CNN contributor Scott Jennings deflected questions about replacing outgoing White House press secretary Karoline Leavitt, but a recent dinner with the president's chief of staff suggests the search is further along than he let on.
Jennings appeared on CNN's "State of the Union" on Sunday and refused to engage with reports that he sits atop the shortlist to take over the White House podium when Leavitt departs at the end of August.
"I don't know what's going to happen. I don't have anything to say about it this morning," Jennings told the program's host, offering praise for Leavitt instead of any hint about his own ambitions. He called her "one of the best press secretaries in the... modern era" and added that "whoever does that job [has] big shoes to fill." The non-denial left the door wide open.
Jennings' careful deflection came days after Newsmax reported that CNN had identified him as an early favorite for the job. CNN reported Thursday that Jennings recently met with White House chief of staff Susie Wiles at Mastro's Steakhouse in Washington, D.C., a detail that moved the conversation from cable-news chatter to something more concrete.
Multiple White House staffers reportedly believe Jennings has Wiles' backing in the search. President Trump, when asked about Jennings, offered a brief but telling endorsement: "Scott Jennings is good."
Trump has also signaled he is in no hurry. CNN reported Thursday that the president told members of his team he wanted to take his time choosing Leavitt's successor, a posture that could stretch the process into September even as Leavitt's last day approaches at month's end.
Leavitt announced Friday that she will leave the White House to return to Trump's MAGA Inc. super PAC, where she worked before joining the 2024 presidential campaign. Fox News reported that Leavitt cited wanting to spend more time with her two young children as a driving reason for her departure.
The field of possible replacements extends well beyond Jennings. The New York Post reported that early front-runners were believed to include Alina Habba, a former acting U.S. attorney now serving as a senior adviser to the attorney general, and Breitbart Washington Bureau Chief Matthew Boyle. Other names floated include Taylor Budowich, Steven Cheung, Katie Miller, Anna Kelly, Monica Crowley, and Kari Lake.
Habba quickly took herself out of contention. "Flattered by the Kalshi odds, but I'm not in the running for any job," she said publicly, referring to the prediction market where she had been listed as the betting favorite at 35 percent odds. After her denial, Jennings moved to the top of the Kalshi board, followed by Leavitt's deputy Anna Kelly.
If Jennings does land the role, he would bring a résumé built across multiple Republican power centers. He worked for former President George W. Bush and advised Senate Majority Leader Mitch McConnell before becoming one of the most visible conservative voices on CNN. Throughout the 2024 campaign and into Trump's second term, Jennings has been a frequent and forceful defender of the president's policies on CNN and on his own radio program.
That track record matters. Former White House press secretary Sean Spicer, who held the podium during the early months of Trump's first term, framed the key qualification plainly. "The next press secretary will undoubtedly be someone who has a strong existing relationship with President Trump," Spicer said.
Jennings checks that box. Trump's four-word assessment, "Scott Jennings is good", may not be effusive, but it is the kind of direct, on-the-record signal this White House tends to send before a decision crystallizes.
Several questions remain unanswered. No one has confirmed that Jennings received a formal offer, or that the Mastro's dinner with Wiles explicitly covered the press secretary vacancy. The White House has not disclosed how many candidates are under serious consideration, and Trump's stated desire to take his time leaves the process open-ended.
Jennings, for his part, stuck to compliments rather than commitments on Sunday. He praised both Leavitt and former press secretary Sarah Huckabee Sanders, who served during Trump's first term, without tipping his hand.
Trump also weighed in on Leavitt's tenure with a statement calling her "one of the best White House Press Secretaries in the History of the Office", high praise from a president not known for handing it out freely.
The White House podium is one of the most visible jobs in American politics, and whoever steps behind it next will inherit a press corps that has spent years sharpening its adversarial edge against this administration. Jennings has spent that same stretch sharpening his own, on their home turf, no less. If the president wants a press secretary who already knows how to handle a hostile room, the CNN greenroom is not a bad training ground.
