Who Will Be Trump’s Next Press Secretary?
Karoline Leavitt is leaving the White House press secretary role at the end of August, and the race to replace her is changing quickly. Alina Habba currently leads the Kalshi market, Scott Jennings has surged into second, and several current White House officials remain in contention.
Donald Trump has one of the most visible jobs in his White House to fill after Karoline Leavitt announced that she will step down as press secretary at the end of August. The decision immediately created a wide-open succession race involving current White House communications officials, longtime Trump allies, political commentators, and several outside names.
The prediction market has moved rapidly since Leavitt's departure became public. Alina Habba now leads at 40%, followed by Scott Jennings at 20%, Anna Kelly at 14%, Natalie Harp at 6%, and Elizabeth Pipko at 4% in the latest market snapshot. Total market volume has reached $918,953.
Those numbers have changed substantially in only a few days. Anna Kelly previously led the market, Jennings has moved sharply higher, and Habba has returned to the top as speculation around Trump's eventual decision grows.
This is exactly the kind of personnel decision where Prediction Markets can change quickly. One credible report, White House meeting, television appearance, or announcement could completely reorder the current prices.
Trump's Next Press Secretary Market Snapshot
Market figures reflect the August 19, 2026 Kalshi snapshot reviewed for this article. Probabilities, contract prices, bid-ask spreads, and available quantities can change at any time.
Karoline Leavitt Is Leaving at the End of August
Leavitt's departure surprised Washington because she had become one of the most recognizable members of Trump's second-term White House.
Trump announced that she will leave the press secretary position at the end of August so she can spend more time with her two young children and family. Leavitt said the decision was bittersweet and that she had concluded she could not balance the demands of the job with the kind of mother she wanted to be.
She is expected to remain connected to Trump as an outside adviser rather than severing ties with the president and his political operation.
The timing makes the succession decision more important. The next press secretary will inherit the briefing room during the closing months of the 2026 midterm cycle, while the administration continues managing domestic policy, foreign affairs, economic issues, and a highly confrontational national media environment.
How the Kalshi Market Resolves
The market asks who will be the first new person to begin serving as White House press secretary after the contract was issued.
Acting and interim service counts. That is important because the White House does not necessarily need to announce a permanent appointment for one of these contracts to resolve.
The market resolves based on who actually begins serving in the position, not simply who Trump announces, considers, interviews, or reportedly prefers.
If no new person begins serving before the market's final expiration date, the individual candidate contracts resolve to No and the separate "No new person" outcome resolves to Yes.
Who Is Favored to Replace Karoline Leavitt?
Alina Habba
40%Trump's former attorney is the current market favorite, with Yes contracts currently displayed around 40¢.
Scott Jennings
20%The CNN senior political commentator is second in the market, with Yes contracts currently displayed around 21¢.
Anna Kelly
14%The principal deputy press secretary already works inside the White House press operation and previously led the market.
Natalie Harp
6%The longtime Trump aide remains a lower-priced contender because of her close working relationship with the president.
| Potential Press Secretary | Current Chance | Displayed Yes Price | Displayed No Price |
|---|---|---|---|
| Alina Habba | 40% | 40¢ | 61¢ |
| Scott Jennings | 20% | 21¢ | 80¢ |
| Anna Kelly | 14% | 14¢ | 89¢ |
| Natalie Harp | 6% | 5¢ | 96¢ |
| Elizabeth Pipko | 4% | 5¢ | 96¢ |
| No new person | 3.7% | 3.8¢ | 96.3¢ |
| Lara Trump | 2% | 3¢ | 98¢ |
| Steven Cheung | 1.8% | 1.6¢ | 98.9¢ |
| Kari Lake | 1.3% | 1.2¢ | 99¢ |
| Sage Steele | 1.1% | 1.2¢ | 99¢ |
| Katie Miller | Below 1% | 1¢ | — |
The displayed chance and current contract offer can differ slightly because prediction markets use live order books. Prices may move between the time this article is updated and the time a reader views the market.
Why Alina Habba Is the Current Favorite
Habba has several characteristics that make her an obvious candidate for Trump.
She has represented Trump personally, served as one of his most recognizable legal and political surrogates, worked as a counselor to the president, and later served as the administration's acting U.S. attorney in New Jersey.
More importantly for the press secretary role, Habba already understands Trump's communication style. She has spent years defending him in television interviews and responding to aggressive questioning in high-profile legal and political disputes.
The New York Post identified Habba as one of the early frontrunners after Leavitt's departure became public. Her existing relationship with Trump gives her something an outside communications professional would need time to develop.
