Talk Radio host Charlie Sykes is the gatekeeper to Wisconsin Republicans, and he may be keeping Donald Trump out. | AP Photo Why Wisconsin’s 'Never Trump' movement is different And how one radio host used his influence to make it that way.

MILWAUKEE — Charlie Sykes left his Monday interview with Donald Trump even more unimpressed with the New York billionaire than he was going in.

As Sykes was trying repeatedly to get Donald Trump to declare wives “off limits,” the morning radio host was prepared for the GOP front-runner to bring up Sykes’ own ex-wife. In February, after the death of former Justice Antonin Scalia, Trump had mentioned two names of judges he might nominate to the Supreme Court. One was Diane Sykes, a judge on the 7th Circuit Court of Appeals and the conservative radio host’s wife of nearly 20 years before their divorce in 1999 — not that Trump seemed to know that during the 17-minute phone interview he did with Charlie Sykes on Monday.


“He had no idea,” Sykes said Wednesday during a commercial break inside his WTMJ AM620 studio. “I think someone handed him a card with her name on it. He never made the connection.”

Trump's unfamiliarity with Sykes demonstrates that the GOP front-runner knows little about the lay of the political land here because if Wisconsin is where his wave finally breaks, it will be in no small part because of Charlie Sykes.

Sykes is Wisconsin’s leading conservative radio voice after 23 years on air and a leader of the #NeverTrump brigade since long before it had a hash-tag. He might also be the single biggest impediment to Trump's winning Wisconsin’s primary next Tuesday and putting the GOP nomination on ice.

“I’m Masada,” Sykes joked, referencing the desert fortress where Israelis made a stand against an encroaching Roman empire.

In Wisconsin, every conservative knows Sykes’ voice, which airs for three-and-a-half hours weekday mornings on the state’s biggest AM talk station. Many credit him for playing a major role in their recent victories, from Scott Walker’s defeat of the state's unions and the subsequent effort to recall him to the rise of Speaker Paul Ryan and Republican National Committee Chairman Reince Priebus, and he has close relationships with both.

“Sykes has had a big hand in creating Scott Walker and Ron Johnson, who was a nobody,” said Matt Batzel, executive director of the conservative advocacy group American Majority Wisconsin.

It’s happening again, this time in unity behind Ted Cruz, who holds a 10-point edge over Trump here, according to a Marquette University poll released Wednesday. “Sykes is one of the leading factors, if not the leading factor, as to why Cruz is surging,” said Mark Graul, a GOP strategist here who oversaw George W. Bush’s 2004 Wisconsin campaign. “The trusted, respected conservative voices in the state have been anti-Trump from the start, and they’ve become very pro-Cruz in the last few weeks.”

Sykes is aided by a special brand of unity among Wisconsin Republicans, where the party grass roots and their talk radio avatars are on far friendlier terms with their party leaders than in other states.

As much as Walker’s hard-fought legislative and electoral victories accentuated the partisan divide, they served to unify Republicans in Wisconsin. “All the different factions within the conservative coalition have gotten on board in the past,” said Graul. Trump, he continued, “threatens that unity just with his tenor and tone, and because none of us who value conservative principles really know what he stands for.”

This time, a victory by that united front would leave a mark on the national stage.

If Cruz wins Wisconsin’s primary, it would serve notice that the Texas senator can win widely outside the South and embolden the super PACs that are finally pumping millions into a campaign to stop Trump to fight on. It would be a point of pride for Walker, who endorsed Cruz Tuesday morning live on Sykes’ show.

But if Cruz does ultimately find fertile soil in Wisconsin, it’ll be due largely to Sykes’ spadework and the anti-Trump broadsides he’s been delivering almost daily to an audience of 100,000 conservatives in southeastern Wisconsin going back to last summer.

Circuit Judge Terence Evans (left) administers the oath of office to Judge Diane Sykes in 2004 for a position in the United States Court of Appeals for the Seventh Circuit. | AP Photo

“Talk radio’s impact can’t really be understated,” Batzel said. “And it’s first and foremost anti-Trump. There have been such tough battles here with the bargaining reforms, the recalls and Walker’s re-election, and talk radio has been a key outlet for informing the voters and informing the electorate.

“You can literally see the lines of voting for Republican where the radio waves literally end. Their listenership is certainly very high and informs the voters’ decision making.”

