Mike Tyson vs. Buster Douglas—30 years later

Thirty years ago Mike Tyson faced off against 42-1 underdog Buster Douglas and found himself in the fight of his life.

Douglas was expected to be chopped up by the baddest man in the planet. But motivated by the passing of his mother, combined with Tyson being less than ready for action, the underdog laid Tyson out in the 11th round to score one greatest upsets in sports history.

The story didn’t end there, and the epilogue is just as much of a roller coaster.

Douglas' victory shocked the world

The world was reeling when it discovered Iron Mike was mortal, and the spotlight shifted to Douglas. Now the undisputed heavyweight champion of the world, Douglas soon found the trappings of fame and success too hard to resist.

Douglas was as far removed from the ring as possible and loved it. Just two months after his victory, Douglas replaced Tyson as the guest referee for the WrestleMania V rematch between Hulk Hogan and Randy Savage and lent his likeness to Sega for James "Buster" Douglas Knockout Boxing, but duty called him back to the ring.

Holyfield brought Douglas back to earth

After he spurned a rematch with Tyson because of his dislike of Don King, Douglas immediately pursued the next-best payday he could find later that year.

Unfortunately for him, that was Evander Holyfield, who was ringside when Douglas stopped Tyson and ruined what could have been the most lucrative fight in boxing.

A flabby, out-of-shape Douglas was no match for Holyfield, who drilled him in three rounds, which ended Douglas' title reign and his stint as boxing royalty.

Douglas retired after that $24 million payday and lived the carefree life—no longer enduring the stress and confines of professional fighting.

He had a brush with death, when he got to 400 pounds and slipped into a diabetic coma, led to a minor comeback in 1996.

Douglas had moderate success in his return. He won six of his seven bouts and retired for good in 1999, back in shape and satisfied with his career.

Douglas has dedicated his life outside of boxing to charity, and trains children in Columbus, Ohio.

Tyson bottomed out

Tyson’s shock defeat was only the beginning of a frightening downward spiral. Though he fought his way back to earn a title shot against Holyfield, Tyson was sentenced to six years in prison for the rape of Desiree Washington and was paroled after three.

Tyson became a media sensation. He fought against putrid opposition and regained the WBC heavyweight title with a knockout of Frank Bruno in three rounds.

When Tyson finally got his chance to face Holyfield, Holyfield withstood Tyson’s early attack. Holyfield controlled the action from that point forward, dropped Tyson in the sixth round, and stopping him in the 11th.

Tyson never fully recovered 

Though Tyson continued to fight until his retirement in 2005, his career as an elite fighter never recovered from the loss to Douglas and was finished when Holyfield knocked him out six years later.

There was the infamous bite fight, a beating from Lennox Lewis, and the constant barrage of external events that defined his career, but Tyson was never Iron Mike after Douglas took his aura of invincibility.

Tyson vs. Douglas changed everything

That night in Tokyo changed boxing forever, and while neither man truly recovered from that historic event, their story stands tall as one of the greatest and most unexpected results in sports history.

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