalculate its entire approach to this conflict. And that is something that we have to take into account.

So for all these reasons, we are much better off continuing the entire range of hybrid warfare, gray zone warfare and driving forward to continue to undermine and shake the confidence of the West. And allow nature to take its course, President Trump wants to undermine weaken and potentially even one day withdraw from NATO. Don’t give him any reason or excuse, especially at this moment of weakness for him to decide to go against those instincts and double down on NATO. Which I believe would happen if you listen to the silly advice of my fellow advisor. So for all these reasons, I think not escalating at this moment, continuing in the same course is the right way to go. And I hope you make the right decision.

Jon Finer:

Full of cheap shots, but well played. The point that I really was struck by, because I think it’s also relevant to what the United States has done with Iran, is that once you play the card of military action, it’s kind of a spent thing. And the threat can actually get you quite a bit as I think it had from Iran for the United States over the years. And now is getting the United States much less since they have seen it-

Jake Sullivan:

Haven’t used it.

Jon Finer:

... and are unbowed. Yeah.

Jake Sullivan:

Yeah.

Jon Finer:

Yeah. Do you think they’re going to do any of these things that are reported in these articles or that are speculated about by people like us?

Jake Sullivan:

I guess what I believe is that they will escalate every vector in ways that could be more damaging, destructive, and even deadly. But I find the idea that Russian troops actually will in some meaningful ... They could step across the border, but will actually conduct an incursion and hold territory. Or that you will see a clear, unambiguous Russian strike on NATO territory that they don’t immediately disclaim as an accident.

I think it’s a real risk, which is why we’ve done this segment. We’re not doing this because we think that that is a silly proposition and we think it has to be taken seriously. Scenario planned against war gamed against vigilance has to be at a high right now. But if I had to put my thumb on the scale, I would say it is more likely than not that they will continue down and intensify the current course than take this step change. But do you have a different view?

Jon Finer:

No, I guess I agree with that. My problem is more that I think their strategy has been the entire time to try to impose as much of a cost on the country supporting Ukraine as they can without triggering a war because they don’t want a war with NATO. And the problem with that approach is every time they impose some sort of cost and there isn’t a response, they decide, okay, that’s below the threshold. So where is the threshold? Let’s try something a little bit further up the escalatory ladder. And at some point, something like what happened in Romania or one of these sabotage attacks is going to kill a significant number of people.

And to my mind already, we’ve reached a point where the alliance really is facing some credibility problems. When Russian drones are flying over European airports, shutting down air traffic for a day in some cases, and not being shot down. These are unmanned aircraft that have violated sovereign airspace. To my mind, that sends a message that this stuff maybe isn’t tolerated, maybe isn’t okay. But ultimately is something that Russia can get away with and leads to the question in their minds of what else they can get away with. And I think that’s a very dangerous part of the current dynamic.

Jake Sullivan:

So I think you’ve put your finger on kind of where I think this will go is I think there will be this intensification. And it could cause actually a much more dramatic incident than we’ve seen so far. And it could come from a vector that we’ve seen less of. It could come from something they do on the high seas. It could come from a form of sabotage that causes a plane to fall out of the sky or a ship to sink or what have you. It could come from a swarm of drones that causes a lot more casualties than we’ve seen so far. That to me seems a lot more likely than what has been reported in The Telegraph, than a more direct attack on NATO territory.

The one place where you could see them say, look, we may take some conventional strike because we see it as just directly defensive, would be an attack on supply lines. In some ways, it’s surprising they haven’t done that. Hit railroad tracks, potentially hit a port where material is coming in on cargo ships. You could see a world in which they say, we need to defend ourselves against this onslaught. So if they were to go down this road, I think they would try to do it in a way that they cast within a broader context of pure defense.

And then the last thing to keep in mind to watch for is they have repeatedly warned about drones being launched, not just from Ukraine into Russia, but from other NATO countries into Russia. Or the use of other countries’ airspace as corridors for Ukrainian drones. So another defensive move they could possibly consider is to say, we are in fact responding to what we have seen as an attack originating from Finland or Poland or the Baltics or Romania. Even if it’s not true, that that could be a pretext for them to take a strike that was specific and targeted to say, we’re only doing this because we feel we were directly hit from a point of origin or airspace of origin of a NATO country.

These are the kinds of scenarios that I think they’re probably gaming out as ways they could choose to take action. But it would be in my view, couched in a very particular defensive logic. And in a way that tries to deter a specific response from NATO by basically saying, we’re responding to you. Now that’s the end of the game.

Jon Finer:

I think that’s very well put. I think the only other thing that we haven’t covered either in the debate or in this wrap up conversation is what will happen if Ukraine actually stops making incremental progress and starts making more substantial progress on the battlefield? And what sort of escalation could that lead to up to and including? And we have to say it because this is a part of Russian doctrine, a major breakthrough in the Russian lines that leads to a threat on what Russia considers to be Russian sovereign territory, either its own territory or Crimea, which we consider to be a part of Ukraine, but Russia doesn’t.

Does that lead Russia to contemplate again as we believe they did at least contemplate in 2022 the use of a nuclear weapon, maybe a tactical nuclear weapon on the battlefield, maybe a nuclear test somewhere else to send the message, “Hey, just a reminder, we have this capability and can use it if we decide to.” I don’t think that can be totally ruled out. It’s crept back into some of the discourse as Ukraine has made progress. And so that’s another thing that we’ll just have to watch.

Jake Sullivan:

It’s interesting in the fall of 2022, we faced this. At some point we can reflect on that more fully. And it was very much in the public commentary back then. As you said, it has come back into the public commentary really for the first time since then now because of the possibility at least that there could be a catastrophic collapse of Russian lines at some point along that very long front in Ukraine. And that’s something again that I guarantee you in the situation room and in NATO capitals they are war gaming and scenario planning against. It would be, of course, the first use of a nuclear weapon since Hiroshima and Nagasaki at the end of World War II.

So these are all things to watch. This whole conversation has a bit of a deja vu all over again quality to it for you and me. But it’s back. And it’s back in a way in which after multiple years of war, the Russians have already done a lot of things, have already kind of pushed the envelope on escalation. As you say, have kept seeing the line in their sense get blurrier and blurrier in terms of what they can get away with without a very robust response for NATO. So we will have to see what calculus Putin makes. And which of the two very erudite arguments, cases that you made and I made he chooses to listen to here in the coming weeks and months.

Jon Finer:

Mine was a little obsequious, but the way to his heart.

All right. Thanks everybody. Diverse set of issues on this episode, but I think a lot got covered and thank you for sticking with us.

That’s all for today. We’ll be back next week with a new episode of The Long Game.

Jake Sullivan:

Subscribe to our YouTube channel and follow the audio feed so you never miss an episode.

Jon Finer:

For additional content, episode transcripts and exclusive podcast segments, subscribe to The Long Game on Substack or join The Long Game Plus on Apple Podcasts.

Jake Sullivan:

This week we covered new developments on Iran and broke down the big strategic questions emerging from the collapsed ceasefire. And President Trump’s announcement that the US will reimpose the blockade of Iran’s ports and Iran ships in the Strait of Hormuz.

Jon Finer:

We’ve kind of gone from strategic failing to strategic flailing at this point.

Jake Sullivan:

Nice.

Jon Finer:

Do you like that? It’s really true though.

Jake Sullivan:

I like it.

Jon Finer:

We are trying the spaghetti at the wall technique of national security policy. They don’t seem to know what to do. And I agree with you very much that this all stems from the United States making an agreement with Iran that it did not really understand.

Jake Sullivan:

Head to thelonggame.substack.com or subscribe to The Long Game Plus on Apple Podcasts. The links are in the show notes.

Jon Finer:

That’s it for this episode of The Long Game.

Jake Sullivan:

If you like the show, please follow, share with friends and leave a review. It really helps listeners find us. The Long Game is a Vox Media podcast network production.

Jon Finer:

Executive producer, Tamara Sepper.

Jake Sullivan:

Senior producer, Matthew Billy.

Jon Finer:

Video producers, Nat Wiener and Adam Harris.

Jake Sullivan:

Supervising producer, Jake Kaplan.

Jon Finer:

Associate producer, Claudia Hernandez.

Jake Sullivan:

Marketing manager, Leanna Greenway.

Jon Finer:

Music is by Nat Wiener.

We’re your hosts, Jon Finer.

Jake Sullivan:

And Jake Sullivan. Thanks for listening.

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A NOTE FROM THE PRODUCER

is the Executive Producer of The Long Game

You may have seen the latest news that the fragile U.S.-Iran ceasefire has effectively collapsed, and the Strait of Hormuz is once again at the center of the crisis. After days of renewed tension, President Trump announced this morning that the U.S. would reimpose its blockade of Iranian ports and charge a 20% protection fee on all cargo moving through the Strait.

In a special segment for paid subscribers, Jake Sullivan and Jon Finer break down the latest developments and the bigger strategic questions now facing the U.S., Iran, and the region, including:

• Did the hostilities resume because the U.S. and Iran never had a true meeting of the minds about what their Memorandum of Understanding (MOU) actually required?

• Can President Trump successfully renegotiate or walk back the terms the U.S. already agreed to?

• What is the “balance of pain” between Iran and the U.S., and which side can better withstand economic and political pressure?

• What happens if the Gulf countries increasingly bypass Washington and cut their own deals with Iran to protect their interests?

• And, how likely is it that global companies and countries reroute shipping, build pipelines, or otherwise “engineer around” the Strait – and on what timeline?

If you’re a paid subscriber, thank you for supporting the show. Please share your thoughts and questions in the comments; we’re collecting them for our future special Mailbag segments where Jake and Jon answer listener questions.

And if you’re not yet a paid subscriber, now is a great time to join. You’ll get access to special segments like this one, Mailbag episodes, recommendations from Jake and Jon, and other exclusive subscriber-only content.

