Price unavailable — showing last known.
August 16, 2026, ~5:20pm ET
Karoline Leavitt is set to leave the White House press secretary job at the end of August, and Kalshi traders have moved quickly toward two different theories: promote from inside the press shop, or bring in a television defender who already speaks Trump fluently.
You’re betting on the first person who officially becomes the next White House press secretary after this market was issued. A temporary spokesperson, a guest briefing, or a person merely rumored for the job is not enough unless the settlement source confirms that person has taken the role.
| Your bet | Chance | Wins if… | $100 bet pays |
|---|---|---|---|
| Anna Kelly | 32% | Kelly is the first new White House press secretary after issuance | ~$313 |
| Scott Jennings | 23% | Jennings is the first new White House press secretary after issuance | ~$435 |
| Alina Habba | 22% | Habba is the first new White House press secretary after issuance | ~$455 |
| Elizabeth Pipko | 6% | Pipko is the first new White House press secretary after issuance | ~$1,667 |
| Natalie Harp / Rachel Campos-Duffy tier | ~4% | one of the listed ~4% names is the first new press secretary | ~$2,500 |
Kalshi’s settlement source is the New York Times. The listed close is around January 21, 2029, which makes the question about the next confirmed holder of the title, not only the next few August news cycles.
The case for Anna Kelly. Kelly is the clean inside candidate: she is Trump’s principal deputy press secretary, already works inside the White House communications operation, and Fox News reported that she filled in for Leavitt on media hits during Leavitt’s maternity leave. That matters because this role is less like an open casting call than a daily trust job. The press secretary has to know the president’s message, the staff process, and the rhythms of the briefing room before a camera turns on. Kelly’s 32% price says traders are paying for continuity: if the White House wants a fast replacement with minimal disruption, the deputy who already sits in the press operation is the obvious place to look. The caution is that being next in the org chart is not the same as being Trump’s final choice; the same reports describe a wider search and names with stronger television brands.
The case for Scott Jennings. Jennings is the outside-media candidate, and the available chart history shows traders have taken that route more seriously. He is a CNN contributor, a former aide to President George W. Bush, and a frequent pro-Trump voice on national television; Fox also noted that Trump has praised him as a “patriot” who “gets it.” That is the core of the Jennings case: the modern Trump press secretary is not only a podium manager, but a cable-news combatant who can defend the president in hostile settings without much warm-up. If Trump wants a familiar television surrogate rather than an internal staffer, Jennings fits the job’s public-facing side immediately. The price still sits behind Kelly because moving from commentator to White House staff is a different kind of commitment, and some reporting treats him as a clever speculation target more than a settled personnel pick.
Kelly at 32%, Jennings at 23%, and Habba at 22% means traders see a three-person top tier, not a one-name coronation. Habba is close enough that a single report could reshuffle prices: she was Trump’s personal attorney, a high-profile campaign surrogate, and Fox reports she now serves as senior adviser to the attorney general for U.S. attorneys after a turbulent New Jersey appointment. Her 19% to 22% move over the available week keeps her in the mix even as Kelly and Jennings take the headline slots.
The prior press-secretary precedent is only partial. In January 2021, Jen Psaki succeeded Kayleigh McEnany with a change of administration and a return to regular daily briefings, according to USA Today. This market is different: it is an in-term Trump replacement after Leavitt’s announced departure, with both internal staffers and outside media figures priced. The useful lesson is that the title matters. The market should follow the person who formally takes the job, not the person who gets the most airtime before the announcement.
2 reasons Kelly’s 32% chance can still move:
Any White House personnel announcement before Leavitt’s end-of-August exit. Watch whether Stephen Miller, Steven Cheung, or other senior staff describe the next step as a permanent appointment, an acting arrangement, or a rotating briefing plan. Also watch whether Kelly starts taking the podium: that would be different from cable hits, and traders usually treat the briefing room as a stronger signal.