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How Mike Tyson’s legendary party with R&B icon led to greatest upset in sporting history

Mike Tyson was undoubtedly one of the most ferocious heavyweights who ever lived, ending 88 percent of his 50 professional boxing victories inside the distance.

Of course, this was long before the 58-year-old legend faced YouTube star Jake Paul, losing a wide unanimous decision in an uninspiring affair last month.

But while several comments have since been made about his legacy, the former heavyweight champion, in his prime, was perhaps the closest thing to an unstoppable force.

And yet, shortly after his ruthless surge throughout the 1980s, Mike Tyson was forced to suffer a stunning defeat at the hands of James ‘Buster’ Douglas.

Weigh-in For LIVE On Netflix: Jake Paul Vs. Mike Tyson
Photo by Brett Carlsen/Getty Images for Netflix © 2024

Mike Tyson partied hard with Bobby Brown before losing to Buster Douglas

‘Iron Mike’ made history in 1986, becoming the youngest heavyweight champion of all time with an emphatic second-round stoppage over Trevor Berbick.

Sure enough, the 20-year-old went on to defend his WBC title against the likes of Larry Holmes and Frank Bruno, before colliding with Douglas in 1990.

Having established himself as a murderous puncher with explosive hand speed, though, Tyson entered their showdown at the Tokyo Dome, Japan, as an almighty favorite.

But then, after nine rounds of back-and-forth action, the Brooklyn-born bruiser was compelled to pick himself off the canvas following a lethal tenth-round combination from Douglas.

And while he eventually scrambled to his feet after a lengthy count from the referee, the writing was seemingly already on the wall in arguably the biggest upset in sporting history.

Thirty two years after the shocking moment unfolded, however, iconic musician Bobby Brown revealed exactly what happened before the fight.

“Me and Mike Tyson are friends to this this day, but there was a time when we partied in Japan right before his fight with Buster Douglas,” Brown said in an interview documented by A&E.

“We partied like really, really, really hard. There must have been two dozen girls in the room with me and Mike… we partied.

“And I was trying to tell him to get some sleep. Eventually he got some sleep [in the ring]! Do not put that part in there please, he is going to kill me.”

Will Mike Tyson continue fighting after Jake Paul defeat?

Immediately after his seventh professional defeat against Paul, Tyson insisted that he will continue fighting – and even called out his opponent’s brother, Logan Paul.

That said, his lacklustre performance at the AT&T Stadium, Texas, would indicate that resuming his career is far from the most sensible option.

Tyson has, after all, revealed that he nearly died after suffering an ulcer flare-up ahead of his controversial showdown with Paul.

But still, so long as he remains one of the biggest names in boxing, Tyson will no doubt be presented with plenty more lucrative, and indeed dangerous, opportunities.