The Buster Douglas Upset: Inside the Turbulent World of Mike Tyson’s 1990 Preparation


When Mike Tyson landed in Tokyo in January of 1990 to defend his world title against Buster Douglas, the heavyweight champion was not in the right frame of mind.

To many, the bout was seen as a complete walk-over; some bookmakers even refused to take bets on the fight. The Mirage, the only casino in Las Vegas bold enough to offer odds to punters, rated Douglas as a 42-1 underdog. Basically, those wanting to bet 32 years ago were told don’t bother with the upset.

However, as Tyson recalled in his autobiography, all was not well behind the scenes and the fighter, who had previously rendered so many opponents unconscious in his wake of devastation would soon be humbled.

“On January 8, 1990, I got aboard a plane to fly to Tokyo,” he wrote. “Kicking and screaming. I didn’t want to fight; all I was interested in then was partying and f****** women.

“I didn’t consider Buster Douglas much of a challenge. I didn’t even bother watching any of his fights on video.

“I had easily beaten everybody who had knocked him out.”


Tyson barely even trained for the fight, with Don King having to pull him out of a public sparring session after just one round when partner Greg Page started to make him look silly.

King had charged anyone willing to attend the session a handsome $60 for the two-round showcase, but was forced to halve the main act. ‘Iron Mike’ instead decided to do his training in slightly less orthodox style.

He said: “Besides having sex with the maids, I was seeing this young Japanese girl who I had had sex with the last time I was in Japan.

“Robin [his wife] would go out shopping and I would go downstairs to the back of the hotel where this young girl had a room… So that was my training for Douglas.”

Tyson arrived in the Far East a mere 30lbs overweight. Ever the businessman, King bet his cash cow he would not be on weight for the fight.

On the eve of the bout on February 10, 1990, Tyson hit 220lbs and collected his winnings before celebrating in his usual manner.

“The day before the fight I also had two maids at the same time. And then two more girls, one at a time, the night before the fight.”


Unfortunately for him, it would be the last time he enjoyed success in Tokyo as the world witnessed one of the biggest sporting upsets in history.


At the end of the fifth round, Tyson’s eye was in awful shape due to the thudding jab of Douglas repeatedly finding a home and disrupting the champion’s rhythm.


With his face grotesquely swollen, Tyson stumbled back to the corner to learn his team had not even bothered to bring an ice pack as they could not foresee a situation where they would need it.

Instead, they filled up a large latex glove with ice water and prop it against his face to try and stem the swelling.

“It wasn’t the usual Tyson going into the ring,” he admitted. “It was obvious to anyone who was watching that I really didn’t want to be there. The fight started and I fought horribly.”

After cumbersomely following the challenger on wobbly legs until the eighth, a trademark right uppercut landed and seemingly Douglas was finished.

But confusion between the Japanese timekeeper and the Mexican referee owing to the language barrier proved to be a massive issue and the count of 10 never managed to materialise.

Two rounds later, Douglas infamously stopped Tyson for the first time in his career and the heavyweight landscape was changed forever.

The seemingly invincible Tyson did not know where he was.


“I knew that God didn’t pick on any small animals, that lightning only struck the biggest animals, that those are the only ones that vex God.

“Minor animals don’t get God upset. God has to keep the big animals in check so they won’t get lofty on their thrones.

“I just lay on my bed and thought that I had become so big that God was jealous of me.”


As Tyson contemplated his mortality, Douglas took the chance to capitalise on his underdog win and went for the quick buck. Rather than rematch Tyson, he made $24million fighting Evander Holyfield and meekly surrendered his WBA, WBC, IBF and Ring Magazine titles.

As for Tyson, the brawler from Brownsville would eventually regain heavyweight championship status after his stint in prison, but he was never the same after that fateful night at the Toyko Dome.


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