× Expand James Gill Donald Trump sent Sykes this signed copy of The New York Times soon after their contentous on-air exchange of March 28, 2016.

“Charlie ought to be going out in a wave of glory.”

So wrote fellow conservative Milwaukee radio host Mark Belling on the occasion of Charlie Sykes’ retirement from the airwaves last December. Belling noted that, as of Sykes’ final radio show, Republicans were about to take full control of both the federal and state governments for the first time since the 1950s. That fact should have made this moment the pinnacle of Sykes’ 23-year radio career.

Sykes’ final week of broadcasts on WTMJ-AM included tributes from virtually every Republican political star in Wisconsin. Ron Johnson jokingly blamed Sykes for his ascent to the U.S. Senate. And Gov. Scott Walker gushed, “You have had a tremendous impact … on the conservative movement, not just here in Milwaukee, but across the state.”

Despite the glorious send-off, the 62-year-old Sykes’ political identity was in a state of upheaval. Significant swaths of the once-cohesive Wisconsin conservative juggernaut, a group that he had both led and served for decades, were now ignoring him or, even, actively shunning him.

A bomb named Donald Trump had detonated within the GOP. And Sykes, who had believed for years that Trump would be an absolutely unacceptable leader of his party, was among its casualties.

The ideological and professional stability Sykes enjoyed through his decades on the air were a contrast to his peripatetic earlier life as a student and journalist. Before radio, he had bounced back and forth between liberalism and conservatism, and from publication to publication, working as a reporter, editor and columnist.

It’s hard, as a matter of fact, to find a veteran journalist in Madison or Milwaukee who has not worked with Sykes. Even after he launched his radio career in the early 1990s, his byline remained a frequent sight in Wisconsin newspapers and periodicals, including Isthmus. “What separates Charlie from 75 percent of the other prominent conservative commentators is that he knows journalism,” says Marc Eisen, former Isthmus editor who later worked with Sykes at Wisconsin Interest magazine. “The guy is a pro.”

No one could have convinced me two years ago that, come 2017, Charlie Sykes and I would be on the same wavelength. But Donald Trump has left me politically homeless, too.

While I was not one of his listeners, Sykes loomed large within the Republican Party of Wisconsin, of which I was an active, but often malcontented, member. My fellow libertarian-leaning activists and I regarded him as an establishment shill, dedicated to the promotion and protection of an ossified party power structure. Belling’s overall assessment of Sykes’ career is positive, but he observes that Sykes “often seemed like a cheerleader rather than a commentator.”

If Scott Walker, Paul Ryan, Reince Priebus and Ron Johnson were the party capos, then Sykes was their muscle. “If you went against the grain,” recalls longtime Sykes adversary Michael Murphy of the Republican Liberty Caucus, “Charlie would call you out.”

I also assumed Sykes was, stylistically, a local version of Rush Limbaugh, his shtick exploiting the darker corners of his listeners’ psyches. Though presumptuous, my distant read of Sykes was not entirely off base. Sykes himself has spent a good deal of time lately reassessing his radio career, and acknowledging mistakes he made.

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In early October, Sykes’ ninth book, How the Right Lost Its Mind, will be published by St. Martin’s Press. The book chronicles the bizarre transformation the conservative movement has undergone since Donald Trump declared his candidacy in June 2015. But it’s also a personal story. The conservative movement has been so central to Sykes’ life, and he so central to it, that the book could hardly not be personal.

While Sykes has come a long way toward making sense of what happened, he is still somewhat bewildered by Trump’s decisive capture of the movement. From Sykes’ perspective, it was a hostile takeover, constituting a “repudiation of the conservative mind.” As Sykes writes in the book, Trump had tapped into “something disturbing that we had ignored and perhaps nurtured — a shift from an emphasis on freedom to authoritarianism and from American ‘exceptionalism’ to nativism.”

When I met with Sykes late this summer, he recalled the strong sense of loss he felt as the conservative movement slid into derangement, and the decision it forced him to make. “If I break with the movement,” he had asked himself, “have I squandered everything that I’ve spent 20 years working on?” Sykes says he understands others’ reluctance to break. “This is who you are, this is your identity, these are your friends. And if you break with them, are you repudiating a real large chunk of your own life?”