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Transcript: Heather Cox Richardson on Democracy, Alliances, and America’s Future

The Long Game with Jake Sullivan and Jon Finer

June 30, 2026

Jon Finer:

Welcome back to The Long Game. I’m Jon Finer. This week, instead of a regular episode, we’re bringing you a conversation that Jake and I had last week with historian Heather Cox Richardson live on Substack. Heather, as I think many of you know, has become one of the country’s most prominent interpreters of American democracy. She’s the author of the very popular Letters From an American, a hugely influential newsletter that distills today’s news and puts it in an historical context.

We hope you enjoy this conversation as much as we did. We’ll be back next week with a new episode, and you can email us your questions or comments at longgame@voxmedia.com, and follow us on YouTube and in your audio feed so you never miss an episode. For exclusive podcast segments and more, subscribe to the Long Game on Substack or join the Long Game Plus on Apple Podcasts. To the many who have joined our community, thank you for supporting the show. Now onto our conversation with Heather Cox Richardson.

Jake Sullivan:

Jon and I are here with Heather Cox Richardson, who really needs no introduction. She’s one of America’s most influential historians and public intellectuals, the author of Letters From An American, which is one of the biggest and most impactful newsletters on Substack. And through her writing and commentary, she really provides deep historical context for current events, I think is a leading interpreter of the moment we are in right now because she can pull that context in.

And especially as the US is coming to mark its 250th anniversary, her work and her insights on the meaning of the American experiment and the relationship, frankly, between America’s democratic institutions and our place in the world, in the universe, is really important. So these are all light topics. We’re going to talk a little about foreign policy, a little about the United States, a little about the present, the future, a little about history in the next bit. So Heather, we’re excited to be with you. Thank you for taking the time this afternoon to join us.

Heather Cox Richardson:

Well, back at you, but I warn you, I have probably more questions for you than you have for me. So let’s see where we go.

Jake Sullivan:

That sounds good. Jon, you want to kick us off, and then Heather, feel free to pose your questions too, but Finer, I’ll turn it over to you to start.

Jon Finer:

I will. And yeah, we love the back and forth. So thanks again for being with us. You issued a pretty stark warning in your Juneteenth essay. I’ll just read it. We are in danger of losing the new nation that it celebrated. That’s pretty striking and just was wondering if you could expound on that a little bit and tell us what you mean and why we should be so concerned.

Heather Cox Richardson:

I don’t think it’s any secret that the Trump administration, not only Donald Trump himself, but his appointees and those people who support him, are actively making war on American democracy, especially the American democracy that we have established since 1933, really the modern world in which we all live.

And you can see that really dramatically, of course, with the Supreme Court decision yesterday, that the Slaughter decision that gives the president a power that he has not had since 1935 when we had the beginnings of this growing government, to remove the heads of agencies, not just political appointees, but other people working for agencies that are housed in the executive branch, despite the fact they’re created by Congress.

So what I meant by that is if you look broadly at the ways in which the Supreme Court and the administration are working to tear apart the machinery of our government, we could lose those fundamental principles laid out in the Declaration of Independence. That in our democracy, we have a right to be treated equally before the law, to have a say in our government, and to have equal access to resources. And I’d love to hear someone make the other side of the argument. I know some people say, “Well, this is just business as usual,” but it certainly is not business as usual. So that’s where I was going with that.

Jake Sullivan:

And do you think, Heather, were talking briefly before we came on, and we just had Bob Kagan. We did a live show at the Aspen Ideas Festival and spent time with him. And he was making the case that how we relate to our democratic experiment at home has an impact on how we approach things in the world. It has an impact on how others see us. It has an impact on how we see ourselves as a global power. Do you think that’s right or would you amend that? How do you relate those observations you were just making about the state of our democratic experiment here to how you see the United States operating as a global power?

Heather Cox Richardson:

So this is a great question because it’s of real concern to me, and I’d love to hear what you have to say about this. It’s a real concern to me that it doesn’t seem to me that the American people spends a great deal of time worrying about foreign policy. Would you agree with that?

Jake Sullivan:

I would say generally, although the one area where they tend to really dial in is if the United States is actually at war.

Heather Cox Richardson:

Okay, that’s a good point.

Jake Sullivan:

And I think there is in the post-9/11 period, in those years, there was more appetite for risk and adventurism abroad, the willingness to go fight over there because people were so worried about security back here. I think now we’re in a phase where this Iran war, for example, was unpopular from the minute it started, which is I think kind of without precedent. Almost every war ultimately becomes unpopular, but starts out with a pretty broad support of the American people. So I think on that issue, the American people have made their opinion pretty clear. On other things, I would tend to agree that it is definitely not at or near the top of the list of folks’ primary concerns, but yeah.

Heather Cox Richardson:

I guess where I was going with that was less the wars, although the story I’m going to tell you I’ve never told before. So I always try to do something new in every interview, so you’re getting a good one.

Jake Sullivan:

All right.

Heather Cox Richardson:

But the general theories behind international relations and foreign affairs are really important to the survival of American democracy and of systems all over the world that support democratic input into their systems. And people sort of seem, I think, to have forgotten that there are those systems, and that we should weigh in on those systems and what effects they have on our lives.

And what I’m really focusing on, of course, is the post-World War II rules-based international order, which I actually don’t want to go into right now because I want to tell you this story. But we’re losing that. And when we lose freedom of the seas, which of course Churchill and FDR laid out in 1941 in the Atlantic Charter, although it had an earlier history than that as well, when we lose the free trade that the freedom of the seas supported, the impacts on the United States are going to be huge.

And Donald Trump came in, and just sort of said, “Well, we’re going back to William McKinley’s era.” I studied William McKinley’s era. There’s no reason to go back, I promise. But in terms of that larger question of whether people are paying attention, I’ve always wondered if it was the 1947 consolidation of the national security state that made so much of what we do secret, or what the United States does secret, that people stopped sort of paying attention. They only saw what was in the news, and they either liked it or they didn’t like it, but they didn’t have that deeper understanding. What do you think of that?

Jake Sullivan:

Was your sense before 1947 that in fact these debates or deliberations in Washington took place with greater transparency than they did after 1947?

Heather Cox Richardson:

Well, with caveats, yes, because of course the presidents have always hidden things. But think about the fact that the last time we declared war was during World War II. And there’s a reason that we’re supposed to have those conversations. And the framers of the Constitution were very clear that they wanted Congress to debate the idea of going to war, not only because it would take people’s lives, but also because having a permanent military or expending cash in war would destroy the economy at home.

And you look at the fact that we are in this war in Iran that nobody approved, except the president and perhaps Pete Hegseth and some of his other advisors. And we’re just pouring money into that. So aside from even the lives at stake, the real fear that we can cripple an economy based on a war that we don’t want is something that the framers would’ve been all over.

Jake Sullivan:

It’s interesting that-

Jon Finer:

Where I think-

Jake Sullivan:

Oh, sorry-

Jon Finer:

Go ahead.

Jake Sullivan:

... go ahead, Jon.

Jon Finer:

Well, where I think you’re right is I do think you can date the beginning of the shift of the center of gravity in national security and foreign policy decision-making from Congress and the executive branch working in tandem to really an executive branch-dominated decision-making process to that post-war period.

But if I’m being candid, and I think Jake would probably agree with this, the people who have actually been responsible for making foreign policy since then, we’d include ourselves I guess in this category, I think bear some responsibility for this disconnect. Because there has been a sort of implicit or explicit leave this to us, I think, mentality that doesn’t necessarily apply to other areas of American policy, maybe in part because some of this is based on classified information that can’t be shared.

But in part, I think because this post-war order that you described, we believed collectively was so advantageous to us that we didn’t really need to make the case to the American people about how great it was. They would just understand it intuitively and implicitly. And they actually, I think, lost track of and came not to believe anymore that this was all in our interest. And along comes somebody like Trump who actually says it’s a raw deal, it’s more of a burden than a benefit. And there was fertile ground for that because we stopped, I think, explaining and making the case for why it was important. That’d be my partial explanation.

Heather Cox Richardson:

I think that’s right. And I’m on board with that. I try and do foreign affairs as much as I possibly can just because it’s so important, and I don’t think people know as much as they should about it.

Let me tell you the story that goes back to your question about the relationship between domestic politics and foreign affairs. And that’s that when the United States gets involved in Cuba, and I’m going to make the argument here that what we know of as the Spanish-American war is really two entirely different wars. There’s the war in Cuba and there’s the war in the Philippines. Because the people who supported those two wars were entirely different groups of people in the United States.

But what’s interesting is that Teddy Roosevelt, for example, and the interventionists in Cuba desperately wanted to go into Cuba because of the humanitarian crisis there. Because you had the Spanish colonial leaders concentrating people. It’s when we get one of the first uses of the word concentration camps. They’re concentrating people into these camps where they’re dying in horrific numbers. And they insist that the United States has become a country of shopkeepers and people who are only interested in money, and that they need to exert moral authority in Cuba to renew their own principles at home.

And of course, we have that very famous scene at the Gridiron Club in Washington DC where the politicians used to go to be roasted by the journalists in which Teddy Roosevelt stands up and he shakes his hand at Mark Hannah, who is really McKinley’s handler, and says, “We will have this war for Cuba even if the moneyed interests don’t want us to do it.” Because the sugar interests didn’t want people to go into Cuba.

But what’s interesting to me about that and the connection to the American domestic scene is that coming out of Cuba, which was for the United States, what John Hay, the secretary of state, called a splendid little war. It was very quick. It was very successful. In fact, at one point the US Navy wins because the other side doesn’t even know they’re at war.

