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Media: July 2023 • Catching up with Mr. Wert

| June 30, 2023

Larry Wert


After more than four decades in the media business as a sales manager/general manager/vice president for places like WLS-TV, The Loop AM & FM radio stations, NBC-5 Chicago, and the Tribune Company, Larry Wert considers himself semi-retired.

“But I’m working way more than I should be, considering I’m semi-retired,” he admits. “I’m working on quite a few things right now. I’m in the spirits business as an investor/owner/advisor in the storied whiskey company named Uncle Nearest.”

He’s also working on a documentary about the radio station he helmed for a decade, the Loop.

“Completion is hopeful for 2023,” he says. “I think it will be fun, interesting, and entertaining for the stakeholders and fan base of the Loop, but I also think it will be interesting for people who weren’t around. They will be blown away by the things that happened at that time.”

Larry came aboard the Loop in the late 1980s when the station was enjoying its second major moment in the sun. The man who brought him in was the architect of that second era, Jimmy deCastro.

“I was the sales manager at WLS-TV,” Larry explains. “The Loop was my client. The Loop’s owner had just bought a station in LA, KKBT, and since I had spent some time in LA, that was what Jimmy wanted me to manage. My second child had just been born, so that idea wasn’t well received at home. So I told him I couldn’t do it. He said, ‘Fine, then I’ll take LA, you take the Loop.’ And before I knew it, he had called Robert Feder, and it was public. I had to sheepishly go into my bosses Joe Ahern and Dennis Swanson at Channel 7, and admit it was true. I was leaving.”

Larry was nervous that first day he met everyone.

“I’ll never forget it. I have a picture of that day that sits over my desk. It was a significant day in my career. We were at Ed Debevic’s. The whole Loop staff was there. As Jimmy deCastro was introducing me to everyone, my heart was beating like a hummingbird. Luckily, Steve Dahl made a joke that broke the ice, and that was the beginning.”

It was a bumpy ride, but it was also exhilarating.

“You had these thoroughbreds and you wanted to let them run, but you had to keep them on the same track. That was the early, broad challenge. And then of course there were daily micro-challenges. You knew something was going to happen, you just didn’t know what. It wasn’t just the obvious ones like Steve & Garry, Johnny, Kevin, Chet, and the accomplished FM jocks. There were also major behind-the-scenes challenges and listener challenges. That’s what my role became. Maintaining trust with the characters involved amidst the chaos swirling all around.”

The ride had to come to an end at some point, and it did in the mid-to-late ’90s. The reasons for the demise are probably too numerous to mention.

“All bright things eventually go dark,” Larry explains. He admits the wounds were probably self-inflicted by nearly everyone involved at the time. “I remember there was a moment when we had a meeting at the top of the Hancock and we said, ‘Boy our momentum is so strong, only we can screw this up.’ And I had no idea how prophetic those words would turn out to be.”

When Larry left radio and returned to television, he didn’t exactly leave the turbulence behind. He joined NBC in Chicago just as the station was dealing with the fallout of management hiring Jerry Springer to do political commentary on the newscasts.

“Yeah, that was right at the beginning. It obviously wasn’t my idea, but I was told I had to fix it. I went to 30 Rock that week, and that began my 15-year career with NBC. Sadly, we just lost Jerry Springer, but I was a big fan of his. Jerry and I went through some turbulence in the beginning, but it wasn’t his fault. The previous management thought it was a good marketing decision, but it was silly journalistically. Carol Marin and Ron Magers left because of that.”

It wasn’t the last time he jumped into a fire.

“When Comcast acquired NBC,” he explained. “I was approached by Tribune leadership after their bankruptcy, and I did that job next. It was the most challenging job I ever had. Right out of bankruptcy. The company was run by the people holding the debt. A great media institution, but with some significant financial challenges. It was difficult but ultimately rewarding.”

It was during those years that Larry and Jimmy deCastro worked together again. This time, technically, Larry was the boss.

“WGN AM needed new leadership, and Jimmy was the perfect one. But I never looked at it like I was his boss. I was focusing on the TV stations, and he was focusing on the radio. WGN was the only radio station in our portfolio. He was in charge of that.”

Now that his media career is in the rearview mirror, Larry is circumspect about how much luck was involved in his ascent.

“I look back and I think about the good fortune I had. I had a series of moments that set up the next moment. In hindsight, they were just plain lucky timing moments.”

And now that he’s “semi-retired” he is working on living up to the second half of that label.

“Don’t worry,” he vows. “I’ll fix that.”

-Rick Kaempfer

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Category: Columns, Featured, Media, Monthly

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