Trump’s search for Karoline Leavitt’s successor remains open following her late-August 2026 departure, with White House Chief of Staff Susie Wiles overseeing discussions and briefings rotating among senior officials. Multiple internal and external candidates have been floated, including Deputy Press Secretary Anna Kelly, CNN contributor Scott Jennings—who met with Wiles but faces some MAGA resistance over past McConnell ties—and communications adviser Margo Martin, whom Trump publicly named alongside Jennings. Reports indicate a broad applicant pool and no settled frontrunner, with traders assigning the highest individual probabilities to Kelly and Jennings while spreading the balance across a long list of aides, commentators, and allies. The absence of a confirmed pick or decisive signals from Trump keeps the field competitive.