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Growing up in Wisconsin, Bart Winkler didn’t listen to much sports radio. Instead, he stayed up to watch late night hosts like David Letterman, Conan O’Brien and Jimmy Fallon and it would be from those legendary personalities that he would learn that you can’t be afraid of trying different things.
Like a bit that Fallon introduced after he took over for O’Brien on the iconic Late Night program. “They did this segment called “Lick it for 10” where he would have people lick something for ten bucks,” said Winkler. “It was so stupid, but I liked it. I thought it was great, but it was so dumb, but I think that kind of mentality where you try something and if it works great but if it doesn’t you learn from it, but you should be able to have the ability to try stuff.”
Today, Winkler is trying out different stuff all the time as the host of The Bart Winkler Show heard nationally from 10 p.m. to 2 a.m. ET on Infinity Sports Network.
Winkler, who graduated from the University of Wisconsin-La Crosse, didn’t aspire to be in sports radio. He wanted to be a television sports anchor, but radio turned out to be the better fit and it was watching those late-night shows on television that shaped the way he would want to deliver content to his audience.
“I grew up watching Conan and Letterman,” said Winkler. “I didn’t go to sleep at night. It would be 12:30 or 1 in the morning and I’d have school the next day. I’m 15 years old but I’m watching reruns of The Simpsons, Cheers or Seinfeld. That’s how I see broadcasting…from that lens.”
From August 2016 to August 2022, Winkler was a host for 105.7 The Fan in Milwaukee as part of Chuck & Winkler and the local version of The Bart Winkler Show. When The Fan ceased to exist, Winkler stayed local hosting podcasts but also embarked on a run as a national sports radio fill-in host.
Part of that run was at CBS Sports Radio, now Infinity, which led to him taking over the full-time late evening to early morning show back in January.
“The show has been great,” said Winkler. “What’s been fun is doing the show that I’ve always done or wanted to do or different versions of past shows but to a completely new audience and a completely different playing field.”
The transition of focusing on hosting local shows to hosting nationally can be a challenge. Winkler has been able to be successful in that transition because he discovered how he wanted it to sound nationally. From predominately talking about the Packers, Bucks, Brewers and the University of Wisconsin, he has been able to find a groove talking about everything going on in sports nationally.
And while the show evolves, his audience is growing as listeners are introduced to the show.
“They’re finding it because I’m on after something else they were listening to whether it’s a Westwood One broadcast or the local affiliate,” said Winkler. “For a lot of people, I’m like the ‘now recommended’ from Netflix after you’ve been watching something for so long.”
Winkler admits that he doesn’t always make a good first impression, but what he’s finding out is that his audience has shown patience and eventually they like what they’re hearing. He’s getting listeners who call the show on a regular basis, but each night is a new adventure when new listeners are tuning in.
“They’ll say at first…I didn’t really like you and now you’ve grown on me,” said Winkler. “I’ve been doing this for 10 months, but there’s a lot of people listening to the show for the first time. While it’s nice to build up some callbacks and recurring bits, it’s like a first date every night where you have to put your best foot forward.”
Winkler has worked with two producers since the full-time show launched on Infinity.
His first producer was David Sheppard who is now a part-time host on Infinity Sports Network. Sheppard played a huge role in introducing Winkler to the listeners and engaging with Winkler on-air.
“He had been with the company for a long time and people know him,” said Winkler. “We had a lot of great spirited conversations which were fun. I’ve worked with a lot of different people and everyone I’ve ever worked with…some of them are my best friends.”
And that includes his current producer, and new friend, Karlos Ortiz. The chemistry has been through the roof because they like a lot of the same things and they both are not afraid to try different things.
“It just clicks,” said Winkler. “He comes up with ideas and there’s a lot of different things we do on the show now. He’s made the show sound and feel a lot bigger than some guy opening up a microphone and talking for four hours and he’s great to talk with. My name is on the show, but I don’t want it to be just four hours of me.”
Inspired by the greats of late-night, Bart Winkler delivers an entertaining form of sports talk to his listeners each night on Infinity Sports Network. He’s not afraid to try different things and his reward has been building a strong audience and attracting new listeners who are not afraid to give him a chance.
Peter Schwartz writes weekly sports radio features for Barrett Media. He has been involved in New York sports media for over three decades, and has worked for notable brands such as WFAN, CBS Sports Radio, WCBS 880, ESPN New York, and FOX News Radio. Peter has also served as play by play announcer for the New Yok Riptide, New York Dragons, New York Hitmen, Varsity Media and the Long Island Sports Network. You can find him on Twitter @SchwartzSports or email him at DragonsRadio@aol.com.
