25 Years Ago Today, Buster Douglas Scored the Biggest Upset in Sports History

James “Buster” Douglas scored the biggest upset in boxing history 25 years ago today.

This perhaps downplays the reality of his knockout of Mike Tyson in Tokyo, Japan. Douglas came out on the winning end of the biggest upset in sports history on February 11, 1990.

The fight started with Douglas a 42-1 underdog. It ended with Mike Tyson searching for his mouthpiece on the canvas.

Nobody, save for Douglas, saw it coming. It’s not as though he lucked into the fight as a nobody. He had decisioned Oliver McCall, Trevor Berbick, and Randall “Tex” Cobb. The former pair both held heavyweight titles; the latter, more famous for his villainous role in Raising Arizona. And with Tyson cleaning out the division, opportunities abounded for hungry unknowns.

But Mike Tyson appeared as an Everest impossible to summit. He had destroyed Larry Holmes, made Michael Spinks look like a scared child, and sent Berbick stumbling into a stupor to win the title more than three years earlier. Tyson entered the fight not only undefeated, but seemingly unbeatable. Winning 33 of his 37 fights by knockout, and never once hitting the deck, Mike Tyson for four years during the 1980s–from when he first appeared on the cover of Sports Illustrated as a smiling “Kid Dynamite”–transcended sports to become the most recognizable athlete on the planet.  Then came divorce from his wife, mental-health and substance-abuse issues, the separation from his small upstate New York crew and adoption of a monstrous entourage, the rape conviction, biting Evander Holyfield’s ear, and the rest of the meltdown. Buster Douglas first demonstrated that Iron Mike could become Aluminum Mike if pushed.

The fight overshadows Douglas’s fight to even fight for the heavyweight championship. A gifted underachiever with great size, athleticism, power, and a pedigree–Douglas’s father fought professionally–the Columbus, Ohio, native never quite lived up to his potential, before or after February 11, 1990. He trained and fought lackadaisically prior to the Tyson fight; he ballooned up to 400 pounds after it. But on one night, he showed himself as the best heavyweight on the planet. Less than a month before the opportunity of a lifetime, Douglas’s mother passed away. He had every reason to fold. Instead, Douglas fought with a fury.

Tyson’s uppercut in the eighth, a fight-ender for lesser fighters, proved that Douglas possessed a chin. Perhaps more amazingly, Douglas proved that Tyson also possessed a chin, something none of Tyson’s previous opponents had even tested. He used a jab effectively and consistently beat Tyson to the punch.

By the tenth round, when Douglas punctuated a perfect a combination with a massive left hook, the ten count appeared perfunctory. The crowd’s response, stunned silence instead of the deafening roar Douglas deserved, quietly announced just how shocking the event was.

“This makes Cinderella look like a sad story,” Larry Merchant opined on HBO. “I would be willing to say it’s the biggest upset in boxing history,” Merchant continued. “In Las Vegas, they wouldn’t even put odds up on this fight.”

A quarter century later, the outcome remains so improbable that viewers on YouTube, convincing themselves of an ending different from the one they know, remain as astonished as the ones on HBO 25 years ago today.