Erick Trickey is a writer in Boston.

Charlie Sykes’ conscience is nagging him.

Since last year, the most influential political talk show host in Wisconsin has found out just how hard it is to be a #NeverTrump conservative on right-wing radio. Ever since Sykes began denouncing Donald Trump on the air—which he does just about every time he talks about the presidential election—he’s strained his relationships with the listeners of his daily radio show.


Sykes’ many arguments with listeners over Donald Trump’s serial outrages have exposed in much of his audience a vein of thinking—racist, anti-constitutional, maybe even fascistic—that has shaken Sykes. It has left him questioning whether he and his colleagues in the conservative media played a role in paving the way for Trump’s surprising and unprecedented rise.

A few days before the Wisconsin congressional primary in early August, Sykes seized on remarks by Speaker of the House Paul Ryan’s opponent, Paul Nehlen, that raised the idea of deporting all Muslims, even American citizens. It’s the kind of inflammatory rhetoric that has become the norm during a presidential cycle that has featured Trump’s calls for immigration bans on Muslims, loyalty tests and mass deportations. A friendly and round-faced guy with glasses, Sykes, 61, doesn’t even try to conceal his disgust, but a large segment of his listeners, like Audrey from Oshkosh, are eager to defend ideas that Sykes believes violate fundamental conservative principles.

“Yeah! Let me make a comparison, and I don’t mean this in a bad way,” Audrey says. “They’re talking about phasing out breeding of pit bulls. Well, not all pit bulls are bad.”

“You’re comparing American citizens, Muslims, to rabid dogs,” Sykes responds.

“No, I’m saying, they’re talking about phasing out the breed because so many are bad. No one wants to phase out poodles! I mean, there’s no Lutherans doing this! We never know when one of these people are going to be radicalized.”

“One of these people,” says Sykes.

Sykes ends the call. He’s silent, broadcasting dead air. He looks upset, like he’s stopped breathing. He goes to a commercial break.

“OK, that doesn’t happen very often,” he says off-air. “I’m not usually absolutely speechless.” He says his listeners never talked like this until recently.

“Were these people that we actually thought were our allies?” he asks.

Sykes remains confident that Trump will lose badly in November, and he is equally fearful that Trump will drag longtime Republicans, like Senator Ron Johnson of Wisconsin, down with him. This has Sykes thinking about the long-term future of the party and what might have precipitated its looming collapse. He wonders: Did “the faux outrage machine” of Breitbart.com and other right-wing outlets foment the noxious opinions that Trump has stoked so effectively on the trail?

“When I would deny that there was a significant racist component in some of the politics on our side, it was because the people I hung out with were certainly not,” Sykes says. “When suddenly, this rock is turned over, there is this—‘Oh shit, did I not see that?’

“I kind of had that reaction this morning, with that woman: Did we ignore this? There’s got to be some serious introspection, because of the things that we either didn’t see, or that we ignored, or that we enabled.”



***

Few people outside Wisconsin had heard of Sykes until this spring, when his explosive interview with Trump became national news. In the 17-minute confrontation a week before the Badger State’s primary in April, Sykes exposed several flaws in Trump’s candidacy, including his lack of preparation and obsessive grudges. “Before you called into my show, did you know that I’m a #NeverTrump guy?” Sykes asked. “That I didn’t know,” Trump replied. Sykes gave Trump several chances to back off his feud with Ted Cruz over online insults about each other’s wives, but Trump couldn’t let it be. “He started it,” Trump kept saying. “We’re not on a playground,” Sykes replied. “We’re running for president of the United States.”

When Cruz beat Trump—the #NeverTrump forces’ last big win—many credited Sykes with a key role. “Midday with Charlie Sykes,” on 620 WTMJ-AM, where he’s been a host for 23 years, reaches 200,000 listeners a week in the Milwaukee area alone, and more beyond. Sykes is Wisconsin’s most prolific conservative media personality: He also hosts a weekly TV show and edits the website Right Wisconsin and the Wisconsin Policy Research Institute’s magazine Wisconsin Interest. His support has boosted conservative candidates across the state, most notably Scott Walker. Sykes and the governor are close, often exchanging texts and emails. Sykes supported Walker throughout his rise to power, the fierce backlash to Wisconsin’s 2011 anti-union law, and the failed 2012 gubernatorial recall.

“[Sykes’] contributions to the conservative movement in Wisconsin cannot be overstated,” Walker said in a written statement. “I value his friendship.” Walker’s support for freezing tuition at Wisconsin’s state universities parallels the ideas in Sykes’ eighth book, published this month: Fail U.: The False Promise of Higher Education, a thoughtful critique of the spiraling cost of college and the “culture of victimization on campus.”

So on this Friday in August, Sykes is juggling his many conservative roles—radio host, thinker, translator of Wisconsin political mores for the outside world. Young reporters from Vice and Milwaukee Public Radio interview him about his book’s argument that spiking student debt isn’t worth it. New York Times, Wall Street Journal, and NBC political reporters ask him about the Ryan-Nehlen race and whether Trump will endorse Ryan. Meanwhile, he’s wrestling with his listeners, from whom he is feeling increasingly estranged.