Despite the high price, “There was not a single moment when I thought, ‘maybe I should go along.’” Today, he adds, “The infrastructure that I had is completely gone.”

From a distance, Sykes’ decision might not seem so self-sacrificial. He has, since Trump’s election, had multiple op-eds published in The New York Times. He co-hosted Indivisible, a WNYC radio series that explored the early Trump administration’s impact on American life. And, most notably, he is now an official contributor on MSNBC. Would any of these opportunities with big-time media have come his way had he not so publicly and vehemently refused to board the Trump Train?

At the time of his retirement, Sykes told The Cap Times that he had decided to end his radio show over a year earlier. So throughout 2016, as he relentlessly bashed Trump, he knew that he would be scouting for new opportunities.

“Charlie looks out for Charlie,” says the Republican Liberty Caucus’ Murphy. “This latest act is just him hoping to stay relevant, and maybe even go national.” Others, like Isthmus columnist and Urban Milwaukee editor Bruce Murphy, assert that Sykes’ political beliefs have often tracked with career opportunities. The reality, Murphy wrote earlier this year, “is that Charlie Sykes has been changing his views, over and over, throughout his life, and has always been rewarded for it.”

× Expand Joeff Davis "While Paul Ryan and Reince Priebus gained influence, Charlie Sykes’ opposition to Donald Trump kept him out in the cold."

Sykes seems dumbfounded by accusations that his steadfast opposition to Trump is driven by expediency. While people with whom he was closely associated — like Paul Ryan and Reince Priebus — moved into positions of great influence, Sykes’ uncompromising stance against Trump kept him out in the cold. “An opportunist goes with the power, not into exile.”

Sykes does appreciate the “strange new respect” he is getting from corners of the media world that used to dismiss him. But he is still quick to criticize the “liberal media,” arguing that their shabby treatment of conservatives fueled the rise of the right-wing propaganda machine. Conservative news-seekers, he writes, “were drawn to safe places, but also pushed.”

At some point, conservative talk radio hosts discovered that traditional news sources make perfect foils. So the talkers pounced, and kept pouncing, until, Sykes writes, “We had succeeded in convincing our audiences to ignore and discount any information whatsoever from the mainstream media.” He regrets that this strategy of delegitimization served to “destroy much of the right’s immunity to false information.”

Sykes devotes a substantial section of How the Right Lost Its Mind to the ascendance of “Alt-Reality” propaganda, how it nurtured “Post-Truth” politics, and its role in Trump’s electoral triumph.

It’s a chilling read. A sizable chunk of the American electorate is astonishingly susceptible to fabrications, even patently absurd ones. In Sykes telling, things got so weird during last year’s campaign that a cottage industry of fake fake news sprung up. Pranksters began fashioning reports just to test the limits of credulity. One tweeted out a contrived Clinton Foundation expense report that showed payees like ‘Sharia Law Center’ and ‘Bill Ayers,’ to see if the Twitterverse would bite. (Spoiler alert: the pranksters were unable to detect any limit to credulity.)

President Trump has, in a stroke of propaganda genius, co-opted the term “fake news,” applying it to legitimate media outlets that he considers unfriendly. In our conversation, Sykes noted that for each of his op-eds, The New York Times assigned a fact-checker. When he hears the president call the Times a “fake news joke,” he remembers the extreme rigor the paper has subjected his work to.

Toward the end of his book, Sykes urges fellow conservatives to “confront the conservative media that boosted and enabled Trumpism and created a toxic alternative reality bubble.” I asked him what non-conservatives might do to help. Because false beliefs are protected by extremely stubborn psychological barriers, Sykes thinks only “still-trusted conservative voices” have the power to stop the madness. “The right’s going to have to clean up its own house.” He laments that, as of now, “We’re not seeing a lot of that.”

Though an “optimist by nature,” Sykes concedes that his book is not terribly uplifting. At a forum in which he recently participated, he relates, a fellow panelist referred to him as “the prince of darkness.”

