To this day, James ‘Buster’ Douglas retains a place in folklore for his stunning heavyweight title defeat of Mike Tyson in the Tokyo Dome, Japan, on February 11 1990, now a full 30 years ago.

A rank 42-1 outsider with an undistinguished professional record, Douglas was meant to be an easy scalp for 37-fight unbeaten, 10-time heavyweight champion Mike Tyson on his unstoppable march towards a showdown with Evander Holyfield.

That night in Japan, when the faults of Tyson’s hard-partying lifestyle were laid bare for the world to see, was the culmination of a wild ride featuring geisha girls, 3am parties, family tragedy and one Donald Trump.

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The legendary moment, 30 years ago, when James ‘Buster’ Douglas knocks out Mike Tyson

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Tyson, then considered unbeatable, looks stunned and badly swollen during the fight

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Douglas celebrates the biggest shock in boxing history, in Japan on February 11 1990

James ‘Buster’ Douglas knocks out Mike Tyson in 1990

Much like Andy Ruiz’s upset of Anthony Joshua 29 years later, there was little doubt from the travelling journalists about who would come out on top.

When asked by a customs official how long he expected to be working in Japan, Associated Press correspondent Ed Schuyler quipped: ‘Oh, about ninety seconds’.

Ranked as the No 7 heavyweight at the time, Douglas had suffered a TKO in his 1987 title fight against Tony Tucker, but a string of six straight victories earned him the right to face Tyson.

The defending champion was nothing short of a phenomenon.

Iron Mike’s stunning combination of hand speed, defensive prowess and awesome power had seen him become the youngest heavyweight champion in history, aged 20 years and four months, in November 1986. Less than a year later he became the first heavyweight to own all three major belts – WBA, WBC, and IBF – and become undisputed champion. Coming into the fight against Douglas, 33 of his 37 straight wins had been by knockout.

The entire world knew, and feared, Mike Tyson.

But his destructive victories – including a 93-second win over Carl Williams in the fight before Douglas – papered over many of the cracks appearing both professionally and personally in Tyson’s life.

While much commentary reflects on Tyson’s troubled approach to the fight, Douglas also endured a difficult build-up.

His mother, Lula Pearl, died 23 days before the bout, while his son’s mother battled serious kidney problems that would later be diagnosed as cancer, and his wife left him.

In fact, it was a death-bed promise made to Lula Pearl that inspired Douglas to victory, often running on raw emotion to overpower the greatest puncher on the planet at the time.

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Tyson’s training for the fight was shambolic and undermined by sex sessions with local girls as he struggled with mental illness, which would lead to years of turmoil in his life

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In a rare public sparring session before the fight, here Tyson throws a punch at his opponent

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Tyson admitted having sex with Japanese women as his marriage to wife Robin (above) had disintegrated before the fight against Douglas

Tyson, by contrast, was rarely seen training in the build-up to the fight having sacked long-term coach Kevin Rooney. His marriage to Robin Givens had also ended acrimoniously shortly beforehand.

 Upon arrival in Japan – he arrived 11 days before Douglas – he was 30 pounds overweight and suffering from addiction and depression.

In his memoir, R&B singer Bobby Brown recalls how he partied with Tyson until 3am the night before the fight, and there were plenty more women beside in Tokyo where his exploits with local geisha girls became the stuff of legend.

Reflecting on his time in Japan, Tyson said: ‘Besides having sex with the maids, I was seeing this young Japanese girl who I had had sex with the last time I was in Japan.

‘Robin would go out shopping and I would go downstairs to the back of the hotel where this young girl had a room… so that was my training for Douglas.’

By the time Douglas landed in Tokyo, Tyson had been in Japan for 11 days but was barely seen in public. One rare open sparring session ended with Tyson so exhausted the spectators had to be sent away. During another training exercise, Tyson was knocked down heavily by his partner Greg Page but neither the fighter nor his entourage heeded the warning signs.

A growing presence around the Tyson camp was Donald Trump, by then a hugely influential figure in American life.

Trump and Tyson initially enjoyed a fruitful relationship in the late 1980s after the real estate tycoon spent a reported $11million to make the 91-second fight between Tyson and Michael Spinks in 1988.

In the immediate aftermath, the future US president was hired as an adviser amid a rift with long-time manager Bill Cayton and was still a key player at the time of this fight.

The relationship, having briefly burned brightly, would later fizzle out just as quickly after rumours of an affair between Trump and Tyson’s wife, Robin.

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During the late 1980s, Tyson employed future president Donald Trump as his financial adviser

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Trump split with Tyson soon after the Douglas fight and has been the US president

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Don King played a key role as promoter throughout Tyson’s reign as heavyweight champion

Don King was the man who would oversee the divisions in Tyson’s camp that ultimately led to his downfall and, in an act of brazen arrogance, announced a title fight between Holyfield and Tyson a month before the bout with Douglas.

Even with the chaotic build-up, no-one expected Douglas, then 30, to pose the slightest threat to 23-year-old Tyson in front of 40,000 in Tokyo Dome.

Yet Douglas’ entrance gave everyone pause for thought, as he almost ran into the ring..

‘Who had ever seen a fighter run to the ring to fight Tyson? He wasn’t walking to an executioner’s chair. He was jogging to a throne,’ Larry Merchant told Bleacherreport. ‘It was the first sign something different was going on. We didn’t know it. But it revealed itself soon enough.’

From the very first bell, Douglas showed no fear in the face of a man whose reputation was by now his biggest weapon.

Tyson’s performance in the early rounds was enough to spark concern among King – who also promoted Douglas – and Trump, with the two power-brokers quick to arrange a deal for a rematch to be hosted in a Trump property in Atlantic City.

