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The departures this week of two legendary Philadelphia media personalities got me thinking about different ways the hosts are ending their terms. So what’s the best way to deal with the on-air talent changes that have drawn large audiences for decades?

Audiences often feel like they’re going through a rift when stations and personalities go their separate ways.

“Think about everything we’ve been through and breaking up is hard to do,” said Neil Sedaka.

This week’s events and the impending retirement of one of the market’s most prominent figures provide opportunities to investigate the mood as they pull away. So let’s start by looking at the personalities who chose to walk away – how they decided and how it worked out.

Ray Didinger was the first to leave the Philadelphia media this week. He retired from 94.1 WIP, where he had been a staple of the station since becoming All Sports. He was a co-host and made numerous appearances on WIP shows throughout the week. Simultaneously, Didinger moved away from NBC Sports Philadelphia, where he was a staple during Eagles coverage.

Didinger was a sportswriter in Philadelphia for more than five decades.

If you’re unfamiliar with Philly, this information undoubtedly demonstrates the extent of adoration for Didinger. As COO of WIP (2008 – 2016), I found Didinger’s universal, non-polarizing appeal to be unparalleled.

Didinger, who was never the hottest guy on the airwaves, was also affectionately known as “Ray-Diddy”. His unparalleled expertise in the NFL earned him the nickname “The Godfather”.

As his radio partner of over 20 years, Glen Macnow, explains, “During an Eagles pre-game show, Ray said something brilliant, and Ike Reese (nine NFL seasons, seven with Eagles , current WIP PM reader) said, That’s why you’re the godfather of football in this town.’ Ray is the highest authority on football in Philadelphia.

I wondered how hard it was to leave. Ray told me he knew when the time was right.

“Several times in the last Eagles season I went to the stadium and thought I’d rather be doing something else,” Didinger said.

“For the first time, it felt like work. I had never had this feeling before. That was when I realized something had changed and it was probably time to leave. This information would have stunned anyone who knew Didinger, listened to him or watched him on the air.

I wondered if Didinger was afraid of being asked to leave. He replied, “That was part of it. I’ve seen a lot of good friends in the media kicked out. They weren’t exactly fired but offered a buyout. They took the bundle and “retired” even though they wanted to continue working. After 53 years, I didn’t want to leave with this bad taste in my mouth.

Family played an important role in Didinger’s decision. “He has four grandchildren, all in the area,” Macnow said. “His nine-year-old grandson plans to teach him to play mad, which I think will be hysterical.

Didinger told Macnow in February of his intention to retire when his contract expired at the end of May. Shortly after, he alerted WIP management. Next comes the discussion of how to inform a loyal audience for decades.

“Ray’s instinct was to tell listeners just a day before his last show,” Macnow recalled. “He had no idea people would have such good feelings about him. Ray just wanted to say goodbye and get out. I said, ‘You can’t do this. It would be unfair for the listeners to deny them the chance to say goodbye.

Eventually, under what Didinger called ‘much restraint’, he agreed to announce his retirement in early May. Macnow scheduled retrospectives and feature stories on Didinger to fill the final eight shows.

“I squirmed through it all,” Didinger said, “but Glen kept it from getting too teary.”

For the final two shows (Saturday and Sunday, May 28 and 29), Macnow planned out each break. The station hosted a party at Audacy’s Performance Center on Saturday. Macnow & Didinger simultaneously performed their show with an audience of around 50 people.

The assembly included some of the show’s top callers and colleagues, including Dick Vermeil, Seth Joyner, Phil Martelli and Ed Rendell (who each mean a lot to Philadelphia) and three generations of Didinger’s family. The station provided a cake in the shape of yellow notepads – Didinger took numerous notes on stacks of these tablets.

After Saturday’s big start, Sunday’s show was the opposite – just Glen and Ray in the studio one last time. “Saturday was the stadium gig,” Macnow explained. “Sunday was the cozy, unplugged version.”

They only took a handful of callers on Sunday. Since the pandemic, the two have made a feature film called “Tell Us Your Story” (a lengthy biographical interview with a top athlete, coach or broadcaster). Sunday Didinger told his story, recounting his fascinating and accomplished life.

The last 15 minutes were moving and powerful. The two shared memories and stories of their partnership, accomplishments, and friendship. Didinger also spoke of the bond established with the community for more than half a century.

When asked if they would have done something different, Macnow and Didinger said they wished their voices hadn’t broken at the end. I found their trembling voices: poignant, raw and authentic to listen to.

Didinger concluded that giving the public a month’s notice before retiring “was about right.” I didn’t want a “Victory Tour”. I wanted something respectful but not overdone. I think we have accomplished that.

The phrase “Victory Tour” brings us to an upcoming retreat. Angelo Cataldi will wrap up an incredibly successful 30-year run as WIP’s morning man at the end of the year. In a profile piece, the Philadelphia plaintiff once said, “Every morning, Cataldi sets the agenda for local sports fans while making them laugh.”

After working with Angelo for eight years, I feel compelled to tell you about him. Initially one of the hardest people to learn to coach, but ultimately one of the easiest. His preparation and intelligence are second to none.

Here is an example of Angelo’s character and loyalty. He was set to retire at the end of 2021 but was convinced to do one more year after some management concessions. One was to reinstate a marketing employee laid off due to budget cuts at the start of the pandemic.

The woman had been with the cluster for 28 years before being circumcised. Angelo thought his release was unfair. He also recognized the value she could bring to his show. She went back to work on the morning show for her senior year. This is who Angelo is.

Cataldi’s retirement was long in coming. “The decision to retire has weighed on me for at least six years,” he told me. After all these years, like most people on the morning shows, he never got used to the hours.

What motivates Cataldi, especially if he has been considering retirement for six years? Always honest, Angelo admits: “Two things kept me going at 71: the first is ego. People care what I have to say. It’s not easy to give it up. And second, fear. I can’t wait to get rid of the burden of doing a show every day, but be careful what you wish for. How am I going to spend my days when the mic is off? He is in my thoughts every day.

For years I’ve told those I coach that they don’t do well unless they’re exhausted at the end of a show. I commented on Angelo’s preparation and dedication to his craft. I NEVER heard him “phone” a show. When it comes to work ethic, he is uncompromising and aware of the price he pays for this standard.

“Giving your all every day is non-negotiable, so the toll gets heavier every year. Often, at the end of shows now, I am not lucid. Fatigue is so much more crippling now,” Cataldi said.

Like Didinger, the grandchildren took Cataldi’s plans into account. He used to talk about moving to California, but that has changed. “There was a time when I considered moving to the West Coast to end my days in the splendor of sunshine and In’n Out burgers. Then I met my three new grandchildren, and that plan changed dramatically. With age comes wisdom, I suppose.

Cataldi’s impending retirement comes up frequently on his show. If it’s not a “Victory Tour”, it’s at least a “Goodbye Tour”. He says he has no regrets, “at least not yet.” However, he is introspective about his heritage: “How do I want to be remembered? Watching the outpouring of adoration for (Jim) Gardner (longtime ABC-6 TV news anchor who recently announced his intention to retire) and Didinger makes me wish for a much different sendoff.

I never really yearned for the love of our listeners. Loyalty and respect are much more important to me. I want to go out with one lasting impression. I worked hard every day, as hard as I could. I never removed a segment, much less a show. I won the audience I had until the end.

There are the stories of two unique and exceptional talents, Ray Didinger, who just walked away on his terms, and Angelo Cataldi, who is expected to do so at the end of the year. Next week we’ll continue the topic with the end of Mike Missanelli’s run on 97.5 The Fanatic and the tougher example where personalities don’t choose to leave on their own.

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