Mike Tyson: 5 Defining Moments of His Hall-of-Fame Career

Iron Mike Tyson is back in the news, now that he has his plaque hanging in the International Boxing Hall of Fame in Canastota, NY.

But Tyson was never out of the public eye, even though his boxing career ended in 2005. He was back on the front page when his daughter died tragically in a treadmill accident. He starred in his own reality show on the Animal Planet about pigeon racing. And he nearly stole the show in the movie The Hangover, with two scenes in which he played—and parodied—himself.

His life has been a roller-coaster ride, a death-defying journey down a rickety track that is one horrific crash away from injury and scandal. Exhilarating? Yes. Masochistic? Absolutely.

In a career (and a life) that is part tragedy/part comedy, there are a few moments in time that have defined Tyson, a larger-than-life character that we just can’t seem to take our eyes off—like the freak on the circus midway. True to form, they weren’t all events that happened in the ring.  

1. Steamrolling through the Division and Becoming the Youngest Heavyweight Champion in History

After winning his first 19 pro fights by knockout and individually unifying the WBA, WBC and IBF titles at the age of 20, Tyson proceeded to establish himself as one of boxing’s most devastating punchers, disposing of much of the sport’s top heavyweights in short order.

When he knocked out former light heavyweight champ Michael Spinks with a crushing body shot in 91 seconds (less time than it took to announce the dignitaries at ringside) in 1988, he captured the lineal championship. Spinks, who was undefeated prior to the bout, never fought professionally again.

It was at this point in time that the mystique and aura around Tyson proved real. Like Ali during his prime, Iron Mike was the unofficial king of the world.  

2. The Deaths of Cus D’Amato and Jim Jacobs

D’Amato, the legendary trainer who took Floyd Patterson to the heavyweight crown and Jose Torres to the light heavyweight title, was more than that to the young Tyson. He was the fighter’s mentor and father figure (who formally adopted him).

When he died in 1985 (before Tyson became champ), Tyson lost the one individual with whom he could discuss his innermost thoughts. When Jim Jacobs, Tyson’s co-manager with Bill Cayton, died three years later, Iron Mike lost the person who introduced him, via his collection of fight films, to boxing’s colorful history.

While not particularly close to Tyson, Jacobs’ death meant that the men who watched over his growth and development, in and out of the ring, were now gone from his corner.  

3. Buster Douglas

Journeyman James “Buster” Douglas’ knockout victory over Tyson in Tokyo in 1990 is considered one of the biggest upsets in sports history, as Douglas was a 42-1 underdog coming into the fight.

The outcome changed the course of Tyson’s career in the ring. After the loss, he was no longer “the baddest man on the planet.”  

4. Desiree Washington

Eighteen-year-old Desiree Washington was Miss Black Rhode Island when she claimed Tyson raped her in an Indianapolis hotel room.

On March 26, 1992, Tyson was found guilty and received a sentence of 10 years. He went to the Indiana Youth Center, where he served three years. Nothing was the same for him upon his release.  

5. Evander Holyfield

It was during their second fight, on June 28, 1997, when the punchline that was becoming Mike Tyson took an even more surreal turn.

This highly anticipated rematch, marketed as The Sound and the Fury, was held in Las Vegas, at the site of their original fight. This one never made it past the third round, as referee Mills Lane disqualified Tyson for biting Holyfield on both ears.

One bite was so severe that a piece of Holyfield’s right ear was found on the ring floor after the fight. Following a melee in the arena once the decision was announced, everything else in Tyson’s life began to unravel as well.

These are all defining moments in a life and career that isn’t easy to categorize. Tyson is a tragic hero to many—an anti-hero to the rest. But it’s no coincidence that we haven’t had a heavyweight champ worth talking about since he stopped throwing leather.

Will we ever?