That familiarity may matter because the press secretary is not simply a television spokesperson. The person needs to understand how Trump wants an issue presented, when he wants the White House to push back, and which messages he considers most important.
Scott Jennings Has the Television Experience for the Job
Jennings presents a very different option.
He is a CNN senior political commentator and has been part of the network's political coverage since 2017. He is regularly placed in live panel discussions where he argues the conservative position against journalists, Democratic strategists, former government officials, and other commentators.
That environment requires quick responses, message discipline, and the ability to defend a position while several people are challenging it at the same time. Those are skills that translate naturally to the White House briefing room.
Jennings also has previous government and Republican political experience. He served in the George W. Bush administration and has spent years working in Republican politics before becoming one of the most recognizable conservative voices on CNN.
The question is whether Trump wants an outside media personality or someone who has already spent years working directly with him.
For readers unfamiliar with how contract prices translate into probabilities, our Kalshi Prediction Markets page explains the basic structure of these markets.
Anna Kelly and Natalie Harp Remain Serious Possibilities
Anna Kelly
Kelly may have the most conventional path to the job. She is already the White House principal deputy press secretary, making her the highest-ranking member of the press operation directly below Leavitt.
She previously served as a spokesperson for Trump's 2024 campaign and as national press secretary for the Republican National Committee.
Kelly led the prediction market earlier in the succession process. Her price has since fallen, but her existing role means she cannot be dismissed simply because traders have shifted toward Habba and Jennings.
Natalie Harp
Harp offers something different. She has developed an unusually close working relationship with Trump and has served as one of his most constant aides.
Her experience is much less centered on briefing reporters than the backgrounds of Habba, Jennings, or Kelly. Still, Trump's personnel decisions have often placed substantial weight on loyalty, personal trust, and an individual's ability to communicate his views accurately.
At roughly 6%, the current prediction market considers Harp possible but clearly less likely than the top three names.
Trump May Not Name a Permanent Replacement Immediately
There is another possibility that complicates every candidate contract.
The Independent reported that Trump was caught off guard by Leavitt's decision and that the White House did not initially intend to name an immediate permanent replacement.
According to that report, senior administration officials such as Vice President JD Vance, Secretary of State Marco Rubio, and Treasury Secretary Scott Bessent could continue appearing in the briefing room, as they did during Leavitt's maternity leave.
That does not mean Trump will ultimately leave the position vacant. It does mean traders need to distinguish between speculation about a permanent successor and the specific Kalshi settlement rule, which also counts acting or interim service.
When Will Trump Announce the Next Press Secretary?
Kalshi also has a separate announcement-date market. These contracts ask whether Trump's next press secretary will be announced before a series of specific dates.
The latest snapshot shows traders assigning a 40% displayed chance to an announcement before August 28, 64% before September 15, and 77% before October 1. The Yes contract prices do not always match the displayed chance exactly because each date has its own live order book.
| Announcement Date | Displayed Chance | Yes Price | No Price |
|---|---|---|---|
| Before Aug. 14, 2026 | Resolved No | — | — |
| Before Aug. 18, 2026 | Resolved No | — | — |
| Before Aug. 21, 2026 | 9% | 6¢ | 97¢ |
| Before Aug. 25, 2026 | 7% | 14¢ | 93¢ |
| Before Aug. 28, 2026 | 40% | 24¢ | 79¢ |
| Before Sept. 1, 2026 | 36% | 36¢ | 65¢ |
| Before Sept. 8, 2026 | 43% | 43¢ | 64¢ |
| Before Sept. 15, 2026 | 64% | 64¢ | 43¢ |
| Before Oct. 1, 2026 | 77% | 83¢ | 24¢ |
These are separate cumulative date contracts. The displayed chance and current Yes or No offer can differ because each contract has its own order book, liquidity, and bid-ask spread.
What the 100-Contract August 28 Example Looks Like
The supplied Kalshi order screen shows 100 Yes contracts on the outcome Before Aug. 28, 2026 at an average price of 24¢.
100 contracts: estimated total cost of $25.28, maximum payout of $100, and displayed potential profit of $74.72 if the announcement occurs in time for that contract to resolve Yes.
That example uses the live order screen rather than a simplified calculation, so it reflects the estimated transaction cost shown by Kalshi at that moment.
There Are Still Plenty of Other Names in the Race
The field extends well beyond the four people currently drawing the most attention.
