Look Who The White House Is Courting

CNN commentator Scott Jennings is reportedly emerging as a serious contender to replace Karoline Leavitt as White House press secretary as President Donald Trump weighs who should become the administration’s next public face.

According to the Daily Mail, White House Chief of Staff Susie Wiles is pushing for Jennings, 48, to take over the job after Leavitt steps down to spend more time with her family.

“It’s his if he wants it,” a source told the Daily Mail. “And he does.”

The report suggests Jennings has been under consideration for some time. Jennings and Wiles were reportedly meeting before Leavitt’s plans to leave the position became public, indicating that discussions over a possible transition may have started well before the broader search became known.

Jennings has become a familiar presence on CNN, where he regularly offers a conservative perspective during political panel discussions. His combative but measured television style has made him one of the network’s most recognizable Republican commentators, which could make him a natural fit for a job that requires frequent exchanges with an often-hostile White House press corps.

Still, Jennings is far from the only name being discussed.

The Daily Mail reported that Trump met with several possible candidates at his Bedminster golf club over the weekend. Among those reportedly seeking consideration were former Trump attorney Alina Habba, real estate executive Bill Pulte and Trump aide Natalie Harp.

“They were all trying to get in front of him this weekend. It was like The Apprentice,” one source said. “It reeks of desperation.”

Other names reportedly in the mix include former Department of Homeland Security press secretary Katie Zacharia, former DHS spokeswoman Tricia McLaughlin, Breitbart Washington bureau chief Matthew Boyle, Republican National Committee spokeswoman Elizabeth Pipko, White House communications chief Steven Cheung and former Kennedy Center spokeswoman Roma Daravi.

Shock Frontrunner–Scott Jennings, to Replace Leavitt Holds Secret Meetings With White House
USING HIS WILES
Donald Trump’s top White House aide is backing the president’s pet pundit.https://t.co/AsWEX98zNr

— moonbreeze (@moonbreeze2) August 19, 2026

CNN has reported on an even broader field of possible replacements. Its list included principal deputy press secretary Anna Kelly, former Fox News host and current chief of protocol Monica Crowley, Trump adviser Jason Miller, former principal deputy press secretary Harrison Fields and former ESPN anchor Sage Steele.

Lara Trump, the president’s daughter-in-law and wife of Eric Trump, has also been mentioned as a possible choice.

The selection process appears to remain fluid, with Trump himself publicly entertaining possibilities.

During a Sunday interview, Trump turned the question back on Fox News correspondent Alexis McAdams when he was asked who he might select.

“You,” Trump told her. “How about you?”

He then turned to Leavitt and added, “She could do the job. What do you think, Karoline? I like it. I’ve always liked you. That’s why I’m doing this. I don’t do this that often.”

For now, Jennings appears to be one of the more prominent names in contention, particularly if the Daily Mail’s reporting about Wiles’ support is accurate. But the crowded field, combined with Trump’s preference for making personnel decisions on his own terms, means the outcome remains uncertain.

Whoever gets the job will inherit one of the most demanding communications roles in Washington, serving as the administration’s primary spokesperson while handling daily scrutiny from reporters and defending White House policy in real time.

The Western Journal