Alina Habba, briefly a favorite among bettors to replace Karoline Leavitt as White House press secretary, publicly said she is not being considered for the role, cooling speculation that had swirled after Leavitt announced she would step away to focus on her family. Kalshi odds shifted quickly, placing Scott Jennings and Leavitt’s deputy Anna Kelly in the spotlight, while Habba’s past roles and a federal court decision that affected her career history added texture to the conversation.
Karoline Leavitt, 28, surprised few when she revealed she would leave the podium at the end of August to spend more time with her two young children, and that departure sparked an immediate scramble. In conservative circles that value toughness and loyalty, who fills that megaphone matters a lot, and bettors pounced on possible names almost instantly. One of the early favorites to step in was Alina Habba, and that caught attention given her close ties to the former president.
Kalshi traders gave Habba a roughly 35% shot at the time, which only made the rumor mill louder and the media narratives more breathless. That kind of betting momentum can feel like an endorsement to casual observers, but in politics the wagers often reflect chatter more than reality. Habba moved to cut through that chatter fast to avoid the optics of being parachuted into a role she didn’t want.
“Flattered by the Kalshi odds, but I’m not in the running for any job,” Habba posted on X. “However, if I’m getting a new one, I’d love for one of these anonymous sources to let me know first,” she continued. “Fake news remains the undefeated champ…well…until I come at them.”
Habba’s path in the Trump orbit has been uneven and public. She once served as counselor to the president for a short stint and was later appointed interim U.S. attorney for the District of New Jersey before a federal appeals court ruled that her service as acting U.S. attorney was unlawful, prompting her resignation. After that episode she landed a senior adviser post to the attorney general for U.S. attorneys, a role that kept her visible inside the conservative legal ecosystem.
She also had a high-profile run as the former president’s personal attorney and was a vocal surrogate during his 2024 campaign. When her name first came up after the election, she acknowledged the attention with humility while signaling where she thought she fit best. At the time she said she was “flattered” by the consideration but believed she would “be better served in other capacities.”
Once Habba publicly denied interest, the money and attention shifted again, with CNN political commentator Scott Jennings taking the lead on Kalshi and Leavitt’s deputy Anna Kelly close behind. Jennings, a former aide to President George W. Bush, has long existed in the mix of conservative commentators who know how to communicate for a Republican audience. He’s someone Trump has praised publicly, and that kind of presidential imprimatur matters in these decisions.
Trump has touted Jennings’ recent book and referred to him as a “patriot” who “gets it.” That shorthand from the president signals a lot about the kind of voice and loyalty the White House will favor if it wants a press office aligned tightly with the administration’s priorities. For anyone tracking personnel moves, those offhand endorsements are often more informative than betting lines.
Former White House press secretary Sean Spicer captured the conventional wisdom when he said, “The next press secretary will undoubtedly be someone who has a strong existing relationship with President Trump.” That’s a straight, no-nonsense way to frame the pick: proximity and trust beat fancy résumés in an environment where messaging must be unified and unswerving. Expect the process to reward allies who have already earned the president’s confidence.
Meanwhile, the day-to-day work at the podium will continue to be important, and names will keep getting floated until a formal announcement is made. Campaigns and administrations alike know the value of a steady messenger, so whoever steps into that role will be watched closely by both critics and supporters. The guessing game has only just begun, and the next chapter will depend on which loyal voice the president chooses to amplify.
Graduate Student, wife, engaged political and legal writer.