President Trump posted an AI-generated image of himself at the White House podium captioned "The Best Press Secretary", a pointed bit of humor as the scramble to replace departing spokeswoman Karoline Leavitt heats up.
The Thursday night Truth Social post landed days after Leavitt, 28, announced she would leave the White House at the end of the month, citing the demands of raising two young children while holding one of the most visible jobs in Washington. Trump had already called her departure "a decision I totally understand and respect" and praised her as "one of the best White House press secretaries in the history of the office."
But the AI image, Trump standing behind the briefing room lectern, grinning at the assembled press corps, carried an unmistakable message: the president is enjoying the guessing game over who comes next. And the field of contenders, according to the Daily Mail's reporting, is already crowded with competing factions and quiet lobbying campaigns.
CNN political commentator and Daily Mail columnist Scott Jennings, 48, is the reported frontrunner. White House chief of staff Susie Wiles has been courting Jennings for the role, and Trump himself is described as a "fan" of the former George W. Bush aide who built a reputation for sharp, combative defenses of the president on CNN's own airwaves.
Picking Jennings would carry a particular sting for CNN. The network's most reliable conservative voice would walk straight from the studio into the briefing room, a move guaranteed to generate headlines and deprive the left-leaning network of one of its few right-of-center regulars.
But Jennings is not the only name circulating. Former U.S. Attorney Alina Habba is understood to have lobbied Trump directly for the job. Elizabeth Pipko, a former model and ex-spokeswoman for the Republican National Committee, has supporters pushing her candidacy as well.
One complication: insiders say Trump has expressed a preference for a woman to replace Leavitt. If that preference holds, it could sideline Jennings despite his frontrunner status. CNN and Semafor both reported that Trump is in no rush to make a decision, a posture that leaves room for the jockeying to continue.
Leavitt's departure does not happen in isolation. The White House communications operation is losing depth at a moment when it can least afford to. Deputy press secretary Abigail Jackson left last week. Director of media affairs Sonny Joy Nelson departed earlier in the year. The team that will face the press through the fall midterm campaign is thinner than it has been since Trump returned to office.
Leavitt posted her resignation statement on X on Wednesday, writing plainly about the tension between the job and motherhood:
"Being a mother and welcoming a new baby while working in one of the most demanding jobs in the world has been the most rewarding yet challenging season of my life, to say the least. The truth is since returning to the White House after the birth of my daughter, I have felt in my heart that I cannot be the best mom my two young children deserve while devoting the constant time, energy, and attention required of the White House Press Secretary, and that is why I have ultimately made the bittersweet decision to depart the White House and embark on a new chapter in my life."
She gave birth to her daughter Vivi in May and returned from maternity leave on July 16, barely a month before announcing her resignation. She also has a two-year-old son, Niko. Her husband is real estate developer Nicholas Riccio, 60, whom she married in January of last year.
Leavitt first entered Trump's orbit during his first administration in 2018, starting as a presidential writer before rising to assistant White House press secretary. She joined his 2024 re-election campaign as national press secretary and was named to the top communications job when Trump returned to the Oval Office. Her tenure included attending classified briefings in the Situation Room, an unusual distinction for a press secretary, and counseling the president through major crises including the Jeffrey Epstein scandal.
She was last seen publicly with the president and his team on Tuesday, aboard Air Force One for a trip to Ohio for the Patriot Games.
During Leavitt's maternity leave, the White House took an unorthodox approach to the daily briefing: cabinet secretaries stepped in. Vice President JD Vance, Secretary of State Marco Rubio, and Treasury Secretary Scott Bessent all took turns at the podium. The arrangement, first reported by the Daily Mail, turned the briefing room into a rotating showcase for the administration's top officials rather than a platform for a single spokesperson.
That experiment may have given Trump a taste for variety at the lectern, and may explain the playful AI image. The president's Thursday night posting spree also included a repost about the Keystone XL pipeline and a separate image placing an outline of his face in the Lincoln Memorial Reflecting Pool. The press secretary image was the one that drew attention, but the broader pattern was pure Trump: a late-night social media session mixing policy, self-promotion, and provocation in equal measure.
Trump said Leavitt would remain a "top outside adviser" and an "influential voice" at the top of the Republican Party after her departure. Whether that means a formal role in midterm campaign operations or a looser advisory arrangement remains unclear.
The open questions around the replacement are piling up. Jennings has not publicly confirmed or denied interest. Habba's lobbying has been reported but not confirmed by her directly. Trump's stated preference for a female successor could reshape the field entirely. And the White House has not offered a timeline for a decision, the Daily Mail reached out for comment and received no response.
With midterm elections in November and a communications team already thinned by departures, the vacancy is more than a staffing question. The press secretary is the administration's daily voice to the country, the person who frames every policy fight and deflects every attack. Leaving the role unfilled, or filling it with the wrong pick, carries real cost heading into a campaign season.
Trump may be in no rush. But the calendar is.