“I am dealing with the daily flood of emails on how we’re never going to listen to you anymore,” Sykes says. Longtime listeners write him to say conservative talk radio should criticize Hillary Clinton and not Trump.

“If I lose listeners, that’s a price I’ve just got to pay,” he says. He’d rather say what he really thinks than fall in line with other broadcasters’ embrace of Trump. “I feel dumber every time I listen to Sean Hannity. I don’t want to be that guy.”

***

Paul from D.C. is on the line.

“This is not the U.S. Constitution; this is not the Bill of Rights,” the speaker of the House responds after Sykes plays him Nehlen’s anti-Muslim comments. “This is not Wisconsin conservatives, Wisconsin Republicans. That kind of dark, grim, indefensible-thinking comment is going to be thoroughly rejected and repudiated Tuesday, I believe.”

Sykes sees an opening. “OK, so here’s my question: What would you say if Donald Trump is asked about this comment and refuses to disavow it? Would that be disqualifying for you?” Sykes’ face has turned red. He’s smiling.

“I’m not going to go into hypotheticals,” Ryan answers testily. “You and I have had these conversations. By the way, with any endorsement of anybody, there’s never a blank check. And you know that.”

This is how Sykes’ show has gone since Trump clinched the nomination: The biggest names in Wisconsin Republican politics call in—like Walker and Johnson—and the normally sympathetic host grills them about their support of Trump.

This time, Sykes reads from an especially punishing New York Times column, in which Ross Douthat claims Trump has “laid waste” to Ryan’s reputation for “moral and substantive authority.”

“I’m the speaker of the House,” Ryan replies. “With this job comes different responsibilities than, say, if I were just a congressman from Wisconsin. … This man won the votes fair and square. … As part of my responsibility for this job, I have the duty and obligation to honor this process.”

Sykes met Ryan when the speaker was first running for Congress, and he’s always been impressed with Ryan’s talent and intellect. They’ve matured together, Sykes says. For instance, they’ve both moved away from their earlier rhetoric about a country divided between “makers” and “takers.”

Shots around the office of radio host Charlie Sykes. | Darren Hauck for Politico Magazine

Wisconsin’s conservative talk-radio hosts are closer to Republican elected officials than radio populists elsewhere. They share pride in the successes of the state’s brand of conservatism: They brag about Ryan being the national Republican Party’s intellectual leader, and they celebrate Walker’s sharply conservative agenda. Decency is also a big part of the Wisconsin Republican self-concept, which clashes with Trump’s self-aggrandizing bombast.

“The elected officials in Wisconsin are all pretty much anti-Trump,” Sykes says. Nevertheless, nearly all of them endorsed Trump once he became the presumptive nominee. Sykes thinks none of them have their heart in it.

“Walker and Ryan have no illusions whatsoever about who Donald Trump is,” Sykes insists with the authority of a confidant. “They could have a conversation for an hour and a half with me, and everything [I] say about Donald Trump, there would be no disagreement. It’s just, at the end of the conversation, they would say, ‘Yes, but we can’t elect Hillary Clinton.’ I would say, ‘I can’t bring myself to vote for Donald Trump. I think he’s unfit to be president.’”

Sykes sympathizes with Ryan's and Walker’s political quandary, but he’s unsparing in his critique of Reince Priebus, who, as the state GOP chairman, boosted Ryan and Walker’s careers before he ascended to the chairmanship of the Republican National Committee. After Priebus declared Trump the presumptive GOP nominee, Sykes stopped talking to him for a couple of months.

“I just didn’t want to hear about the Kool-Aid,” Sykes says after a long sigh. “Reince is a friend. Reince has no illusions about Donald Trump, but made this decision not just to support him, but to go all in. It was painful watching somebody who I knew knew better. That’s why I describe him as a tragic figure.”

Priebus, he notes, commissioned the famed post-2012 election “autopsy” that called on the GOP to become more inclusive. “To watch him bow and scrape before the Orange God King—it was difficult!”

***

The reluctant right’s most powerful argument for supporting Trump, the future of the U.S. Supreme Court, doesn’t persuade Sykes—even though it affects someone close to him. His ex-wife, Diane Sykes, is on Trump’s short list for the U.S. Supreme Court.

Since their 1999 divorce, Diane Sykes has risen from local judge to federal appeals court judge and has developed a national reputation as a respected conservative jurist. In a February debate, Trump offered her as an example of a judge he might appoint to the high court.

Sykes says he’s “very close” to his ex-wife. “She would be absolutely fantastic for the court,” he says. “That would be an outstanding choice.” There’s just one problem. “I don’t trust [Trump] that he will appoint the people he says. I don’t believe the promises he’s making aren’t negotiable. He’s backed off virtually everything.”

