Q&A: A Kentucky gentleman in the lion’s den

Nationally renowned conservative commentator and writer Scott Jennings tells American Experiment’s John Hinderaker what it’s like to be the conservative black sheep at CNN, what the future holds for news media, and what he thinks of Pres. Trump’s second term in office.

Kentucky native Scott Jennings is a senior political contributor at CNN with daily appearances on a number of CNN programs. He served as an advisor on four presidential campaigns, as Special Assistant to Pres. George W. Bush, and played pivotal roles in high-profile U.S. House and Senate races.

Jennings has taught at Harvard’s Kennedy School and is a founding partner of RunSwitch Public Relations, Kentucky’s largest PR and public affairs firm. He is a regular columnist for Gannett and hosts his own weekly podcast, “Flyover Country with Scott Jennings.”

John Hinderaker: Scott Jennings, you’ve been in politics for a long time. You must have started out in politics at the very beginning of your career and stuck with it.

Scott Jennings: The earliest experiences I had in politics came as a boy when I was young. My grandfather was a local elected official in western Kentucky. He was a Democrat. I came from a family of Democrats, and that’s really where I learned about politics. But when I was a teenager, I fell in love with the Republican Revolution under Newt Gingrich in the 1990s. So I became a Republican and went off to college and was a McConnell Scholar at the University of Louisville.

You were active in both of George W. Bush’s campaigns, and you worked in the Bush White House.

That’s right. After the 2004 campaign, I was recruited by Karl Rove to join the White House Office of Political Affairs, where I served as a special assistant to the president, handling a wide range of issues.

In addition to all of that, you founded and run a political consulting firm?

Yes. I went home to Kentucky after the 2008 cycle and got into the public affairs and public relations business, and I’ve been in it ever since. I joined a firm that was already in existence when I went home, but in 2012, a couple of my colleagues and I decided to form our own firm called RunSwitch Public Relations.

The outlet through which you’ve really become famous in recent years is CNN. When did you start there?

I was hired in 2017. During the 2016 presidential campaign, I spent most of my time on FOX News working principally on “Special Report with Brit Hume.” I was doing a lot of analysis for Brit during his coverage of the 2016 election, but in June of 2017, CNN recruited me and offered me a contributorship, and I’ve been there ever since. I always joke because around that same time, CNN had also hired JD Vance. You can see that I’m still putting on makeup for a living, and he’s now the Vice President of the United States. I’m not sure who got the better end of the deal, but it’s a great job.

When you started at CNN, did you think of them as the kind of liberal network that most of us consider them to be today, or was it closer to the middle?

CNN was the news network that I grew up watching. I watched the Gulf War unfold as a boy on CNN. I thought of it as the place you go to get the news. And obviously, in the years since Donald Trump came on the scene, I think they have become known as a little bit more of a liberal network in their political commentary. But I did and still do consider them to be the home for breaking news. Trump changed the nature of cable news, and I think that’s true for CNN and for every other outlet. And they’ve really treated me well and given me the space to do what I do, which is giving authentic conservative representation of how half — or more than half — the country is analyzing the news on any given day.

What programs are you on at CNN, and how do you describe your current role?

I’m a senior political contributor, so I’m apt to be on any show. The show that I’ve probably become most known for lately is the 10 o’clock show: “News Night” with Abby Phillip, which is essentially a debating show. Everyone sits at a round table, of all political persuasions, who come from a lot of different walks of life. I think it’s the only show like it on TV, and my instinct is that there’s a lot of hunger for actual, authentic debate.

I don’t have a script. There’s nothing on the teleprompter. We’re out there just debating in the moment. I also appear often on Wednesday nights with Kaitlan Collins. I do “State of the Union” on Sunday mornings with Jake Tapper and Dana Bash fairly often. On Friday nights, I’m usually on with Laura Coates, who has the 11 o’clock show. And throughout the day, I’m apt to pop up in the morning or the afternoon — it just depends on what’s going on. At least once a week, I’ll be on “The Arena with Kasie Hunt” at 4 o’clock. So, I really appear across the network. But I think the show that generates the most viral content that people probably see is the show Abby Phillip hosts and we’re slugging it out on the issues of the day.

It seems you have really burst onto the scene in the last couple of years to become one of the main faces of conservatism nationwide. Do you feel that way?

I do feel that way. I think a couple of things happened. Number one, for a lot of my time at CNN, there were other people there, such as Rick Santorum. And then in the 2020 election, it wasn’t a real campaign. We were all stuck inside. The campaign did not happen in a way that allowed people like me to fully flourish. But then 2024 came along, and this presidential campaign was full-blown from the beginning of the primaries all the way to the end.

Through the course of that election, I became, for CNN, the representative of what half the country was thinking and how they were analyzing this contest between the Democrats and the Republicans. Then we reinvented this 10 o’clock debating show. It was a convergence of circumstances that just gave me the platform to grow into the commentator that I am today, and I have to give a lot of credit to CNN. A lot of shows you see are just six people agreeing with each other, and I think it’s boring. I don’t need six people to confirm what I already think. I love to hear some conversation and debate, and I have to credit CNN for seeing the wisdom in that. Now, it is true that I’m often outnumbered in these settings, but that’s okay. I think I’m more than capable of interjecting the conservative viewpoint in these conversations, even if three or four people are yelling at me while I’m doing it.

When people see clips of you, it’s always you against two or three liberals. How does that feel — like the Lone Ranger?

