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Scott Jennings is CNN’s breakout pundit. Could he be Trump’s White House press secretary?

A.Davis34 min ago

It's the Monday morning after the second attempt on Donald Trump's life and Scott Jennings is seated inside a climate-controlled CNN studio on the west side of Manhattan ready to stand as a vessel for red state America.

When anchor Rahel Solomon raises the inflammatory rhetoric "on both sides" pervading the 2024 presidential campaign , Jennings sees his opening.

"I know after something like this happens, it becomes fashionable to talk about rhetoric on both sides," he interjects, taking a short beat. "Donald Trump is the target, OK? He's the current target."

To turn down the political temperature, the 46-year-old Dawson Springs, Ky., native then suggests Democratic leaders do something he knows most could never swallow: Tell their voters the country won't be irreparably damaged if Trump wins a second term.

Online, the clip of his quip attains swift virality, racking up 3.3 million views on the site formerly known as Twitter. Hundreds of replies pile up from irate liberals, including former MSNBC host Keith Olbermann.

It's clear Jennings, who shares a hometown with former Democratic Gov. Steve Beshear, cut his teeth in Kentucky politics and still heads the state's leading Republican public relations firm, has the political world's attention — and is relishing his moment.

His ascent as a pundit has been supercharged.

"It's pretty thrilling to be honest," he says. "I'm doing more with my time and my opportunity than any other Republican on television right now."

Later that night he'll appear on "Newsnight" with Abby Phillip in the 10 p.m. hour only to return on Tuesday for a trio of hits on CNN International, "The Situation Room" with Wolf Blitzer and another evening panel with Phillip. On Thursday, it's "The Source" with Kaitlin Collins before another three-show run on Friday, chatting with Kasie Hunt at 6 a.m., Blitzer around dinnertime and Collins again in primetime. Even Saturday isn't an off day.

An average week for Jennings is a dozen different segments, which means if you leave CNN on for any protracted period of time, you're likely to catch him.

"I am apt to appear on any show," he texts in between hits. "There's nothing I don't do at least some of the time."

In a news sea awash with talking heads in rectangular boxes, Jennings has managed to swarm the screen and punch through it in this convulsive campaign cycle. As CNN's resident Republican analyst, he is often so outnumbered on the network's panels that Bill Maher half-jokingly referred to him as "lonely Scott."

And yet it's that singularity that's allowed Jennings to break from the pack. His crisp, agile argumentation and zeal for confrontation — all delivered with a hint of a southern affect — reverberates in a way that might be lost on a more politically comfortable outlet like Fox.

"I think he's a godsend for CNN because he is able to communicate various Republican positions in a way that the CNN audience can digest," said Van Jones, one of the network's most recognizable Democrats who frequently panels with Jennings. "[He's] the CNN Republican that exacerbates our liberal viewers, but doesn't antagonize or infuriate our liberal viewers — and that is hard to do ... It's like watching an Olympic level gymnast."

Balls & strikes, or MAGA?

Jennings says his No. 1 duty as an on-air analyst is to call "balls and strikes," but in the next breath acknowledges the obligation he feels to represent what most Republicans are thinking on any given issue.

It's an inherently contradictory goal.

The latter half of that mission has earned him an unabashedly "pro-Trump" tag, even as he was bred as a Mitch McConnell-Mitt Romney-George W. Bush Republican who served as Karl Rove's deputy in the White House.

"He was one of the better people I was able to work with during the seven years I was there, but if you told me he was going to turn out to be a rock star on cable news, I would've said, 'Well maybe,'" Rove said in an interview. "It strikes me that he's come into his own."

But while Rove described himself as an analyst, he called Jennings "an advocate."

"So I'm in a somewhat different place than he is. He tends to be on the opinion panels," said Rove, who has incurred Trump's wrath for his commentary.

As the presidential campaign intensifies into the final stretch, Jennings has largely assumed the role of calling out Democrats' hypocrisies, skewering Kamala Harris' skills as a candidate and defending Trump. It's the last leg of that stool that is undoubtedly the trickiest, particularly for someone who grew out of the traditional wing of the GOP.

But it's also engendered warmer feelings toward him among Republicans who were turned off by his closeness to McConnell, both in Kentucky and beyond.

"Sometimes I think Trump deserves to be commented on or defended in a way that no one else is doing," Jennings says.

But Jennings' harshest critics believe that Trump's penchant to lie, distort and disparage often doesn't merit a defense and are angry that CNN even provides a regular platform for one.

"He is completely MAGA and ... a really duplicitous person," said Norm Ornstein, a scholar at the American Enterprise Institute who has urged CNN to fire Jennings. "I think it's a bad model, and I think he represents the worst of it."

"I don't believe any journalistic organization is under the obligation to tell both sides of a lie. Scott often performs that role on CNN," said Stuart Stevens, who ran Romney's presidential campaign. "Scott Jennings has decided he's a Trumper. I can't believe he will not regret it."

Appear on live television most days of the week and you're bound for moments you'd like to have back.

On a recent "Newsnight" panel, when professor Michael Eric Dyson asked Jennings if there were any lies told by Trump that disturbed him, Jennings glanced down at the table in the direction of Dyson and stated his desire that no politician would lie.

It was a sidestep that Jennings himself would've seized upon.

When another panelist, Jay Michaelson, accused him of a "Kamala Harris evasion" it set him off.

"I don't answer to you, and I don't answer to you," Jennings said, pointing his index finger at Michaelson before lifting it toward Dyson's face.

It was a rare instance in which the normally congenial Jennings displayed a flash of anger when placed on the defensive.

His name began trending on X, powered by incensed viewers who suggested Jennings could be justifiably clocked for his physical gesture at Dyson. Jennings can see online the ire he inspires on the air, which is what led him to recently install a home security system.

