Angelo Cataldi has a little less than six months left before he walks away from WIP. The Philadelphia sports radio legend was a guest on The Press Box this week, The Ringer’s podcast focused on the media.

Host Bryan Curtis asked Cataldi how he is doing with the end in sight and what he thinks he will feel on his last day on air.

“A sense of closure,” Cataldi answered. “I’m hoping to receive that in the next six months. A sense of relief. And to some extent, a sense of accomplishment. I’ve done this a long time, but I still have a sense of trepidation. I still think about it and go ‘maybe tomorrow is the day I fall flat on my face.’”

That last part is why he says he knows it is time to say goodbye. Angelo explained that it’s harder to be great at 71. He preps more than he ever did before to ensure he doesn’t forget an important name or thought in the moment.

He also spendt part of the podcast looking back on his highlights and struggles. Curtis asked Cataldi how he would characterize his relationship with fellow Philadelphia sports talk icon Howard Eskin.

Cataldi said that Howard deserves all of the respect he gets, but they have a classic love/hate relationship.

“‘Love’ in that I really respect what he has done for sports talk, especially in Philadelphia. I respect his work ethic and respect his love for sports. I don’t respect that he’s never been a great team player. He’s never looked out for you. More now than before, but, he’s a big talent, a big talent. 

“All of us that are doing talk radio in Philadelphia took something from Howard’s approach to it. He was very provocative and interesting. I think we’re in a pretty good place right now, but the next time I say something he doesn’t like, we will not be in a good place, and he will come after me, I will retaliate, and then we will have two old men fighting like little children.”

Cataldi also talked about the demise of the famous WIP Wing Bowl. In its 26-year run, the event went from being contested in a hotel ballroom for a cheap hibachi to competitors entering a sold-out Spectrum Center to compete for $75,000 worth of prizes.

It was an event Angelo Cataldi described as full-on debauchery.

“It was the closest thing as you would get to a public orgy. It was bad. By the end, it had gotten completely out of control and it was time to end it, especially given #MeToo and all that’s going on now. We got out at the right time. It would not be acceptable, what was going on in those buildings. But it was a hell of a radio promotion for a long time.”

One interesting moment in the podcast came when Curtis asks Cataldi about his accent. The Providence, RI native said that he wishes he was better at hiding it, but it is about as good now as it is going to be.

He has been on the air in Philadelphia for 33 years, but because of his voice, he knows there are some listeners that will always think of him as an outsider.

“People knew I wasn’t one of them, so when they wanted to hate me, it was easier to hate me.”

Outsider or not, Cataldi is feeling the love from the audience right now. He says the most rewarding thing that has happened since announcing his impending retirement is that strangers are more likely to stop him on the street to tell him how much they have enjoyed his show.

“They reinforce in you that what you did had some value,” he said. “If you’re doing that and they’re paying you well, what more are you gonna ask for? It was a good deal.”