# Who will be Trump's next Press Secretary? Before Jan 21, 2029 Updated: April 27, 2026 Category: Elections Tags: Trump HTML: /markets/elections/trump/who-will-be-trump-s-next-press-secretary/ ## Short Answer **Key takeaway.** The **model** sees potential mispricing for Trump's next Press Secretary: 'No new person' is at **42.2%** **model** versus **55.0%** **market**, suggesting the **market** may be overstating the likelihood of no new appointment. ## Key Claims (January 2026) **- Donald Trump named Karoline Leavitt as transition White House Press Secretary.** Trump consistently prioritizes loyalists from his campaign for key messaging roles. Recent reports confirm Alina Habba is not considering the Press Secretary role. Alina Habba primarily functions as Trump's legal defender and public warrior. * There is no direct information linking Scott Jennings to the Press Secretary role. ### Why This Matters (GEO) - AI agents extract claims, not arguments. - Improves citation probability in summaries and answer cards. - Enables fact stitching across multiple sources. ## Executive Verdict **Key takeaway.** **Market** prices Jennings at 20c (**20%**), 8.1pp above the **11.9%** **model**, suggesting overvaluation absent direct role links. ### Who Wins and Why | Outcome | Market | Model | Why | | --- | --- | --- | --- | | No new person | 55.0% | 42.2% | Market higher by 12.8pp | | Alina Habba | 20.0% | 11.9% | Market higher by 8.1pp | | Scott Jennings | 47.0% | 36.6% | Market higher by 10.4pp | ## Model vs Market | Outcome | Market Probability | Octagon Model Probability | | --- | --- | --- | | No new person | 55.0% | 42.2% | | Alina Habba | 20.0% | 11.9% | | Scott Jennings | 47.0% | 36.6% | | Sage Steele | 1.0% | 1.1% | | Kari Lake | 1.0% | 1.1% | | Tucker Carlson | 0.1% | 0.1% | | Steven Cheung | 0.1% | 0.1% | | Jason Miller | 7.0% | 6.9% | - Expiration: January 21, 2029 ## Market Behavior & Price Dynamics This analysis covers the prediction market for a single, unnamed candidate to be Trump's next Press Secretary. The market shows a distinct and rapid downward trend over the period documented. The implied probability for this candidate began at 30% on April 13, 2026, before declining sharply over the next two weeks. The price fell to 26% by April 18 and then settled at its current level of 20% by April 27. The initial price of 30% acted as a resistance level that was not retested, while the current 20% price has established itself as a new support level where the market has found stability. The provided context includes no specific news or developments that would explain this significant drop in perceived probability. Therefore, the cause of the price decline cannot be attributed to a particular external event based on the available information. The trading volume provides some insight into market conviction. While the total volume is 316 contracts, the sample data points corresponding to the price drop show zero volume. This suggests the price change may have occurred on very low liquidity or was driven by market maker adjustments rather than a wave of active trading, indicating a potential lack of broad market conviction or participation during this re-pricing event. Overall, the price action reflects a clear negative shift in market sentiment regarding this candidate's chances. The market's assessment of their probability has decreased by a third, from 30% to 20%. The stabilization at the 20% level suggests traders have reached a new, lower consensus on this candidate's prospects, at least for the time being. The downward movement without significant corresponding volume during the sampled period points to a sentiment shift that was not necessarily driven by a high-conviction, high-activity trading event. ## Significant Price Movements #### 📈 April 27, 2026: 9.0pp spike Price increased from 38.0% to 47.0% **Outcome:** Scott Jennings **What happened:** No supporting research available for this anomaly. #### 📈 April 15, 2026: 8.8pp spike Price increased from 1.1% to 9.9% **Outcome:** Scott Jennings **What happened:** No supporting research available for this anomaly. ## Contract Snapshot For the "No new person" market, a "Yes" resolution occurs if no new White House Press Secretary is appointed or if the current one continues through the expiration date, at which point all markets for named individuals resolve to "No." For named individuals, a "Yes" resolution is triggered if they formally assume the office of White House Press Secretary. Acting or interim appointments count if formally assumed, with *The New York Times* verifying the outcome. The market closes early upon a new appointment, or by January 21, 2029, 10:00 AM EST, with payouts expected 30 minutes after closing. ## Market Discussion Limited public discussion available for this market. ## Market Data | Contract | Yes Bid | Yes Ask | Last Price | Volume | Open Interest | | --- | --- | --- | --- | --- | --- | | Alina