Jennings, a native of Kentucky and a former advisor to both McConnell and President George W. Bush, is said to have made his intentions known in a candid moment at an afterparty for the White House Correspondents’ Dinner. According to the Daily Beast, Jennings stated, “If the president wants me, I’ll run. If he wants somebody else, I’ll support that candidate.”

Though he hasn’t officially declared his candidacy, political observers believe Jennings could be a serious contender for the seat, especially given his rising national profile. Over the past year, he has become one of CNN’s most prominent conservative commentators, regularly appearing on “NewsNight with Abby Phillip,” where his spirited debates and defense of conservative policies have made him a standout voice on the network.

In fact, his role on CNN has grown so significantly that the network recently renewed his contract and gave him a substantial raise. Still, Jennings has not been given his own show, prompting speculation that he might pursue a broader political platform. According to the New York Post, his potential Senate run is “certainly not fake.”

Trump himself acknowledged Jennings’ balancing act on national television during a rally in Michigan, joking, “He defends me all the time on CNN, and he defends me really well, but he can’t go too far because he’ll get fired.”

During that same rally — marking Trump’s first 100 days back in office — Jennings was called to the stage by the former president. Embracing the moment with humor, he quipped, “I’ve 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.” The lighthearted jab drew laughter from the crowd and further showcased Jennings’ ability to play both a political insider and media personality.

Support for a Jennings candidacy is already taking shape among conservative figures. Prominent radio host Erick Erickson tweeted in February, “Could I nominate [Scott Jennings] for the United States Senate from the Commonwealth of Kentucky? He’d be a hell of a McConnell replacement.”

Even some of his ideological opposites have acknowledged Jennings’ effectiveness on TV. CNN colleague and former Obama adviser Van Jones once described him as a “likable rascal,” saying Jennings understands the need for a commentator to be sharp without crossing into villainy. “He knows how to dance that dance. It’s a rare gift,” Jones told the Daily Caller earlier this year.

Still, Jennings is not the only Republican eyeing McConnell’s seat. Former Kentucky Attorney General Daniel Cameron quickly threw his hat in the ring after McConnell announced his retirement in February. Congressman Andy Barr, another established GOP figure, also recently joined the contest.

Meanwhile, Lexington businessman Nate Morris, another potential candidate, has publicly criticized his rivals, painting both Barr and Cameron as “puppets” of McConnell. In a February social media post, Morris wrote, “I’m not gonna let Mitch McConnell dictate whether I run or not… He’s turned his back on President Trump.”

Amid these early maneuvers, the one figure who could immediately reshape the field is Donald Trump. So far, the former president has not endorsed anyone in the race. Jennings, it seems, is waiting to see which way the political wind blows from Mar-a-Lago before taking the plunge.

Adding to Trump’s unpredictable streak, he made headlines the same day in Michigan by unexpectedly praising Democratic Governor Gretchen Whitmer during a speech at Selfridge Air National Guard Base. “You know, I’m not supposed to do that. She’s a Democrat. They say, ‘don’t have her here.’ I said, ‘No, she’s going to be here… she’s done a very good job,’” Trump told an audience of service members.

That moment of bipartisanship contrasted sharply with the calculated moves happening in Kentucky’s GOP primary battle — where candidates and hopefuls like Jennings know that Trump’s endorsement could determine their political future.

As Jennings weighs his decision, his unique media experience and close ties to both McConnell and Trump put him in a rare position. But whether he enters the race may ultimately depend on one question: Will Trump give him the nod?