Coming out of that, the people who become known as the imperialists, who want to spread American values overseas, and that’s going to include Teddy Roosevelt and people like Henry Cabot Lodge out of Massachusetts, but crucially it’s going to include Albert Beveridge in Indiana. Most of us read him in high school, the March of the Flag speech about how we have to go take over all these poor benighted countries. That’s his words, not mine.

Their big argument for that was partly about, oh yeah, we got to spread democracy and religion and so on. But an awful lot of their argument was if we’re going to do these things, if we’re going to spread American values, we must clean up the United States at home. And so one of the big arguments behind the progressive reforms under Theodore Roosevelt in the early 20th century was we can’t preach citizenship and capitalism and religion and all these things and citizenship overseas unless America looks like we’re doing it at home.

And that was actually really powerful as an argument for taking over the rest of the world. Not the entire rest of the world because the US isn’t involved in the fight for Asia, for example. But that whole working backward of we’re going to go take other countries, but if we’re going to go take other countries, we got to fix up America first, is kind of a backward approach to imperialism, but it really was a driving force behind progressivism. Is that going to happen now? I haven’t seen a single person making that argument.

Jon Finer:

Well, you could make the argument in fact that we are in some ways not preaching democracy and citizenship abroad, but actually preaching and befriending authoritarianism abroad as we impose it at home. So almost the inverse of what you describe, a less democratic, more authoritarian society in America that is bleeding us into league with less democratic and more authoritarian countries around the world under this president.

Heather Cox Richardson:

Josh Marshall yesterday called it greater MAGA. Putin in Russia, and of course, Viktor Orban is no longer in control of Hungary, but the different authoritarian regimes across the world. But maybe that gives us a different way to think about the relationship between foreign affairs and the domestic scene now if you think about it.

Because Putin’s in real trouble. He’s in real trouble. And if he goes down, Rick Wilson was saying that, of course, aside from the economics of whether or not he goes down and Belarus has just refused to enter the war, and appears to have appealed to China for protection against Russia, it’s unclear to me what’s really going on there. This is your field, not mine.

But if Putin goes down, aside from anything else, all the files that are in his administration’s possession suddenly seem to me, as Rick Wilson suggested, to become extraordinarily valuable for getting people out of legal trouble or possibly out of the country. And I wonder if him going down is going to do great damage to those other countries that have relied on him for money or propaganda support. And I’d be shocked if that didn’t include the US. What do you think?

Jake Sullivan:

Well, a few things here. One, it’s definitely the case, and we saw it during our time in government, that Russia continues to put money into commentators, political figures, other people, including in the US, but across the world, to try to shape the debate, sow division, undermine democracy, and also support far right movements. And I think Putin is a critical player in that because he’s sort of the avatar, the symbol, for a lot of these folks across Europe and folks including in the MAGA movement here in the United States. So that’s definitely a real factor.

And it is interesting, Heather, that people who are not prone to hyperbole or prone to exaggeration are now saying about Putin’s position in the Kremlin in Moscow that, look, he’s not maybe going to fall tomorrow, but that he is in a weaker, more pressurized place than he has been in a long time. So I definitely think that that bears watching.

When you were talking earlier, I just wanted to put a plugin for Mary Dudziak’s book called Cold War Civil Rights, because the story you were telling about the progressive era, she tells about the civil rights movement and the Cold War. And how the Cold War actually led to a series of arguments here at home about how we had to make progress on civil rights because how could we make this case of freedom versus communism if we weren’t cleaning up our house at home? So this has a long pedigree. And as Jon was saying, we may be seeing it in exact reverse today, but I thought that was really quite striking.

Not to jump all over the place, but before we actually pressed the live button, we started a conversation about Mark Carney’s speech at Davos where he talked about a rupture in the international system. And he said, “The old order is not coming back.” That was his phrase. And basically said Canada and countries like it, middle powers like it, are going to have to build these new coalitions that frankly don’t depend on America. In some way could be seen as adversarial to America, depending on how things develop. And used this phrase variable geometry, which we were talking about. What’s your read on that? You were talking about this postwar era, how it’s changing. Mark Carney’s essentially declared it dead. Did you read Carney’s speech, and what was your take on his observation or the strategy that he was putting forward?

Heather Cox Richardson:

I did. I actually wrote about his speech as well. I’m following Carney really closely. Because if you’re in a period in which something’s falling apart, you want to watch for the people who are articulating a new way forward, not simply doing it, but articulating it. At least because of the way I see the world, it takes people’s ability to articulate a new vision for others to join it. So I have been watching him.

Before I want to say that though, I want to pick up what you just said about the idea that the Cold War amplified the drive for civil rights. And I want to make a caveat to it that I think really matters. 100%. Yeah. I mean, it was just a no-brainer that you couldn’t fight against fascism and then live a version of it at home.

But the Cold War actually did not advance civil rights for women. It tended to reinforce traditional rights for women because as one historian has very famously said, you could see on TV that all of the women in Russia, this is her phrase, not mine, looked like Mr. Potato Head. And this is when you get the whole idea of women in poodle skirts and so on. So there’s a real disconnect there between civil rights for Black and Brown men and for women that the Cold War really divides.

So the reason I’m interested in Carney actually goes to your work, the two of you, and what happened during the Biden administration and having Antony Blinken at the State Department, the secretary of state. Because to me, one of the best speeches and most important speeches that Biden gave was in February of 2021 when he was introducing, I mean-

Jon Finer:

At the State Department.

Heather Cox Richardson:

At the State Department. So it’s like February 4th or something. And he talks about the fact that a couple of things. The old order, the post-World War II order is dead, he says, which we could talk about because that’s interesting. But he was trying to replace it with the idea, first of all, that you had to make democracy work at home. And that I mean, I think the Biden administration was ideologically extremely coherent and it just didn’t get the play in the media for people to see that it was coherent. He wanted to make democracy work at home.

But then he also said that in order to combat, and I’m reading slightly into this because I don’t think he used the word colonialism, but one of the things about post-World War II, the rules-based international order, is that it inherently had a colonial mindset. That is a few groups of wealthy countries were going to dictate to places like Africa, which until the Biden administration did not have a seat on the G20, which is bonkers. I mean, you know that.

So what they came up with, in my understanding, is they looked at how a bunch of countries could jockey and come up with coherent policies in what became the EU, where instead of having a largely top-down version of how they would cooperate, they would use variable geometry to say, listen, these three countries care about, I’m making this up, cheese, and these six countries care about shoes. And instead of everybody saying, we’re all going to have to be alike, you get these different people in different countries in ad hoc committees. But Biden and Blinken added the word diplomatic, that they were variable diplomatic geometry with the idea, through diplomacy, you were going to be able to do this at a world level.

And there were some profound successes in that the way they treated fentanyl, for example. I actually think that a lot of the work that they did in Latin America, you, I’m sorry, did in Latin America got almost no press, but it was very successful. Vice President Kamala Harris’s trip to Africa was one for the ages that got almost no press in the United States.

But the problem with it always seemed to me was it was just a ducky idea until you had to force somebody to do something. And in that case, what the Biden administration rolled out were dramatic economic sanctions and expulsion from the SWIFT banking system that enables countries to exchange money. But it didn’t work in the case, for example, of Israel and Gaza, where Biden was not willing to put those economic sanctions on Israel. That’s my sense of it anyway.

But then you’ve got Carney stepping in and saying, we’re going to do this. We’re going to do this variable geometry. What a terrible name by the way. But we’re going to do it without those big powers. Us middle powers are going to do it. And it’s a very similar idea to what was going on at the EU. But I’m still back on that idea that if you try and put this together, you need teeth. And where are the teeth? Canada and the EU, of course, have been working very closely together in trade, but is that enough teeth that you can force the United States, for example, to do something? And I don’t know. I feel like getting that piece in place would give us a foreign policy for the future, but I don’t see that piece yet. What do you think?

Jon Finer:

So I guess my answer to that would be you definitely need both carrots and sticks. It’s a bit cliche, but it’s actually the reality. And I think sometimes we, the United States, struggle on both ends of that. You’re right that sometimes we lack maybe the political will to muster sufficient sticks when it’s our friends who are involved. But we also, I think, have struggled to offer sufficient carrots sometimes to incentivize countries to work with us.

In the modern era, it’s a lot harder, for example, to offer countries access to the American market than it used to be because of the politics around trade in our country. What countries really want from us are closer economic ties, much more than almost anything else. They want American investment in their countries. We don’t have the ability to direct that investment, to tell American companies, you will go here and you will go here. We don’t have state-owned enterprises. We don’t have sovereign wealth funds here the way some countries do to channel large amounts of capital. So we have to use incentives, we have to use persuasion, but it’s never direct and immediate in that way. Similar on the coercive side.

And so I do think what’s going to be interesting about this variable geometry of the middle powers that Carney is trying to muster is will countries that are working together, almost to try to reduce their reliance and dependency on the US, be willing to use these sorts of tools that we have used sometimes against them, sometimes with them, against us in the current moment? And I think they are trying to gauge whether they have the collective will and the willingness to take on the pain that will come with that because sometimes it means imposing costs on your own population to try to coerce and change American decision-making. Not clear to me that they will get there, but that is the conversation I think they’re having right now.

Jake Sullivan:

And similarly, if you go to Europe now, they’re having that conversation with respect to the US. They’re also having that conversation with respect to China. And they are very worried about the extent to which basically China’s overcapacity, the flooding of European markets with products across a range of different industries, is leading to the further hollowing out and de-industrialization of Europe.

And I think they have been historically reluctant to use leverage, to have teeth, to your point. They have the latent capacity for it. Their economy’s big enough, they have the leverage, but will they actually use it? I think the combination of what China’s doing and what the US is doing right now may just get us a Europe, Canada, Japan, Korea, even India, a range of these middle powers that are democracies, deciding to ban together and exercise, exert the leverage they have to a greater extent than we have historically seen. But I think you put your finger on the critical question. Because depending on whether they do or don’t, so will go basically this variable geometry theory. If they don’t do it, then their ability to shape or influence events is going to be extremely limited.