“The damage to the political culture is so deep. If you have millions of Americans that learn to accept lies … that’s a degradation that is hard to come back from.

“Everything that’s happening now that’s bad,” he adds, “will get worse.”

On March 28, 2016, about a week before the Wisconsin presidential primary, Donald Trump called in to Sykes’ radio show. It was an unexpected booking, as Sykes was already renowned for his vigorous anti-Trumpism.

Sykes hit the future president with tough questions almost immediately, and things only got hotter as the interview progressed.

Sykes scolded Trump over a tweet that disparaged Heidi Cruz’s looks. “I expect that from a 12-year-old bully on the playground, not somebody who wants the office held by Abraham Lincoln.” After an unsuccessful attempt to elicit some contrition, Sykes asked Trump if he ever apologizes, the way that “most real men, when they screw up” do.

The interview went viral, and was picked up by most major national media outlets.

× Expand Joeff Davis "A bomb named Donald Trump had detonated within the GOP."

Much as I savored hearing Trump get grilled, the exchange reinforced my presumption that Sykes was an archetypally aggressive right-wing talker.

But sampling his radio archives (which are available back to September 2015), I was surprised to hear an almost uninterrupted record of reasonable-sounding, dialogue-based broadcasting. Sykes is clearly a man of strong opinions — a polemicist, even — but I heard none of the childish insults, like “feminazi,” that I expected to.

“Early on … [Sykes] would cut people off and belittle them. But he mostly got over that,” according to West Bend journalist, blogger and businessman John Torinus. “Of the talk show hosts, he has been among the most civil.” Torinus adds, however, “It’s a low bar.”

Sykes has long chafed at being lumped in with figures like Rush Limbaugh and Sean Hannity. To the local media, “we all were alike, [so] we could all be dismissed that way.” He spends an entire chapter of How the Right Lost Its Mind chiding Limbaugh for his support of Trump and various other hypocrisies. At one point during our conversation, in an almost sympathetic tone, Sykes says that Hannity is “dumb as a box of rocks.”

Sykes alludes to his low moments, when he might have been confused with a Limbaugh or a Hannity, in the introduction of How the Right Lost Its Mind, wondering, “Did we — did I — contribute to this prairie fire of bigotry and xenophobia that seemed to grip so many on the right?”

Often, Sykes leaves such questions of personal responsibility hanging, or, in speaking of talk radio’s sins, hedges in distinguishing between ‘we’ and ‘I.’ During our discussion, he firmly declares that “Everything seems so much more toxic, and, of course, talk radio contributed to that.” But then, after a moment, he adds, “… as a national institution.”

Unlike Tea Party firebrand Glenn Beck, who has virtually disowned his former self, Sykes seems not quite ready to go full mea culpa. Maybe that’s because he knows he did push back against the GOP establishment at times, especially when corporate welfare was involved.

But Sykes does regret supporting former Milwaukee Sheriff David Clarke early in his career. And Sykes concedes that, too often, he turned a blind eye to signs that something was terribly amiss in his sphere. Instead of decisively countering those who made bizarre, ugly assertions about, say, President Obama’s nativity or religious beliefs, “we simply rolled our eyes, because we were allied with them. They were still our friends. And then, suddenly, you realize, ‘This is who we are?’”

Sykes is glad to be free of the tribal pressures that came with having to maintain an audience. “I have not had one day when I regretted not being on the air. Because I don’t want to have to think about ‘What’s the backlash on all of this?’”

Tribalism is, Sykes believes, at the root of the right’s debasement. “For many conservatives, a willingness to ignore, rationalize or defend lies has become a test of tribal loyalty,” he writes in How the Right Lost Its Mind.

And tribalism can make deviant political behavior, like intimidation, seem perfectly acceptable. He recounts in the book how prominent Milwaukee-area conservative activist Bob Dohnal called Sykes out soon after the election, branding him and other vocal “Never Trumpers” on the right as “Judases.” “The biggest question we had,” wrote Dohnal, “was how come Sykes and all of his buddies were doing this?”