Reporting has also identified White House Communications Director Steven Cheung, Breitbart Washington Bureau Chief Matthew Boyle, former White House deputy chief of staff Taylor Budowich, Katie Miller, Monica Crowley, Kari Lake, Jason Miller, and several other Trump allies as potential choices. The current Kalshi board also lists Elizabeth Pipko at 4%, Lara Trump at 2%, Steven Cheung at 1.8%, Kari Lake at 1.3%, Sage Steele at 1.1%, and Katie Miller below 1%.
That matters because a 40% favorite is still far from certain. Habba may lead every individual candidate, but the combined probability assigned to everyone else is larger.
Personnel markets can also react dramatically to information that was not previously public. One meeting with Trump, a report from a White House correspondent, or an unexpected person appearing at an administration event could produce an immediate change.
Trade the Next Press Secretary Market
Kalshi lists separate Yes and No contracts for the potential successors to Karoline Leavitt. Current prices change as traders react to new reporting and White House developments.
View the Market on KalshiWhat a Winning Alina Habba Prediction Could Pay at 40¢
Alina Habba Yes contracts are currently displayed around 40¢. If Habba is the first new person to begin serving as White House press secretary, each winning contract pays $1.
The examples below use whole contracts purchased at a constant 40¢ price. They are simplified examples before fees and assume enough contracts are available at that price.
| Investment | Whole Contracts | Approx. Cost | Payout if Habba Wins | Approx. Profit Before Fees |
|---|---|---|---|---|
| $25 | 62 | $24.80 | $62 | $37.20 |
| $50 | 125 | $50.00 | $125 | $75.00 |
| $100 | 250 | $100.00 | $250 | $150.00 |
| $250 | 625 | $250.00 | $625 | $375.00 |
| $500 | 1,250 | $500.00 | $1,250 | $750.00 |
| $1,000 | 2,500 | $1,000.00 | $2,500 | $1,500.00 |
Examples use a constant 40¢ purchase price. Actual fills may occur at several prices, particularly on larger orders, and fees can change the final cost and profit.
The 1,000-Contract Alina Habba Example Shown on Kalshi
The order-entry screen supplied for this article shows a 1,000-contract Habba Yes order with an average price of 42.83¢.
1,000 Habba Yes contracts: estimated total cost of $445.46, maximum payout of $1,000, and displayed potential profit of $554.55 if Habba wins the contract.
This order-screen example is separate from the simplified 40¢ table above. The live order book, available prices, and transaction costs can make the estimated order total different from a simple contract-price multiplication.
What a Winning Scott Jennings Prediction Could Pay at 21¢
Scott Jennings Yes contracts are currently displayed around 21¢. The market's displayed chance is 20%, so the live Yes offer and the displayed probability are not exactly the same measurement.
The examples below use whole contracts purchased at a constant 21¢ price. They are simplified examples before fees and assume enough contracts are available at that price.
| Investment | Whole Contracts | Approx. Cost | Payout if Jennings Wins | Approx. Profit Before Fees |
|---|---|---|---|---|
| $25 | 119 | $24.99 | $119 | $94.01 |
| $50 | 238 | $49.98 | $238 | $188.02 |
| $100 | 476 | $99.96 | $476 | $376.04 |
| $250 | 1,190 | $249.90 | $1,190 | $940.10 |
| $500 | 2,380 | $499.80 | $2,380 | $1,880.20 |
| $1,000 | 4,761 | $999.81 | $4,761 | $3,761.19 |
Examples use a constant 21¢ purchase price. Contract prices can move rapidly, available quantities vary, and actual transaction fees can reduce the final return.
What Could Change the Market Next?
A Trump Endorsement
Any public signal from Trump that one person is his preferred choice could create the largest immediate market move.
White House Meetings
Credible reporting that a contender has met privately with Trump or Chief of Staff Susie Wiles could quickly change expectations.
An Acting Appointment
Because acting and interim service counts, even a temporary assignment could resolve the market before a permanent appointment is made.
Television Performances
Trump places substantial importance on media presentation. High-profile interviews involving Habba, Jennings, Kelly, or another contender could matter.
A New Candidate
The current market includes a long list of possibilities, and Trump has a history of making personnel decisions that were not the consensus expectation.
No Immediate Replacement
If the White House continues rotating senior officials through briefings, the market may remain unresolved longer than traders currently expect.
Our Pick Is Alina Habba, With Scott Jennings a Very Close Second
This section reflects the opinion of Bonus Predictions and Robert Beadle. It is separate from the reporting and prediction-market data above.
First and foremost, we love Karoline Leavitt, and we are going to miss seeing her behind the White House podium.
