Next Press Secretary Odds: Scott Jennings Rising in Odds as Race to Replace Karoline Leavitt Continues
Karoline Leavitt is preparing to leave the White House press secretary role at the end of August after roughly 19 months behind the podium, opening one of the highest-profile vacancies in the Trump administration. Scott Jennings, Anna Kelly and Natalie Harp have emerged among the leading prediction-market candidates as traders react to a rapidly changing succession race.
Peter Alexis - August 20, 2026, 12:13 PM EDT
4 Minute ReadWho Will Replace Karoline Leavitt as Next Press Secretary in Trump Administration
Scott Jennings has surged 15 points to become the new market favorite at 39%, overtaking White House Deputy Press Secretary Anna Kelly at 17%. Natalie Harp sits third among the candidates shown at 6%, while more than $1.15 million has already been traded on a market that includes acting and interim appointments.
The movement has accelerated since President Donald Trump announced that Leavitt will leave at the end of August to spend more time with her family following the birth of her second child. She plans to remain an outside adviser to Trump, ending a tenure that began with his return to office in January 2025.
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Next Press Secretary Odds From Kalshi
Candidate | Implied Probability |
|---|---|
Scott Jennings | 39% |
Anna Kelly | 17% |
Natalie Harp | 6% |
Scott Jennings - 39% Chance
Jennings has become the biggest mover in the market, jumping 15 points to 39% on Thursday morning after Kelly briefly emerged as a leading option. He has not publicly confirmed that he is pursuing the position, giving evasive answers when questioned about the possibility on CNN, but reporting around the search has increasingly connected him with the vacancy.
The 48-year-old currently works as a senior political commentator for CNN and hosts a national radio program on Salem Radio Network. He also brings considerable Republican political experience, having advised Mitch McConnell, worked on both of George W. Bush's presidential campaigns and served in the Bush White House as special assistant to the president and deputy director of political affairs.
Jennings would represent a different type of selection from Leavitt. Rather than promoting directly from Trump's current communications operation, the administration would be bringing in an experienced television personality accustomed to combative live debates and defending conservative positions in an often-hostile media setting. That skill set helps explain why traders have moved so aggressively toward him despite there being no official appointment.
Anna Kelly - 17% Chance
Kelly briefly gained momentum as one of the most natural internal successors before Jennings moved decisively ahead. She currently serves as a White House deputy press secretary, meaning she already works inside the communications operation and would offer significantly more continuity than an outside appointment.
Her résumé is almost entirely built around Republican communications. Before entering the White House, Kelly served as national press secretary for the Republican National Committee and previously worked as communications director for Rep. Derrick Van Orden, Tim Michels' Wisconsin gubernatorial campaign and the Republican Party of Wisconsin. She also served as press secretary for Trump's 2024 campaign operation.
Kelly's 17% probability may therefore undersell how straightforward the transition would be. She already understands the administration's messaging structure, regularly represents the White House publicly and would not require the adjustment period associated with an outside hire. The question is whether Trump wants continuity or a more recognizable national media personality at the podium.
Natalie Harp - 6% Chance
Harp is a much longer shot at 6%, down four points, but few candidates have a closer day-to-day relationship with Trump. The White House's latest staff report lists her as special assistant to the president and executive assistant to the president, a position that keeps her directly involved in Trump's schedule, information flow and communications.
Before joining Trump's political operation, Harp worked as a presenter for One America News Network and became nationally known after publicly praising Trump's Right to Try legislation. She joined Trump's team in 2022 and has since become one of his most constant aides, including helping manage material provided to him and aspects of his social-media operation.
Her biggest obstacle may be that her current job is significantly different from the public-facing press secretary role. Harp operates largely behind the scenes and has far less briefing-room experience than Kelly or television experience than Jennings. Her proximity and loyalty to Trump keep her relevant, but the 6% market price reflects the unconventional nature of moving her directly into the podium role.
Trump Press Secretary Betting Outlook
Jennings' surge has transformed what looked like a much more open succession race. His 39% probability now puts him more than twice as high as Kelly, while his television experience, previous White House service and willingness to defend Trump publicly give him a résumé that fits the communications-heavy position.
Kelly remains the clearest continuity candidate because she is already working directly inside the White House press operation. Harp offers unmatched proximity to Trump but would require a much larger shift in responsibilities. With Leavitt remaining in office through the end of August and Trump yet to announce a replacement, the market still has enough time for another significant move before the next press secretary is formally determined.
Next Press Secretary Prediction
- Lean: Scott Jennings - 39% Chance Bet on the Next Press Secretary with Kalshi Here
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