Dohnal could have looked back at his own email for a clue. He had written, just a few months earlier, that the newly minted GOP nominee should drop out of the presidential race. “[Trump] is a definite split personality: manic depressive if [I] ever have seen one, and I have seen thousands [as a] clinical pharmacist.” In a June 2016 blog post, Dohnal observed that Trump’s speaking style is similar to “Peron, Mussolini, Chavez, Huey Long, [and] other rank populists.”

I contacted Dohnal, in an attempt to understand his speedy conversion from anti-Trump conservative to excoriator of anti-Trump conservatives. Dohnal says things turned for him when, travelling the state, he realized that Trump could actually win Wisconsin. “So … I started beating up on these guys, and saying … ‘if you’re going to be Republicans, that’s fine, then either shut up or back Trump.’” Dohnal continues, “If [Sykes] wants to spend 20 years being a conservative and a Republican, and living off of that, then that’s fine. But once he [turned] against us, I said to him ‘You are the enemy. I have to fight you.’”

Similarly, radio host Belling went from railing against Trump (“lying comes easily to him”), to reluctantly supporting him, to calling prominent conservative Trump critics like Sykes “spoilsport brats who hop in bed with the enemy.”

Belling explains in an email: “[Sykes] clearly is relishing mocking a president who, despite faults, seems to be trying to achieve conservative goals that Charlie and the other anti-Trumpers claim to care about.” He continues, “Some conservatives like Charlie seem more pleased with the approval of The New York Times, Isthmus and the intellectual elite than of those whose political beliefs they purport to share.… Trump was my 16th choice out of the 17 that ran but I refuse to take my rattle and cry in the crib like Charlie and many others.”

Sykes finds it especially disconcerting that conservatives are attacking him on behalf of a politician who, as he argues in his book, “spent most of his career rejecting their values.” He urges those who believe he is a turncoat to “find something I am saying now that I wasn’t saying a year-and-a-half ago.”

I ask Sykes if it comforts him to consider that some who support Trump have genuinely respectable intellects and judgment. Does he ever wonder if he’s overreacting? “You always have to ask yourself that,” he responds. “But ultimately the answer is no.”

Sykes believes that the “corrupting phenomenon of power” has situationally scrambled some people’s judgement. “Power is a drug. It’s seductive. People make compromises to be close to power.” As he thinks back on the mass capitulation he witnessed, wherein close, trusted friends surrendered their political souls to Donald Trump, he wistfully reflects, “The power of the tribe was so intense.”

Sykes’ optimism did make a few appearances during our conversation. He notes that Republican U.S. senators seem more and more willing to break ranks as the administration drags on. “What you’re seeing now is the growing recognition that we made this Faustian bargain, but it’s not working out for us.”

With a hint of cheerful sarcasm, Sykes says that “liberals have suddenly discovered the value of the Constitution and checks and balances” and that “journalists have rediscovered their mission of being adversarial and speaking truth to power.”

I get the impression, though, that Sykes never stays upbeat for long these days. Words like “soul-crushing,” “heart-breaking,” and “painful” make frequent appearances. He has learned some very uncomfortable things over the past couple years. He asks me, rhetorically, “How can the GOP go back to saying that the Constitution matters, that character matters?”

But Sykes has given up on neither his country nor conservatism. He is in talks with WNYC to host a podcast. The prospect of deepening his reach into a liberal-leaning media audience excites him. “At this particular moment, to be an evangelist for rational, principled conservatives in the world is a pretty important thing to do. I get a lot of reaction from people going, ‘Wow, I didn’t know that conservatives thought that way.’”

And How the Right Lost Its Mind will surely garner major national media attention. Brian Williams is already flogging the book on his MSNBC show. Of the coming publicity, Sykes says, “I’m expecting some heavy incoming fire from both the right and left.” He adds, only half-jokingly, “This will probably cost me the remaining friends I have in Wisconsin.”

Charlie Sykes’ upcoming Madison appearances:

Sept. 17: Cap Times Idea Fest, Gordon Dining and Event Center, 10 a.m.

Sept. 18: Wisconsin Writer in Residence talk, UW-Madison’s Discovery Building, 4:30 p.m.

Oct. 16: Wisconsin Book Festival, Madison Central Library, 7 p.m.