Heather Cox Richardson:

Didn’t India and the EU do a huge trade deal-

Jake Sullivan:

They did.

Heather Cox Richardson:

... [inaudible 00:27:02].

Jake Sullivan:

Yeah. Canada and India did one. The EU and India did one. And frankly, they couldn’t get to the finish line for years and years and years because there was always some provision that one side or the other didn’t want to agree to. Nothing creates the get across the finish line momentum like Donald Trump and his trade war. And so they did. And you have, if you just look at what Canada’s doing with diversifying its economic relationships, trying to increase the level of investment into Canada from other countries, trying to create new markets that don’t-

Jon Finer:

Including China, by the way.

Jake Sullivan:

Yeah, exactly. That don’t make them as dependent on the US. I think they’re taking those steps. The question is whether they will add to that these kind of trade countermeasures, targeted tariffs against certain kinds of products that are flooding into their markets, controls on certain kinds of investment. That’s the big question for me as to whether they’re prepared to do that.

Heather Cox Richardson:

So I have a question for you on that. Two questions. First of all, doesn’t it make sense, if you’re trying to protect your supply lines at the very least, to have targeted tariffs? I know a number of countries do. If you can develop your own production, don’t you want to do that?

Jon Finer:

We voted with our feet on this question. We inherited a set of tariffs from President Trump, including some, candidly, that President Biden, when he was a candidate for president, said he didn’t like very much. Ultimately, when we stared hard at this problem, there were some that we wanted to revise and many that we decided to keep in large part for exactly the reason you just identified, which are there are a set of critical industries, critical elements of our supply chain, that have to be made more resilient and more reliable. And tariffs are a part of the process of doing that along with, by the way, some of these positive incentives and partnerships with countries around the world that are essential to those supply chains that are closer to our way of thinking than China, where we had an unhealthy dependency for a long time and still do in some areas.

Heather Cox Richardson:

Can I ask you one... I mean, I don’t know what your time looks like.

Jake Sullivan:

I think we should let you go-

Jon Finer:

We’re getting there.

Jake Sullivan:

... in a sec.

Heather Cox Richardson:

Can I ask you one question though? It’s a little one. It’s a teeny tiny one. If you could design a US foreign policy for the 21st century, simply, not in the weeds, but sort of this new philosophy that we’re talking about here, what would it look like?

Jake Sullivan:

Historically, we had approached our idea of alliances and partnerships in a hub and spoke model. Basically, we would work with countries bilaterally. We would be in the middle and everyone would connect to us. I think my view would be basically we need a lattice work. And this is kind of like variable geometry, but basically connect everyone to everyone so that, for any given international problem, you can collect the right group of countries to go tackle it. And so that if there are periods where the United States pulls back or pulls out, as we see with Donald Trump, and as you put it before with greater MAGA, other countries can work more closely together and sustain the kind of international cooperation that makes for a more peaceful world.

But fundamentally, when it all comes down to it, the core of US foreign policy abroad has got to be work with allies and partners because it is the only way we get the scale and leverage to solve any of the challenges that should matter to people here at home, including supply chain resilience, having the capacity to manufacture and innovate effectively, ensuring that we can deter wars and prevent wars in other places. So for me, it really comes down to a lattice work of allies and partners across the world that is flexible, that is problem solving oriented. And if we could just do that with diplomacy first, it feels to me like we’d be on the right track.

Jon Finer:

I just want to say, I do think we should probably wrap up, I agree with how Jake described things. I wanted to end just by saying something about your work, which I think I appreciate, and an energy that we would like to try to bring to our work as well and that I think you brought to this conversation. You have a way of describing hard things that the country is going through without sounding despairing or hopeless, and while always offering counterpoints and ideas. And I think that’s just so essential and appreciated in this moment. I don’t know if that’s intentional or just something that’s in your nature, but I just wanted to call that out and say thank you for bringing that problem-solving energy to this conversation. And we’re big admirers and love to have you back-

Jake Sullivan:

Bless you.

Jon Finer:

... at some point, but thank you.

Heather Cox Richardson:

Would love to. Thank you so much for having me.

Jake Sullivan:

Awesome. Thanks so much.

Jon Finer:

Take care.

Jake Sullivan:

Take care.

Jon Finer:

Well, that’s all for today. We’ll be back next week with a new episode of The Long Game. Subscribe to our YouTube channel and follow the audio feed so you never miss an episode. And for additional content, episode transcripts, and exclusive podcast segments, subscribe to The Long Game on Substack, or join The Long Game Plus on Apple Podcasts. That’s it for this episode of The Long Game.

Jake Sullivan:

If you like the show, please follow, share with friends, and leave a review. It really helps listeners find us. The Long Game is a Vox Media podcast network production.

Jon Finer:

Executive producer, Tamara Sepper.

Jake Sullivan:

Lead editorial producer, Jennifer Indig. Senior producer, Matthew Billy.

Jon Finer:

Video producers, Nat Weiner and Adam Harris.

Jake Sullivan:

Supervising producer, Jake Kaplan.

Jon Finer:

Associate producer, Claudia Hernandez.

Jake Sullivan:

Marketing manager, Liana Greenway.

Jon Finer:

Music is by Nat Weiner. We’re your hosts, Jon Finer.

Jake Sullivan:

And Jake Sullivan. Thanks for listening.

Jennifer Indig is the Lead Editorial Producer for The Long Game

This week, we have a special bonus segment for paid subscribers featuring a lightning round with historian and foreign policy scholar Robert Kagan, recorded live at the Aspen Ideas Festival.

After conducting a sweeping net assessment of America at 250, from the future of American power and the international order to democratic resilience and great-power competition, Jake Sullivan and Jon Finer shift gears with a series of rapid-fire questions directed at Kagan that reveal a more personal side of one of America’s most influential foreign policy thinkers. Kagan weighs in on the most misunderstood figures in history, the presidents he believes are overrated and underrated, the books that have shaped his thinking, the most unpopular opinion he holds, and even his lifelong allegiance to the New York Yankees, before ending on a surprisingly hopeful note.

This content is exclusively for paying subscribers. Thank you for supporting our work.

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Transcript: America at 250: A Net Assessment (w/ Robert Kagan)

The Long Game with Jake Sullivan and Jon Finer

July 01, 2026

TEASER:

Robert Kagan:

I think that we’re moving into a genuinely multipolar world that looks a lot more like the 19th century than anything, or maybe even the early part of the 20th century, than anything we’ve seen before. And that’s a world in which every nation is basically for itself because nations can no longer rely on the United States to protect them. I know people look at the world and they say, “Well, there’s the United States and there’s China and then there’s Russia and there’s India.” I believe in the world we’re heading into, it’s going to be a much more diffuse world where medium powers become bigger. Iran is about to become a much bigger power in the world. And I think Germany and Japan are going to go in that route too.

Jon Finer:

Hey everybody. Welcome to a special live audience episode of the Long Game Podcast, where every week we dig into the deeper context and drivers behind the headlines in global affairs. This week, it’s our pleasure to be coming to you from the Aspen Ideas Festival in Aspen, Colorado. I’m John Finer.

Jake Sullivan:

And I’m Jake Sullivan and we’re excited to be here at the Aspen Ideas Festival for this episode of The Long Game. We’ve got a great crowd with us and we are thrilled to be joined by an incredible guest, the historian and writer, Robert Kagan. Few writers have done more. Yeah, please. Well, you can please clap. Yeah. Bob, your fan club is here.

Robert Kagan:

Where am I?

Jake Sullivan:

Yeah. Can’t hold him back. Few writers have done more to shape debates about America’s role in the world than Bob Kagan. For four decades, he’s argued that peace, prosperity, and democratic progress rest on a foundation that many Americans have taken for granted, American power. At a time when that power in the international order had helped build or under increasing pressure, Bob has become one of the sharpest, most thought provoking interpreters of the current moment. A little bit of background about Bob. He earned a doctorate in American history from American University. He began his career in the Reagan administration, serving as a speechwriter and foreign policy advisor to Secretary of State George Schultz. One thing the three of us share in common is that we all worked in the State Department’s policy planning shop. Bob left government in 1988 and never looked back unlike John and me who’ve been gluttons for punishment.

Over the years, he’s written too many influential books for me to list them all, but I can tell you I still remember President Obama carrying around his 2010 book, The World America Made. In a recent series of essays that he wrote for The Atlantic, including January’s America Against the World, he’s argued that the international order the United States helped create after World War II is rapidly unraveling and America is squandering its competitive edge. Bob has another very important distinction. He’s the husband of one in John and my treasured colleagues, Toria Newland. Toria is a legendary diplomat who served most recently as undersecretary of state. We’re both excited to have her listen to the podcast and nervous about her listening to the podcast because she’s certainly going to give us her unvarnished feedback.

Jon Finer:

And like Toria, Bob tells it like it is. He certainly has inspired the administrations that Jake and I have worked in, the Biden administration, the Obama administration, from sharp criticism, but it’s always grounded in logic and in principle and never in cheap shots. And so as the U.S. approaches its 250th birthday next week, Jake and I wanted to take a step back and examine the bigger picture. Bob offers a perspective that draws on our country’s past to interpret our present and our future. So he’s the ideal guest for The Long Game at any time, but especially in this moment. So Bob Kagan, welcome to The Long Game.

Robert Kagan:

Well, thank you so much and I can’t do anything after all that.

Jake Sullivan:

We had more, I cut some down.

Robert Kagan:

It’s a pleasure to be here. Be in front of all of you. Thank you.

