In January 2025, Karoline Leavitt became the youngest White House Press Secretary in American history, at just 27 years old. Leavitt’s position as a trusted go-to talent for President Donald Trump was cemented during the 2024 campaign. Once the Butler, Pennsylvania, events transpired, Leavitt returned to her duties as the campaign’s National Press Secretary just four days after giving birth to her first child.
But a lot can happen in two years. Leavitt gave birth to her second child earlier this year. After returning to her White House job two months later, she ultimately resigned her position, citing the need to be with her family. Trump’s loss is a gain for political prediction markets on Kalshi, where roughly $3.5 million has already been traded on who will be Karoline Leavitt’s successor.
At just 26¢ per contract, we see a lot of value in Anna Kelly. This is especially true for traders who have already drawn the conclusion that Scott Jennings’ close ties to establishment politics make him a less viable candidate to function adequately under the unique demands of President Trump.
As a former beauty pageant contestant (who won “Miss State Fair” of Virginia in 2019), Kelly possesses a pedigree that CNN anchor Scott Jennings simply can’t compete with. Kelly, who is already the Principal Deputy Press Secretary, is partially “filling in” for the role Leavitt left open while the president chooses a permanent replacement.
Ironically, Anna Kelly is just half a year older than her former boss, Karoline Leavitt. If she is chosen before January, she will still be in her 20s when she takes over the official duties as the next White House Press Secretary. Trump’s former personal attorney Alina Habba is an intriguing pick and is currently priced at around 10 cents per contract. However, Habba has already publicly stated that she’s not interested in the job.
Hypothetically speaking, Trump’s former lead defense attorney Alina Habba might find it difficult to turn down an offer from the 45th (and 47th) US president. The fact that Trump has given her official responsibilities since retaking office (first as White House Counselor and then as a senior advisor to the DOJ when her role as an acting US Attorney was shot down by a federal court) would put Habba in an uncomfortable position if she were formally asked to take the open position.
But we’re confident that Habba was sincere in her August 19th post on X when she said she was “flattered by the Kalshi odds, but I’m not in the running for any job.” If she truly wished to be the next White House Press Secretary, she could probably make a personal request to the president given the fierce loyalty she’s shown towards him over the past few years.
Those who follow politics closely can forecast who the next White House Press Secretary will be on Kalshi right now. It only takes a couple of minutes to register a new account. All winning contracts settle at exactly $1 and there is no minimum, except for the price of a single contract, on how much can be traded.
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