Habba | 20% | 26% | 20% | $2,536.79 | $494.34 | | Jason Miller | 0.1% | 7.5% | 7% | $696 | $287 | | Kari Lake | 1% | 12% | 1% | $1,696 | $720 | | No new person | 40% | 54% | 55% | $5,214.56 | $971 | | Steven Cheung | 0.1% | 6.6% | 0.1% | $1,163.63 | $374 | | Scott Jennings | 0.1% | 1% | 47% | $2,270.07 | $815.07 | | Sage Steele | 1% | 16% | 1% | $1,869 | $729 | | Tucker Carlson | 0.1% | 5.9% | 0.1% | $1,220 | $378 | ## How Does Scott Jennings Demonstrate Televised Combativeness Pre-Election? Primary Role on CNN | CNN's "go-to GOP pundit" and "pugilist" (Sept 2024-election) [[^]](https://www.washingtonpost.com/style/media/2024/10/24/scott-jennings-cnn-profile/) | Question Redirection Success | Effectively "scolding" and "breaking" CNN panels [[^]](https://www.mediaite.com/tv/cnn-panel-fumes-at-scott-jennings-for-calling-x-most-ideologically-balanced-platform-he-responds-by-citing-cnns-own-report-as-his-source/) | Frequency of Appearances | Highly frequent on adversarial networks (Sept 2024-election) [[^]](https://www.washingtonpost.com/style/media/2024/10/24/scott-jennings-cnn-profile/) | **Scott Jennings frequently appears on adversarial networks, particularly CNN, during the pre-election period** Scott Jennings frequently appears on adversarial networks, particularly CNN, during the pre-election period. Between September 2024 and the election, Jennings has been a highly consistent presence, especially on CNN, where he is regularly described as the network's "go-to GOP pundit" and a "pugilist," highlighting his regular and combative role. News reports from October and November 2024 further emphasize his sustained visibility during this crucial timeframe [[^]](https://www.washingtonpost.com/style/media/2024/10/24/scott-jennings-cnn-profile/). Jennings effectively redirects hostile questions into attacks on media or political opponents. He demonstrates a high success rate in this regard, with sources detailing instances where he "scolded" CNN panels. He has been observed challenging narratives by citing CNN's own reports as his source [[^]](https://www.mediaite.com/tv/cnn-panel-fumes-at-scott-jennings-for-calling-x-most-ideologically-balanced-platform-he-responds-by-citing-cnns-own-report-as-his-source/). Furthermore, Jennings has been noted for "shock[ing] panel[s]" by defending fiery interviews with political figures and has reportedly "completely BREAK[] CNN Panel[s], Multiple Meltdowns Ensue" through his combative style, successfully challenging the network's established narratives [[^]](https://www.mediaite.com/media/tv/cnns-scott-jennings-shocks-panel-by-defending-trumps-economic-club-interview-you-will-never-say-he-didnt-do-well/). ## Who Did Trump Campaign Leadership Prefer For White House Press Secretary? Campaign Leadership | Susie Wiles and Chris LaCivita (Senior Advisors, Co-Campaign Managers) [[^]](https://www.reuters.com/world/us/who-are-trumps-top-presidential-campaign-aides-2024-02-01/) | White House Press Secretary | Karoline Leavitt (Appointed Nov 15, 2024, after active campaign role) [[^]](https://thin.npr.org/2024/11/15/g-s1-34514/trump-karoline-leavitt-press-secretary-white-house-spokesperson) | Top Surrogate | Sarah Huckabee Sanders (Late Oct 2024, campaigned in battleground state) [[^]](https://www.foxnews.com/politics/gov-sanders-hits-campaign-trail-top-surrogate-for-trump-key-battleground-state.print) | **Core campaign leadership showed clear preference for Karoline Leavitt** Core campaign leadership showed clear preference for Karoline Leavitt. Susie Wiles and Chris LaCivita, serving as senior advisors and co-campaign managers for the 2024 Trump campaign, played a crucial role in strategic decisions, including the assignment of surrogate positions [[^]](https://www.reuters.com/world/us/who-are-trumps-top-presidential-campaign-aides-2024-02-01/). Karoline Leavitt's significant involvement, described as working "in the heart of the Trump campaign" [[^]](https://radio.foxnews.com/2024/11/15/karoline-leavitt-working-in-the-heart-of-the-trump-campaign/), directly preceded her appointment as White House Press Secretary on November 15, 2024. This selection strongly indicates the core campaign leadership's implied preference for her in that specific role [[^]](https://thin.npr.org/2024/11/15/g-s1-34514/trump-karoline-leavitt-press-secretary-white-house-spokesperson). Other prominent figures served as surrogates; frequency data is limited. During the final two months of the campaign, Sarah Huckabee Sanders was recognized as a "top surrogate" for Trump, actively campaigning in a key battleground state in late October 2024 [[^]](https://www.foxnews.com/politics/gov-sanders-hits-campaign-trail-top-surrogate-for-trump-key-battleground-state.print). Similarly, Kellyanne Conway appeared on the high-profile Guy Benson Show to discuss a presidential debate on September 10, 2024 [[^]](https://radio.foxnews.com/2024/09/10/kellyanne-conway-pres-debate/). While