President Donald Trump’s Press Secretary Karoline Leavitt’s is leaving the role, opening one of the more active non-election prediction markets in Washington.
With the forward-facing role open, traders have jumped into the action looking to figure out who’s next to take the Trump administration podium.
For now, the market says Scott Jennings.
The CNN contributor and conservative commentator leads Kalshi’s next press secretary contract at 32% on $1.3 million in volume. White House deputy press secretary Anna Kelly is second at 19%, followed by former Trump attorney Alina Habba at 11%.
Polymarket numbers are close, with Jennings trading at 31% on about $90,000, Kelly at 19%, and Natalie Harp and Habba tied at 8%.
Jennings has the market edge
Jennings is the obvious market favorite because he already plays the public-facing role of Trump defender nightly on CNN. He has become one of the administration’s most recognizable outside surrogates, often mixing aggressive attacks on Democratic opponents with a polished television style that would translate naturally to the briefing room.
Trump has reportedly signaled interest in Jennings and discussed replacing Leavitt with a man. However, NOTUS reported that the president is not yet sold on Jennings as the final choice.
This is a Trump personnel market, which means “leading” is not the same as “chosen.”
The odds also reflect a familiar market dynamic. Jennings is a clean and easy-to-understand trade. He has national visibility, a cable-news résumé, access to Trump-world, and a role that already looks adjacent to the job.
But none of that necessarily gives him Kelly’s internal relationships or Habba’s personal loyalty profile.
Kelly and Habba stay alive
Kelly is the institutional option. As principal deputy press secretary, she already understands the briefing operation and would offer continuity after Leavitt’s departure. Her 19% pricing on both Kalshi and Polymarket makes her the clearest alternative if Trump decides the White House does not need a splashy outsider.
Habba is the loyalty pick. Trump’s former defense attorney and former acting U.S. attorney for New Jersey have remained prominent administration allies, and reports have repeatedly placed them in the mix. She is also the kind of candidate who could move sharply in a market like this if Trump signals even a mild preference. On the flip side, she has said she is not in the running.
The difference between the two is the selection logic. Kelly is the smoother transition. Habba is the higher-variance Trump choice. Jennings sits between them as an already aggressive communicator, but not yet an administration official.
Breaking the streak
Trump’s reported preference for a man would end a long run of women in the job. Leavitt has been the only press secretary of Trump’s second term so far, and she followed Sarah Huckabee Sanders, Stephanie Grisham and Kayleigh McEnany in Trump’s first administration.
Trump did begin his first term with Sean Spicer, who held the job for about six months in 2017 before Sanders took over. So the all-women streak is not a continuous Trump-era record from day one.
A Jennings pick would make the personnel decision more than a routine staff replacement. It would signal that Trump wants a different kind of public messenger for the next phase of the administration, someone whose brand was built on argument, cable news combat and defending the president outside the briefing room.
The Scaramucci rule
There is one final reason to take this market with a little caution: The Trump White House has never been a place where a title is confused with job security.
Trump had four official press secretaries in his first term: Spicer, Sanders, Grisham and McEnany. That is plenty of turnover around the broader communications operation. Anthony Scaramucci, of course, remains the benchmark for how quickly a Trump communications job can become a historical footnote.
Scaramucci was communications director rather than press secretary, but the 11-day tenure still stands as Washington’s reminder not to get too attached to the market favorite.
For now, Jennings is the leader on prediction markets. But with Trump reportedly unconvinced, Kelly positioned inside the building and Habba waiting in the loyalty lane, this is less a settled appointment market than a live read on what kind of fight the White House wants to bring to the podium next.