Days later, when asked about the Dyson exchange, Jennings says while he forces himself to self-reflect on tense on-air moments, he didn't see any particular need to resolve anything with Dyson.

"Welcome to the NFL," he said.

Cable news scrums are as fleeting as an autumn snow in Washington. And for every lefty Jennings alienates, there's a MAGA diehard that climbs aboard.

On that same night, Jennings earned conservative accolades for an earlier segment in which he defended Trump for declaring he deserved 100% of the Jewish vote.

Jennings is "without a doubt the best Trump surrogate in America," wrote a columnist for Townhall .

Road to the White House?

In 1998, a controversial proposal rippled through the McConnell Scholars Program at the University of Louisville.

The senator had issued a memo seeking to impose "exemplary standards" for conduct and character, including a potential ban on scholars who had a child out of wedlock.

Jennings, then just a sophomore and a McConnell scholar himself, openly challenged the idea — which ultimately was unanimously struck down — putting him at odds with a powerful mentor and future boss.

"I think a majority of scholars are upset with McConnell," Jennings said, according to an account in the student newspaper. "I'm in a small majority that thinks you can disagree with McConnell's idea, but still remain loyal and supportive to him (and the program) ... Loyalty to someone doesn't mean you have to agree with them 100% of the time."

Jennings has attempted to apply that same independent philosophy to Trump, who he has criticized at chosen points, without ever dipping into "Never-Trump" territory.

In 2019 when Trump floated bringing the Taliban to Camp David for a meeting, Jennings said on air the thought of the idea "makes my blood boil."

The day after the Jan. 6, 2021, riot in the U.S. Capitol, Jennings told Anderson Cooper that Trump "clearly violated his oath of office to preserve, protect and defend the Constitution to the best of his ability."

"And I can't frankly believe there are still Republicans tonight siding with the people who stormed the Capitol by voting for these objections!" Jennings opined.

More recently, Jennings panned Trump's appearance before the National Association of Black Journalists by questioning Harris' race.

"He did crap the bed. ... The only question is whether he's going to roll around in it or get up and change the sheets," Jennings quipped.

Jennings has never spoken to Trump and says he feels no obligation to be an automatic defender of the former president.

But Trump's campaign manager, Chris LaCivita, keeps in touch with him, as do a phalanx of other Trump allies.

And Trump, America's foremost cable-news obsessive, is watching.

"President Trump watches clips of Scott Jennings and David Urban completely eviscerate their Democrat counterparts and biased CNN hosts who are clearly in the tank for Kamala," confirmed Trump spokesman Steven Cheung.

In June 2017 when the Trump administration was going through the first upheaval of its communications shop, senior members approached Jennings about coming aboard to help right the ship.

It was the exact same time he received an offer from CNN to come aboard as a contributor. Jennings chose the bright lights of cable rather than the drama of 1600 Pennsylvania Avenue.

But while Jennings loves his role, he acknowledges, "I sort of wonder what would have happened had I gone the other way."

If Trump wins a second term, there's already open speculation that Jennings will be at the top of the list to be his press secretary or communications director.

Jones says he would be brilliant at the podium job.

"I don't think he would turn it down; I think he would see it as an opportunity to serve the country," Jones said.

Others say the most important voice in that decision would be his wife Autumn, considering the couple has four young children and his family life remains rooted in Kentucky.

Jennings' Louisville-based firm, RunSwitch Public Relations, is the dominant outlet for public affairs work in the commonwealth, but those familiar say he's largely entrusted his two fellow partners with running its day-to-day operations, which largely serve non-political clients.

Jennings also finds himself in ever-increasing demand on the private speaking circuit, the spoils of his newfound television stardom.

When asked if he would accept a White House role the second time around, Jennings didn't rule it out.

"I really have no way to answer that. It would be a major life upheaval," he said, adding, "The job is not an audition tape. I will not go on television and deliver a take I do not believe in."

The CNN family

What many viewers watching at home don't realize is that regular cable news commentators are as likely to grab drinks or watch a ballgame together as they are to spar over Trump's latest outburst or Harris' housing plan.

"These guys are like my family," Jennings says.

On a recent Wednesday afternoon, Jennings spent the afternoon grabbing lunch with David Axelrod and strolling through New York City with the renowned Democratic strategist. Jones professed he loves Jennings like a brother.

Ashley Allison, another CNN Democratic contributor, recalls the last conversation she had with her father, Jennings came up unexpectedly.

"Oh that Scott, oh my god he just works my nerves!" her father told Allison.

To which Allison replied, "Daddy he's fine."

The next day her father had a stroke and later died. When Jennings called to check in, it crystallized to her how their personal relationship transcended their political scuffles.

"Those are moments when it's about the person. It's not about panel anymore. It's about protecting somebody that you work with and that ultimately you realized you care about because you spend so much time together and you don't want anything bad to happen to them," she said.

"He's playing a partisan role at a time when...you have to stretch yourself to do that and feel good about it," Axelrod said of Jennings on The Bulwark podcast, adding, "But I know him as a human being."

As cable news channels grapple with double-digit percentage declines in viewership, CNN has attempted to stake itself out as the last refuge for debate that represents both halves of a bifurcated country.

But at the end of the day, it's still a business putting on a show designed to keep you from clicking away.

"You're putting together a soap opera of personalities that are kind of talking over the dinner table – and the chemistry's got to work," Jones said.

Jennings is undoubtedly one of the stars, or villains, depending on your political perspective, in a story no one can safely know the ending to.

He calls the Trump-Harris election "a jump ball" that could tip either way on Election night.

Whichever way it goes, Jennings will have one of the last words most likely to pop into your media diet.

"Whether they get to me in 20 seconds or 20 minutes," Jennings says, "I think you can bet that I'm going to deliver."

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