Scott Jennings, Conservative Champion on CNN

The Hugh Hewitt Show

Scott Jennings joined me for the first time this AM:

Audio:

10-16hhs-jennings

Transcript:

HH: I’ve been doing this since 1990, and I don’t think I have many equals. But there’s a new guy in town. It’s sort of like the Gunslinger movie. When the old guy says okay, I can put down my weapon, there’s a new sheriff in town. The new sheriff is Scott Jennings. And Scott Jennings works over at CNN. And he’s better at this than I am, because he doesn’t lose his temper as often as I did. Scott Jennings, it is a pleasure to meet you. First time I’ve ever talked with you.

SJ: Yeah, good morning, and you are the legend. And you are the best of all time, and you’re the mentor for all of us. So we appreciate you so much, Hugh. Thank you for what you do.

HH: Well, I’ve got four to six years left, and then I’m just kicking back and saying there are enough youngsters out there over at the Ruthless podcast and Scott Jennings. I want to begin with some bio. Tell us who you are and who you root for.

SJ: Absolutely. I’m a Kentuckian. I was born in Dawson Springs, Kentucky in 1977, and started my political career working for George W. Bush’s campaign in 2000, and have been in politics and in this space ever since. I’ve actually been with Mitch McConnell since his 1996 election when I licked envelopes in an office in Kentucky. And he’s really been my mentor, truthfully. I’ve been with CNN for seven and a half years, and this is the first presidential cycle at CNN that I’ve been there where we’ve really been out and about. You know, the ’20 cycle, we were all stuck in our houses, and it took a back seat, in some ways, to the COVID coverage. But that’s my job in the media right now, is I write occasional columns for the L.A. Times and for the Daily Mail, but I take up my perch at CNN as the resident conservative and contrarian, and try to give half the country a defense of how they’re thinking and feeling about this world we live in.

HH: I like to tell people you’re a common-sense conservative. And I knew you had a McConnell tie. I’d like to go back through the political biography, because I believe the McConnell people are the best communicators. All the Ruthless podcasters, or three out of four, are McConnellists. I am a great admirer of the Leader. I think The Long Game is the most important political memoir ever written. But what did you do for the Leader?

SJ: Well, I started out as a young political volunteer in ’96 when I was a freshman in college. But then in 2002, I was his political director and communications guy for his campaign. In 2008, I was the senior advisor to his very difficult reelection campaign. And then in 2014, I ran the independent expenditure arm of the campaign, which was new then. And then in 2020, I advised him informally as he was coasting to reelection in Kentucky. And over the years, he and I have just had such a great bond. I was also a McConnell scholar at the University of Louisville. He has this amazing scholarship program for ten Kentucky kids a year. And I’m the son of a garbage man. I didn’t really have anything, and then he plucked me, and the program plucked me out of obscurity, and really nothing, and gave me a chance to go to the University of Louisville and get a college education. I’ll never forget. I was with him and Elaine Chao last night in New York City. I interviewed them for a big award they won at the Hudson Institute. And he was in rare form last night, and talking about his view on the world and what he’s going to do for the next two years after he’s finished being leader. And he was as spry and funny and locked in on the issues of the day as ever. So he’s been my mentor, and I wouldn’t be here without him.

HH: You know, Scott, you may not have heard me say this, but for many years, I have said Mitch McConnell is the single best legislative leader the Republicans have enjoyed in my lifetime. I’m 68 years old. I go back a long way. I worked for Nixon in his exile in San Clemente. I worked on the Ford 1976 campaign. So I have a long memory for Republican legislators. Leader McConnell is the most effective. I’m not sure I’d want to succeed him. Do you think anyone really wants that job? I know the two Johns want that job, but my goodness, it’s going to be hard to be as good at it as Leader McConnell’s been at it.

SJ: Yeah, I agree both on the legislative front and on the political front. When you consider what he does for the party in terms of fundraising, candidate recruitment, you know, clear-eyed strategic guidance for a lot of these campaigns, I tell people this all the time. We’re going to miss him when he’s gone. We’re going to miss him for a long time, because all the roles he plays for the party, he’s been so vital not just in Kentucky where he has turned the state totally red, but nationally. He’s our best strategist both in the chamber and in the political campaign world, in my opinion.

