Who Will Trump Pick as the Next Press Secretary?

The hunt for Donald Trump’s next press secretary continues, after former incumbent Karoline Leavitt formally stepped down on August 27th to spend more time with her young family. For now, Trump intends to fill the role temporarily. Various heads of department, including Secretary of State Marco Rubio and Treasury Secretary Scott Bessent, will take turns performing media duties, after Vice President JD Vance stepped up to the podium last week. In the meantime, traders are continuing to speculate on the identity of the next permanent press secretary on Polymarket. Over $420,000 has been traded so far, after the market opened on August 14th. Below, I’ll analyze the field and reveal the best value picks. I’ll also highlight the optimal trading strategy in this type of market. Our exclusive Polymarket bonus code is CORG and will get you $20 after you sign up and deposit $10. If you’re looking for similar options and contracts to trade, check out our list of the best political betting sites. Anna Kelly Odds – The Favorite – But is She Overpriced? Will Anna Kelly be the next White House Press Secretary? Yes 22% · No 78% View full market & trade on Polymarket “Anna Kelly” | “Yes” at 23¢ | 22% Chance Anna Kelly is the favorite in this market. Her price has traded above 20¢ consistently since September 5th, while her current win probability has reached 22%. One of the primary factors in Kelly’s favor is that she currently works as the deputy press secretary. She worked closely under Leavitt and has previously represented the White House in the media. The 29-year-old former beauty queen has extensive political experience outside of the White House, too, previously working as the national press secretary for the Republican National Committee (RNC). She also served as communications director for the Wisconsin Republican Party. Kelly’s status as favorite is built largely on her current role and the fact that she’s a staunch Trump loyalist. She has backed most of the President’s hardline positions on migration, foreign affairs, and even the media, echoing the President’s catchphrase “fake news” and attacking journalists. Ultimately, this may be causing Kelly to be slightly overpriced at the current benchmark of 23¢. However, she remains a key frontrunner and deserved favorite, and media speculation could send her price even higher in the coming weeks. There’s certainly a potential upside here. So, snap up “Yes” shares now and wait for their value to move above 35¢. Did you know? Did you know? Our exclusive Polymarket promo code, CORG, will earn you a $20 trading bonus when you sign up to Polymarket and make a $10 deposit. Scott Jennings Odds – A Political Commentator With Significant Backing Will Scott Jennings be the next White House Press Secretary? Yes 18% · No 82% View full market & trade on Polymarket “Scott Jennings Odds” | “Yes” at 18.9¢ | 18% Chance Scott Jennings may appear to be an outlier in this particular market. A political commentator on CNN, Jennings was previously critical of Trump and his administration, while his close relationship with Senator Mitch McConnell has drawn ire from the President’s MAGA base. However, Jennings’ ties with McConnell were forged during three Presidential election campaigns. Jennings has worked on four Presidential campaigns in total, and has a wealth of political experience to count on. The 48-year-old has also become a fierce defender of Trump on CNN. One recent viral monologue argued passionately that the US had achieved its strategic war objectives in Iran. Jennings aggressively defended Trump’s executive assistant Natalie Harp after criticism of a public security incident, too. Trump has praised Jennings for his backing. When asked recently by reporters about Leavitt’s replacement at Joint Base Andrews, Trump answered directly by saying “Scott Jennings is good”. He also responded positively to a book written by Jennings, with “A Revolution of Common Sense: How Donald Trump Stormed Washington and Fought for Western Civilization” praising the President’s leadership. By showing loyalty to Trump and garnering his support, Jennings may follow the path of Pete Hegseth into a top-tier administration role. Overall, his current price of 18.9¢ offers value and a viable upside, while it’s up from 12.2¢ since September 5th. So, consider buying “Yes” shares now. Alina Habba XIV Odds – A Longshot With a Significant Potential Upside Will Alina Habba be the next White House Press Secretary? Yes 6% · No 94% View full market & trade on Polymarket “Alina Habba” | “Yes” at 7.6¢ | 6% Chance Alina Habba was one of the frontrunners when this market opened, with an initial win probability of 41%. However, the 42-year-old announced that she was “not in the running for any job” on August 19th, causing her odds to plummet to just 6%. However, Habba remains a viable candidate on Polymarket, and has generated $28,733 in trading volume so far. Although many may have traded “No” as they look to lock in a small but reliable profit, there’s still a chance that Habba could be selected for the role. Formerly Trump’s personal lawyer, Habba now works as a senior advisor to the U.S. Attorney General at the Department of Justice. This followed a brief stint as acting U.S. attorney for the District of New Jersey, which was cut short when a local court rejected her nomination. This decision is being appealed, and she may return to the role if the ruling is subsequently overturned. However, she has close ties to Trump and has served briefly as his counsellor, while the President has previously praised her for being “unwavering in her loyalty.” Habba remains a viable longshot, even at a price of 7.6¢ (up from just 1.4¢ on September 6th). Further media speculation or praise from Trump could easily send her price into double figures, creating a potential exit point above $14¢. Photo by LOU ROCCO/American Broadcasting Companies, Inc. via Getty Images Margo Martin Odds – Another Longshot Who Has Received a Direct Endorsement from Trump Will Margo Martin be the next White House Press Secretary? Yes 2% · No 98% View full market & trade on Polymarket “Margo Martin Odds” | “Yes” at 2.6¢ | 2% Chance Margo Martin is another genuine longshot in this market. Like Scott Jennings, however, she has received a direct endorsement from Trump in relation to the role of press secretary. During the same media appearance in which he suggested Jennings as a viable contender, Trump also asked the assembled journalists, “How about Margo? What do you think of Margo?”. This is far from definitive, of course, but it shows that she’s viewed as a key contender by the President himself. This should come as no surprise. Trump places significant stock in loyalty, and Martin was one of the few staffers who stayed by his side after he left office back in 2021. She has also survived numerous administrative reshuffles and retains the absolute trust of the President. Martin currently works as a special assistant to Trump and his communications advisor. So, she’s closer to the President than any rival contender and has strong fundamentals despite her lack of media presence. All these factors count in the 31-year-old’s favor, while suggesting that Martin is underpriced at just 2.6¢. Her price has previously peaked as high as 26¢ on August 15th, and the potential upside here is significant. Martin is a popular MAGA insider, too, so consider buying “Yes” shares now and targeting an exit point of 10¢ or higher. The Last Word – How to Trade this Market Attempting to forecast a winner in this market is incredibly difficult and laden with risk. Not only is there a broad depth of candidates, but it’s hard to accurately evaluate the favorites or pre-empt Trump’s impulsive decision making. Instead, you should look to buy and flip positions for a profit. Price changes in the market are largely driven by media narratives and trader sentiment, so targeting potentially underpriced outcomes and selling them prior to settlement is highly recommended. This also requires you to set realistic exit points for trades. This includes setting an attainable sale price that’s capable of delivering a profit, without risking exposure to low demand or liquidity. You should also note that this market will settle on December 31st, 2026, at 11:59pm ET. It will resolve to “Other” if no individual is chosen to replace Leavitt before this date and time, too. Want to make any of these trades? Use our exclusive CORG promo code on Polymarket to earn a $20 trading bonus when you register and deposit $10. The post Who Will Trump Pick as the Next Press Secretary? appeared first on Casino.org.