In 2016, a month before the presidential election that Donald Trump would win, the longtime Republican strategist Scott Jennings described him as “a vulgar, crude, braggadocious, desperate-to-impress playboy who tends to view most everything through a sexual lens”.
After Trump’s loss in the 2020 election, Jennings excoriated Trump’s conduct during the January 6 Capitol insurrection, saying he “clearly violated his oath of office to preserve, protect and defend the constitution to the best of [his] ability”.
When Trump was in the political wilderness in 2022, Jennings said the party “[needs] a new nominee”, later encouraging the Florida governor, Ron DeSantis, to launch a primary challenge. “There’s only one strategy for getting rid of Trump: it’s to beat his ass,” he said the following year.
So why exactly is the 48-year-old conservative TV pundit being considered “an early favorite” to serve as Trump’s top spokesperson, replacing the departing Karoline Leavitt as White House press secretary?
The answer can be traced to Jennings’s virtuosic ability to pivot (or shape-shift, as some critics might suggest) to land on the right political side.
As soon as it became clear that Trump would in fact win the Republican nomination, in early 2024, Jennings became a bigger supporter than ever . And over the last few years, Jennings has emerged as a star in his own right: CNN’s in-house Maga gladiator who is always game to appear on television and beat up any liberals that challenge him.
Highlighting his transformation, Jennings appeared onstage with Trump in 2025, telling a rally crowd : “Michigan, we were flying in here today and I said: ‘Look at these farms. I got to get a farm in Michigan, because when you own as many libs as I do, you gotta [get] a place to put them all.”
Jennings’s bombastic performances have made him a target of hatred for Democrats but won him praise – and, most importantly, attention – from conservatives, including those in Trump’s circles, even as the president still reportedly holds some reservations about picking him as press secretary.
Ben Ferguson, who served as a conservative contributor on CNN for many years and still occasionally appears as a guest, said Jennings was uniquely talented as an on-air pugilist – and that he could use that experience to serve him well as Trump’s press secretary.
“The more reps you get, the more fights you have, then the better you are, and the better you can serve the president,” he said in an interview. It would also help that Jennings is already well-acquainted with the CNN journalists who cover the administration, he added.
Some longtime politics reporters have vouched for Jennings, who became a known quantity to beltway journalists as a staffer in George W Bush’s administration and a longtime adviser to Senator Mitch McConnell from his home state of Kentucky.
“Not that my opinion matters here, but Jennings would be great in this role,” Rachael Bade, a former Washington Post and Politico journalist, wrote on X last week . “Most reporters in this town have known him for years from his time in McConnell Land – WELL before he was a CNN celeb. He’s also just a nice & fair guy – tho maybe not so nice if you’re on the other end of his slap-down.”
During a May 2024 segment on CNN , Jennings clashed with George Conway, the conservative attorney who had been married to the Trump counselor Kellyanne Conway, after a New York jury found the then ex-president guilty on 34 felony counts.
“You’re lying. You’re lying, Scott. You’re lying about the law,” Conway told Jennings, drawing the objection of a CNN anchor when he asked “why this network is paying Scott to say those lies.”
Conway, who later claimed that he was temporarily “shadow-banned” by CNN after the segment, wrote on X last week that Jennings would be perfect for the job as press secretary.
Asked by the Guardian to explain why he was seemingly endorsing his former sparring partner, Conway responded: “Because it’s a terrible job for a terrible boss and he’s a terrible guy! All around, a great fit.”
Mark Feldstein, a former CNN and ABC News journalist who teaches broadcast journalism at the University of Maryland, noted that Jennings’s background “is mostly as an establishment Republican rather than Maga fanatic, so in that sense he may seem a bit more credible than one of the more obsequious Trump toadies from the rightwing mediasphere”.
“But,” he added, “I don’t think he, or any press secretary for the Trump White House, will carry much credibility with the mainstream Washington press corps because anyone appointed to that position will be expected to defend the indefensible and convey Trump’s habitual lies to the news media. It’s an inherently credibility-diminishing job.”
Jennings’s reputation for embodying a certain kind of folksy charm faced scrutiny this spring, when he told Adam Mockler, a 23-year-old progressive commentator, to “get your fucking hand out of my face” during a contentious segment about Trump’s war on Iran. Despite calls for CNN to punish what former network contributor Keith Boykin called a fireable offense , there is no evidence that he faced any punishment from the network, which has struggled in the past to find credible Trump defenders.
While he’s never expressed interest in working for the Trump administration, he has also never said no – though he told a McClatchy reporter for a 2024 profile that he was not auditioning for the job by taking on the president’s critics on CNN. “It would be a major life upheaval,” he said for the story , which was headlined: “KY’s Scott Jennings is CNN’s breakout pundit. Could he be Trump’s White House press secretary?”
Jennings has continued playing coy in the days since his name was first floated as Leavitt’s potential successor, even when asked directly about it on CNN. (The White House did not respond to a request for comment.)
“I don’t have any comment about that, but it’s an important job, because that person has to represent the most powerful person in the world, and the entire US government,” Jennings told the CNN anchor Abby Phillip , who hosts the evening show that he most regularly appears on. “And what they say matters … whoever gets it, it’s a big responsibility.” (When asked if he would take the job, Jennings replied: “I’m not going to answer that.”)
When asked about the rumors by the CNN anchor and chief White House correspondent, Kaitlan Collins, Jennings said: “I don’t really have anything to say about it, other than, I would get to see you every day, and I would think you’d be happy about this.” (“I already see you every day. … We already work together, Scott,” Collins responded.)
Highlighting the irony of a CNN contributor being the subject of CNN reporting, a recent story about Jennings’s prospects noted that “CNN has reached out to Jennings” for comment.
Some have accused Jennings of using his perch on CNN to lobby for the job, particularly in his recent vociferous defenses of the Trump aide Natalie Harp. A CNN spokesperson declined to comment on Jennings’s potential appointment, but noted that he had been asked about it on air several times.
Were Jennings to take the job, it would leave CNN without its most high-profile and prolific conservative commentator, and it would take a reliable Trump defender off one of the president’s most-hated networks.
But, Ferguson, the conservative former CNN contributor, said: “I think Scott can serve the president in an even better way being his press secretary than he does being at CNN.”
After Trump’s loss in the 2020 election, Jennings excoriated Trump’s conduct during the January 6 Capitol insurrection, saying he “clearly violated his oath of office to preserve, protect and defend the constitution to the best of [his] ability”.
This report is published with credit to theguardian.com. Full available text from the wire is above. Read on theguardian.com →
Source: theguardian.com · Jeremy Barr in Washington. Published 28 Aug 2026, 10:00 am.