HH: He also saved the Constitution. And that is what I really genuinely admire with his No Hearings, No Votes in the aftermath of the untimely death of Justice Scalia. Not only did he get Donald Trump elected by making that an issue, he kept the Court on its originalist court and all of his appointees that he shepherded through the Senate. Now enough about Leader McConnell. Scott, you mentioned you’re the son of a garbage man. So is Tim Russert. Tim Russert’s memoir, Big Tim And, what was his dad’s name? Was it Big Tim and Little Tim? I can’t remember, but his dad was a garbage man. And he became very savvy as a result of that. You learn a lot from a dad who collects trash. Tell me about your father.

SJ: Well, my dad was a blue-collar guy. For many years, he was one of the people who managed what, you know, we didn’t even have garbage pickups, so he had to, like, manage the installation where you took the garbage. That’s how rural it was where I grew up. He also worked in factories and was a union guy at times. He was the biggest Bill Clinton guy I knew, big Democrat. My grandfather was a Democrat. And now, he’s the biggest Trump guy I know. He was the first person to call me and tell me Donald Trump’s going to be the next president of the United States. And of course, me being, you know, from the wing of the party I’m in, I was like oh, Dad, come on. You know, give me a break. But he knew first, and all those Democrats from the 90s, all those blue-collar guys, they’re Republicans now. And you know, I think about my relationship with my dad. He was like the leading indicator of it, and I didn’t even know it at the time. But his journey through life and our relationship means a lot to me.

HH: Well, maybe there’s a book in there. Russert’s book was Big Tim and Little Russ, because he was Big Tim and Little Russ. And that’s what the name of the book is. Now Scott, what did you do for W., who I admire more than any president. I worked very closely with Nixon. I worked in the Reagan White House. I have voted twice for Trump and will vote for Trump again. I get along fine with him. But the best man to be president in my lifetime, and just in terms of the soul and the fiber, is George W. Bush, in my assessment. What did you do for W?

SJ: In 2000, I was the campaign guy for Kentucky. Back in those days, Kentucky was still a swing state. Bill Clinton had won it twice. But then in 2004, they sent me to New Mexico, and I was his campaign director in New Mexico, which we won. He had lost it in 2000. And then after that, I went to the White House and was special assistant to the president. I worked in the Political Affairs office for Karl Rove and had mostly a great experience. We did have a run-in with some Democrats after the ’06 midterms, but that was my job. I was a political guy helping on the campaign side and then getting, honestly, the opportunity of a lifetime to work in the White House, working on the Supreme Court…

HH: Well, now I can yell at you. I’ve yelled at Rove about this. Karl taught me to be a field, I went to field school with Karl in 1974. He was running the College Republicans, and he came to campus. He also then went across the country and taught field school to my wife, and we met at a Pete Wilson fundraiser. So I thank Karl Rove for a lot of things. But deciding to try and reform Social Security in 2005 after the election of 2004 was the biggest political mistake of my lifetime. Do you regret that?

SJ: Well, I certainly was in the middle of it. I mean, it didn’t turn out well for us. I mean, we went all over the country. You might remember Bush had this massive travel schedule. We were going all over the country. Republicans were a little nervous about getting involved in it, but he really believed in it and really tried it. And then of course, all that got upended by other world and domestic events in the fall of 2005. And it was a slog that he never quite made it through to the other side.

HH: 2005 may be the worst political year for any person I’ve ever watched. We had the young lady dying in Florida, and the Republicans passed a law to try and save her life, and that didn’t go over well. Then, we had Katrina. Then we had Iraq go south. It was just a disaster.

SJ: Yeah.

HH: It must have been a nightmare to be in the political operation. So Scott, how did CNN find you? I got offered a job by Jeff and turned him down, because I just didn’t want to work at CNN. I went to work for NBC instead. How did CNN find you? And did you have reservations?

SJ: Well, they found me in 2017. A producer called me. I had done some work on Fox, mostly for Brit Hume in the 2016 cycle, but in an unpaid capacity. And a producer called me in 2017, asked me to come up and do a few shows. I was not under any obligation to say no, so I did it. And within a few weeks, they offered me a contributorship, and I’ve been there ever since. And it’s been, honestly, a great job. I love CNN. They treat me well. They’re pretty committed to political debate right now, which is what I really believe in. I think we need a fair hearing for both sides of this country. I don’t think you’re getting that at a lot of the other media outlets right now, and so they let me do my thing. And you know, we’ve certainly been through a lot of iterations of the network, but right now, when you look at what they’re doing in letting a conservative voice and conservative voices go on the air and make the case and defend half the country’s views, I think CNN ought to be commended for what they’re doing in bringing actual debate and conversation to the airwaves right now.