I enjoy being that person who’s willing to stand in against what I sometimes think is a barrage of silly arguments or uninformed arguments or people who are saying things that I think are frankly just wrong for the country, and maybe just wrong on their face. I think that’s the role I play in trying to deliver common sense into these conversations. I don’t come from the East Coast. I don’t live in New York City or Washington, D.C. I live in Middle America. I live just outside of Louisville, Ky. I’m a mainstream conservative Republican, but I often feel like I’m the only person with those credentials who some of the people I’m debating have ever met. I think there’s great value in that.

It also explains why these clips go viral because it’s so unusual to see that kind of interaction on television. On any given night, we might get 500,000 to 600,000 viewers for that 10 o’clock show, but by the next morning, some of these clips have millions of views. So, I think that there’s a hunger for this idea that some regular guy from Middle America gets to stand in and debate these issues with these elite liberals from the coasts. People like to watch it, and I like to do it.

Many people are seeing you in a two-minute-long clip making good, sensible points against what seem to be silly liberal arguments. It seems like you’re in the middle of a transformation in the way that Americans consume news.

I agree with you. Some people love to watch the whole show, but there are a lot of people — maybe younger people — who consume information of any kind through highlights or these shorter clips. Maybe people don’t have time to watch a whole hour-long debating program, but they’d love to see 90 seconds or 120 seconds of a conservative and a liberal going back and forth on major news of the day.

CNN is still like a lot of legacy media outlets, figuring out how to fully transition into this era. And I’m not sure they knew how it was going to happen at the time, but this 10 o’clock show is one of the most clippable shows on TV because of the debate scenarios that we’re setting up. A lot of shows are still just interview shows. You come on, I interview you, we talk, and then it’s over. On the debating shows, because it’s unscripted, and because it’s in the moment, and because it’s often quite passionate, it lends itself to these extremely watchable moments.

I also think that some conservatives who had turned away from CNN see that there’s a voice that represents their views on the network through some of these clips, and then they’re more apt to turn it on later. If you look at the ratings of the 10 o’clock show, it’s the fastest growing show on the network and one of our highest rated shows, both broadly and in the demo of 25 to 54. I think the reason is because the content we’ve created has generated this buzz, and now people are saying, “I might want to tune in there and see what they have to offer.”

How do you get along with the people at CNN off the air?

Great question. My best friends at the network are David Axelrod — the legendary Democratic strategist and former Pres. Barack Obama’s chief strategist — Van Jones, and Ashley Allison, who is an accomplished Democratic political operative from Ohio. I spend a huge amount of time with those three people. Ashley and I make up a strong core of the CNN election night team. During the 2024 election, we traveled together. In the fall of 2024, David Axelrod and I would be stuck in New York and not have much to do during the day, so we would take these long walks around New York City and talk about life, our families, and the news of the day. We just built this amazing relationship. I love ’em all.

When you see us on the air, you see that we interact with each other in a way that we open our ears and our hearts to each other before we open our mouths. I listen to what they have to say. I think they’re credible people, and I also think they debate the issues in a good-faith way, and I think they believe that about me as well.

Mitch McConnell is stepping down from his Senate seat. I’ve seen your name mentioned as a possible successor. Do you have any interest in your career going in a political direction?

I’ve seen the speculation about it. It’s flattering. I revere people who run for office. I thought it was the most amazing thing that my grandfather had been elected by his neighbors to hold this local office. So anybody willing to put their name on a ballot, I’m enormously respectful of. I think the Kentucky Senate race won’t be decided until next May. And I think, like a lot of Kentuckians, I’m waiting and watching and seeing how it develops. The one thing I’m sure about is that the Commonwealth of Kentucky needs to replace Mitch McConnell with another Republican. It would be a travesty if somehow a Democrat like our governor, Andy Beshear, were able to sneak in there. So yes, I’m paying attention to it, and we’ve got some good people who are looking at it or who are already in the race right now, but I’ll be tracking this closely over the next few months.

Do you have any overriding thoughts about what we’re seeing unfold currently in Washington, D.C.?

Over the last few months, we’ve seen some momentous things happen. Going back to Joe Biden — I still think it’s one of the biggest scandals in modern political history. What happened in that Biden White House, this cover-up of his condition, and now Democrats are fully admitting that the president was impaired. I don’t think we’ve fully absorbed the enormity of this scandal that Biden was debilitated, unelected staff were running the White House, and his staff were also lying to the American people about what was going on behind closed doors.

Donald Trump winning. To me, it was the greatest comeback in American political history, and I think it was the revenge of average, everyday Americans saying, “We’re tired of being lied to. We’re tired of being condescended to. We’re tired of being called Nazis. We’re tired of being brow-beaten because we’ve taken an interest in our kids’ schools.” I mean, people were sick and tired of being force-fed narratives that weren’t true that we could all see with our own eyes. And then the first 100 days of Donald Trump — he hit Washington hard with the executive orders and the momentum that he created, and they were prepared and able to hit the ground running on day one.

It created a massive amount of radical change and, frankly, brought a lot of radical transparency to governance in Washington. It’ll take some time to see what the results of all these policy choices are, but there’s no doubt that Donald Trump revolutionized presidential campaigning and he has revolutionized governing. Not since FDR has a president exercised this much executive authority and executive nimbleness when it comes to reversing just disastrous policies and disastrous choices that were made by the previous administration.

I think we have lived through some of the most historic, noteworthy, and lasting moments in the last year. Not every political cycle produces memorable things — this one did. And Donald Trump continues to produce historic moments every single day, and it’s fun to be right in the front row for all of it. Every day with Trump, there’s never a dull moment.