How a top conservative radio host took on Trump, lost his audience and faith, but gained a new perspective

Reporting from MEQUON, Wis. —  For nearly 25 years, Charlie Sykes was one of the most powerful and influential voices in Wisconsin.

He cheer-led policies that turned this historically progressive state into a model of conservative governance. He made and destroyed political careers, using his perch on Milwaukee talk radio to help vault figures such as House Speaker Paul Ryan and Gov. Scott Walker to national prominence.

But for the moment Sykes was speechless. He sank into the brown leather banquette of a suburban steakhouse. He stammered. He sighed.

“When you’ve devoted your whole life to certain beliefs and you think now they have been undermined and that you might have been deluded about things,” he began. “So. So. Um...”

In 2016 Sykes emerged as one of Donald Trump’s most prominent critics, a stance that outraged listeners, strained longstanding friendships and left him questioning much of what he once held true.

What it means to be a conservative. The role of race in politics. The wisdom of voters.

More troubling, Sykes believes he and others in the shoutrageous world of talk radio contributed mightily to the rise of Trump, to the contagion of fake news that abetted his presidential candidacy and to invigorating the racist, sexist and xenophobic elements drawn to his caustic campaign.

“Reaping the whirlwind,” Sykes calls it, and though his heresy has opened new avenues, including a commentary role on left-leaning MSNBC, many erstwhile foes question both his motivations and avowedly sudden self-awareness — the leitmotif for a book due out in October.

They liken him to a pyromaniac grieving over the ashes he created, or, as former Wisconsin Democratic Chairman Mike Tate put it, “a guy who slowly fed poison to his dog for 10 years then, when the dog dies of poisoning, throws up his hands and says, ‘My God, how did that happen?’”

For Sykes, it presents something of an existential crisis. Reviled by old allies on the right — “Judas goat!” “Benedict Arnold!” — and distrusted by many on the left, he quit his radio show and finds himself a bit at sea.

“Kind of the man without a country at the moment,” Sykes said.

::

For Trump supporters, Inauguration Day was a glorious pageant. Detractors called it Black Friday.

Others who opposed Trump believe it signaled time to move on, swallow their qualms and, however grudging, hope for the best. In a word, surrender.

“I campaigned against him and I was beaten,” said Katie Packer, who ran a political action committee that spent more than $18 million trying to stop Trump. “I may find things that he does to be objectionable but I don’t really have it in me to spend the next four years just hating on the guy every single day.”

Rob Stutzman, another outspoken Trump critic, has taken solace in his conservative Cabinet picks and the promise of tax cuts and a rollback of environmental regulations. “I’ve adopted more the notion of wait and watch at this point, but the first week was mostly appalling,” said Stutzman, a Sacramento-based GOP consultant.

Some, however remain firmly dug into their never-Trump trenches.

John Weaver, who managed Republican John Kasich’s White House bid, has never met Sykes, but expressed admiration. “He hasn’t been one of those so-called conservatives who modified their belief system in order to curry access or favor,” said Weaver, who offers a steady stream of anti-Trump vituperation on his Twitter feed.

Sykes’ own feed has become a catalog of contempt; recently it’s been filled with criticism of Trump’s immigration ban and the failure to mention Jews in a White House statement observing Holocaust Remembrance Day.

Sykes, who broadcast for 23 years before ending his radio show, gained national notice in March when an unwitting Trump called into his radio program a week before the Republican primary. “Here in Wisconsin we value things like civility, decency and actual conservative principles,” Sykes said by way of welcome, implying Trump lacked all three.

For the next 16 minutes, a polite but persistent Sykes prodded the GOP front-runner about his history of supporting Democrats, his disparagement of women and “playground” behavior. “Do you ever apologize?” Sykes asked, suggesting it was something “most real men” do.

Trump responded with rare equanimity, and no apologies. Afterward, he derided Sykes as a “low life” and “whack job.”

He lost the primary — a fact Sykes mentions with pride — but the setback barely slowed his march to the nomination. (Trump narrowly carried Wisconsin in November.)

The big loser, arguably, was Sykes.

