Trump Sent Shockwaves With One Name to Replace Karoline Leavitt
Karoline Leavitt is leaving the White House press secretary job, and the search for her replacement is already underway.
One name has floated to the top fast — and it comes with a lot of baggage most people aren’t talking about.
And Trump sent shockwaves with one name to replace Leavitt.
How Jennings Worked His Way Into the Conversation
Chief of Staff Susie Wiles recently sat down with CNN commentator Scott Jennings at Mastro’s Steakhouse in Washington, DC, at the request of the White House, according to two sources familiar with the meeting cited by CNN. Multiple staffers believe he has her backing to take Leavitt’s place as White House press secretary.
The meeting came after Jennings went after US Senator Jon Ossoff (D-GA) over comments Ossoff made at a campaign rally referencing Natalie Harp, President Trump’s executive assistant. Jennings called Ossoff’s remarks “disgusting” on CNN and called the senator a “coward.”
And here’s where the audition part becomes obvious. According to Politico, Jennings sent clips of himself defending Harp directly to White House senior staffers. He was not waiting to be discovered. He was packaging himself and shipping the product to the people who make decisions.
Trump has reportedly told his team that Jennings “looks the part” and handles himself well on television. One senior White House official told CNN simply: “He’s competent and good on TV.”
But some inside the White House are not sold. One Trump adviser told CNN: “Can he do all the closed door legwork that has made Karoline so effective? No one knows.” Another official put it more bluntly: “She’s thoughtful, she’s not impulsive, she actually understands the job. Some outside person doesn’t understand the way it works.” A third added: “It feels like her and Susie (Wiles) are the only people holding this place together sometimes.”
No offer has been extended to Jennings. Wiles plans to meet with several other potential contenders before any decision gets made, and Trump is reportedly not rushing the process.
Alina Habba, Trump’s former personal attorney who had been speculated about for the role, took herself out of the picture. “Flattered by the Kalshi odds, but I’m not in the running for any job,” she posted on X. The president has also joked to advisers that maybe Natalie Harp herself should get the job, according to one source familiar with those conversations.
The Record Jennings Wants You to Forget
Before anyone gets too excited about a Jennings press briefing, it’s worth spending a moment on who Scott Jennings actually is — because his current CNN persona and his actual record are two very different things.
Jennings spent years as a key operative for George W Bush and for Senator Mitch McConnell (R-KY). He has publicly called McConnell “my mentor,” saying on CNN: “He’s been my mentor, and he changed the trajectory of my life.”
Both Bush and McConnell opposed Trump at critical moments. That is not ancient history. That is the world Jennings came from, the relationships he built his career on, and the institutional orbit he operated inside for decades.
And then there is January 6.
In a CNN op-ed written that same day in January 2021, Jennings wrote: “These are domestic terrorists, and they ought to be treated like any other terrorist uprising with the full force and fury of the US government.”
That language — “domestic terrorists,” “terrorist uprising,” “full force and fury” — was not a slip of the pen. It was a fully constructed argument. It adopted the framing that the Democrat Party and its media allies used to turn a chaotic and contested day into a permanent political weapon against Trump supporters, millions of ordinary Americans who had legitimate questions about how the 2020 election was conducted.
The partisan January 6 committee and the impeachment proceedings that followed were political exercises, not dispassionate investigations. Democrats who cheered that process said nothing while American cities burned in the summer of 2020, federal courthouses were attacked, and a police precinct was seized and torched. The double standard was not subtle. And Jennings handed them the language to use.
He has since repositioned himself as a Trump defender on CNN. His current on-air posture — combative, pro-Trump, reliably good for a clip — sits in uncomfortable proximity to that 2021 record. That is not a long-held principle. That is a reinvention.
What This Means for the Press Secretary Search
Karoline Leavitt set a high bar. She was effective precisely because she understood the internal machinery of the White House, not just the television mechanics of a briefing room. The unnamed official who said she and Wiles are “the only people holding this place together sometimes” was not being hyperbolic. Leavitt’s departure, announced last week ahead of her planned exit at the end of the month to spend more time with her young family, leaves a real gap.
Jennings knows how to perform on television. That part is not in dispute. But the press secretary job is not a television job. It requires knowing what you can say, what you cannot say, what the President actually wants communicated, and how to navigate a briefing room full of reporters who are not asking questions in good faith. It requires trust built over time, not clips sent to senior staffers after a viral moment.
There is also the question of whether a man whose defining public statement about January 6 used the phrase “terrorist uprising” to describe Trump’s supporters should be the person standing at the podium as the face of a Trump White House. The President’s voters — the people who sent him back to Washington in 2024 — remember that framing. They lived it. They watched federal agencies, Democrat prosecutors, and a compliant press corps use exactly that kind of language to target ordinary Americans who raised legitimate questions about the 2020 election.
Jennings calling Ossoff a “coward” on CNN is fine television. But it does not erase what he wrote.
The White House is right to take its time. The press secretary position is not a reward for a good audition tape. It is one of the most consequential communications roles in American government, and the person who fills it needs to be someone the President trusts, someone who has been in the fight, and someone whose record does not require a lengthy explanation before the first briefing even starts.
Jennings may get the job. The process is far from over, and the White House has made clear it is looking at multiple candidates. But anyone paying attention to the full picture — not just the CNN clips — has reason to ask whether the establishment Republican who called Trump’s supporters “domestic terrorists” in 2021 is really the right person to speak for a President those same supporters sent back to the White House by a landslide.
That question is not going away, no matter how many steakhouse meetings happen first.
Sources: CNN, Politico, Mediaite, The Daily Beast