HH: Well, you are getting a lot more time than any other conservative I have ever seen get time on CNN, so that’s good. I want to talk to you during the break and after the break about big media generally and how underrepresented people like you and me and conservative men and women, and center-right people, are underrepresented in the Beltway-Manhattan media elite. Stay tuned, America.

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HH: Part two of my four-part conversation this morning with Scott Jennings. Scott, it is my rule, and maybe you practice this as well, never to speak ill of anyone with whom you’ve worked, no matter how mad you are at them. And so I’m not going to trash any of your colleagues at CNN, because I get along with Dana and with Jake. Mark Preston and I were buddies. Mark almost got me smoking again, though. He is a chimney, and he’s a New England fan, and he’s a Boston Red Sox fan. So there’s everything that could possibly be wrong with Mark is wrong. But I love all the people over there. But you’re the only one. I mean, name for me any other conservative who’s on the air as much as you are.

SJ: Well, we have a few other voices. There’s a fellow named David Urban who is on as well…

HH: Oh, David, you’re right.

SJ: Contributor, and yeah, and knows a lot about Pennsylvania politics. And we have a very young guy named Shermichael Singleton, who’s on sometimes and who does a nice job. You know, for better or worse, I’ve taken up my slot at the end of the desk on most nights as the resident contrarian, and it’s been a great gig, honestly. And my family of Axelrod and Van Jones and the rest, we really have forged this amazing bond. And I think it’s led to some pretty interesting moments on the air.

HH: Well, you just mentioned the smartest leftist out there, Van Jones. There are some very smart leftists on CNN. And there are some hosts who are pretty fair, like Dana and Jake. But you weren’t there in the Lemon era. And Don and I used to fight on the air. That’s not a secret, because I just thought he was unfair to people. Have you run into any of that where someone is unfair?

SJ: No, I don’t, I wouldn’t call it unfair. You know, you certainly run into panels where you know, you feel like you didn’t get your full, you wanted to make one more argument about something. And I was on the air a lot with Don Lemon, too. I cut my teeth a lot on those 11:35pm panels with Don late in the night, you know, talking about goodness knows what. But no, like I said, I feel treated very well. I mean, they don’t censor me. No one tells me what to say. Nobody, you know, tries to steer me in one director or the other. They’ve only ever told me just to give my authentic opinion based on my values and experience, and I’ve tried to live up to that. So no, I feel like it all goes pretty well. And I know my role, and they know what their role is, and I think we all have a fair understanding of how it works.

HH: No one ever told me what to do on any network. I mostly worked for NBC. I never took a dime from CNN, but I never worked for anyone but NBC. And no one ever told me what not to say. However, have you ever been on a panel that was 3-1 conservative to liberal ever in your entire life? Have you ever had two other conservatives against one liberal?

SJ: No, I don’t remember any panels like that. You know, they have had panels where they put a couple of conservatives on, just conservatives with no dissenting opinion to talk about something going on in the Republican Party. But no, no, I don’t really recall it being set up that way.

HH: Yeah, it doesn’t exist.

SJ: Most of the time…

HH: It doesn’t exist.

SJ: Yeah.

HH: Now do they ever ask you for programming advice? They never asked me for programming advice, so I always gave it to them. But have they ever asked you?

SJ: You know, they do ask me and talk to me about what the segments are going to be on the shows that I’m going to be on. And this Abby Phillip show, which is at 10:00 at night, does something kind of miraculous. They give each panelist 30 seconds at the end of the show to give a hot take of the day. And I turn it in, and they let me have 30 free seconds to do my thing, which is the first time that’s ever happened.

HH: This is the difference between being a young man and an older man. Abby has invited me up to New York repeatedly, and I won’t go, because I just don’t need to go to New York anymore at 68 and for 30 seconds, and a 10 o’clock show or an 11 o’clock show. But she’s pretty smart. Is she fair?

