It’s become Washington’s hottest new parlor game: Who will be Karoline Leavitt’s successor?
Names started circulating at dinner tables and over text chains after President Donald Trump announced on Wednesday his press secretary’s plans to depart at the end of the month to spend more time with her young family, upending his press operation with less than three months until the midterm elections.
For a president who believes he’s his own best spokesperson, replacing Leavitt — who took a proactive, public-facing role but also became one of his most trusted advisers — will be a challenge.
“She is one of one. Nobody will ever be able to do what she did,” White House communications director Steven Cheung told CNN in a text message Thursday.
It was not immediately clear to some White House staff who would fill the role, a source told CNN. One source close to the White House suggested the president might not name a replacement until after the midterms, while some predicted the role might stay unfilled for the duration of Trump’s two and a half years left in office.
But one GOP operative granted anonymity to speak freely suggested the job should be filled — and soon.
“It’s another deployable asset for the midterms,” they said.
Potential candidates
The president has yet to weigh in on who could fill Leavitt’s shoes.
But about a dozen names emerged as potential options from CNN’s conversations with several communicators and advisers in Trump’s orbit. The White House downplayed any shortlists as speculation or wish casting, and CNN hasn’t confirmed to what degree Trump is considering any of these people or whether they’re pursuing the job.
Some names are current or former Trump staffers, many have cable news experience, and at least one is a Trump family member.
Among the names circulating is Scott Jennings, who served in the George W. Bush White House and has made waves as a CNN contributor sparring on the president’s behalf. Jennings — who had the backing of Donald Trump Jr. for the top spokesperson job during the presidential transition, according to a source with knowledge — has deflected about interest in the role this time around.
“I don’t know but I’ll tell you this: Karoline Leavitt has been maybe the greatest White House press secretary in the last 30 years at least. She’s been nothing short of brilliant,” he said Wednesday on CNN’s “NewsNight with Abby Phillip.”
Alina Habba, a former lawyer and political adviser to Trump who briefly served as acting US attorney for the District of New Jersey, has been floated as an option with Trump’s trust.
And then there’s Leavitt’s number two, principal deputy press secretary Anna Kelly, who’s one of a small handful of staffers authorized to speak as a surrogate on outlets including Fox News.
Tricia McLaughlin, who became a frequent presence on cable news during her time aggressively defending Trump’s border policies as Department of Homeland Security spokesperson, could be another option who’s earned Trump’s confidence.
Elizabeth Pipko, a former model and Republican National Committee spokesperson, has close ties with the Trump family and was under consideration for the job before Leavitt’s selection, a source close to Trump said.
Monica Crowley, a former Fox News analyst now serving as the US chief of protocol, often travels with the president and plays host to world leaders visiting Washington.
Allies of Roma Daravi, who worked in Trump’s press shop in his first term and now is communications director for the embattled Kennedy Center, have been promoting her on social media as a contender. The president’s daughter-in-law, Lara Trump, could also be an option. She served as Republican National Committee chair during the 2024 presidential campaign and now hosts a weekly show on Fox News.
Other names that came up in CNN’s conversations include longtime Trump communicator Jason Miller, former principal deputy press secretary Harrison Fields and former ESPN anchor-turned-MAGA-ally Sage Steele.
Prediction markets have also begun prognosticating. Kalshi Politics ranked Habba, Kelly, Miller and Daravi at the top of its list Thursday morning. (CNN has a partnership with Kalshi and uses its data to cover major events. But CNN editorial employees are not allowed to use prediction markets.)
It’s also entirely possible that the president goes in another direction altogether.
“There will be plenty of people who try to drum up noise. If anybody seems too eager or like they’re pushing too much, that could turn the president off,” said Erin Maguire, a Republican strategist and spokesperson for Trump’s 2020 presidential campaign.
No heir apparent
One of the reasons a replacement wasn’t immediately clear, multiple sources familiar with the matter said, is because the timing of Leavitt’s decision caught the president and the White House off guard.
Prior to the birth of her second child in May, Leavitt had privately suggested she might stay in the role for the entirety of Trump’s second term. That didn’t sit well with some staffers, with one source familiar raising concerns that Leavitt did not create a pipeline of talent in her press shop — which is now becoming a problem.
“The team didn’t really get the latitude to be seen as heir apparent,” that source said, adding that Leavitt’s predecessors in Trump’s first term had been intentional about empowering lower-level staffers.
Leavitt — who Trump said will remain an outside adviser — will likely have some influence over Trump’s eventual decision, that source suggested.
In the short-term, multiple sources suggested the White House could return to the playbook used during Leavitt’s maternity leave, deploying Vice President JD Vance and Secretary of State Marco Rubio, among other top officials, to deliver the day’s messaging and field questions — although they handled the pressure of the podium with various levels of success.
What Trump’s prioritizing
Trump isn’t a traditional president who needs a traditional press secretary to interface with the media — he often speaks directly to the press and has also been known to respond to reporters’ calls and texts.
Regardless of whether he goes for someone who’s on TV or who operates more behind-the-scenes, his pick will have to have his trust.
“I don’t see an instance where someone from outside the orbit comes in. That’s the biggest hurdle — it’s a small pool of people qualified and enough in the orbit to be considered,” Maguire said.
There’s also the question of presentation.
“Everything is viewed through the eyes of ‘central casting,” said one source close to Trump, adding, “I don’t think he cares who can actually do the job. I think it’s about what he or she looks like.”
But another source suggested he may want someone who’s “less of a celebrity” than Leavitt, who became a household name and built an Instagram following of more than 3 million during Trump’s second term.
Many of the potential contenders have promoted the president and his policies on right-leaning outlets, and Leavitt solidified a practice of turning to friendly reporters during her briefings, including the establishment of a “new media” seat.
But the source close to Trump suggested that any viable contender should spend some time defending the president on other networks to prepare for the rapid-fire of the briefing room.
“I don’t think people grasp how much studying is required to do that job, how much reading, how much thoroughly understanding every topic you could possibly be asked — I don’t think everybody recognizes how much work that is,” the source said.
But ultimately, Leavitt’s successor will have to perform for an audience of one.
“It is the biggest podium in the world, so filling that role is one of the biggest calculations the president is going to make — because he cares about message, he cares about the messaging, and he cares about the messenger,” Maguire said.
By CNN
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