Jon Finer:

So Bob, on the podcast we sometimes use a concept drawn from governments and really pioneered by the U.S. military of a net assessment, which is essentially an evaluation of relative capacity across a number of key metrics. And we want to start by going through where America stands at nearly 250 years old, across the key areas of national strength and health, starting with our power and influence in the world. But we will also get, of course, to the home front, which you’ve written about quite a lot. When you look around the world on one level, you could make the argument that the basic metrics of American power look very good compared to everybody else. Our military is still stronger than anyone’s, our economy too. We remain the most innovative country on earth with the deepest capital markets. We have better relationships with more countries than our competitors have, et cetera, et cetera.

But if we’re being honest, this all feels a bit more fragile than that would indicate and that it has in many decades. And you warned back in 2012 in The World America Made that reports of American decline were exaggerated and that maintaining our strength and even supremacy was critical to global order. But what about now? Is American power stagnating? Is it in decline? Are we on some other trajectory?

Robert Kagan:

I was getting ready for these kinds of small questions that you were going to ask. And I thought, if you don’t mind, if I could just sort of try to set things in a little bit of a broad historical context because it’s very easy to look at what’s going on and think this is an unprecedented situation. And in many ways it is. We have an unprecedented person running the country and the circumstances are always different. History doesn’t repeat itself. But I do think you can see patterns in American foreign policy and we may have thought that those patterns were over, not just American foreign policy, but also domestic politics. We may have thought those patterns were over, but now here they are sort of repeating themselves again. So just as a way of maybe beginning this conversation, I just wanted to look at American foreign policy over history on two vectors.

There’s a million ways to think about American foreign policy. These two vectors are not the only ones, but I think they’re really critical and they help explain what’s happening right now. The first thing, in my view, most important vector is the struggle over American identity. What is the United States? And that’s always been a contested issue since the very founding. There was the founder’s vision, which was of a country based on universal principles. They had a chance to create a country that was built for white Anglo-Saxon Protestant men, which is what they were, but they deliberately, deliberately chose not to do that and to make it clear that it didn’t matter what your religion was, et cetera, et cetera. Those are the principles of Declaration of Independence that we’re about to celebrate. But from the very beginning, from the moment of the declaration, there’ve been millions of Americans who didn’t accept that, didn’t accept the principles of declaration, didn’t accept the principle of human equality.

Obviously there was a slaveholding part of the country that explicitly rejected the declaration and instead looked at the United States as a white Christian country. And we’ve gone through oscillating periods about that. So you had the Civil War, then you had the end of the 19th century and you had a lot of advancement and then you had a reaction against that and immigration, which always plays into this in the 1920s and ‘30s. And then as a result of the Depression and World War II, we moved into a totally liberal phase. If you think about liberal as being sort of more aligned with the declaration versus a blood and soil nationalism, we very much moved into this liberal period, but it turns out it was temporary. So we are now back to a struggle over our identity. I think this administration, whatever the president himself may think about anything, this administration is definitely engaged in the process of turning the United States into a white Christian country, which is what they believe that it was founded in.

And this always affects foreign policy. This is the thing that I think we often lose sight of. These internal battles over American identity play themselves out in foreign policy terms. And this has been true from the beginning. Hamilton and Jefferson had a huge argument about whether to be more supportive of France or more supportive of England that was entirely rooted in what they wanted to build at home with Jefferson being on the more radical democratic side and Hamilton being in the more sort of, let’s try to look more like England except without a king. So this struggle has gone on and on and on and is happening now and you can see the effects of the periods where we moved into this conservative way that this conservative approach was also the ‘20s and ‘30s. The other vector, and one of the things about that reality is that the reason the United States can do this, that it can play out its identity on the world stage when it chooses to, is that it doesn’t really require to do anything else.

The United States has been essentially secure since the end of the 19th century and really not facing the prospect of foreign attack. And therefore everything the United States does in foreign policy to some extent has been voluntary, which is why we can go back and forth like this. And this just gets me to the second vector and then I’m going to shut up. The second vector is an oscillation between periods of high end intervention and periods of retrenchment. And if you look at American foreign policy beginning, let’s say in the 1890s, period of high foreign overseas involvement is followed by a period of rejecting that approach, regretting that approach and retrenching, which was then followed by another uptick. And it seems to me that oscillation has been pretty the continuous element of America. And we have been in this mode of, when we want to retrench, it’s because we don’t know why we’re doing all the things that we got out there to do.

We undertake large projects, almost always driven by an ideological concept. Even when we succeed as in World War I, we wind up regretting it and then retrenching. And this seems to be a constant in American foreign policy. So we’re right now, just to conclude, we’re in a double cycle. We’ve moved into a conservative anti-liberal anti-declaration period in our politics and we’ve moved into a unhappiness with the extent of our global involvement at the same time. And Donald Trump is sort of presiding over this, but I can’t say that he caused it.

Jake Sullivan:

So Bob, I want to ask you a question about each aspect, each of those cycles in the double cycle. On the first one, I’ll put a plugin for your book, The Ghost at the Feast, where you write about a lot of these dynamics before World War II and what it meant for the United States then, and frankly, how it echoes to the present. So to get out of that cycle in the 20s and 30s, it took a depression and a world war. Is there a way out of this cycle without a depression and a world war?

Jon Finer:

Can you give us any hope?

Robert Kagan:

I knew you were going to ask me that question. So normally I would say that the oscillation continues and I think I would have said that had it not been for the domestic political direction and the sort of victory of anti-liberalism in 2016, I would say the country was already beginning to head up that oscillating ladder toward greater concern. Usually what happens is as what happened in the ‘20s and ‘30s, Americans have decided they washed their hands of the world and then as a result of the United States washing its hands of the world, the world begins to behave in a way that Americans don’t like until finally Americans decide, “Hey, we got to do something about it.” So I think Americans were already moving in that direction, but now it has been completely stymied. Eventually, I believe, we will respond to the growing threats in the world, but if the history is any guide, we will respond too late to avoid the sort of catastrophe that then allows us to go back to what you’re talking about. So it’s hard to imagine snapping back short of much worse disasters ahead.

Jake Sullivan:

Okay. That’s very encouraging.

Robert Kagan:

Listen, if you’re looking for optimism, everybody should go find another place to-

Jon Finer:

That’s the other panel.

Jake Sullivan:

Okay. So let me take you to this oscillation on the retrenchment piece and in addition to the oscillation on the nature of American identity, you have been an outspoken critic of the war in Iran. In fact, you were one of the first people to come out and basically say, “America fought this war and lost.” You have recently wrote a remarkable paragraph that I actually want to read for the audience here about America’s broader involvement in the Middle East. And this is a quote from your piece.

“Even the threat of terrorism from the Middle East region was a consequence of American involvement, not the reason for it. Had the United States not been deeply and consistently involved in the Muslim world since the 1940s, Islamic militants would have little interest in attacking an indifferent nation 5,000 miles and two oceans away. Contrary to much mythology, they have hated us not so much because of ‘who we are, but because of where we are’.

In Iran’s case, the United States was deeply involved in the politics from the 1950s until the 1979 revolution, including as the main supporter of the brutal regime of Shah Mohammad Reza Pahlavi. The surest way of avoiding Islamist terrorist attacks would have been to get out.”

So can I ask you, Bob, as somebody who has been an advocate for getting in, not just getting out, do you now believe actually the United States, if you were to operationalize that, should pull out of the Middle East in a kind of real military way, shut bases, reduce our presence, reduce our engagement in the domestic politics of those countries? Can you convert that into what your actual idea would be for what the U.S. should do in the years ahead?

Robert Kagan:

Yeah. Let me be clear about what I was trying to do in writing that paragraph. The thing that I find surprising about Americans is that we’re constantly shocked that others are reacting to us. Pearl Harbor is the same thing. We brought on Pearl Harbor. We took the steps that we knew that if we embargoed Japan, it was very likely that they would start a war. We didn’t think they were going to hit Pearl Harbor, but we thought there was a real chance of war. And the American people went polled, by the way, four months before Pearl Harbor said, “We’re okay with a war with Japan.” Now, they thought that Japanese were little people that they didn’t have to worry about. So I just want us to be conscious as we wield power that it is going to have an effect. And then the question of whether to be in the Middle East or not, to my mind, has to do ...

Robert Kagan:

... question of whether to be in the Middle East or not to my mind has to do with what is your overall goal in the world. When America was solidly behind the American world order, when we were solidly behind supporting our allies in Europe and Asia, when we took it on as responsibility to maintain the overall security of our allies, but in the general sense of the world, that’s what made that region critical to us. The United States by itself, if the United States is in isolation and not involved in the world, it doesn’t need to be the hegemonic power in the Persian Gulf. It was as a consequence of our overall strategy.

So if I thought that the world order that we have held on to rested on our ability to open the strait, for instance, I would say, “Okay, we have to do whatever is necessary,” but at the time when we are actively abandoning any thought of supporting the international system we’ve supported, as we pull troops out of Europe at a time when Europe is at war with an aggressive Russia, as we increasingly abandon all of our commitments around the world, the one place we’re going to go to war is in the Persian Gulf? That’s what makes no sense to me.

But in general, I think that Americans have to stop being naive. If we’re going to exercise power, we’re going to get a reaction. Then we have to decide, is the reaction worth it or is it not worth it? But it has to be for something, and that’s what I feel like this was for nothing.

Jon Finer:

Maybe to put a slightly finer point on it then, given you’re an historian, we can go back a little bit in time, is that meant to suggest, was this paragraph meant to suggest, is your answer meant to suggest that we overreached in the Middle East in the immediate aftermath of 9/11, in the global war on terror, in the Iraq war, or is that a separate question from the one you were trying to answer here?

