Karoline Leavitt's run behind the White House podium officially ended last week, and the search for whoever takes her place has only gotten louder since.
The press secretary job remains one of the most exposed and demanding roles in American politics. Whoever holds it becomes the executive branch's main public voice, running the daily briefings, handling the communications side of any crisis, and putting the administration's policies into words the public can follow.
The Kalshi market for “Who will be Trump’s next Press Secretary?” reflects uncertainty and volatility surrounding a question whose market trajectory can be altered at any moment.
The Press Secretary Odds: Anna Kelly is the Favorite
Anna Kelly, the principal deputy who has been Leavitt's right hand since the start of the term, has moved to the top of the Kalshi board at 26%, a clear few points ahead of second place. The move fits a pattern several outlets have picked up on: Kelly already handles a good chunk of the briefing-room and cable-news workload, so promoting her from within would be the path of least disruption for a White House with plenty else on its plate this fall.
Scott Jennings, the CNN commentator who briefly looked like the pick after reports of a sit-down with Chief of Staff Susie Wiles, has slipped to 19% after repeatedly sidestepping questions about his own interest in the role during on-air interviews.
Alina Habba, the early front-runner in the days right after Leavitt's announcement, has settled into third place at 7.4% following her own public denial that she's angling for the job.
Margo Martin, meanwhile, brings her own case: she has served since January 2025 as special assistant to the president and communications advisor, after leading press operations for Trump's team during the transition and working on his political action committee.
Why a Deal Still Looks Weeks Away
Kelly's lead doesn't mean the pick is close to final. The process has already produced one false start: Jennings' rise faded once the White House pushed back on reports that the Wiles meeting meant he had the job locked up, with a person familiar with the search telling NOTUS that Trump was "not quite sold" on him.
There's a fresher signal, too.
Tuesday marked 40 days since the White House's last formal press briefing, and a briefing is reportedly now being scheduled for Thursday, without, as of this writing, a confirmed name behind the podium.
Cabinet officials and even the vice president have taken turns fielding questions in Leavitt's absence, which is its own hint that no successor has been locked in yet. Wiles is still said to be working through the full list of candidates before bringing a recommendation to Trump, so the contract's next move is anyone's read.
What Moves the Press Secretary Odds?
Prices in executive personnel markets do not move at random. They react swiftly to specific operational and political signals that you have to monitor to correctly recalibrate your trading strategy.
Cable News Presence and Media Performance
In second-term personnel decisions, public performance during high-stakes television interviews serves as a primary vetting ground. Candidates who land frequent primetime appearances or gain praise from key figures often see immediate speculative buying in their contract prices.
High-Profile Surrogacy and Travel Rosters
High-level surrogate scheduling, press pool reports, and campaign/administration travel rosters are major catalysts for movement. When potential candidates accompany executive trips or lead briefing calls, event contracts frequently experience upward momentum.
Reporting from National Media Outlets
Because Kalshi settles contracts based on primary news reporting, leaks or sourced reporting from major outlets (The New York Times, Politico, CNN) cause instant repricing. A single sourced report naming a potential successor can cause a candidate's share price to surge.
Personnel changes in the executive branch can happen abruptly. When relying on delayed news feeds, you risk buying at the top of a rumor cycle or holding losing positions after official announcements are made.
Market Rules and Dates
First of all, Kalshi operates under Commodity Futures Trading Commission (CFTC) oversight. Individuals holding material non-public information or employed by relevant government entities are strictly prohibited from trading these contracts, or else it would be considered insider trading.
The outcome will be verified by The New York Times.
The market resolves based on the first individual who officially assumes the duties of White House Press Secretary, not merely who is nominated or announced. Acting or interim service counts toward resolution.