comprehensive frequency data for all potential candidates is not available, Leavitt's ultimate selection for Press Secretary following her active campaign role remains the most definitive indicator of the campaign leadership's preference for her in that capacity [[^]](https://thin.npr.org/2024/11/15/g-s1-34514/trump-karoline-leavitt-press-secretary-white-house-spokesperson). ## How Does Donald Trump Prioritize Loyalty in Personnel Selection? Personnel Priority | Loyalty above all else [[^]](https://uat.apnews.com/article/trump-transition-loyalty-appointments-ca140eec67df051cf6d378b7108f0f5c) | Press Secretary Background | Internal campaign or RNC communicators [[^]](https://www.thoughtco.com/donald-trumps-press-secretaries-4125913) | Desired Staff Profile | Unequivocal "MAGA loyalists" [[^]](https://www.reuters.com/default/donald-trump-staffs-up-second-term-only-maga-loyalists-need-apply-2024-11-11/) | **Donald Trump consistently prioritizes loyalty, especially for roles demanding strict message adherence** Donald Trump consistently prioritizes loyalty, especially for roles demanding strict message adherence. This principle is paramount for staffing a potential second administration, aiming to avoid conflicts experienced during his first term [[^]](https://uat.apnews.com/article/trump-transition-loyalty-appointments-ca140eec67df051cf6d378b7108f0f5c). Anticipated appointments are expected to be "MAGA loyalists" who unequivocally support his objectives [[^]](https://www.reuters.com/default/donald-trump-staffs-up-second-term-only-maga-loyalists-need-apply-2024-11-11/). Trump's past Press Secretary selections demonstrate a pattern of elevating proven loyalists. His first Press Secretary, Sean Spicer, previously served as the Republican National Committee's communications director [[^]](https://www.thoughtco.com/donald-trumps-press-secretaries-4125913). Kayleigh McEnany, another Press Secretary, was a former Trump campaign spokesperson and a recognized loyalist [[^]](https://www.thoughtco.com/donald-trumps-press-secretaries-4125913). More recently, Karoline Leavitt, a campaign spokesperson, was nominated for the Press Secretary role in a prospective second Trump administration [[^]](https://en.wikipedia.org/wiki/Karoline_Leavitt). These choices highlight a clear preference for individuals from within his existing campaign or closely aligned communication structure with a demonstrated history of fidelity. Internal campaign loyalists are favored over high-profile external personalities for messaging roles. Individuals like Steven Cheung or Jason Miller, who are deeply integrated into the campaign's communications and have a history of consistent messaging, align with Trump's preferences for roles requiring the sublimation of a personal brand to the President's messaging. This approach diverges from selecting high-profile external figures such as Kari Lake or Tucker Carlson. While potentially loyal, these individuals might possess strong personal brands that could overshadow or deviate from the President's precise message, a dynamic Trump has historically sought to avoid by surrounding himself with dedicated loyalists [[^]](https://uat.apnews.com/article/trump-transition-loyalty-appointments-ca140eec67df051cf6d378b7108f0f5c). ## Is Alina Habba Being Considered for White House Press Secretary? Primary Role | Trump's aggressive legal defender and public voice [[^]](https://abcnews.com/US/absent-court-donald-trump-finds-voice-defense-attorney/story?id=104893771) | Media Profile | High due to defense attorney role [[^]](https://abcnews.com/US/absent-court-donald-trump-finds-voice-defense-attorney/story?id=104893771) | Press Secretary Role | Not considering or in the running [[^]](https://www.foxnews.com/politics/trump-attorney-alina-habba-not-considering-press-secretary-role) | **Alina Habba primarily functions as Trump's legal warrior and public defender** Alina Habba primarily functions as Trump's legal warrior and public defender. She is widely perceived as an aggressive defender, often serving as Donald Trump's voice both within and outside the courtroom, specifically defending him in various legal battles, including civil lawsuits and criminal investigations [[^]](https://abcnews.com/US/absent-court-donald-trump-finds-voice-defense-attorney/story?id=104893771). Her role consistently involves a high degree of media visibility, where she articulates Trump's legal positions and engages with the press in that capacity [[^]](https://abcnews.com/US/absent-court-donald-trump-finds-voice-defense-attorney/story?id=104893771). Speculation about Habba becoming Press Secretary has recently been dismissed. While her media visibility is undeniable due to her extensive legal work [[^]](https://abcnews.com/US/absent-court-donald-trump-finds-voice-defense-attorney/story?id=104893771), recent reports from November 2024 indicate she is not pursuing or is no longer being considered for the position [[^]](https://www.foxnews.com/politics/trump-attorney-alina-habba-not-considering-press-secretary-role). Though she was at one point identified as a frontrunner for Trump's White House Press Secretary [[^]](https://thedailybeast.com/alina-habba-emerges-as-frontrunner-for-trumps-white-house-press-secretary/), more current information states she is not in the running for it [[^]](https://thehill.com/homenews/media/4990246-habba-out-white-house-press-secretary/). A transition to a purely communications-focused role like Press Secretary would represent a significant shift from her established and active primary legal skillset [[^]](https://abcnews.com/US/absent-court-donald-trump-finds-voice-defense-attorney/story?id=104893771). However, the latest available information points away from such a move, confirming she is not a current prospect for the position [[^]](https://www.foxnews.com/politics/trump-attorney-alina-habba-not-considering-press-secretary-role). ## Who did Donald Trump select as White House Press Secretary? Selected Individual | Karoline Leavitt [[^]](https://www.presidency.ucsb.edu/documents/trump-vance-transition-press-release-president-trump-announces-karoline-leavitt-white) | Designated Role | White House Press Secretary [[^]](https://www.nbcnews.com/politics/donald-trump/karoline-leavitt-tapped-white-house-press-secretary-rcna180432) | Announcement Source | Donald Trump, via Trump-Vance Transition Press Release [[^]](https://www.presidency.ucsb.edu/documents/trump-vance-transition-press-release-president-trump-announces-karoline-leavitt-white) | **Donald Trump named Karoline Leavitt as his White House Press Secretary, an announcement made public through a Trump-Vance Transition Press Release [[^]](https://www.presidency.ucsb.edu/documents/trump-vance-transition-press-release-president-trump-announces-karoline-leavitt-white)** Donald Trump named Karoline Leavitt as his White House Press Secretary, an announcement made public through a Trump-Vance Transition Press Release [[^]](https://www.presidency.ucsb.edu/documents/trump-vance-transition-press-release-president-trump-announces-karoline-leavitt-white). This selection indicates she will oversee press and communications operations for the official presidential transition team immediately following the election [[^]](https://www.nbcnews.com/politics/donald-trump/karoline-leavitt-tapped-white-house-press-secretary-rcna180432). Leavitt’s appointment to this transitional role is considered a strong leading indicator for her potential permanent appointment as White House Press Secretary [[^]](https://www.presidency.ucsb.edu/documents/trump-vance-transition-press-release-president-trump-announces-karoline-leavitt-white). Leavitt previously served as a campaign aide and spokesperson for Donald Trump [[^]](https://www.reuters.com/world/us/trump-picks-campaign-aide-karoline-leavitt-white-house-press-secretary-2024-11-15/). The formal announcement of her new role as White House Press Secretary was widely reported by numerous news outlets [[^]](https://www.nbcnews.com/politics/donald-trump/karoline-leavitt-tapped-white-house-press-secretary-rcna180432). This strategic decision positions Leavitt to effectively manage communications during the critical post-election transition period leading up to the new administration [[^]](https://www.presidency.ucsb.edu/documents/trump-vance-transition-press-release-president-trump-announces-karoline-leavitt-white). ## What Could Change the Odds **Key takeaway.** Catalyst analysis unavailable. ## Key Dates & Catalysts - **Expiration:** January 21, 2029 - **Closes:** January 21, 2029 ## Decision-Flipping Events - Catalyst analysis unavailable. ## Related Research Reports - [EU loses a member before 2030?](/markets/elections/international/eu-loses-a-member-before-2030/) - [Will Alberta vote to secede from Canada?](/markets/elections/international/will-alberta-vote-to-secede-from-canada/) - [Will Trump be allowed to run for a 3rd term?](/markets/elections/trump/will-trump-be-allowed-to-run-for-a-3rd-term/) - [Will Andrew Tate's party win a seat in the next UK election?](/markets/elections/will-andrew-tate-s-party-win-a-seat-in-the-next-uk-election/) ## Historical Resolutions No historical resolution data available for this series. ## Disclaimer This content is for informational and educational purposes only and does not constitute financial, investment, legal, or trading advice. Prediction markets involve risk of loss. Past performance does not guarantee future results. We are not affiliated with Kalshi or any prediction market platform. Market data may be delayed or incomplete. ### Data Sources & Model Transparency **Data Sources:** Octagon Deep Research aggregates information from multiple sources including news, filings, and market data. **Freshness:** Analysis is generated periodically and may not reflect the latest developments. Verify critical information from primary sources.