Robert Kagan:

It’s obviously not a separate question, but at the time, and history is such that you can’t wind it backwards from everything you know, we were all in a state about the perils of the world after 9/11 and I think that therefore we were sort of less tolerant of existing threats that we knew existed, and Iraq was a preexisting threat. I think, in the terms that I was talking about, I think it made sense to do that, and I will say, for all the failures of the Iraq War, it did actually remove the person in power. It did lead to regime change. There’ve been six Democratic elections in Iraq. Iraq is no longer a threat to its own people or to the region, which it was before.

We can all argue about these things, but I don’t really regret that decision, except for the effect that it has had on the American public’s attitude towards the world, and that is a separate issue.

Jon Finer:

Also came at enormous cost in Iraq, and we don’t need to-

Robert Kagan:

No, we can’t. Right.

Jon Finer:

But it’s worth not letting that pass. You’ve also been a student of the US-Israel relationship, which is another major factor that has kept the United States as invested in the Middle East as we have been. You’ve been quite critical of Israel under Prime Minister Netanyahu, noting as far back as 2016 that the interests of the US and Israel can sharply diverge at times, which may be more self-evident now, but was not, I would say, widely acknowledged back then. You’ve criticized Israel for intervening in a partisan way in American politics for democratic backsliding at home for cozying up to authoritarians abroad.

Two questions about how the US should view Israel given that. First, given the assault on democratic institutions like courts and the fact that there are still now millions of Palestinians living under occupation without basic rights, is Israel a democracy? That’s one. Easy question, simple question. Second, given the increasingly divergent interests you’ve noted, is Israel under Netanyahu still a US ally?

Robert Kagan:

Israel was founded on something of a contradiction. It was going to be the Jewish state, which meant obviously it had to privilege Jews in the state, but it was also going to be a liberal democratic government, and I think there’s always been a question as to whether those two things were ultimately compatible. I would say long before, certainly within... I mean, I wrote that in 2016 and I think it was obvious before then that Israel was increasingly becoming more of a Jewish state and less of a liberal democracy. I don’t have an opinion about that. It’s just a reality, but I don’t think that necessarily had any particular bearing on America’s relationship with Israel, except that we had to understand what that relationship was about.

We have all kinds of allies who we not necessarily share all common values with, not perfectly, and certainly Israel is at least an imperfect democracy. Our discussion of Israel became one in which we began to believe that we had a vital interest in supporting Israel. We started supporting Israel out of a sense of moral obligation. That was the reason for American support for Israel ultimately, and I think that was a noble thing to do after World War II and the Holocaust, et cetera, but we never were supporting Israel for strategic reasons.

In fact, much of our strategy in the region came to be about defending the interests of Israel because they were an ally and because we felt an obligation to them. I’ve always felt about Israel roughly the way I feel about Taiwan, that we have an obligation as a defender of a country that we have their responsibility for, but not that it somehow transcends basic understanding of our interests. And I would say clearly Israel is not operating in the interest of the United States because that’s not what Israel is supposed to do. It’s supposed to operate in the interests of Israel, but those interests are definitely...

In my view, Israel’s vision for the Middle East has never been a vision that the United States should sign up to, because Israel’s attitude is basically the Arab Muslim peoples can’t... we don’t want them in democracies, we want them ruled by strong men who can control them, we fear a public opinion among Arabs and Palestinians, and therefore we don’t want to give them that opportunity, and I just don’t think that is a sustainable position to take over the long run in the Middle East, and it should never have been America’s position.

Jake Sullivan:

So Bob, you were, in answer to an earlier question, talking about President Trump’s indications, early movements that he’s going to pull forces out of Europe, reduce the overall commitment to the transatlantic alliance to NATO. You’ve also talked about how Vladimir Putin is waging a shadow war to test just how strong Article 5 is, that he’s probing and poking drones in Poland more recently in Romania, a campaign of sabotage, the potential that he will escalate in the Baltics or somewhere else. Can you talk for a minute about how you see that threat, how you see Putin perceiving the way that President Trump is approaching the transatlantic relationship, what you most worry about, and how Europe should be interpreting this and how they should respond?

Robert Kagan:

Well, look, I think that you have to be living on another planet not to see that Trump’s goal is to pull out of Europe. I mean, they say it every day. The Europeans obviously have such a powerful interest in that not happening that they are as much in denial as they could possibly be for as long as humanly possible, but I don’t really think they’re in denial anymore. I think that it’s clear that the United States is pulling away. I believe it was right after the mistaken drone attack in Romania that the United States pulled forces out of Romania.

So the signals are clear. If you’re Putin, it seems to me it’s likely that Putin believes that he has a once-in-a-millennium opportunity here to take advantage of a moment that he can’t be sure is going to last forever in which the United States is really pulled away from the Europeans and left them to themselves. At the same time, of course, he’s doing very poorly in the war, so then what you’re basically asking is, what’s his next move?

Jake Sullivan:

Yeah.

Robert Kagan:

I think I’ve always been surprised that, and maybe this was your brilliant policies that prevented this from happening. I’ve always been surprised that he did not attempt much more seriously to cut off supply roots into Ukraine. Those supply roots are vulnerable. They go across borders. You could threaten the people on the other side of the border. Even if the Romanian drone attack was a mistake, it served its purpose, it seems to me.

So I would anticipate that he, on the one hand, he can still wait for Trump to make the next move on Ukraine, which I think is going to happen at some point. Trump is going to cut Ukraine off entirely, including of intelligence-sharing at some point, and Putin may want to just wait for that, but I also think that he wants to weaken European support for the Ukrainians. And he’s got reason to be optimistic. Polish politics now and the dispute, I don’t know whether you’ve followed the dispute, I know you have, but the dispute that’s going on between Poland and Ukraine, which has to do with their ugly history, and particularly in this case Ukraine’s ugly history, but it’s just what Putin needs at this moment.

The shadow war, which is increasingly out of the shadows, is definitely designed to intimidate the Europeans at a time when they are losing their great protector. The question is, how risk-averse does he continue to be? He was relatively risk-averse, has been relatively risk-averse up until now, but he may not feel that that’s in his interest, especially if things are going poorly for him. So I worry about Putin’s next move very much.

Jon Finer:

You mentioned the supply lines to Ukraine as a potential target. Are you not also surprised that Putin has not yet tested Article 5 more than he has in a very direct way given, let’s just say at least lukewarm support for Article 5 that sometimes emanates from the current White House?

Robert Kagan:

I don’t know what his plans are. He obviously had a long-term plan for invading Ukraine, so we don’t know what his long-term plan might be for a Kaliningrad scenario, for instance, all of which is possible. More deployment of intercontinental ballistic missiles, more... In the past, he’s used this. I don’t know how available it is to him now. The Russian populations in some of the Baltic States sometimes feel that they’re being mistreated and he can always claim that there is something there that he needs to defend the Russian people in these various countries. I think the opportunities are there. I just don’t know whether he feels that he wants to avail himself of them or not.

Jon Finer:

As dangerous as it remains, and this conversation makes that clear, Russia is today, I think you’d agree, a declining power, at least, that can’t-

Robert Kagan:

It’s been declining for 500 years.

Jon Finer:

For quite some time. They can’t compete directly with the United States in any meaningful sense, though it can obviously cause a lot of problems and is currently doing that, but for net assessment’s purposes, just to come back to this concept, the real elephant in the room is China. So I’m wondering how you rate the relative power influence of the world’s two strongest nations across the most important metrics at this point.

Robert Kagan:

Look, the reason I was generally sanguine about American decline and why I didn’t think it was going to happen was because the structure of international relations established after World War II is very hard for a country like China to deal with. The fact that the United States had ironclad alliances with the strongest nations surrounding China was a huge obstacle. I know that people are talking, and I think it was one of the premises of the Biden administration that China aimed to ultimately rule the world in some way, or at least its ambitions were global, but it was always very hard for me to imagine how they could exercise global power if they were not even able to exercise hegemony in their own region. That to me seemed like a prerequisite. The fact that the United States denied both Russia and China a real sphere of influence was always a huge blow to their ultimate aspiration. So it seems to me China must gain control of its region first, and it is a long way from being able to do that.

However, now, I think that it is a real prospect given American policy, but then if we start moving into the world that I think we’re moving into, it’s not going to be a world of just the United States and China. I think that we’re moving into a genuinely multipolar world that looks a lot more like the 19th century than anything, or maybe even the early part of the 20th century than anything we’ve seen before, and that’s a world in which every nation is basically for itself because nations can no longer rely on the United States to protect them. I don’t think a great power like Japan is going to go easy into that good night of regional Chinese hegemony.

So the next challenge is going to be a return to the dynamic that existed before World War II. In those days, it was Japan beating up on China. In this period, it might be China beating on Japan, but that dynamic is going to return. Similarly in Europe, I believe it is just a matter of time before Germany returns to being something like Germany, and I don’t mean that in a negative...

Robert Kagan:

... or Germany returns to being something like Germany. I don’t mean that in a negative sense. Germany has been many things over the past century and it can be a liberal great power, but I think it’s going to be a great power. I know people look at the world and they say, “Well, there’s the United States and there’s China and then there’s Russia and is India.” I believe in the world we’re heading into, it’s going to be a much more diffuse world where medium powers become bigger. Iran is about to become a much bigger power in the world. And I think Germany and Japan are going to go in that route too.

Jake Sullivan:

Bob, a couple of things off of what you just said. First, on this question of whether China could become the global leader, maybe not hegemon, but surpass the United States as the overall world’s leading power if it can’t dominate its own region. If your notion of power rests very heavily on military power, that makes a lot of sense. If however, the exercise of power has shifted to a certain extent to be more about economics and technology than pure military power, then there maybe is a pathway for them, even if we still have allies in Asia.

As one of the foremost historians of power, do you think that these other forms of power have become more relevant in 2026 than they were in 1926 or is this still really, at the end of the day, mostly about the hard power of military projection?

Robert Kagan:

I don’t want to poo-poo what you’re saying. I think-

Jake Sullivan:

It was a question.