That would never go ahead after Douglas broke his contract to fight Holyfield in a big-money payday, but King and Trump would still pocket $4.5m each for their troubles.

WBC president Jose Sulaiman was also worried.

After the fight, referee Octavio Meyren told Playboy: ‘Five minutes before the start of the fight, Jose Sulaiman spoke to me,’ . ‘… As we walked from the dressing rooms to the ring, Sulaiman took my shoulder and he told me, “If you see Tyson hurt, be nice with him. If you see Douglas hurt, stop the fight immediately.”

‘I said, “I’ll never do that. I’m an honest man and I never do that.” Then he told me, “OK, go out to the ring and do your job the best you can do.”‘

The contender controlled the fight into the middle rounds, allowing only the occasional shot past his dominant jab.

So lackadaisical was the approach from Tyson’s backroom team that when he returned to his corner at the end of round five with a swollen eye, cuts man Taylor Smith did not have the right tools to fix the problem.

Instead, trainer Aaron Snowell improvised with a condom – or a rubber glove, depending on who you believe – packed with ice, and the lack of vision in his right eye would prove costly.

In contrast, Douglas had a plan. Assistant trainer John Russell had told him in training: ‘You step to the side. You don’t back up because the train runs right over you. If you back up against Tyson he’s going to run right over you. Just keep moving to the side. Don’t let him get set.’

Still, Tyson fought on and felled his rival in the ninth round with a trademark upper-cut, but Douglas made the most of communication difficulties between the Japanese timekeeper and Mexican referee for what was effectively a 15-second count.

Douglas, who was earlier knocked down, lands the vicious left hand that felled Tyson

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The referee counts out Tyson as he lays on the floor after being stunned in the 10th round

As Douglas told Steve Bunce: ‘I knew he would break if I kept on hitting him and what did I have to lose?’

He also told Sportsmail back in 2015: ‘It was just great – I have great memories of that night, the preparation, just focusing, feeling good about going in there and doing something everybody thought was impossible,’ he said.

‘I fought hard that night, I was in shape and he went down.’

The tenthround would see Douglas batter Tyson to the floor, knocking him over for the first time in his career. That would be that, and the world reeled. Jeff Powell, reporting the fight for the Daily Mail, wrote: ‘The Invincible Man, a boxing myth worth countless millions, lay sprawled across the floor as senseless as a crumpled dollar bill. One eye close by swelling as big as a fist, the other glazed open, gumshield gone, tongue lolling, the monster was well and truly slain. Here was the biggest upset since David killed Goliath.’

The belts were snatched from Tyson’s grasp – eventually.

But he, inevitably, has his own view: ‘I shoulda won that fight.

‘That ref [Octavio Meyran] hated my guts. I knocked [Douglas] down in the eighth but that a**hole gave him 13 seconds to get up!’

King, out of sheer desperation, immediately lodged an appeal over the decision and within six hours the man used his considerable power to ensure both the WBC and WBA had withdrawn their ratification of the new champion. 

Douglas himself has admitted his enjoyment of victory was somewhat tainted by King’s appeal and the four-day delay between the knockout and the WBC and WBA finally recognising his new status as champion.

‘He’s a big time sore loser,’ Douglas told Sportsmail about Tyson. ‘He was upset that night I beat him. He was whining and complaining like a baby in a crib.

‘It was an enjoyable win, having everyone chanting my name, but after that I was stuck in a legal battle for about four months trying get the right to call myself champion of the world so that was pretty difficult.

‘I still celebrated with my trainer and stuff but it did spoil it.

‘I met Tyson in Cincinnati a couple of years ago at a boxing event and took pictures and stuff. He didn’t say much – we didn’t speak much at all in fact.’

Even Trump was quick to evade Tyson in the aftermath.

‘I’m not going to Tyson’s dressing room,’ Trump reportedly said. ‘I can’t go near him. It might rub off. The same thing could happen to me.’

‘They came to see Godzilla, but the wrong guy turned out to be the monster,’ Merchant added.

Douglas would also move quickly to secure a $24m match-up against Holyfield, entering the ring overweight and lasting three rounds before defeat.

Despite much speculation, a rematch between Douglas and Tyson would never materialise with both men facing sharp declines physically after what would prove to be a defining night for the sport.

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Tyson gained more infamy for biting Evander Holyfield’s ear during their fight in 1997

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Tyson (right) would suffer defeat by Kevin McBride in his final professional fight in 2005

Following the Douglas fight, Tyson’s career would continue to plumb new depths culminating in a six-year prison sentence for rape in 1992.

Tyson didn’t win back the WBC and WBA titles until 1996, following his prison sentence.

Having pulled out of a 1991 fight through injury, it would be another five years before Tyson eventually met Holyfield in the ring for the first of two victories, the second known only for his infamous bite, which took a chunk out of Holyfield’s ear, that will mar boxing forever.

Drink, drugs and depression would continue to afflict Tyson even following his eventual retirement in 2005.

Likewise, Douglas would never scale the heights again the boxing ring and endured some troubles outside of the sport during the intervening years.

At one point Douglas ballooned to almost 450 pounds (32 stone) and slipped into a diabetic coma that nearly killed him, but is now enjoying a much quieter retirement.

‘Life is definitely harder than fighting Tyson or anyone else,’ he told Sportsmail.

‘Life outside the ring is real, it’s hardcore.

‘But you know once I came out of my depression, and quit drinking all the time, I felt like I got a second lease at life.

‘I look forward to every day now.’

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Tyson, pictured in August last year, remains a legendary boxer despite his turbulent life

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Douglas is pictured here this month teaching a young girl boxing in Columbus, Ohio

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