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On the Sly
After a "Sly" move (ahem), the lefty Madison talker will share a megaphone with a conservative host. Wait, wait, we've got more puns ...


"Sly" Sylvester
John “Sly” Sylvester
is that rarity in Wisconsin talk radio – a mostly left-leaning on-air personality in a field dominated, as it is nationally, by conservatives.


Next week, he becomes something just as rare – a talker on a station that is willing to mix it up ideologically.


Popular among Madison liberals, Sylvester has been doing opinionated talk in the state capital for a quarter century. But his profile escalated sharply starting in 2011 as he swung solidly behind the opposition to Gov. Scott Walker’s controversial Act 10 stripping public employees of most union rights. Sylvester regularly took the governor and the Republican-dominated legislature to task on his show and in public appearances.


That all skidded to a halt late last year when the news/talk station where he’s worked for the last 15 years – WTDY, 1670 AM – fired virtually all of its staff the day before Thanksgiving in the first step of a format conversion. (After playing Christmas music through the holidays, owners Mid-West Family Broadcasting on Jan. 2 switched the station to its new call letters and format as WOZN, a sports/talk station.)


Almost immediately Sylvester’s fans in Madison rallied to get him back on the air, targeting Madison’s progressive talk station, WXXM, 92.1 FM. Had they succeeded, it might have been an interesting story. But what actually happened may be even more interesting.


Last week, Sylvester announced he would join WEKZ, 93.7 FM, a locally owned station in Monroe. WEKZ’s broadcast reaches Madison – but it also has an audience as far as Dubuque, Iowa, and in the northern Illinois cities of Rockford and Freeport. The station doesn’t subscribe to the Arbitron radio rating service, so the data on how it stacks up in those markets isn’t readily available.


To find local ownership at all in an industry so dominated by major corporations is unusual enough. More striking, though, is that Sylvester’s new employer is interested not in making the station hew to one side of the ideological spectrum, but rather to mirror the diversity of opinion among listeners.


Glenn Grothman
That would be station owner Scott Thompson, who practices law in Monroe while hosting a morning talk show, “The Morning Mess,” on his station. “My show happens to be right of center, and Sly will be a good balance because he’s left of center,” Thompson tells me. “We will have both the yin and the yang. Regardless of whether it’s progressive or conservative, I think everybody wants to hear good talk.”


Sylvester, who debuts Monday, Feb. 4, in the 3 p.m. afternoon drive slot, agrees.


“I’ll be doing what I did on my previous two stations where I did talk,” he says. “Taking calls from people who disagree with me – they’ll be at the head of the line. This isn’t an echo chamber.”


He points out that State Sen. Glenn Grothman – who may be, for liberals, the most vilified and ridiculed Republican Wisconsin legislator currently in office – regularly appeared on his show.


“Even though I have a point of view, when you have someone on that disagrees with you, I just think the conversation’s more interesting,” Sylvester says. “When you have everybody on a station where everybody has the same point of view, it becomes monotonous.”


Sylvester’s new home on the airwaves has an interesting story of its own. Owner Thompson is a self-described “radio rat” from when he was still a teenager who went into law because “I needed a career that had a future in it.” After getting his law degree in 1984 he joined a small firm in Monroe, but his love for radio wouldn’t let go. So he started doing play-by-play sportscasting on the local station.


Eventually in the mid-1990s the station’s five owners decided it was time to sell, and Thompson represented them in the deal with the Rockford-based would-be buyer. That buyer backed out, though, and a few months later, Thompson offered the owners an alternative: sell to him, at the same price, and carry the financing; they readily agreed, he says.


That fetched Thompson the first two of what would become a total of five stations. A station in Lena, Ill., west of Freeport, followed. Then he bought another pair of stations after their out-of-town owners offered to buy him out. “I wasn’t interested,” says Thompson. “I said, ‘I’ll buy your two stations in Freeport if you want.” It was a deal.


When WTDY’s staff was shown the door in November, many figured the high-profile Sylvester would wind up at WXXM, nicknamed “The Mic” and owned by Clear Channel.


How that would have gone is anyone’s guess. “The Mic” may be most famous outside Madison for having backed away in 2006 from a plan to drop its progressive talk format after a massive pushback from listeners. Despite that, or perhaps because of it, the station has very little in the way of locally produced programming.


But even as Madison fans ginned up their campaign to “Give Sly The Mic” late last year, Thompson put out feelers to Sylvester. Sylvester was interested and the deal came together in early January.


Thompson says with his own morning show and with a lot of sports programming in the evenings, adding an afternoon talk show was natural.


Being independent and privately held gives him freedom that large publicly traded station owners lack (although it’s worth noting that Sylvester’s former employer, Madison-based Mid-West Family Broadcasting, is also locally based operation, albeit one with 28 stations instead of just five.)


“When I see an opportunity for a good, solid radio person, I can make that decision in five minutes,” Thompson says. “I don’t have to worry about my profit in the first quarter and am I going to please Wall Street.”


But Thompson also has grown weary of the uniformity that characterizes so much of talk radio. His own media habits reflect that: “I’ll watch Fox for a while, but I probably watch Rachel Maddow more than I watch whoever’s opposite of her,” Thompson says. “I get tired of everybody parroting the party line, right or left.”


In that respect, he perhaps has something of a kindred spirit in Sylvester.


Originally a rock deejay, Sylvester, a Milwaukee native who grew up in Madison, sidled into talk radio at rock station WIBA-FM in the late 1980s. There, in his morning slot, he interspersed music with “a daily ‘Morning Dilemma’ segment,” the Madison weekly Isthmus wrote last year, “where he allowed callers to debate each other and/or himself on the air.” Isthmus continued:


When he moved to the talk-only WTDY, he seemed to deliberately avoid being classified as a liberal or conservative. He publicly backed former U.S. Sen. Russ Feingold, but also famously (and crudely) disparaged former Madison mayors Sue Baumann and Dave Cieslewicz and raged against gun control.


Or as Sylvester himself notes, “I have a point of view on a variety of issues. They’re generally left of center, but they don’t all comport with that.”


Indeed, WTDY’s own talk-radio profile has been eclectic. It was one of Rush Limbaugh’s first stations, and before conservative talker Mark Belling joined Milwaukee’s WISN-AM, he was on the Madison station.


Sylvester, though, certainly brought WTDY a more liberal audience. And he’s been particularly outspoken on workers’ rights, even before the battle over Act 10 pushed that issue front and center.


“I’ve been very involved in the fight to keep jobs in America,” he says – speaking out against free-trade agreements, which he blames for devastating American living standards. “I have walked countless picket lines. I was very passionate about labor rights – I think they’re important, not just for workers’ rights but for a middle class economy.”


When word surfaced during last fall’s presidential campaign that Sensata Technologies, a company owned by Mitt Romney’s former private equity firm Bain Capital, was moving 170 high-tech jobs from Freeport to China, Sylvester visited Freeport to speak to workers who would be left behind. “I did my show from across the street from where the plant was,” says Sylvester.


Back before he was governor, “Scott Walker used to be a regular guest on my show,” he says. “The night he ‘dropped the bomb’” – Walker’s own words in describing the introduction of Act 10 – “I emailed him and said, ‘I will fight you with every last breath.’”


Come next week, Sylvester will get to fill his lungs again.



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(note: a previous version of this story incorrectly identified WTDY's position on the AM dial.)

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