Robert Kagan:

It’s a serious question. But I also want to say I’ve heard this question before. After the fall of the Berlin Wall and the end of history, the key attribute of the end of history was they were moving into a period of geoeconomics and away from a period of geopolitics. I remember reading in the 1990s about the end of the nation state and how power had become meaningless.

I’m afraid the lessons of the past 30 years have tended to contradict that. So is it going to be different? Now, what you’re saying is somewhat different. I understand. And I can’t tell you if the nation that wins the AI race therefore becomes the most powerful-

Jake Sullivan:

Or dominates all the supply chains. Where geopolitics is right there in the middle, but the way it’s exercised is through rare earths, not necessarily through missile.

Robert Kagan:

No, that’s true. But I guess I do believe that international politics will still be determined by nations seeking to maintain their sovereignty rather than falling under the sway of greater powers. So whether or not China is making gains in that if Japan is feeling threatened by China, that is going to raise an unavoidable geopolitical problem for China that it will have to deal with.

And if Europe rearms, it’s going to have an effect on what Russia does. And so I would be very wary of saying we’ve moved away from raw military power. I would say if anything, recent years have demonstrated that raw military power, including something we thought was completely off the books, which was territorial gain.

Everybody assumed that those days were over because what do you need to have territory for? Because it’s all about AI and economics and yet China’s still obsessed with what flag is flying over Taipei. That makes no sense in the world you’re talking about.

Jon Finer:

We talk about territorial acquisition in America too now.

Robert Kagan:

And we talk about territorial acquisition in America. So yeah, that’s why I say for all of everything you’re saying being true, the world still looks like it’s behaving much like a 19th century world.

Jake Sullivan:

So one other thing I wanted to pick up on what you said was that it won’t be bipolar in whatever sense. It will be multipolar. It’s really multipolar. I have been one more in the camp of show me the other polls beyond the US and China. But I think there really is something to what you’re saying. The thing that most struck me though about your comment was you focused in on Germany, not the European Union. Now I can understand why, but do you see Germany really exercising its power in the world more as a nation state than as a member state of the European Union?

Robert Kagan:

Look, now we’re into my desire side. My desire is that Germany do this entirely within the EU and as much as possible, the Germany rearm in a way that reassures the other countries of Europe rather than unnerving them. But let’s face it, even when the world order was healthy, but Germany was getting too economically dominant for a lot of Europeans. There’s a lot of tension in Europe about Germany.

I lived in Europe for six years. I was stunned at a degree, you don’t have to scratch very deep to find some old feelings and you’re going to see it between Germany and Poland and whatever. And after all, Germany has the capacity for nationalism and we’re seeing that obviously in the strength of the AFD. So while my obvious preference would be that it do so within the sort of liberal context and somewhat constrained by the EU and that’s always what Germany has wanted was to be constrained.

But when countries get serious about the threats they’re facing and the EU was born in the American paradise. There would’ve been no EU if the United States had not solved Europe’s security problem by basically keeping Germany and France off each other and allowing Germany to prosper in a way that was not threatening.

Now we’re going to experiment with going back to the way it used to be where there is no deus ex machina and Europeans have to deal with it themselves and Germany once again has to deal with the problem that as it proved earlier, it’s too big for the continent. It would require great statesmanship on the part of Germany to avoid doing it itself. But if you made me put my money down on Polymarket, I would say it’s more likely that Germany will do it leading on its own preferably with others than doing it within the context of the EU.

And you’re seeing that already with weapons decisions that they’re making. I think Mertz has been very clear about saying, “Whatever else is going on, we’re going to take care of German capabilities.” And I think he even said this, “We’re the ones who will be called on if something happens in the Balts.” I think what he means is not the French. And-

Jon Finer:

He may mean not the Americans too at this point.

Robert Kagan:

No, no, definitely not the Americans. That’s the whole point. Germany is not rearming to make Trump happy. They’re rearming because they face a very serious threat to their East and they know the United States is not going to be there for them.

Jake Sullivan:

Bob, do you bet on Polymarket?

Robert Kagan:

No, I hate Polymarket.

Jake Sullivan:

Okay.

Robert Kagan:

But I know people say that all the time so I decided to say it.

Jon Finer:

Now we have to put one of those gambling addiction disclaimers at the bottom of the video. So if anybody has a problem, I’ll get the 800 number around.

So there’s a wise aphorism about not making predictions, the folly of doing that, especially about the future. But I’m going to ask you two sort of future oriented applications of some of the theories you’ve been putting on the table. And the first is about China. So we have a president who seems a lot more interested in stability, even collegiality, congeniality with China than he does in competition with China.

You’ve written, “There are a few people who don’t think that if Trump could get a trade deal with China that he liked, that he would not be willing to sell out a lot of things including potentially Taiwan,” which you mentioned earlier in this conversation. How concerned are you about PRC military action against Taiwan, let’s just say over the next few years? And is this a vital interest of the United States that we should be willing to defend with force?

Robert Kagan:

By the way, I wrote that before I think the Beijing Summit and before Trump on the air flight back-

Jon Finer:

Really called this into question.

Robert Kagan:

... totally made it clear that the $14 billion aid package was up for grabs as far as the... And the Chinese have been taking advantage of that ever since because it’s the art of the deal. He’s a brilliant negotiator.

It’s always been their preference and their expectation that Taiwan would fall naturally under their sway. And I’m sure that especially given what’s... I don’t want to say I’m not sure, but I feel generally confident that because of what happened to Russia and Ukraine, if she thinks that because the United States is gradually abandoning Taiwan anyway, that the Taiwanese are ultimately going to have no choice, but basically to enter the relationship on China’s terms. And he’s obviously playing the KMT card in that regard, that he would prefer to do it that way.

Having said that, I also think his calculation has got to be similar to Putin’s in the sense that he can’t know that the United States isn’t going to turn around in four years and become the United States again in a way that he’s not going to like and that maybe he has a window of opportunity.

And after all, even before any of this happened, I think there was all this kind of, he wants to get it done by 2027. I don’t know whether that was ever... how serious that ever was, but it certainly is something to consider. And now given the Trump phenomenon, I would think that he might be even more willing to do it.

And in some ways I do think he’s going to be more aggressive and they’re already doing... I mean, it’s hard to say when they’re being more aggressive in the China Sea than not, because they’re always being somewhat aggressive, but I think they’re being more aggressive right now. And the thing that he can be sure about is that Trump is not going to play hardball with him on all those little details because Trump really just does really want just to deal with him. So she has a choice. I guess I would say on balance, he’ll probably would rather see Taiwan fall naturally as a result of American neglect.

Jon Finer:

And on the vital interest question.

Robert Kagan:

Again, it’s only of vital interest if we think we have a vital role in global security. I guess you could say that the chip manufacturing is a vital interest, but that’s like saying oil is a vital interest. Sure, anything that you need is a vital interest in theory, but I would say all of our perceptions of what... The truth is Taiwan was never a vital interest to the United States. It was an as necessary interest if we were trying to maintain this global order, but if we’re not trying to maintain the global order... Put it this way, would Warren Harding have thought Taiwan was a vital interest of the United States?

Jon Finer:

I don’t know enough.

Robert Kagan:

Not a question I’ve considered.

Jon Finer:

Warren Harding to-

Robert Kagan:

Not a question you’ve given any thought to.

Jon Finer:

If the president asked us-

Robert Kagan:

But I have.

Jon Finer:

... that we’d say, “We’ll get back to you. We’re going to look into it.”

Jake Sullivan:

We’ve talked about a number of countries under threat in this conversation, Japan, Germany, Poland. These are all countries that are not nuclear weapon states, that are under threat potentially from nuclear weapon states. Do you expect that there will be nuclear proliferation? Leave aside the adversary side of this, which we’re trying to deal with very clumsily in Iran, but even among our friends and partners in the years ahead?

Robert Kagan:

Absolutely. Again, you have to look at this from the position of countries. Every nation’s number one priority is protecting its own security. For decades, the United States has been protecting these nation security. Now the United States is not a reliable protector. They have to make the decisions necessary to defend their own countries. And I think that the nuclear... we are also entering a period in which nuclear diplomacy, shall we say, is going to be a much bigger factor and having a nuclear weapon or weapons is going to be regarded as an essential prerequisite to playing in a game where everybody has to defend themselves because they can’t rely on anybody else to defend them.

So I think we are going to be living in a world of many more nuclear weapons. I know John Mearsheimer thinks that’s a wonderful thing, but I think it probably greatly increases the likelihood that they will be used at some point.

Jake Sullivan:

That was the positive part of the program?

Robert Kagan:

Okay, good.

Jake Sullivan:

We’ve moved. We’ve moved. Bob, in one of your earlier answers to Jon, you used a turn of phrase that I thought was really interesting. You said Xi Jinping and part of his calculus around Taiwan has to be, will America become America again in four years? Something along those lines. Let’s imagine it does. Let’s say you get a president after Trump who wants to reinvest in alliances as a core pillar of American strength, who wants to reengage in international cooperation.

Of course, the rest of the world is going to sort of say, “Can we count on that because we just saw what happened?” So what advice would you give a president who actually wanted to reinvest in alliances after what we’ve seen for how to do that effectively and what advice would you give to allies about how they should engage a United States on the back end of the Trump administration?

Robert Kagan:

It’s the same advice to both in a way, which is we can’t go back to the way things were. We’re not going to go back to a world in which everybody relies on the United States for their basic security. So what we’re going to need now is to learn how to manage a multipolar world where like-minded states can work together and cooperate. And the United States in that situation would still be the strongest of those nations.

