Karoline Leavitt, the youngest White House press secretary in American history, announced Wednesday she's leaving the podium at the end of August. She's 28 years old, has two young children — including a daughter born in May — and says she can't serve both the "around-the-clock demands" of the job and her family at the same time.
So she picked the family. Good for her.
President Trump didn't exactly let her go quietly. He called Leavitt "one of my most trusted aides," "a real leader in the White House," and — in true Trump fashion — "one of the best White House Press Secretaries in the History of the Office." Capital H, capital O. He said she'd transition to an outside advisory role as "an influential voice within the Republican Party," which is the kind of send-off most political staffers would trade a kidney for.
Leavitt has held the job since Trump's January 2025 inauguration, after being named to the role in November 2024. She walked into a press room that spent four years lobbing softballs at Karine Jean-Pierre and turned it back into a contact sport. The reporters didn't love it. We did.
Now the jockeying begins. And the list of potential replacements reads like the VIP section at CPAC.
Anna Kelly, the principal deputy press secretary, is sitting at the top of prediction markets with 19 to 23 percent odds, according to Newsweek. She's the conventional pick — already in the building, already knows where the bathrooms are. Harrison Fields, another principal deputy, is in a similar lane. Sometimes the best replacement is the person already doing half the job.
Then there's Alina Habba, Trump's former defense attorney who served as counselor to the president in the West Wing and previously held the role of acting U.S. Attorney for New Jersey. She built her reputation on TV defending Trump through his legal gauntlet, and the camera likes her. Scott Jennings, the CNN commentator and former Bush aide, is pulling around 17 percent in the betting markets — which is interesting, because he's spent the last two years being the lone conservative on CNN panels who actually fights back.
Steven Cheung, the current White House communications director, is another name floating around. He already handles behind-the-scenes press secretary duties, so the promotion wouldn't require a learning curve. Katie Miller — wife of Stephen Miller, former press secretary to Vice President Pence — brings institutional knowledge and name recognition. Roma Daravi, currently VP of public relations at the Kennedy Center, is pulling 14 percent on the prediction markets.
The longer shots are more colorful. Matthew Boyle, Breitbart's Washington bureau chief, has deep ties to Trump and has conducted multiple interviews with the president. Natalie Harp, the former OAN anchor, is at roughly 13 percent. Kari Lake is on the list because of course she is — decades of journalism experience and a current role at the U.S. Agency for Global Media. Even Rachel Campos-Duffy and Jason Miller have been mentioned.
Trump hasn't settled on anyone yet, per White House sources. That means the auditions are still open, which means every name on this list is going to spend the next two weeks being very visible and very available.
The left-wing press is already trying to frame Leavitt's departure as chaos. It isn't. A 28-year-old mother of two decided that the most demanding communications job on the planet wasn't compatible with being present for her kids, and a president who's never had trouble finding talent is now sorting through a bench that most administrations would envy.