SJ: She’s been very fair to me. I love Abby, and I think what she’s doing with this show, putting people in a roundtable setting in the heat of this election, it’s been a great revelation, I think, for the network. The show is terrific. She’s fair to me and gives me a totally fair hearing. And we joust a little bit about things, but I think Abby’s doing a terrific job. It’s been a breakout thing for me. This has been one of the most fun shows I’ve done in seven years.

HH: You have broken out. And I want to talk about that when we come back live on the network, so stand by. Scott Jennings is my guest.

— – – – —

HH: Scott Jennings is my guest, and I’m about to put him on the spot, but he’s used to it, because he is the conservative on CNN. Scott, have they offered you your own show?

SJ: No. No, I’m a senior political contributor. I show up when they ask me to for all the shows, but no, never been offered that.

HH: If they offered you your own show, would you do it?

SJ: Oh, 100%. Absolutely. I mean, look, I think half the country needs more conservative speech and more conservative content. I think, so of course. And I think the CNN audience would like it. I mean, look, I think there are conversations to be had that are being had all over this country that just aren’t being fully represented in most media. And the more we can represent that, I think the better off we’d be as a country. And so 100%, would do it.

HH: So you’re a free market guy. I’m a free market guy. I do not understand why none of the major networks, the legacy networks, and I include CNN into that, have one conservative host, just one. We’ve got lots of left-wingers. And Margaret Brennan is my favorite punching bag right now because of the disastrous debate that she hosted between on the vice-presidential debate. But my question to you is why don’t you think the networks have one conservative host between them? Just one anywhere.

SJ: Yeah, I don’t know. I guess it’s a little above my pay grade to know the vagaries of television production decision making. But I will say this for the network that I work for, not knowing how they make those decisions. But knowing the decisions they’ve made to feature conservative voices in this cycle, and to let, you know, people over the years give a viewpoint for half the country. I do think that is good, and I think they are the one network actually committed to doing that. I don’t really think you’re getting these kinds of debates at the other places. So I need to speak up for my…

HH: No, I left NBC because they weren’t having those debates. They promised them. Andy Lack left, and then it ended. And ABC’s gone over a cliff.

SJ: Yeah.

HH: CBS has gone over a cliff. So I’m glad to see you out there. Are you amazed at how many people retweet your posts?

SJ: Yeah, it’s been kind of amazing, actually, to see these clips going viral. But I think it’s a testament to the product that CNN is making that people want to watch it. And I mean, I get messages all the time saying you know, I don’t watch CNN, but I will now. And I think that’s a good thing. But it is kind of incredible that all these moments have been created that people have really latched onto in this cycle, and I’m proud to do it, because I think half the country needs a representative. And I’m trying to deliver that every day, an authentic representation of what the average conservative is thinking. There’s obviously a marketplace for it, and people are responding to it.

HH: And you are unafraid. I like that. Fair and unafraid. Now Scott, in terms of the McConnell gang that’s out there, I’m sure you listen to Ruthless podcast. Do you think podcasting is going to destroy broadcast?

SJ: You know, as an old radio guy, my first job ever as a teenager was as a radio guy back in rural Western Kentucky.

HH: Oh.

SJ: And I was the news anchor on WHAS radio in Louisville, Kentucky for, when I was in college. So I’m a huge radio guy and a proponent for radio. No, I don’t think it’s going to destroy it, because I think there’s always going to be a place in America for live radio, and for what people like you do, and for what radio does in local communities. And my job was in community radio. And I just know the impact of it on communities. I still think it exists. I don’t think podcasts can meet that live demand, that instant demand. So no, I think radio’s going to be with us. It may take different forms, but I think it’s so unique that it’s irreplaceable.

HH: Now we disagree. I think podcasting is going to chew up broadcasting and spit it out, because it’s, you find smart guys like Holmes and Ashbrook and Duncan and Smug, and you put them together, and you get more content, and you actually get expertise like you have, because you come out of the world of politics. Most journalists don’t. And here’s where I want to close. In fact, I should close after the break. Pause for a second, Scott.

— – – –

HH: So I’m back with Scott Jennings for the last part of my long conversation with him. How do you stay abreast of the news, Scott? How do you keep up with what’s going on?

