A Q&A with Charlie Sykes
By Chuck Melvin
Oct. 20, 2024
It was never just about numbers, although Charlie Sykes had thousands of daily listeners on Milwaukee’s WTMJ radio from the 1990s through the mid-2010s.
It was about influence — the right-wing audience he nurtured, the conservative candidates he validated. He played undeniable roles in the elections of Scott Walker as Wisconsin governor and House Speaker Paul Ryan as congressman, among others.
He took special pleasure in driving liberals crazy.
But never, ever during those years did Sykes foresee what he is about to do:
Vote for Kamala Harris.
Not to worry. Sykes hasn’t suddenly turned into, God forbid, a Democrat. Since leaving his radio show, he has co-founded conservative websites, created conservative podcasts and newsletters, contributed countless conservative articles to prominent newspapers and magazines, and become a regular commentator on MSNBC.
For Sykes, the bridge too far wasn’t conservatism.
It was Donald Trump.
In an hourlong video chat from his Mequon home, Sykes — a Never Trumper since 2016 — told me about his endorsement of Harris and why he thinks the race remains tight despite the defections of so many prominent Republicans.
This conversation has been edited for clarity and length.
Q: Why are you voting for Kamala Harris?
A: I understand how surreal it seems for somebody who spent a quarter of a century being a conservative talk show host to vote for a Democrat. But this is not a normal presidential election. This is not a choice between liberals and conservatives. It is a choice about democratic norms.
I think it is absolutely essential to keep Donald Trump from the White House again. America deserves better than a chronic liar, a convicted felon who tried to overturn a legitimate election and incited a violent attack on the Capitol, and who openly talks about terminating the Constitution. So, as a conservative, this is ultimately not a difficult choice.
Q: Before she became vice president, Harris was very liberal on some issues. What’s it like to endorse someone who once supported the Green New Deal?
A: There’s no question that I disagree with her on a wide variety of issues. But at this point, I cannot tolerate someone who wants to shred the Constitution. There comes a point where you say, all right, we are not ideologically aligned, but we are united in our respect for the Constitution. And this does feel like a moment to put country over party.
I’m really struck by the degree to which Kamala Harris has reached across the political aisle and has made it very clear that she wants the votes of centrist and center-right voters who have not changed their principles, but are disgusted by what they see on the Republican ticket.
Q: With so many conservative leaders and former Trump officials insisting that he is dangerous, clueless, or both, why are the polls so close? Why isn’t your former radio audience coming along with you? This is a razor-thin race.
A: I think that’s a tribute to the hyper-polarization of our politics. And I look back on my days on the radio and recognize that I did contribute to that.
In Wisconsin, I think we foreshadowed some of that extreme partisanship during the fight over Act 10 (AUTHOR’S NOTE: Passed in 2011, Act 10 restricted collective bargaining and wages for thousands of Wisconsin public employees, including teachers. It led to massive protests and an unsuccessful attempt to recall then-Gov. Walker).
I regret a lot of that because I’m seeing the way it plays out, the way in which Republicans have been willing to shed one value after another in the name of party loyalty.
The fight becomes about the fight. The specifics of the issue matter less than our side winning and the other side losing. It’s been translated into just “owning the libs.”
Q: Are there other reasons that Republicans and Democrats remain so entrenched?
A: There’s the media ecosystem that we see today. I was part of this.
We’ve created these alternative reality silos that are almost impossible to penetrate. So Donald Trump is able to spread disinformation, to spin his lies and advance conspiracy theories, to an audience that is increasingly immune to any sort of fact-checking. This explains the political moment where half of America is looking at the other half of America and thinking, “Who are you? How can you possibly think these things?”
You used to have people in the Republican Party going all the way back to Abraham Lincoln who said that we need to appeal to the better angels of our nature. Those voices have either been silenced or exiled now from the Republican Party.
Q: Fox News launched in 1996. Now we see in the Dominion settlement that Fox News is brazenly dishonest, beyond any doubt. We saw the text messages, the emails. And yet they still seem to be the go-to place for the right.
A: When I started in conservative talk radio, we were a relatively narrow band of information. Now we have created these vast empires that have figured out that disinformation can get you more clicks and higher ratings than simply telling the truth. Fox News is only one part of this vast constellation of people, of outlets.
I think the most disturbing thing about this development is not just that we have so many politicians and so many media outlets that spread lies. It’s that tens of millions of Americans are OK with that — by which I mean, it’s one thing to lie to someone. It’s another thing for that person to realize they’re being lied to and decide they don’t care.
What happens if a segment of the American people simply do not care whether a politician or a media outlet is telling them the truth, as long as it tells them what they want to hear or advances their political agenda?
Q: How did you deal with this on radio.
