LEXINGTON, Ky. — Scott Jennings has become one of the most beloved — or loathed, depending on your political perspective — conservative commentators in America.

A favorite of President Donald Trump and billionaire Elon Musk, the Kentuckian and CNN pundit has earned praise in the president’s MAGA World with his vigorous advocacy for Trump’s agenda and quippy rebuttals to Democratic pundits.

Could that translate into entering the race to replace Sen. Mitch McConnell in 2026? Several Republican strategists and political insiders say Jennings is definitely weighing a potential run.

Jennings has not responded to multiple Herald-Leader requests for comment.

But others are talking about a possible Jennings’ Senate campaign, and it’s more than empty chatter.

Five individuals deeply involved in Kentucky Republican politics, who were given anonymity to speak freely about the race given their connections to the field, confirmed to the Herald-Leader the 47-year-old communications professional is eyeing a run.

And while Jennings has not said anything publicly, some Republicans acknowledge much is being said behind the scenes.

In fact, Jennings is being lobbied by Washington power brokers to seek McConnell’s seat.

“I think he’s carefully observing the field as a possible contender,” one GOP insider said. “People are seriously talking about it.”

Another Republican told the Herald-Leader: “In conversations I’ve had with serious Republican donors in Kentucky, it’s evident he’s making moves for a potential run.”

The question of who will replace McConnell in 2026 has grabbed headlines and interest from the commonwealth to the Capitol.

The longtime senator, who was first elected in 1984, said in February he would not seek reelection in 2026. Former attorney general Daniel Cameron announced his run the same day McConnell broke the news, and 6th Congressional District Rep. Andy Barr entered the race Tuesday.

Another GOP candidate, tech entrepreneur Nate Morris, is considering joining the race, too.

Campaign officials for Barr and Cameron declined comment about Jennings' potential entry.

Jennings would make the GOP field even more crowded should he take the plunge from political punditry to seeking political office.

An additional Kentucky Republican, who is affiliated with Jennings, told the Herald-Leader he is “listening” and “flattered” by the encouragement he’s received to run for the post.

They indicated Jennings will defer to Trump on who should come out of the GOP primary field, adding he doesn’t think a “nasty primary” would help given the possibility of Democratic Gov. Andy Beshear running for the seat.

Beshear, however, has shut down the possibility of running for the seat on multiple occasions.

The Democratic governor won reelection in 2023 by 5 percentage points over Cameron, but Trump won Kentucky by 30 points in the 2024 presidential race.

“Ultimately, I believe Scott thinks the primary is and ought to be in the president’s hands,” the person affiliated with Jennings said. “And nobody is doing more for President Trump on the national stage right now than Scott.”

Kentucky Republican strategist T.J. Litafik said the talk of Jennings as a potential contender has persisted in the weeks since McConnell announced he would not seek reelection in 2026.

He pointed out that Jennings’ perch at CNN is highly influential and lucrative. According to the media industry newsletter Status, Jennings received a “substantial pay increase” earlier this year as the Trump 2.0 administration took office.

Spokespeople for CNN did not respond to questions related to Jennings’ compensation.

“I have trouble imagining he’d want to walk away from that, but for a lot of people, it’s their lifelong dream to be in the Senate or Congress. I don’t know how burning that desire would be, but I have heard it from a few channels,” Litafik said of Jennings’ potential.

A week ahead of the Kentucky Derby, Litafik put Jennings’ odds of entering the race in horse racing terms: 15-1.

“It’s not great odds, but it’s not 50-1, either,” he said.

“I don’t know if he’s ever seen himself in the Senate or Congress. I know what my answer would be if I had to choose between a sweetheart gig on a major network versus the way politics works now.”

In Kentucky Republican circles, Jennings has been showing up at local party events where one usually expects potential candidates.

For instance, he headlined the Boyle County GOP Lincoln Day Breakfast event in March, where he hyped up the potential 2027 gubernatorial run of expected candidate 1st Congressional District Rep. James Comer.

He predicted that Kentucky voters would “recall” Comer from his current job because of their satisfaction with Comer’s handling of the House Committee on Oversight and Reform.

“We’re going to have a new governor soon enough, and one that isn’t accustomed to letting the Democrats get away with all their corruption. So I’m just going to go out on a limb here and say the next governor of Kentucky is in this room and his name is Jamie Comer,” Jennings said to applause at the event.

Those appearances have fueled the speculation about his potential political future. And Jennings has another one planned: A May 9 Jefferson County Republican Party “Evening with Scott Jennings” fundraising event for the GOP at a downtown Louisville restaurant. Tickets are $250.

“It kind of went from a, ‘Haha, that’d be interesting,’ to a, ‘Oh, wow, he might actually be interested in it,’” one of the Kentucky GOP insiders told the Herald-Leader.

“I think if he got in, he’d bring a lot to the race . … There wouldn’t be any training wheels with him if he got elected.”

His own personal website, scottjenningsky.com, has been noted by some Kentucky Republicans for its splashy campaign-esque presentation and content.

While he’s never sought office before, Jennings is an Oldham County resident and longtime power player in Kentucky and Washington Republican circles.

A native of Dawson Springs, the same Western Kentucky ancestral small town as the Beshear family, Jennings graduated from the University of Louisville as a McConnell Scholar.

He worked as a campaign manager to state-level operations for George W. Bush and McConnell in Kentucky in the early 2000s before joining the the Bush White House, where he was a deputy under Karl Rove, a top strategist for both of Bush’s successful elections, during Bush’s second term.

In 2012, Jennings founded RunSwitch PR, a Louisville-based consulting and public relations firm. It claims to be the biggest PR firm in Kentucky, touting business and political clients.

In 2023, RunSwitch’s services were used by four of the seven GOP statewide office candidates in the general election, according to records with the Kentucky Registry of Election Finance.

Though known best nationwide for his support of Trump, here in Kentucky, Jennings is associated with the McConnell network.

He has mostly avoided the direct criticisms of Trump offered by McConnell following the president’s first term, but Jennings has offered some critiques of Trump and Trump supporters at pivotal moments, such as the Jan. 6, 2021 insurrection at and inside the U.S. Capitol.

“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 said on CNN one day after the riot.

Jennings joined CNN in 2017 as an on-air contributor. His ties to the network, and prominence within it, have grown exponentially during the first Trump presidency and the Biden presidential term.

In late 2024, Jennings joined the editorial board of the Los Angeles Times. The newspaper’s owner, billionaire Patrick Soon-Shiong, announced the move touting the organization’s commitment to recruiting “experts who have thoughtful balanced views.”

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