CNN commentator Scott Jennings could soon move from analyzing the White House on television to speaking for it.
Jennings, 48, is being pushed by White House Chief of Staff Susie Wiles to replace outgoing White House press secretary Karoline Leavitt, according to a new report from the Daily Mail.
“It’s his if he wants it,” a source told the outlet. “And he does.”
Leavitt is stepping down to spend more time with her family, setting off a scramble among potential successors for one of the administration’s most visible positions.
The report indicates, however, that President Donald Trump has not settled on Jennings. Trump reportedly has a preference for a woman in the role, and the field of possible replacements remains crowded.
Jennings nevertheless appears to have a significant advocate in Wiles. According to the Mail, Jennings and the White House chief of staff had been meeting even before Leavitt’s departure plans became public.
A longtime Republican political operative, Jennings has become one of CNN’s most recognizable conservative commentators, regularly defending Trump administration policies and challenging liberal panelists during the network’s political discussions.
But Jennings is hardly the only person being considered.
Trump met with several possible candidates at his Bedminster golf club over the weekend, according to the report. Among them was Alina Habba, 42, who previously served as one of Trump’s attorneys.
Federal Housing Finance Agency Director Bill Pulte, 38, and Trump aide Natalie Harp, 35, also reportedly met with the president.
One source gave the Daily Mail a colorful description of the competition.
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
“They were all trying to get in front of him this weekend. It was like The Apprentice,” the source said. “It reeks of desperation.”
The list extends well beyond those weekend meetings.
The Mail identified 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 director Steven Cheung and former Kennedy Center spokeswoman Roma Daravi as other potential candidates.
CNN reported still more possibilities.
Principal deputy press secretary Anna Kelly is reportedly in the mix, along with Monica Crowley, the former Fox News personality who currently serves as chief of protocol. Trump political adviser Jason Miller has also been mentioned.
Other names include former principal deputy press secretary Harrison Fields and former ESPN anchor Sage Steele.
CNN even floated Lara Trump, the president’s daughter-in-law and wife of Eric Trump, as a possible choice.
With that many candidates circulating, Trump does not appear interested in conducting anything resembling a conventional hiring process.
That became particularly obvious Sunday when Fox News correspondent Alexis McAdams interviewed him and the subject of Leavitt’s replacement came up.
Asked whom he might choose, Trump turned the question directly back on McAdams.
“You,” he said. “How about you?”
Trump then addressed Leavitt while discussing the Fox correspondent.
“She could do the job,” he said. “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.”
Whether McAdams was receiving a genuine invitation or simply experiencing Trump’s improvisational approach to personnel speculation was not immediately clear.
Jennings presents a very different possibility.