In our opinion, she has been the best press secretary in American history. She understood President Trump, she knew exactly what message the administration wanted to communicate, she was extremely quick on her feet, and she never seemed intimidated by a difficult question or an aggressive exchange with reporters.
Replacing that is not easy.
Looking at the current field, we agree with the two names at the top of the Kalshi market. Alina Habba and Scott Jennings both make a lot of sense, and we think either one could do an excellent job.
If we had to choose one, though, we would probably take Alina Habba.
The biggest reason is that she already knows Trump. She has represented him, defended him publicly, worked around him, and spent years learning exactly how he communicates and what he expects from the people speaking on his behalf.
That is a major advantage in this White House.
Habba is also tough. She does not back down easily, and we have already watched her handle adversarial television interviews and difficult press exchanges without losing control of her message. The White House briefing room can become confrontational very quickly, and we do not think she would have any problem handling that environment.
There would be almost no learning curve when it comes to Trump's brand, communication style, priorities, or expectations.
Scott Jennings, though, may be almost perfectly built for the media side of this job.
He has spent years sitting on CNN panels where he is often the only conservative voice in the discussion. He regularly has to defend his position in real time while other commentators challenge him from several directions.
That is valuable experience.
Jennings understands how television news operates. He understands how reporters and political commentators frame stories. He knows how to identify the weak point in an argument quickly, and he is comfortable responding without needing a prepared script.
He also knows many of the journalists, anchors, commentators, and political figures who shape the Washington media conversation. He would enter the briefing room already understanding the personalities and the dynamics around him.
That could make him extremely effective.
The choice between the two comes down to what Trump values more for this specific appointment.
If he wants someone who already knows him personally, understands his instincts, has defended him for years, and will aggressively push back against a press corps that often challenges his administration, Habba makes a tremendous amount of sense.
If he wants someone whose biggest advantage is live political debate, media strategy, and years of experience taking on opposing viewpoints on national television, Jennings may be the better choice.
Our pick today is Habba, but not by much.
Either way, we think these are the two strongest choices in the current field, and we would be very comfortable seeing either one behind the podium.
The Current Favorite Is Still Far From Certain
Habba's 40% market probability makes her the favorite, but it still leaves most of the market's combined probability spread across Jennings, Kelly, Harp, Pipko, and the rest of the field.
Personnel markets are especially sensitive to private information becoming public. The next major report could move these prices considerably in minutes.
The Kalshi settlement rules also make acting and interim appointments important. Traders should review the complete market terms rather than assuming the contract only resolves after a permanent appointment.
Who Will Be Trump's Next Press Secretary?
Alina Habba currently has the clearest lead, but the race is not settled.
Her 40% probability puts her ahead of Scott Jennings at 20%, Anna Kelly at 14%, Natalie Harp at 6%, and Elizabeth Pipko at 4%. At the same time, reporting suggests Trump may not be in a hurry to choose a permanent replacement.
Habba has the direct Trump relationship. Jennings has the television and debate experience. Kelly has the strongest existing position inside the press office. Harp has a close personal working relationship with the president.
Those are four very different cases for the job, and the market is currently giving the biggest advantage to the person who already has years of experience speaking publicly for Trump.
That makes Habba our pick today, but this is one of those prediction markets where the answer could change quickly.
Follow the Next Press Secretary Prediction Market
Prices can change quickly as new reporting develops. You can view the current market on Kalshi or review our Kalshi Promo Codes page for current Bonus Predictions promotion information.
View the Press Secretary MarketSources
- USA Today: Who Could Replace Karoline Leavitt as White House Press Secretary
- The Hill: Trump Faces Near-Impossible Task of Replacing Karoline Leavitt
- The Independent: White House Has No Immediate Plan to Replace Karoline Leavitt
- New York Post: Karoline Leavitt's Possible Successors Emerge After Surprise Departure
- Dr. Steve Turley: Karoline Leavitt Replacement Leaves Dems Spiraling
Robert Beadle
Robert Beadle leads Bonus Predictions editorial direction, content strategy, research structure, and digital publishing. His work covers prediction markets, event contracts, government markets, political developments, bonuses, and the factors influencing live market prices.
Bonus Predictions may receive compensation when readers create an account through an affiliate or referral link. Compensation does not change the prediction-market data, source reporting, or editorial content presented in this article. Kalshi market prices and probabilities can change at any time. Personnel decisions can also change without advance notice. Author-opinion sections represent the named author's personal viewpoint. This article provides general information and is not financial advice.
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