On Wednesday morning, Sykes sat at his microphone in a white shirt and blue tie and took call after call from listeners who couldn’t believe Trump had the audacity to show up in Paul Ryan’s hometown and trash Walker. “Trump is criticizing our leaders,” said Mark on Milwaukee’s west side. “He has no idea what the state went through,” said Todd from Menomenee Falls, who told Sykes he volunteered on Walker’s behalf in his last election. “I take it personally. I want to go vote for Ted Cruz more than ever.”

Sykes, like any seasoned radio host with a loyal, like-minded audience, stoked his listeners’ outrage. “You can’t parachute in here from Manhattan and crap on everything we’ve been doing for the last 20 years,” said Sykes, before pivoting to a more reassuring tone. “But people here have a well-attuned BS meter,” he said. “Donald Trump’s approval rating in southeast Wisconsin is extremely low because people pay attention.”

Not once during the three-and-half hour show did a caller disagree with Sykes, but many praised him and his grilling of Trump that’s raised his national profile and filled his evenings with cable TV hits. “I watched the CNN town hall last night and I told my husband, Anderson [Cooper] was taking Charlie’s lead and finally being tough on Trump,” said Mary in Elkhorn.

Warning his listeners about splitting the anti-Trump vote, he urged them to support Cruz mainly as a means to an end — keeping Trump from securing the nomination. “I’m more anti-Trump than pro-Cruz,” he told listeners, asking them to think long and hard before casting a vote for John Kasich, the Ohio governor who is poised to play spoiler. “It’s a binary choice,” Sykes continued. “Either Ted Cruz is going to win, or Donald Trump is going to win.”

“Ted Cruz was not our first choice or second choice,” Sykes continued as we stood outside his studio during a commercial break. “He’s not the best fit for Wisconsin. I know a lot of people coming on board in favor of him are swallowing hard and recognizing that this is it — this is our firewall, our firewall of sanity.”

Sykes is outwardly confident that the Wisconsin firewall he’s helped build will hold next week, telling listeners he gives Cruz an 80 percent chance to beat Trump here. But whatever happens here, Sykes is deeply unsettled by Trump’s appeal and the existential crisis laid bare for conservatives and the party they have long called home.

He wrote a blog piece months ago outlining why he would refuse to support Trump as the GOP nominee, calling the candidate a “cartoon character” of every left-wing stereotype about Republicans. “I’ve spent decades defending Republicans, trying to convince people that conservatives are not racists, that we’re not misogynists,” he said. Trump’s campaign “upends everything.”

“Party loyalty only goes so far,” he told listeners, shrugging off Trump’s statement Tuesday evening that he will no longer promise to support the GOP nominee and offering his own reasoning for refusing to back Trump. “When the Republican Party ceases to be a vehicle for conservative values, there is no entitlement to people’s support.

“I don’t mean to put pressure on him, but how does a Paul Ryan embrace a Donald Trump nomination?” he continued. “How do you as a party go back to Hispanics, how do you go back to women, how do you go back to millennials and wash that stain off after this?”

In his final hour Wednesday morning, Sykes spent an entire segment trashing Trump for defending his campaign manager, Corey Lewandowski, who was charged with misdemeanor battery on Tuesday for grabbing a female reporter earlier this month to keep her away from Trump. “He is going all in in ridiculing and attacking,” Sykes told listeners. “He is saying things that are fundamentally false and untrue and maybe it doesn’t matter, but it ought to matter.”

Taking his headphones off, Sykes continued the thought during the next break, explaining that Trump’s “shtick” bothers him less than its resonance with his unwavering supporters — or as he calls them, “Trumpkins.”

“It’s the people who don’t care that he’s lying. It’s what he unleashes that bothers me,” he said. Suddenly, the conservative radio host was lamenting a country beset by “these media silos where we’ve all created these alternative realities — that it is possible to live in a media reality where you either never encounter a counter argument.

“We bear some responsibility because we beat on the mainstream media for so long and now there are no credible sources anymore,” said Sykes, before pausing mid-thought and putting his headphones back on as the bump music signaling the start of his next segment filtered into his studio.

Sykes has been unable to move the “Trumpkins” — although the man wandering around the parking lot of the Holiday Inn Express in Janesville Tuesday afternoon after Trump’s rally there with a sign that read “Charlie Sykes SUCKS” seems an indication that at least some of them know who he is.

In his final minutes on the air Wednesday, he spoke directly to the Trump supporters he’s thus far failed to convince — if any of them happened to be tuned in.

“Do you understand the implicit contempt the man has for you?” he said. “When he says he could shoot someone and you’d still support him, he’s saying he thinks you’re a sucker.”