A: I understand how liberals were unhappy with my radio show, but one of the things that I really tried to do was, with the audience, push back against disinformation and misinformation.
For years, I had a good enough relationship with them that when somebody sent me a story about Hillary Clinton’s “murders” or just some bizarre theory, I would be able to send them factual information saying, OK, this is not true. We don’t need to support Hillary Clinton, but there are not bodies stacked up in a warehouse in Ohio.
In 2015 and 2016, it became increasingly difficult to push back against that, even with people that I had known for years. You’d send them a clip from the Washington Post or NPR, and they would say, well, that’s the liberal news media.
Q: I was shocked when Trump, during the debate with Harris, brought up the absurd story about Haitian immigrants stealing and eating pets in Ohio. Do you think he really believes something that outrageously false, or is he using it somehow? And then JD Vance repeated it.
A: Well, I think the fact that JD Vance repeated it is the real tell here.
Donald Trump is utterly indifferent to the truth. He will say anything that he thinks will advance his cause.
In the case of the Haitian immigrants, it’s been debunked, it’s been refuted by local officials, including by the conservative Republican governor of Ohio, and it doesn’t matter, because the lie becomes the weapon, and they are unwilling to give up the weapon.
I’ve been asking people, why are the poll numbers shifting (toward Trump)? What’s going on here? And this is what’s terrifying: You have these lies and the lunacy, and it’s effective.
Q: I also have been perplexed by Republicans’ blitz regarding transgender issues. Is this really a serious national problem that we somehow missed until now?
A: This is the ultimate wedge issue of 2024. There’s crime, there’s immigration, there’s minorities — but then there’s transgenders. It is the other. And it basically is the way in which they can define Kamala Harris and the Democrats as extremists who are doing something that is not, quote-unquote, “normal.”
I hesitate to give Donald Trump credit for strategic thinking, but he’s always had this reptilian instinct about what fires people up. And he’s recognized that this issue, particularly with children and with sports, actually does help define his value universe versus the Democrats.
And I’m really sorry to say that it’s working. The airwaves are absolutely being flooded with this. It tells you something about what they’re willing to do.
Q: Do you see other, more fundamental issues getting overlooked?
A: I haven’t even raised the fact that the Republican nominee for president is not only a convicted felon who has called for terminating the Constitution, but also is someone who has been found liable for sexual assault by a federal jury and judge, a judge who has described it as rape.
Maybe our capacity for being shocked has been eroded. We’re no longer shocked by something like the Access Hollywood video or his lies or his sucking up to Vladimir Putin, or the fact that hundreds of thousands of Americans died because he lied about COVID.
I mean, you’re watching millions of evangelical Christian voters look at this man who has paid hush money to a porn star and go, “Yeah, I’m voting for him because I’m concerned about moral values.” It feels as if the country has lost its mind.
Q: Another subject that has flown under the radar is January 6.
A: Oh, God. This is why I’m taking the same position as Liz Cheney, somebody who has been a Republican all of her life, and going, “No, this is a uniquely disqualifying event.”
This is a man who actually incited a violent attack on the Capitol and was willing to sacrifice the lives of police officers in order to overturn the election.
As we’ve seen from the (special prosecutor) Jack Smith indictments, this was a concerted conspiracy that culminated in acts of violence. Donald Trump tried to get the courts to overturn the election, failed miserably, tried to get legislatures to overturn it and wipe out tens of millions of votes, failed, then came up with a conspiracy of election fraud to use fake electors. That didn’t work.
And then, having failed all of these other attempts, he turned to violence.
Q: Have Trump’s rambling speeches figured into your thinking?
A: One of the biggest stories of 2024 was the withdrawal of Joe Biden after his very poor performance in the debate. There were legitimate questions about his decline. So, if that was the most important issue in the presidential race when it dealt with Biden, why is it not the central issue when it comes to Donald Trump?
So you’ll have Donald Trump come out and spend 45 minutes with pure incoherent gibberish, and you will still have media commentators the next day wringing their hands about what we got in the latest policy white paper from Kamala Harris.
Q: Have the media given Trump a mulligan on the pandemic?
A: Oh my God, yes. It’s like we’ve said that year doesn’t count. And I don’t understand that.
One of my other big issues is, are we really going to turn Ukraine over to Vladimir Putin? Are we really going to dismantle NATO?
Q: What about this election keeps you up at night?
A: It’s an excellent question. What keeps me up at night: Just think that 70 million or 80 million of my fellow Americans look at Donald Trump and think that this is somebody who should have the office once held by George Washington and Abraham Lincoln. That’s what really shocks me, that with all the lies, with all the failures, with all the betrayals, with all the crimes, that 70 million or 80 million people will cast their votes for him.