5 Biggest Heavyweight Boxing Upsets

#1: Mike Tyson v James ‘Buster’ Douglas

February 11th, 1990 | Tokyo, Japan

10am on a quiet Sunday morning in Tokyo was a strange time and place for the scene of not just the biggest upset in boxing history, but perhaps the biggest shock in all of sporting history.

As is so often the case when big fights take place outside America, the action was scheduled at an incongruous hour to accommodate a primetime US TV audience.

In February 1990, the 23-year-old Mike Tyson was at his peak. In 1986, aged just 20, he’d become the youngest heavyweight champion of all-time, ripping the WBC title away from Jamaican hard man Trevor Berbick in two one-sided rounds.

He seized the WBA title in his next fight against James ‘Bonecrusher’ Smith, before claiming the IBF belt from Tony Tucker to become undisputed heavyweight champion just a month after turning 21 years old. He was already being spoken of as - potentially - the greatest heavyweight of all time.

Tyson’s path from Brooklyn street thug to heavyweight championship of the world is well documented. Both his parents were drug addicts and dead by the time he was 16. A lost child running wild in the ghetto, he found boxing while serving time in a youth detention centre in upstate New York.

There, he came to the attention of the wizened old boxing guru Cus D’Amato, the former trainer of the previous youngest heavyweight champion, Floyd Patterson. D’Amato was in Patterson’s corner the night he lost his heavyweight crown in traumatic fashion to the unstoppable Sonny Liston.

Cus and his lifelong companion Camille Ewald, originally from Ukraine, became the orphaned Mike Tyson’s legal guardians in 1982. Their home was a place of refuge for many young boxers including Kevin Rooney, who would become Tyson’s first professional trainer, and Teddy Atlas.

Turning pro in 1985 aged just 18, over the next five years Tyson laid waste to an entire generation of heavyweights. No flashy dressing gown, no tassels, no gimmicks. Just his trademark black shorts, black ankle boots and white cut-out towel. A human wrecking ball, leaving a trail of destruction in his wake. Boxing fans, and the media, couldn’t get enough of him.

In the 1980s, boxing was still a mainstream sport and in the pre-internet age, Tyson was a genuine global star every bit as famous as Madonna, Michael Jackson or Michael Jordan. This was before jail, before the bite, before all the lurid headlines.

A 1987 UK promotional tour featured an appearance on prime-time TV chat show Wogan. It revealed a rather sweet, softly-spoken, effeminate and intelligent young man quite at odds with the violent force of nature who stepped through the ropes.

Tyson continued his relentless march through the division. An aging Larry Holmes briefly showed flashes of the old magic before being ruthlessly dispatched in four. Most memorably of all, the exceptional Michael Spinks – one of the all-time great light-heavyweights – was blasted out in 89 seconds, in the fight which came to define Tyson at his most destructive, terrifying best. Two more routine wins, including a fifth-round stoppage of Frank Bruno in 1989, meant that Tyson arrived in Tokyo boasting a perfect 37-0 record, with 33 knockouts.

But despite his problems, Tyson was still seen as invincible, and potentially on his way to becoming the greatest heavyweight of all time. Douglas had been knocked out three times already, and was regarded as nothing more than a warm up before a Tyson super fight versus Evander Holyfield – ringside in Tokyo – already signed and sealed for later in the year.

Famously, Douglas was made a 42/1 underdog, in a two-horse race, by the only casino that put up betting odds for the fight. And most of the money still came in for Tyson.

“Just another day at work for Mike Tyson, he looks almost bored, as they’re called to the centre of the ring by the referee”. So said the great Bob Sheridan, calling the fight for HBO.

But standing 6’4” to Tyson’s 5’10”, it wasn’t long before Buster had Tyson’s attention. He started strongly, ramming out stiff jabs and throwing hard right crosses, showing aggressive intent and taking the fight to Tyson from the opening bell. That in itself was something of a shock.

The James ‘Buster’ Douglas story was altogether less dramatic, and rather more wholesome, than the chaos which shaped the young Mike Tyson. Fortunate enough to enjoy the peace and quiet of a stable family upbringing in Columbus, Ohio, Buster’s childhood was nevertheless not without its challenges.

As a bullied, 10-year-old boy returning home in tears one day, his mother demanded he go back outside to confront his tormentor. Resolving never to be pushed around again, he started boxing under the guidance of his father, former 70s middleweight contender, Billy ‘Dynamite’ Douglas. The old man was a hard taskmaster.

Buster forged a solid if unspectacular pro career. In a 1987 challenge for the IBF title against Tony Tucker, he was stopped in the tenth when leading on the scorecards. His most notable wins were decisions over Trevor Berbick and Oliver McCall, in the two fights immediately preceding Tyson. Buster headed for the Tokyo showdown with a professional record of 29 wins, four defeats.