SJ: Yeah, I’ve cultivated a pretty diverse feed using X, truthfully, as my principal go-to source. But in terms of newspapers, I read the Wall Street Journal cover to cover every single day. And then I read the New York Times, as much as it pains me to say it out loud every single day. And then I have a, I just have a whole flood of things that I’ve curated that I keep up with. I also watch a lot of video, honestly, especially in the presidential election. I watch a lot of the Trump stuff. I watch a lot of Harris. And I just try to watch them directly and how they’re presenting things. And I’m doing it mostly so I can predict what’s going to happen on TV that night. But there’s a lot of reading that gets done by me every day. And I keep up with it throughout the day, because you never know when something’s going to break, and you’re going to have to pop on the air and comment on it.

HH: So two last questions. What do you think’s going to happen when the voting closes on November 5 and we get the results?

SJ: Gosh, I’ve been saying the same thing for 18 months. I have no idea who’s going to win. I think Trump is very close, but I don’t think he’s over the hump, and I don’t think she is, either. If I were either of them, I wouldn’t be too confident right now, because I don’t think either of them have it in the bag. But it’s true. He’s more popular than he’s ever been. His administration is retroactively more popular than it’s ever been. She is a disaster every time she opens her mouth in an open media setting. And she’s apparently committed to continuing to do that. So I think he’s right on the cusp of winning, and she’s got real problems. But Hugh, truthfully, I’m not sure. I usually have a pretty good instinct for these things. I’m conflicted on this one. I don’t know how you feel, but I’m a little conflicted.

HH: I don’t know. After 2016, I don’t make predictions. Last thing I want to talk to you about. In the spring, CNN and Salem, and I work for Salem, we jointly presented to the RNC to do debates. And I thought Ronna McDaniel and Bossie were going to give us four debates like we had in 2015-2016, because Salem-CNN is a pretty good combination. And I got to know Chris Licht a little bit, and I was looking forward to suggesting to him, not for me, I’m too old for this, but for someone like you the return of Crossfire. Chris got blown out, obviously, in the unfortunately Atlantic expose which never talk to the Atlantic ever. But I want Crossfire back. I want it back with young people who know what they’re talking about. Do you think they’ll ever go back to that? Jon Stewart blew it up, and that’s on him. But it was unfortunate, because Crossfire did a lot of good for America when it was done well. Do you think it will ever come back?

SJ: I don’t know if it’ll come back with that branding. And again, that’s above my pay grade. But I will tell you this. If you’re not watching it, this 10 o’clock show with Abby Phillip might be the closest thing that we have to that right now. I’ve had a few people suggest to me that it reminds them and gives them the same feeling that they got on Crossfire. So if you want to check out something that’s perhaps comparable, the 10 o’clock show with Abby might be what you’re looking for. So great question. I grew up watching that, too, and loved it. Loved the format and loved the people and the way the show was handled. So I’m in the boat with you. I love Crossfire. And honestly, doing the 10 o’clock has given me the feeling that I imagine it was like to be on that show.

HH: Do they ever allow two conservatives on the Abby show?

SJ: Yeah, we often have two conservatives, actually. Sometimes, it’s a journalist or someone from a different background than me, but yes, they often have two on there. And then they’ll have two Democrats. And then there’s usually a fifth chair that’s sometimes a journalist, sometimes somebody from culture. You know, it varies. But yeah, they actually have, it’s pretty balanced most nights.

HH: Well then, maybe I will say yes to them on the condition that we do it for five nights in a row, and that you are there. I would just be a guest. I don’t like to go to New York too often, but if you were there and Abby’s that good and they’re trying to do Crossfire, maybe I’ll say yes. Because Scott, you’re awfully good at this. Congratulations. The only thing I’ve got to ask you, do not go into radio for the next six to eight years, for as long as I hang around doing this. I don’t want you in radio.

SJ: I totally understand. I’m more than happy to be on your show, and by the way, if you come to New York and sit across from me at the table, that will be a dream come true to be on TV with Hugh Hewitt. Are you kidding me? That would be like getting to be on TV with a legend and somebody you looked up to for so long?

HH: I’ll bring a baton along, because I don’t know anyone else who’s been as willing to be a punching bag as me other than you. Scott Jennings of CNN, thank you for joining us. Follow Scott on X @ScottJenningsKY. Follow me to the next segments, America. I’m Hugh Hewitt.

End of interview.

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