On the Sly

    “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…

 

 
“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.

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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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Milwaukee Magazine Contributing Editor Erik Gunn has written for the magazine since 1995. He started covering the media in 2006, writing the award-winning column Pressroom and now its online successor, Pressroom Buzz. Check back regularly for the latest news and commentary of the workings of the news business in Milwaukee and Wisconsin.