CNN commentator Scott Jennings is the leading contender for White House Press Secretary.
That bombshell landed after Karoline Leavitt revealed she would step down at the end of August to focus on raising her two young children. Now, with roughly two weeks left before she walks out the door, the behind-the-scenes jockeying has reached a fever pitch, and one name keeps rising to the top.
Chief of Staff Susie Wiles has been personally courting Jennings, the 48-year-old conservative firebrand known for going toe-to-toe with liberal panels on CNN. The two shared a steak dinner at Morton's in Washington, D.C., while other contenders were busy trying to schmooze the president at his Bedminster golf club, according to reports. That dinner speaks volumes about where Wiles' loyalty lies in this particular talent search.
"It's his if he wants it," a source close to Jennings told reporters. "And he does."
Here's where it gets spicy. Three White House insiders confirmed that Jennings actually sat down with Wiles before Leavitt even made her official announcement last Wednesday. These two have apparently been chatting regularly, and the steakhouse rendezvous was just the latest meeting in what looks like a done deal in the making.
But there's a wrinkle. President Trump has reportedly said he'd prefer a woman to succeed the 28-year-old Leavitt. Still, he's apparently a big fan of what Jennings brings to the table, especially his reputation for delivering razor-sharp comebacks against hostile media figures.
Meanwhile, the Bedminster scene over the weekend sounded like absolute chaos. Former Trump attorney Alina Habba, 42, real estate executive Bill Pulte, 38, and White House aide Natalie Harp, 35, all showed up hoping to catch the president's eye. One source who knew about the weekend gathering put it perfectly: "They were all trying to get in front of him. It was like The Apprentice. It reeks of desperation."
The White House officially denied any meetings took place. Classic.
Leavitt's exit carries extra weight because it comes less than three months before the November midterms, making the selection of a battle-ready communicator even more critical. In her departure statement, Leavitt called returning to work shortly after having her second child "the most rewarding yet challenging season of my life."
Insiders painted a more stressful picture. One source revealed that Trump constantly messaged Leavitt during her maternity leave, calling it "overwhelming." The grueling demands combined with caring for two young kids meant she barely slept. She reportedly stuck it out as long as possible because she refused to let her performance suffer.
"The president did everything he could to keep her," the insider added.
Jennings, a former George W. Bush administration staffer and newspaper columnist, has built a reputation as a conservative gladiator willing to fight alone on hostile terrain. Whether Trump ultimately picks him or bows to his own stated preference for a female replacement remains the million-dollar question. But right now, every sign points to Jennings holding the winning hand.
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