PoliticsDonald Trump's Press Secretary Search Turns Into a Fight Over Who Can Survive the Podium
Donald Trump faced growing speculation over who would replace Karoline Leavitt.
Aug. 19 2026, Published 6:29 a.m. ET
President Donald Trump has not named Karoline Leavitt’s replacement as White House press secretary, and the guessing game is already becoming its own Washington spectacle.
Leavitt, 28, stunned insiders by announcing she will leave the role at the end of August to spend more time with her two young children. Trump praised her as one of his “most trusted aides” and “one of the best White House Press Secretaries in the History of the Office.”
Speculation, and even betting, over a possible successor has focused on a very Trumpian shortlist: loyalists, TV regulars, and conservative media figures.
The Names in Play
Alina Habba was reportedly among the early names under consideration for the position.
Sources told the New York Post that early contenders include Alina Habba, Trump’s former attorney and former acting U.S. attorney for New Jersey, and Breitbart Washington Bureau Chief Matthew Boyle.
Other names reportedly being discussed include Steven Cheung, Taylor Budowich, Katie Miller, Anna Kelly, Monica Crowley, Scott Jennings and Kari Lake.
Several conservative media figures and Donald Trump allies were also floated as possible replacements.
Kalshi betting markets have also swung toward more unexpected names, including Rachel Campos-Duffy and Spencer Pratt.
Trump could also use senior officials more sporadically instead of naming an immediate replacement. JD Vance, Marco Rubio, Scott Bessent and Trump himself have all previously handled briefing-style moments.
- Donald Trump Repeatedly Called Karoline Leavitt Asking When She Would Be Back From Brief Maternity Leave Before Her Resignation, Insiders Claim
- Donald Trump Throws Karoline Leavitt Under the Bus and Claims She's 'Doing a Bad Job'
- Alina Habba's Bedminster Sighting Fuels Press Secretary Rumors After Karoline Leavitt Announces Exit From Trump Administration
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The First 60 Days
Christopher Lee said the first 60 days would be crucial for building trust inside the White House.
“The first 60 days are not about being at the podium — whether you are already on the White House staff or as an outsider,” said Christopher Lee, founder of Foresight Strategic Advisors.
“They’re about building relationships inside the building with the president and the staff, especially the Chief of Staff or Communications Director,” he explained. “In the first month, if you don’t have the trust and respect of those three individuals, the next thirty are going to be a Stephen King-level nightmare.”
Lee said the next press secretary may assume the White House press corps is easier than managing Trump’s volatility.
“They would be wrong,” he said. “This press corps has grown weary of Trump’s antics and the next person in this job is going to feel that heat.”
The Gladiator Problem
He warned that Donald Trump’s preference for confrontation could make the press secretary role especially difficult.
Lee said a normal administration would let the chief of staff shape the decision, weighing political skill and press relationships, but he argued this White House is different.
“The internal politics are dictated by the whims of a reality show president who cares little for these important elements and just wants to see combat in the press room,” Lee said. “The only person that matters is Trump — and that’s the biggest red flag for anyone who takes this job.”
Lee said viral moments may be inevitable because Trump’s ideal spokesperson is built for confrontation, “to distract and delay” coverage of the administration’s scandals.
“Trump’s press secretary he envisions as gladiator when, in fact, they are merely cannon fodder,” he said.