Another small yet significant factor was the fact that Douglas had also fought on six Tyson undercards. He’d seen him up close already. He wasn’t scared by the ‘Iron ‘Mike’ image or distracted by the circus which surrounded the champion. He knew what to expect.

For all his dominance inside the ropes, outside the ring, Tyson’s life was unravelling. He’d been through a messy, expensive and very public divorce from Robin Givens. He’d been hospitalised in a car-crash and broke his hand in a bar brawl with former opponent Mitch Green.

Most damaging of all – in pure boxing terms – his long-time trainer and fellow Cus D’Amato disciple Kevin Rooney had been ditched as Tyson came under the ever more malign influence of Don King. Shortly before the Douglas fight, Tyson had been dropped in sparring, with TV cameras there to witness it.

But by the sixth round against Douglas, he wasn’t doing much more than just plodding forward looking for the one single shot. Just about claiming the seventh, Sheridan stated that was the first round he’d given Tyson all night.

In the eighth, both boxers dished out and took some telling blows. But after being forced back on to the ropes, Tyson connected with a signature uppercut to finally floor the gutsy challenger. A shot that would have ended the fight against many others, Buster made it to his feet at the count of 9, when the bell sounded to end the round.

It looked like Tyson had landed the big shot he so desperately needed to turn the fight around. Instead the knockdown turned out to be his last stand. A huge ninth round for Douglas swung the fight decisively in his favour, Tyson surviving several crunching combinations and barely making it out of the round. As he wobbled on unsteady legs back to his corner, nobody could quite believe what they were seeing.

But if the sight of Tyson in trouble was shocking enough, what happened in the tenth was nothing short of seismic. 35 seconds in, Douglas unleashed a huge right uppercut stopping the advancing Tyson dead in his tracks.

The finish was emphatic, Douglas landing four more bombs right on the money as Iron Mike Tyson was sent crashing to the canvas. He was up just as the count reached 10, but in no condition to continue. The referee waved it off. There was a new heavyweight champion.

Those pictures of a groggy Tyson on all fours, fumbling for his gumshield, trying in vain to beat the count, somehow seem as unreal today as they did for that gobsmacked global audience back in 1990.

The sheer shock factor of the result often clouds the fact that it was an absolutely tremendous fight. Tyson, the great champion, took a terrible beating but showed incredible heart and bravery to keep coming, defiantly searching for a way through.

It quickly became apparent that this was not going to be the early blowout which everyone expected. Douglas was letting his hands go, and every time Tyson did get through, Buster was quick to return fire.

With swelling around Tyson’s left eye apparent from the fourth, Douglas gained further confidence. He picked up the pace, controlling the middle rounds against a flat-footed Tyson who displayed none of his customary head movement out of his trademark peek-a-boo stance.

Tyson’s boxing skills are often underrated, but he was an excellent technician. Short for a heavyweight, he had to be. Usually giving away plenty in reach, his footwork, hand speed and head movement all had to be on point for him to get close enough to do his damage.

He almost managed it with that knockdown in the eighth, but on this night, or rather this morning, nothing and nobody was denying Buster Douglas. He produced an epic, punch perfect performance, and it changed his life forever. The citizens of Columbus came out to salute their new, undisputed, unexpected heavyweight champion of the world.

In the immediate aftermath there were some predictable shenanigans from promoter Don King, who tried to claim that the fight should have been stopped after the first knockdown, as the referee gave Douglas too long to recover. That shameful attempt to deny the worthy Douglas his deserved recognition dragged on through the courts for a while, but was eventually dismissed.

Everyone wanted a piece of the new champ, but Douglas wasn’t much one for the fame game, saying some years later “There was a lot of demands. I got to do the talk shows, that was alright. But I’d have much rather been just at home, just chilling”. Buster seemed far too easy going to be a fighter.

Eight months later, he faced the man Tyson was supposed to fight, had he taken care of Douglas - Evander Holyfield. But Buster’s edge had gone. Fighting for the memory of his mother and for the opportunities his boxer father never got, he’d put absolutely everything into dethroning Iron Mike, and had nothing more to give.

He was bombed out in three rounds by the Real Deal and promptly retired. And having pocketed $24 million for his night’s work, why wouldn’t he.

The turmoil in Mike Tyson’s private life was soon to catch up with him. Within two years of losing to Douglas, Tyson was locked up, released in 1995 to resume the second phase of his turbulent career.

As for Buster, one of boxing’s true gentlemen, after some serious health issues and a brief return to the ring, things worked out just fine. Content to blend into the background in his beloved Columbus, that’s where he remains today, as happy as can be.