He is 62, with the tidy, all-American looks of the dad in a store-bought picture frame. His own father died of a heart attack at 63, so the age has long been a kind of benchmark; Sykes says even before Trump’s rise he planned to end his radio show to pursue new interests.

But the antipathy of old friends and allies made the decision much easier.

“Basically the music score of my last six months was ‘We’re not listening to you again,’ ‘What’s up with you?’ ‘Betrayal,’” Sykes said with a small, mirthless laugh. “Some could have been trolls from Macedonia. Others were prominent Republican women from Waukesha I’ve known for 20 years.”

His last show was Dec. 19, drawing a series of tributes, including Walker’s declaration of “Charlie Sykes Day” in Wisconsin. Ryan was among the luminaries calling in; he pointedly ignored the host’s jocular plea to prove him wrong about Trump.

The speaker, who hails from the policy wing of the GOP, is one of Sykes’ longtime political soulmates. Reince Priebus, a former state party chairman serving as Trump’s White House chief of staff, has also been a friend, which only underscores Sykes’ estrangement from his old bedfellows.

He speaks of a Faustian bargain — “What are you willing to sell out in order to get tax reform?” — and likened those around Trump to the dupes who surrounded Adolf Hitler, convinced they could control him once he gained power. “So this is the Franz von Papen plan, right?” Sykes said, referring to the German chancellor who preceded the Nazi dictator.

“I think ultimately it’s the triumph of hope over experience,” he said, with another cheerless laugh.

::

Before he was a talk-radio titan, Charlie Sykes was a hotshot journalist and, before that, a Eugene McCarthy-loving young Democrat.

He followed his father in both directions.

Jay Sykes was a reporter and editorial writer at the Milwaukee Sentinel before leaving the paper to teach journalism. As the Wisconsin director for McCarthy’s 1968 presidential campaign, he helped lead the anti-Vietnam War candidate to victory in the primary; 13-year-old Charlie was a volunteer.

But he was no scruffy-haired radical; a 2000 Milwaukee Magazine profile describes him as “a freckle-faced teenager in a button-down Oxford” with hair conservatively shorn above his ears.

By his 20s, Sykes had become increasingly alienated from the Democratic Party, put off by its permissive stance on abortion and the violence of the anti-war movement. His disenchantment grew as a City Hall reporter, covering what he considered costly but ultimately failed government programs.

His evolution from Democrat to Reagan-era conservative is cited by skeptics who see Sykes’ latest incarnation as another case of expedient rebranding.

“There’s a fortune to be made going out speaking to liberals and telling them how evil and awful conservatives are,” said Mark Belling, Milwaukee’s other major talk radio personality, who gave Sykes his start as an occasional fill-in host. (Sykes jumped to a rival station and began his own show after about a year.)

However heartfelt his mea culpa, Belling said, “It’s undeniable that it has opened doors for him that otherwise would not have existed.”

Sykes doesn’t disagree. “I don’t like it,” he said quietly. “But I understand why people say that.”

::

Regrets? Sykes has a few and as Frank Sinatra sang from the speakers overhead, he listed some.

He remains devoutly conservative, so it’s not as though his political philosophy changed.

But he wishes he had opened his show to more divergent viewpoints, instead of feeding the preconceptions of his audience. He wishes he hadn’t done so much to denigrate legitimate news sources, to the point where listeners automatically dismissed facts if they were reported by outlets such as the Washington Post or New York Times.

He wishes he had done more to try to bridge the vast racial gap between Milwaukee and its suburbs, which makes this perhaps the most segregated metropolitan region in the country. He wishes he more forcefully dismissed the Trump-peddled fiction that President Obama was born in Kenya.

“If I contributed to this, I got to own up to that,” he said. “When you have something this big… it’s time for some serious introspection.”

Sykes had hoped to be somewhere far off on Inauguration Day, in the north of France, visiting family. But a book deadline disrupted those plans, and his obligation to MSNBC forced him to watch Trump’s speech, painful though it was.

Not in real time, however. He watched it on YouTube, pedaling furiously on his exercise bike to help ease his blood pressure.

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Twitter: @markzbarabak

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