Everything eventually fades with time—strength, persistence, mobility, IQ—even for legends this is true. Just like every other fighter, Mike Tyson is aging now. If you happened to catch him fighting Jake Paul back in November last year, you will understand what we’re talking about. And honestly, it’s only fair. But we know that wasn’t the real Tyson. Prime Mike Tyson? He was an absolute force of nature. A destroyer par excellence. Comparing him to someone like Oleksandr Usyk? Iron Mike was in a whole different league. Let’s rewind the clock before we get to the important bit.

Tyson kicked off his pro career in 1985 and came out swinging—literally. He racked up 19 straight knockout wins! That’s not just impressive—that’s terrifying. By 1986, just a year in, he had already made history. At only 20 years old, he knocked out Trevor Berbick in the second round to become the youngest heavyweight champion ever. That record? Still untouched. But he didn’t stop there. In 1987, he unified the heavyweight division by defeating WBA champion James Smith, and then less than five months later, he took down IBF champ Tony Tucker to become the undisputed heavyweight champion. Tyson wasn’t just winning—he was dominating. Over the years, he went toe-to-toe with some of the best heavyweights to ever lace up the gloves including the legendary Larry Holmes. But why the history lesson now? Well, for Larry, decades later, he still regrets stepping into the ring against Mike Tyson, which he did for only one reason.

In a 2022 interview with The Telegraph, The Easton Assassin got real about his 1988 fight against Mike Tyson. And you could just feel the regret in his words. “I shouldn’t have come out of retirement against him. I fought Mike Tyson and I lost. He stopped me,” Holmes lamented. And yes, he did lose, badly. But Holmes still had to give credit where it was due. “Tyson could punch, you can’t take that away from him,” he admitted.

But Holmes also threw in an interesting what-if: If they had met in Holmes’ prime, things would’ve been different. He said, “He would stand in front of you, try and push you against the ropes, but he wouldn’t have been able to do that to me in my prime. I would have beaten him.” And honestly? That’s not too wild a claim when you understand the reality of the situation. Holmes in his prime was a beast—many considered him one of the greatest heavyweights ever.

The fight with Tyson? It was Tyson’s second defense of his undisputed title, and Holmes was already 38 years old—ironically, the same age Muhammad Ali was when Holmes beat him back in 1980. And this is why, the victory was all the more sweeter for Iron Mike. You see, Mike Tyson was 14 years old when he traveled with his mentor Cus D’Amato to watch his hero Muhammad Ali fight Larry Holmes at Caesars Palace in Las Vegas. Ali, 38 at the time, was already showing reduced mobility, a probable early symptom of his Parkinsons. Despite repeated attempts by his former doctor Fergie Pacheco to halt the bout, Ali and his team went ahead with the fight. In the fight, a reluctant Larry Holmes put a shellacking on the aged Ali with his corner eventually stopping the fight in the 10th round. That was a terrible night for both Ali and Tyson.

A tale of vengeance 8 years in the making for Mike Tyson

“I was offended by how bad he beat up Ali,” Tyson admitted to ESPN years later. “When we drove home to Catskill, nobody in the car said a word. We were all so upset.” The next morning while on a call with Muhammad Ali, Cus D’Amato introduced the young Mike to Ali. Here, the young kid vowed to avenge Muhammad Ali for what Holmes did to him. “I’m a revenge you. I’m a restore your honor. When I get big, Im’ma get him for you,” Tyson reportedly told Ali. And when fight night in 1988 came around, Tyson was ready. The best part—Ali was in the audience to watch him exact his revenge. Before the fight, Muhammad Ali stepped into the ring and after shaking hands with both the combatants, whispered into Tyson’s ear: “Get him for me!” And “Get him” Iron Mike did. The beating was even more brutal than the one Holmes gave Ali. Talk about poetic payback.

But let’s not forget, there was a 17-year age gap between Holmes and Tyson when they fought and Holmes was coming off of two back-to-back losses to Michael Spinks. So yeah, it was basically a young wrecking ball crashing into an aging legend. So why did he take the fight against Tyson? Holmes didn’t sugarcoat it. “Money. It’s the money,” he admitted regrettably in the interview.

And let’s get one thing straight—Larry Holmes wasn’t just some washed-up ex-champion stepping into the ring with Tyson. Nah, this was the heavyweight force in the late ’70s and early ’80s. We’re talking about a guy who made 20 successful title defenses. That’s more than Ali. More than Tyson. More than any heavyweight ever, except the legendary Joe Louis. Holmes went a mind-blowing 48-0 before he lost two razor-close (and honestly, controversial) decisions to Michael Spinks. And let’s not forget—he went the distance with Evander Holyfield in a world title bout in 1992. That’s no easy feat. Out of his 75 career fights, no heavyweight ever stopped Larry Holmes—except one—Mike Tyson. This just goes to show—no matter how great you are, time, it comes for us all—even the legends.