In a way, no one ever did more for football than John Madden. A torn knee ligament ended his NFL career before it could take off. But after that setback, he built a coaching career spanning 18 years, and at its twilight, became one of the most prominent broadcasters in the history of football sportscasting – even bringing the iconic Turducken into football lore. But at the same time, Madden faced something that probably hurt him more than that busted knee in 1959 – impersonations by Frank Caliendo.

The year was 2008. Caliendo, having already established himself as a master of impressions, was making waves in advertisements and landed an opportunity to be the voice of the popular game, Blitz: The League II. Caliendo lent his voice to the game – which was supposed to be direct competition to Madden (the game) – as the color commentator as well as the voice of an offensive coordinator. But John Madden didn’t care for the impression Caliendo made in that game, and reached out to NBA legend and sports analyst Charles Barkley to do something about it.

Appearing on The Sage Steele Show last week, Caliendo revealed how a conversation with Barkley led to a secret he had to keep bottled up for nearly two decades.

“Charles came up and told me about that, and he’s like, ‘You know John Madden wants to sue you, right, man?’” Caliendo said on the show. “And he tells me the whole story. And I would never tell that story out in public because I didn’t know if I had permission from Charles. He told me that in confidence; I’m not going to tell somebody that.

“Even though it probably would have been good for me to tell it, I held on to that story for like 10 – 15 years. And then Charles just told it recently on a couple of podcasts and people are like, ‘Did you know this?’ I’m like, ‘Yeah, I’ve been holding it as a secret for 20 years. It’s crazy.”

Caliendo went on to tie the possible lawsuit to the ads he did alongside the video game. He had even appeared on The Late Show with David Letterman once, dressed in a suit, complete with a gray wig, answering questions as Madden. All of this put together perhaps drove Madden over the edge, as Barkley told the story in 2023 on Barstool’s Spitting Chiclets podcast.

“I remember this phone call I got from my agent,” Barkley had said. “He says, ‘Hey, John Madden wants to talk to you.’ He called me, I said, ‘Hey, you’re the best. It’s an honor and a privilege.’ He says, ‘Thank you… I want to talk to you about a lawsuit I’m thinking about filing on this a**hole Frank Caliendo.’ I’m like, ‘What?’ He says, ‘This a**hole, have you seen the impersonation he does? I hate it, and I’m thinking about filing a lawsuit.’”

Barkley asked Madden if he didn’t consider the impersonations “flattering.” Madden said he didn’t, and not wanting to disrespect him, Barkley told him he’d speak to his agent and call Madden back. Barkley never made that call. Back on the Sage Steele Show, after recounting the story, Caliendo explained that he understood where Madden was coming from.

“Those football coaches can be really weird about that stuff. I do understand where a football coach has to have the attention of the players,” Caliendo said. “The players have to trust this because their lives are on – NFL is different than any other sport. If you’re a lineman and you got to trust that your coach is not putting you in harm’s way, you have to trust in that.

“So, you can’t be just laughing at the coach, especially with an outsider. In somebody inside the team, it’s a little different. You’re in a brotherhood, that type of deal. But as soon as some little guy from outside that looks like he – I did play sports growing up but not anywhere near that level that they’re like, who are you to be making fun of me?”

Interestingly, even Dish Network – where Frank Caliendo’s ads were featured – once took pre-emptive legal action against John Madden and Charles Barkley because they thought a lawsuit was coming from them. The lawsuit never came. And even though Madden was at odds with Caliendo for years, it eventually got better.

In 2011, at Super Bowl XLV, legendary NFL coach Jimmy Johnson introduced Caliendo to Madden face-to-face. When Madden realized it was Caliendo, things looked like they were about to explode. Caliendo apologized to Madden for impersonating him, saw that he was talking to his grandkids, and decided to break the ice with them.

He did an impression of Madden in front of his grandkids, and after some awkward silence where the kids stared at their granddad unsure whether to laugh, they cracked up. Madden’s reaction, as Caliendo recalled it on one instance, was “like a light bulb went on over his head, like, ‘I get it now. This guy makes small children laugh, he’s a saint, just like Drew Brees.’”

Years later, Caliendo’s clip from The Late Show, along with all the other impressions of John Madden he did over the years, has remained a lasting tribute to the coach who gave his life to football. As for that lawsuit, it has become a funny anecdote for those like Caliendo and Barkley who remember it with fondness.