Karoline Leavitt spent two years walking into a room full of reporters who wanted her dead and walking back out with Trump's message intact.
The race to replace her now has a frontrunner.
One TV star just jumped to the top of the list – and the White House is not saying a word.
Scott Jennings Was Already Meeting With Susie Wiles Before Leavitt Announced Her Departure
Karoline Leavitt's exit last week caught Washington off guard – but not Susie Wiles. Insiders say Trump was messaging Leavitt constantly through maternity leave after the birth of her second child. The job was grinding her down and she refused to let it show – until she couldn't anymore.
Wiles had already moved on her behalf before she did.
Three sources told the Daily Mail that White House Chief of Staff Susie Wiles had already met with CNN conservative commentator Scott Jennings about the press secretary job before Leavitt even formally announced she was leaving.
They've since met again. They "speak often," per one source. And the clearest signal of all: "It's his if he wants it. And he does."
Jennings is not sitting back and waiting, either.
According to Politico, he sent clips of himself defending Trump aide Natalie Harp – after Georgia Democrat Jon Ossoff made a crude insinuation about her at a campaign rally – to multiple senior White House staffers.
People close to the president called it a "fairly obvious public audition" for a job he has been eyeing since the transition.
Jennings, 48, is a Kentucky native who served as special assistant to President George W. Bush and built RunSwitch PR into the largest public relations firm in the state. For nearly a decade, he's been CNN's resident conservative – the lone voice on panels that run four-to-one against him, going viral week after week when he refuses to budge.
Trump has praised him by name at rallies. At a campaign stop in Warren, Michigan, the president told the crowd: "We have a man here that I don't know, but he's defending me all the time on CNN. And he defends me really well – but he can't go too far, because if he goes too far, he'll get fired."
Trump then addressed Jennings directly: "Don't worry, we will take care of you Scott."
Turns out, that wasn't a throwaway line.
Alina Habba and a Dozen Rivals Swarmed Bedminster While the Frontrunner Was Already at the Table
Trump's New Jersey golf club in Bedminster turned into something one source called "The Apprentice" this past weekend.
The hopefuls included White House communications chief Steven Cheung, former Trump attorney Alina Habba, Breitbart Washington bureau chief Matthew Boyle, aide Natalie Harp, RNC spokeswoman Elizabeth Pipko, real estate mogul Bill Pulte, former DHS press secretary Katie Zacharia, ex-DHS spokeswoman Tricia McLaughlin, and former Kennedy Center spokeswoman Roma Daravi.
"They were all trying to get in front of him this weekend," one source told the Daily Mail. "It reeks of desperation."
The White House officially denies that any meetings between Wiles and Jennings took place. Jennings hasn't confirmed them publicly either – though when CNN anchor Abby Phillip pressed him on air about whether he was throwing his name in the ring, he shook his head, then pivoted to praising Leavitt without ever saying no.
Scott Jennings Built His Name Beating Liberals on CNN – Now He May Own the Briefing Room
The media establishment cannot process a Jennings appointment for one simple reason: he's been beating them on their own network for nine years.
CNN put him on panels to provide the token conservative voice – outnumbered, surrounded, with anchors who wanted a punching bag. Instead, he became one of the most clipped, shared, and argued-about commentators on television.
Every viral moment the Left celebrated as a "takedown" became a fundraising clip for the Right.
There is one complication. Trump has made clear he'd prefer a woman behind the podium – and Wiles knows it.
Politico reports the president is "not quite sold" on Jennings. The president loved what Leavitt represented: young, female, fearless, unbreakable under fire. Jennings is none of those things.
Wiles was at Mastro's before Leavitt's departure was public knowledge. In Trump's White House, she is the one who actually controls personnel – not the chaos at Bedminster, not the hopefuls angling for face time on the golf course.
She doesn't make social calls. Jennings has already decided. The question is whether Trump will get there too.
Sources:
- Elina Shirazi, "TV star emerges as shock frontrunner to replace Karoline Leavitt," Daily Mail, August 18–19, 2026.
- Ahmad Austin Jr., "Scott Jennings Sent His Natalie Harp Remarks to White House in Bid to Succeed Leavitt as Press Secretary," Mediaite, August 20, 2026.
- Jack Davis, "Late Breaking: Scott Jennings Being Courted to Replace Karoline Leavitt," Western Journal, August 19, 2026.
- Staff, "Scott Jennings Doesn't Deny White House Press Secretary Speculation," Barrett Media, August 14, 2026.
- Matt Margolis, "Scott Jennings for Press Secretary? I Dig It," PJ Media, August 14, 2026.