This does not mean he can contemplate voting for Trump’s opponent. (When pressed, he says he’s willing to consider voting for Libertarian Gary Johnson.) “Hillary is awful and potentially corrupt within historically understandable parameters,” says Sykes. He holds his hands about a foot and a half apart. “She’s awful like that.”

Then Sykes throws his arms out wide. “Trump is potentially awful at this level,” he says.

In Sykes’ eyes, Trump is “a serial liar, a con man, a fraudster, a narcissist and authoritarian.” Clinton, meanwhile, is “a welfare-state liberal Democrat” and “big government” supporter with her own character problems.

“In any other scenario, Hillary Clinton’s lying about her emails, and her pay-for-play relationship with the Clinton Foundation would be disqualifying issues,” he argues. “The only reason they’re not disqualifying is because Donald Trump is a fundamentally more repellent, dishonest figure.” He predicts Trump will lose Wisconsin, take Ron Johnson’s Senate reelection bid down with him, and poison the Republican Party’s chances to ever make inroads with women, minorities and the young.

He predicts doom for the GOP ticket in Wisconsin in November. Trump, he says, is “uniquely unpopular in the biggest Republican areas of the state”—meaning the Milwaukee suburbs, where Sykes’ show has its deepest reach. Though Sykes thinks Johnson is an “outstanding” and “fantastic” U.S. senator, he thinks the Tea Party favorite will lose to liberal Russ Feingold, who’s running to take his old seat back. Trump’s unpopularity will trickle down the ballot and wound Johnson, Sykes thinks: “It’s not going to be pretty.”

Besides, Sykes notes, Wisconsin’s conservative revolution is based almost entirely on success in off-year elections. The Badger State hasn’t gone for a Republican presidential candidate since 1984. (George W. Bush lost Wisconsin by less than 1 percent in 2000 and 2004, but Barack Obama won it overwhelmingly in 2008 and 2012.)

“After November, the #NeverTrump conservatives will basically find themselves in the wilderness,” Sykes says. “Our role is going to be opposition to whatever is the ruling regime installed next year. I don’t want to be complicit in it one way or another.”

Charlie Sykes recording live. | Darren Hauck for Politico Magazine

Instead, Sykes wants to help Ryan-style conservatives take the Republican Party back from Trump’s angry nationalists. “I hope to spend next year writing my next book,” Sykes says, “which will be titled How the Right Lost Its Mind.” He wants to figure out why, in his opinion, things went so wrong for the conservative movement. One problem, he thinks, is his fellow talk-radio hosts.

“Talk radio made itself relevant by beating up on other Republicans, vilifying other Republicans,” he says. “It fed this faux outrage machine that raised expectations unrealistically”—for instance, asking why Congress didn’t repeal Obamacare, though Obama’s veto pen made it mathematically impossible. Later, he would tell Business Insider’s Oliver Darcy that talk radio’s attack on mainstream-media bias has backfired, because its listeners now dismiss legitimate media fact-checking as untrustworthy.

Sykes warns his listeners to step outside the “alternative reality bubble” of Breitbart.com and other right-wing websites. Part of his audience thinks he’s sold out, he complains, because he won’t parrot dubious claims they’ve read on such sites. “A lot of the conservative talk shows around the country embrace almost whatever comes over the transom,” he says.

***

Eight days after the Nehlen show, a Milwaukee policeman fatally shot an armed black man, 23-year-old Sylville Smith, after he fled from a traffic stop. Rioters burned down stores, injured police, threatened and even attacked reporters, fired gunshots, and shot an 18-year-old white man in the neck. On the following Monday, the first day back on the air, Sykes drops his coverage of the presidential race and devotes his entire show to the unrest, Milwaukee’s story of the year.

“A riot—not an uprising, a riot,” he says. Sykes sounds like a conventional conservative on this issue, blaming cultural and family breakdowns and criticizing a black Milwaukee alderman for rhetoric that he thinks excuses violence. But he also subtly challenges himself and his audience by bringing on Mikel Holt, a columnist for the Milwaukee Community Journal, the city’s black newspaper, and taking callers from the city, not the Republican-leaning suburbs. Holt pushes back against some of Sykes’ assertions that city politicians have provided poor leadership, and he argues for drawing clear distinctions between the rioters on one side and idealistic activists and law-abiding city residents on the other.

“This was a really important message for my audience to hear,” Sykes says the next day, “that some of stuff they’re seeing on TV is not representative of anything more than a small minority of the community.”

A week earlier, Sykes had said Milwaukee’s racial divisions would also be a part of his coming reevaluation of the conservative movement. He’s thinking again about a 2014 New Republic piece that depicted Scott Walker’s political base in the Milwaukee suburbs as a hostile racial environment and argued that conservative talk radio hosts such as Sykes play a role. Sykes calls the piece “ridiculous,” “tremendously overblown” and a “really, really negative hit job.” But he says he’s going to grapple with it when he writes his next book.

“I’m going to reread it and go, ‘OK, as much as I really seriously hated this story’—this is the nagging thing in the back of your head—‘Is there some grain of truth in the criticism that I spent 20 years denying?’”