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Harry Teinowitz was a unique talent in a unique time in Chicago sports radio

You can judge the heart of a person in the workplace by the way they treat interns.

At ESPN 1000, Harry Teinowitz treated them as if they were at the top of the org chart.

“He used to treat first-run interns the same way you treat bosses or producers,” said Adam Delevitt, a former producer and program director at the station. “He used to bring interns in locker rooms with press passes. And these interns are bright-eyed, they’re meeting athletes. And Harry’s just walking them around like it’s normal.

“Harry always looked out for the other guy.”

Teinowitz, who grew up in Glencoe and was part of the famed “Mac, Jurko and Harry” show from 2001 to ’09, died Tuesday at 64. He suffered from complications from a liver transplant in 2023 and heart problems. He lived hard, but he lived for the enjoyment of others. Upon the news of his death, many of those interns took to social media to express their gratitude:

“Harry was always kind.”

“He was very welcoming and extremely nice to the interns.”

“What a hilarious, loving soul.”

As funny as he was, Teinowitz didn’t make it as a stand-up comedian. He’d tell you he almost made it as an actor, saying he was the runner-up for a top role in the film “Better Off Dead.” But he did appear in “Risky Business,” and he had a bigger part in “Up the Academy.”

Though Teinowitz wanted to be seen, he made his mark being heard. In 1994, he began his first radio show, “Harry and Spike,” with Spike Manton at The Loop. He later appeared as the sports guy for Loop hosts Danny Bonaduce, Steve Cochran and Jonathon Brandmeier, then reunited with Manton at ESPN 1000.

But he’s known best for co-hosting “The Afternoon Saloon” with Dan McNeil and John Jurkovic. The trio jump-started a station that had been lagging behind sports-talk rival The Score, racking up listeners and raking in money. Their authenticity and boisterous exchanges captured an audience that spanned demographics.

It took some time, though, for the show to find its footing. Teinowitz was the third wheel. He didn’t have the radio chops of McNeil, who helped launch The Score, and he wasn’t a former athlete like Jurkovic, who had a nine-year NFL career. But Teinowitz was fanatical about sports, and he had a deep, eclectic knowledge of them. So he didn’t take to being the foil so fast.

“After a couple of years, he finally accepted being a punching bag a little bit more willingly,” McNeil said. “He pushed back against our teasing early on, like that he had a junior partnership with us because he was only a fan, and how much love can you give a failed comic? That’s important to remember in this: Harry was the one who always said comedy is cruel.”

As a result, tension permeated the show. That led to several incidents that led to several suspensions, but it made for rollicking radio.

“It was at times entertaining because if you like workplace drama, there was plenty of it,” said Ben Finfer, a former show producer. “Other times it was just tough.”

Teinowitz would come to work every day with a list of ideas for the show, including guests and bits. But McNeil wasn’t the type of host who did bits, and as the show’s driver, it was his call. So a lot of Teinowitz’s ideas didn’t fit within the show.

“They fought a lot on the air and off the air,” said Delevitt, who was the executive producer. “There was a lot of tension. But they were able to drum it up for four hours. Jurko was great at kind of breaking the silence. If Jurko wasn’t in there, I don’t know what would have happened.”

Though McNeil and Teinowitz could be at each other’s throat, they learned from each other.

“He made me a more productive employee behind the scenes,” McNeil said. “He taught me some sales techniques on how to remember names of our clients. He was extremely genteel. And I learned from that because I didn’t wanna talk to sponsors after shows. But Harry figuratively grabbed me by the shirt collar and said, look, this is part of it.”

ESPN 1000 fired McNeil in 2009 and replaced him with Carmen DeFalco. In 2011, Teinowitz’s hard living caught up to him when he was arrested in Skokie for driving under the influence. The station suspended him, and he entered rehab. Two years later, ESPN 1000 let him go.

Teinowitz hung around radio, rejoining Manton on the short-lived sports station The Game and filling in on WGN. It was a frustrating period for Teinowitz, but he turned it into another endeavor, writing the play “When Harry Met Rehab” with Manton and earning rave reviews.

Meanwhile, Teinowitz and McNeil had grown close. They spent a lot of time together around the period of the transplant, and McNeil brought some of Teinowitz’s radio brethren back into his life. Though Teinowitz’s health was failing, his spirit was not.

“Harry was happy for most of the last two years of his life,” McNeil said. “So I’m taking some solace in the fact that he never got that microphone he wanted so bad again, but he laughed again in the last couple years, and he hadn’t laughed much since he got fired a long time ago.”

That laugh sprung from an almost-cartoonish voice, another quality that set Teinowitz apart from traditional radio talent.

“There aren’t a lot of Harry Teinowitzes out there,” Finfer said. “He had fun talking sports and hanging out with people. He was fun to be around and to listen to. Because of that, he got himself an opportunity to be on the radio and to have several other media opportunities.”

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