On February 11th, 1990, “Iron” Mike Tyson lost his championship to James “Buster” Douglas.

It was the biggest upset in heavyweight boxing history until Anthony Joshua was taken out by Andy Ruiz, Jr.

The fight was billed as “Tyson’s Back!” and took place in Tokyo. Going into the fight, Tyson was the undefeated and undisputed heavyweight champion of the world. He held the WBC, WBA, and IBF titles and was considered the baddest man on the planet.

He hadn’t fought since 7 months earlier, which was rare for Tyson. During this time he fought 3-4 times a year. However, the abuse allegations from his wife Robin Givens hung overhead. Many other things were going on at the time but Tyson flew to Tokyo to the fateful match.

At 42-1 underdog, Buster Douglas hadn’t a prayer in the minds of the Las Vegas bookmakers. At the time Tyson was 37-0 with a slew of first-round knockouts.

He was already a legend and this was supposed to be a cakewalk. Until it wasn’t. The Columbus, Ohio native that was ranked #7 at the time who lost his only other title shot via TKO to Tony Tucker did the impossible.

In the 10th round, after a back and forth match that saw Douglas hit the canvas in the eighth round, Tyson was knocked down from an uppercut.

It was the first time in his career and he wouldn’t survive the count. The fight is now the most cautionary tale for any boxer who is winning; a testament that anything can happen.

Now thirty years later, it is more relevant than ever.