White House Press Secretary Karoline Leavitt announced last week that she will leave her position at the end of August to spend more time with her two young children, setting off speculation about who Trump will select to replace her.
With only about two weeks remaining before Leavitt’s departure, rumors have been swirling about who might replace Leavitt.
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In a significant development for the Trump administration, CNN political commentator and staunch conservative voice Scott Jennings has positioned himself as the leading candidate to succeed Leavitt.
Sources close to the process reportedly told the Daily Mail that Chief of Staff Susie Wiles has actively engaged Jennings in private discussions about the critical communications role.
While several ambitious figures sought face time with President Trump at his Bedminster golf club over the weekend, Wiles focused her efforts elsewhere.
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The influential chief of staff dined with Jennings at a Washington, D.C., steakhouse, underscoring her preference for the seasoned media fighter known for his unapologetic defenses of the president against left-leaning cable news attacks.
“It’s his if he wants it,” one source close to Jennings said of the press secretary job. “And he does.”
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Jennings, 48, a former George W. Bush administration aide and Daily Mail columnist, has earned widespread respect in conservative circles for routinely standing alone against hostile liberal panels on CNN.
His track record of sharp, effective rebuttals makes him uniquely equipped to handle the White House briefing room’s aggressive press corps.
Three White House sources familiar with the selection process confirmed that Jennings met with Wiles before Leavitt’s formal announcement of her departure last Wednesday.
The pair connected again this weekend at Morton’s and ‘speak often,’ a source told the Daily Mail.
President Trump has expressed a preference for a female successor to the 28-year-old Leavitt, yet he remains a strong admirer of Jennings’ capabilities.
EXCLUSIVE: White House Chief of Staff Susie Wiles was at DC steakhouse Mastro’s blocks away from the White House having dinner with her chosen candidate to replace Karoline Leavitt.
Read all the details about their private dinner last weekend: https://t.co/8pIjPRlZdt
— Elina Shirazi (@elinashirazi) August 19, 2026
The timing of Leavitt’s exit, coming less than three months before the pivotal November midterms, has intensified the search for a battle-tested communicator who can advance the administration’s agenda without flinching.
As Wiles and Jennings conferred, Trump hosted competing aspirants at Bedminster.
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Among them was Alina Habba, 42, the president’s former attorney recognized for her tenacity and media presence.
Also present were real estate executive and close Trump ally Bill Pulte, 38, and White House aide Natalie Harp, 35.
“They were all trying to get in front of him this weekend. It was like The Apprentice,” one source who was informed about the weekend said. “It reeks of desperation.”
Jennings stands out as the clear frontrunner.
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His willingness to break with conventional narratives when necessary has not diminished the confidence Trump’s team places in him.
The White House officially denied to the Daily Mail that any meetings occurred. Jennings and Wiles were contacted for comment.
Leavitt’s departure created an urgent scramble within the administration.
In a statement, she described returning to work soon after the birth of her second child as “the most rewarding yet challenging season of my life.”
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Insiders explained that the intense demands contributed to her decision.
“It was a constant stream of messages from him [during maternity leave] and it was overwhelming,” one insider explained.
“It was a very stressful job to do with her children. She never got any sleep, and she didn’t want her performance to slip either, so she decided to stay as long as she could and do the job well. The president did everything he could to keep her,” the source added.
This article may contain commentary which reflects the author’s opinion.
