Gerry Cooney held on to his money, but not his regrets

In the boxing ring, it doesn’t matter how far ahead you are, how many rounds you’ve banked – there’s always a risk, until the final bell sounds, that the other guy can suddenly erase all the good work you’ve done with one punch.

The same applies to a fighter and his money. Countless boxers have built what looks like an insurmountable lead, making millions, tens of millions, even hundreds of millions, and found a way to lose it all.

You know that famous line from Ernest Hemingway’s The Sun Also Rises, where Mike is asked how he went bankrupt and says, “Gradually, then suddenly”? With boxers, either adverb is possible. Some go broke gradually. Some go broke suddenly. But the sad truth is quite a few of them who make what sure looks like enough money to last several lifetimes still wake up one day with nothing.

Gerry Cooney is one of the exceptions to that rule. 

Cooney battled his share of demons, no doubt. He’s had his struggles and his low points. But once he made his money, he was never in danger of running out of it. And as he nears the 35th anniversary of his final fight, he’s still living comfortably without ever having to get a 9-to-5.

For a guy who did more than his share of punching and clocking, he’s proud and relieved to have avoided ever needing to punch a clock.

There are several smart decisions the former heavyweight title challenger made, but at the center of it all was the attitude he developed toward money at a young age.

“I always said, ‘The rainy day is coming,’” Cooney, 68, reflected this week. “I knew from growing up poor – or some might call it the poor side of middle class, whatever you want to call it – but I knew there was gonna be a rainy day. I’ve seen it many times with other people, especially with athletes, that they think it’s never gonna end. But, boy, does it.”

In a pro career that spanned from 1977-1990, “Gentleman” Gerry went 28-3 (24 KOs) and earned total purses – before managers and trainers took their cut, and before taxes – in the neighborhood of $15 million. He says the purse for his biggest fight, his unsuccessful 1982 challenge of heavyweight champ Larry Holmes, was not quite the widely reported $10 million, but rather $8.5 million. He had a few other low-seven-figure paydays against Ken Norton in 1981, Michael Spinks in 1987 and George Foreman in 1990.

Add it all up and Cooney made considerably more money than the average working man will see in a 50-year career, but just a tiny fraction of the estimated $400 million that Mike Tyson made in the ring. And yet Tyson filed for bankruptcy in 2003, reportedly in debt at the time for more money than what Cooney made in all his time as a fighter.

Tyson is an extreme case, of course. But the broad strokes of what he experienced are shared by so many fighters who make it big. Cooney, however, avoided all of those pitfalls.

“I wasn’t a big spender,” Cooney said. Did he live the celebrity lifestyle? Yes, to an extent. He partied with Elton John (“The only guy that ever kissed me on the lips,” Cooney laughed) and became friends with Bob Hope. But, he noted, “I never cared about having Rolls-Royces and all that stuff.”

That’s obviously helpful when it comes to remaining financially stable, but it takes more than that – especially if you want to at least spend some money to make your life enjoyable. Cooney has no trouble identifying the key moment for him:

“I hooked up with a good guy who had a couple of seats on Wall Street, Don Scanlon. He was a boxer [in the Golden Gloves], an Irish guy, [and] he wanted me to train his son. We became friends, and he turned me on to his finance people – and that was the best thing that ever happened to me.”

The path to get to that point wasn’t always smooth. When Cooney turned pro at age 20, he signed a 16-year contract with managers Mike Jones and Dennis Rappaport. 

“They didn’t give a fuck about me,” Cooney said bluntly. “I had to have one guy watch the other guy. They were two real estate guys, and the thing that I liked about them was they had [Olympic gold medalist] Howard Davis, so I felt like, well, I could fight on all his cards, I could be showcased around the country.

“And little did I know I signed a 16-year contract. My father had just died [the year before]. My father didn’t know anything about contracts. My mother didn’t know anything about contracts. I didn’t know anything about contracts. So I signed this contract. I felt locked up with them, but for a while I just accepted it.”