And if we were well-behaved, I think we might be able to work it out so that there is some element of at least trust and cooperation. But I could not advise the Europeans to throw in their lot with the United States again and simply because I’m not even that optimistic that even if we get... let’s say we get our Democratic president of a choice and I’m going to be voting with both hands for Democrats in every election for the foreseeable future, you may have a different view of this than I do.

This is not Dean Atcherson’s Democratic Party. This is not the party that says, “Oh my gosh, look at the state of the world. America needs to lead again. We need to be out there.” It’s been very divisive in this country for a long time. The Democratic Party has been at least as dubious overall about America’s role in the world as the recurrent Republican Party is. In fact, the Republican Party used to be more wedded to the world order than the Democratic Party was in some ways. So that’s one problem. I don’t think we’re going to... we’re not electing Harry Truman in 2028 assuming we can. And similarly, a lot of things that Trump has done are going to be hard

Robert Kagan:

And similarly, a lot of things that Trump has done are going to be hard to reverse. The tariffs alone. There’s going to be an income stream that if you cut off that income stream, you’ve got to find some other way to get the money. And by the way, again, with all due respect, the Democrats are not exactly averse to some protectionism themselves. And then of course, MAGA’s not going away and certainly the sentiments about foreign policy that MAGA has represented are definitely not going away. And so that’s why I feel like for a real revolution to occur, things are going to have to get a lot worse. But that doesn’t mean I don’t welcome a change in ‘28, but I don’t think we should even try to go back to the world that was created in unique circumstances after World War II and look instead for a much more cooperative, equal relationship with our partners going forward.

Jake Sullivan:

By the way, even when we inherited much more limited tariffs on China and the Biden administration, it was extremely difficult to change them because so much reliance invested interest get built up around them. And like you said, you also get revenue, but you also have companies coming in and say, “I now count on these tariffs to keep my jobs in America.” So I think this question of what happens to the Trump tariff wall in the future is a very real and live question.

Jon Finer:

You’ve been one of the most prescient and persuasive voices sounding the alarm about the health of American democracy. I do want to end on things here at home. You’re also an historian and across the broad swath of 250 years, I guess we’re interested in how you rate our current democratic health and maybe more parochially why you think there aren’t more people as outraged as you are and maybe as we are about the current condition of our democracy?

Robert Kagan:

Well, I mean, that’s a question I’ve been asking myself from the beginning and I still ... I can come up with, there’s a multitude of reasons that you can explain. One of the things I’ve been struck by is how much a person’s reaction to what’s going on gets into the almost very personal qualities that people, or life experiences, because people who look exactly the same have wound up on completely different sides of this issue, so I find it’s very baffling. But what I don’t find baffling is the fundamental movement that we’re seeing play out. And it’s really wrong to think of this as the failure of our democracy. This is an ongoing, as I mentioned at the outset, that’s why, because I tied all this together for you guys, that the struggle of American identity has been ongoing.

We’ve just come out of a period in which there was a fundamentally liberal consensus, that consensus is broken down. And what we’re seeing is a movement that is basically fighting against I think what most of us regards as the gains of the Civil Rights Movement over previous decades because it has led to a breakdown of privileges for people who are used... And by the way, this doesn’t mean economic privileges because many of the people who feel this way are not economically advantaged at all. But one thing that’s been clear to me is that the Trump movement is much more motivated by these what we call cultural issues, but I’m sorry, which are really racial religious issues than they are about economic issues. Trump is doing nothing for these people, but what he’s doing for them is hating the right enemies. And the enemies he hates are mostly people of color. And that’s what this immigration thing is all about. It isn’t about illegal immigration. It’s about changing the complexion of this country and trying to turn it back.

As it happens, this is all married up to an individual who is a true megalomaniac. I don’t know what a narcissistic personality is and I don’t care, but I do know someone who is trying to maximize his personal power at all times and is riding this attack on our system because it is giving him power.

So on the one hand, I see ... The historical roots of this are clear. There have been many periods in American history when fundamentally, as I say, anti-liberal forces have been in the ascendant. They definitely were ascended in the 1920s and early ‘30s when the eugenics movement was the most popular thing in America. And so I just think a lot of us thought it was over and that we’d gone past all that and it turns out that we never really did. So that’s the threat. The threat is, it’s interesting that we’re even going to have this big celebration about the Declaration of Independence because Lincoln made the declaration the founding document. Most Americans have not regarded the Declaration as the Founding Document. And certainly people who share the views of the people in this administration, people like Russell Vought and others and their sort of intellectual guides do not believe in the Declaration of Independence and are trying to overturn a system that is based on it. I know that’s worth cheering.

Jake Sullivan:

So I just want to say, you’ve given us a lot to sit with in that diagnosis, but listening to it, one way of interpreting that is to say this is about a person as much as it’s about structural forces. So how do you kind of net that out?

Robert Kagan:

You mean it’s about Trump as opposed to ...

Jake Sullivan:

Yeah. Yeah.

Jake Sullivan:

You kind of described both, but if you had to tell us the extent to which you see this as a kind of once in a blue moon force, this guy, as opposed to it really being a true underlying structural force that’s pushing against the declaration and the kind of core precepts of the American republic.

Robert Kagan:

I mean, that structural force is there and was there to be captured. And he set out to capture it, just to be clear and he ran on one issue and that was Obama is not a real American. Our first Black president is not a real American and he knew exactly what he was doing. I don’t think that qualifies as a dog whistle, okay. Everybody then knew ... And that’s how he collected his movement. So in some ... It’s not an accident. He didn’t just step into this. But to have a person of Trump’s personality, that is once in a blue moon. And I think that with absent someone who is as megalomaniacal as Trump is and therefore willing to break everything, that movement, the movement that he represents now is a spent movement.

One of the reasons they’re doing this right now in such desperation is of course they’re losing. There is no white majority left in America. There’s no white Protestant majority left in America. They’re trying to cling to an America that no longer exists. They wouldn’t have an opportunity to do that if they didn’t have Donald Trump in the White House. I don’t even think if it were Ted Cruz, if it were almost anybody else, it’s hard to imagine that we would be at much risk. So it’s both, but we should not lose sight and I want to be very clear about this, about the ugliness at the core of us, okay We can blame Donald Trump all we want, but this is also us and we need to face up to it and address it. Thank you.

Jon Finer:

All right, we’ll end on this and because we need it, what gives you hope?

Robert Kagan:

Sports apparently -

Jake Sullivan:

Are you a Knicks’ fan?

Robert Kagan:

Pardon?

Jake Sullivan:

Are you a Knicks’ fan?

Robert Kagan:

I am a Knicks’ fan and from way back folks, I just want to say. And it’s been two things over the last couple of months that have really struck me, and one was watching New York celebrate and I thought, “My God, thank you. That is the America that I love right there.” You look at any picture of cheering New Yorkers and there weren’t three people in a row who have the same skin color. It was the ultimate melting pot.

And then the other thing is the way Americans have greeted the World Cup Americans go through periods where we really hate the rest of the world. In the 1920s, really hated, we just hated everybody and you could think looking at the way we’re behaving now that xenophobia was a big part of what we are and it is. And yet here we are and you hear these great stories about people in Lawrence, Kansas who are falling in love with the Algeria... Don’t [inaudible 00:53:41] them, they’re Muslims. They’re falling in love with the Algerian team and it’s sort of like, “Yes, thank you. This is the America that we love.”

And so is it possible that this America can ultimately triumph? And by the way, you’re not asking me this and the time is out, but I am going to say this is the last thing because it is sort of related to hope. The challenge is going to be the 2026 elections folks. I have absolute confidence that the Trump administration, if the Democrats look like they’re going to win, which I’m sure they will, is going to try to stop that. And that is going to be the moment when we need that America to come out and defend its principles.

Jake Sullivan:

Bob Kagan.

Jon Finer:

All right. We will defer to the flashing red light and thank Bob for his time and thank you all for being with us.

Jake Sullivan:

Please give it up for Bob Kagan. Thank you, Bob, for joining us on The Long Game.

Jon Finer:

Well, that’s all for today. Thanks for listening to our live recording with Robert Kagan at the Aspen Ideas Festival. We’ll be back next week with a new episode of The Long Game.

Jake Sullivan:

Subscribe to our YouTube channel and follow the audio feed so you never miss an episode.

Jon Finer:

For additional content, episode transcripts, and exclusive podcast segments, subscribe to The Long Game on Substack or join The Long Game+ on Apple Podcasts.

Jake Sullivan:

This week we wrap up our conversation with Bob Kagan with a lightning round where Kagan offers some quick takes on everything from presidents and power to books, baseball, and a few questions he definitely didn’t see coming.

Robert Kagan:

I think Wilson’s gotten a very raw deal. It’s ridiculous to say that Franklin Roosevelt is underrated, but the way he managed American opinion on the foreign policy question and gradually shifted the country out of its isolationist mood into deciding that something needed to be done, that is one of the great acts of presidential leadership.

Jon Finer:

Be on the lookout. Head to thelongame.substack.com or subscribe to The Long Game+ on Apple Podcasts. The links are in the show notes. That’s it for this episode of The Long Game.

Jake Sullivan:

If you like the show, please follow, share with friends and leave a review. It really helps listeners find us. The Long Game is a Vox Media Podcast Network production.

Jon Finer:

Executive producer, Tamara Sepper.

Jake Sullivan:

Lead editorial producer, Jennifer Indig.

Jon Finer:

Deputy editor, Celine Rohr.

Jake Sullivan:

Senior producer, Matthew Billy.

Jon Finer:

Video producers, Nat Weiner and Adam Harris.

Jake Sullivan:

Supervising producer, Jake Kaplan.

Jon Finer:

Associate producer, Claudia Hernandez.

Jake Sullivan:

Marketing manager, Liana Greenway.

Jon Finer:

Music is by Nat Weiner. We’re your hosts, Jon Finer.

Jake Sullivan:

And Jake Sullivan. Thanks for listening.