Until he fought John Dino Denis in November 1979, Cooney says he never saw any money – he was living on a $200 weekly stipend from his managers until the Denis fight earned him a big enough check to pay them back for fronting his expenses. But then he started to make good paydays.

“And around then I realized I need my own personal attorney, I need my own personal accountant,” he said. “That’s the biggest advice I’d give to any boxer now who’s starting to make money. Go to the athletic commission in your state. Tell them that you need help. You’ll want to find a good accountant separate from your managers and promoters, and the commission should be able to help with that. Go to a lawyer and find out where your money is going, who’s taking it, what’s happening with it.

“And I have to say, I think the boxers are getting better with this than they were when I was fighting. These guys are holding on to the money better.”

Boxing experts often hold up Cooney as an example of a mismanaged career, in that he positioned himself for the title shot by knocking out Jimmy Young, Ron Lyle and Norton, and then sat idle for 13 months waiting for the Holmes fight. He was competitive against Holmes but gradually came undone and was stopped in the 13th round – leaving everyone to wonder if he could have become champ with more rounds and less rust leading up to the life-changing payday.

Cooney himself has mixed feelings on the matter.

“Sometimes, I wish I would have had a Bob Arum to manage me the right way, put me in the right fights,” Cooney said. “Or if I had gone with Don King, maybe I could have fought the right guys and gotten the best experience. But who knows? I could be punchy if it had gone that way.

“It turned out the way it did for me, and I have regrets, but I don’t hold on to them. I forgave the people that were sucking the life out of me, because all I’m doing otherwise is I’m holding on to it. They’re not even thinking about me, right? And so I turn the page. I move on. Does it bother me sometimes? Yeah, but what am I gonna do now? What can you do? What do you hold on to it for?”

Anyone who’s familiar at all with the Gerry Cooney story knows about his toughest struggle. It wasn’t with regrets or wishing he’d become champion of the world, and it certainly wasn’t with managing his money. For him, the roughest fight was with the bottle.

“I stopped drinking 36 years ago,” Cooney said. “Listen, we make mistakes. We get up, we dust off our pants, we move forward. We fall down, we get up again, move forward. I stopped drinking April 21, 1988. And my life changed.

“I’ve learned so many things that I wasn’t available to learn at other times in my life. I read books now that I read 10 years ago and it’s a completely different story. I understand a lot more now, through the process of putting down the booze and getting to know yourself and not blaming yourself. No one picked me up. I picked myself up. I turned the page. I got on with my life.”

Cooney’s life these days includes co-hosting At the Fights on SiriusXM radio with Randy Gordon, and he also makes money giving talks, doing corporate gigs, and even teaching a little boxing. And he’s long been involved with philanthropic pursuits. His most noteworthy endeavor on that front was the formation in 1998 of FIST – Fighters Initiative for Support and Training – which provided counseling and job services to boxers.

All the pieces interlock for Cooney. His financial stability helps with his mental health and his ability to stay sober. Giving up drinking helped him stay strong of mind and wallet. Learning to let go of regrets fueled his happiness and success on the other fronts.

And then there’s one other factor at the center of it all: his marriage for more than 30 years to his wife, Jennifer.

“I am a very rich man in so many ways,” he said. “I’ve got a great wife. I’ve got a great family. We have a beautiful home. We’re lucky, and we’re able to do the things we want to do. So, honestly, I feel like I am the richest man in the world.”

Eric Raskin is a veteran boxing journalist with more than 25 years of experience covering the sport for such outlets as BoxingScene, ESPN, Grantland, Playboy, Ringside Seat, and The Ring (where he served as managing editor for seven years). He also co-hosted The HBO Boxing Podcast, Showtime Boxing with Raskin & Mulvaney, The Interim Champion Boxing Podcast with Raskin & Mulvaney, and Ring Theory. He has won three first-place writing awards from the BWAA, for his work with The Ring, Grantland, and HBO. Outside boxing, he is the senior editor of CasinoReports and the author of 2014’s The Moneymaker Effect. He can be reached on X or LinkedIn, or via email at [email protected].