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Back in June, Andy Ruiz Jnr dropped Anthony Joshua four times on the way to scoring a dramatic seventh round knockout and one of the great heavyweight boxing upsets.

As shock results go, it was one of the biggest we’ve seen in recent years. But the long, rich history of the fight game is littered with such upsets.

We take a look back at five other heavyweight shocks. AJ is in good company with Lennox Lewis, Mike Tyson and Tyson Fury among those who feature. We’re counting down from the least surprising shock, as it were, to the biggest.

First up, it’s the ‘Gypsy King’.

Wladimir Klitschko v Tyson Fury, November 28th 2015, Dusseldorf, Germany

A 6’9 fighting gypsy named Tyson Fury was always likely to make headlines, one way or another.

Even in the chaotic and colourful history of the fight game, few journeys can match for sheer improbability that trodden by Manchester’s self-styled ‘Gypsy King’.

Leaving school before his teens with no qualifications, Fury soon found boxing and despite his awkward, gangling frame, discovered he was a natural.

Perhaps that’s no great surprise for a man born into a travelling community whose extended family includes notorious gypsy bare-knuckle boxing champions Uriah Burton and Bartley Gorman.

After picking up several medals as an amateur, including super heavyweight gold at the 2008 English National Championships, Fury turned pro later that year. Scoring a 1st round KO on debut, the Gypsy King was on his way.

Wladimir Klitschko meanwhile, 12 years Fury’s senior, was by this time a veteran of 54 professional contests and held three versions of the world heavyweight title.

Stepping out from the not inconsiderable shadow of elder brother Vitali, and under the tutelage of legendary trainer Emmanuel Steward, Wladimir had overcome a couple of early setbacks and developed into a fine world champion in his own right.

Derided in some quarters as an old fashioned, stand-up eastern automaton, the sage-like Steward maintained that Klitschko had all the tools necessary to go down as one of boxing’s very best.

Certainly that pulverising right-hand was a thing to be feared, the mere threat of it enough to dissuade David Haye from showing much aggressive intent in his hugely anticlimactic bid for Klitschko’s world titles in 2011.

Two years later, Fury himself was to cross paths with Haye, but two scheduled bouts never came to pass, the ‘Hayemaker’ citing injury and pulling out of both.

That period of inactivity with Haye cost Fury his place in the pecking order for his own crack at Klitschko’s titles.

Regarded as one to watch from his early days – not that he was easily missed – Fury was considered an accomplished if eccentric talent, but it was by no means certain he would make it to the top.

He’d already been floored twice and was rather unkindly labelled as a bit of a lummox for having memorably punched himself in the face in one of his early contests.

Nevertheless, he was 24-0 by the time he entered the ring against Klitschko, with two victories over Dereck Chisora (one on points, one stoppage) his career highlights to date.

‘Dr. Steelhammer’ although by now 39 years old, entered the ring with a professional record of 64-3, 53 knockouts, and hadn’t been beaten for over 11 years.

Even by the standards of professional boxing, Fury’s performances in the pre-fight press conferences were something to behold.

Despite’s Klitschko’s best attempts to keep things civil (boring, according to Fury), the Gypsy King was having none of it, infamously turning up to one of them dressed as batman, because, well, Tyson Fury.

Fury, the natural showman, appeared to rile the more polished champion who was taken aback by Fury’s antics and insults. The barely disguised contempt in which Klitschko held the challenger was plain for all to see.

Come fight weekend, yet more drama was to unfold before the first bell had even sounded. The Klitschko camp, on ‘home’ territory in Germany, started playing power games in an attempt to unsettle Fury and show everyone who was in charge.

After the Klitschkos reneged on previously agreed stipulations regarding the gloves and the ring canvas, a livid – ok, furious – Team Fury threatened to pull out of the fight with the arena already filling up.

They refused to back down. Fury had made his point and the fight was on.

Facing one of the most formidable champions in history, away from home and infront of a 55,000 sell-out crowd, most expecting an easy Klitschko win, Fury was showboating less than 90 seconds in.

Throwing feints and snapping out jabs with the champion in pursuit, Fury won the first, had plenty to say to Klitschko at the bell and walked back to his corner, arms aloft.

The pro-Klitschko crowd voiced their disapproval at such audacity, but there was a point to it. Fury had shown he could handle the occasion and the pattern of the fight had been set.

Jabbing from the hip, switching stance, using his height and reach effectively, Fury succeeded in unsettling the champion who couldn’t do much more than paw tentatively for an opening which never came.

Fury was executing his game plan perfectly, bamboozling Klitschko, despite the ever-present threat of the champion’s big right hand. Although the challenger appeared to be in complete control, Klitschko hadn’t been seriously hurt and there was still the nagging doubt about how the judges might be scoring it.

In the ninth round, Klitschko finally let the right hand go but Fury took it well and responded with a left-hook of his own as the champion failed to press on.

Then in the eleventh, more drama as Fury finally managed to rock the increasingly ragged Klitschko, before being docked a point for consistent blows to the back of the head. Both fighters came out swinging in the last looking to finish strong, and the outcome was left to the judges.

Most ringside observers had Fury ahead, and in the event the judges agreed, with the challenger winning by unanimous decision. In true gypsy tradition, the new champion celebrated with a song .

From campsite caravan to the heavyweight championship of the world. The Gypsy King could now lay claim to the lineal title held by boxing royalty from Lennox Lewis, Mike Tyson, Muhammad Ali, Rocky Marciano, Joe Louis, Jack Dempsey and Jack Johnson, all the way back to John L. Sullivan.

As is so often the case in boxing, the pre-fight nonsense gave way to a mutual and genuine respect after the fight. Ultimately, Fury was a puzzle that Klitschko could not solve and the great champion acknowledged as much. Fury for his part, apologised to his vanquished foe.

A rematch was agreed, but never took place. Soon after Dusseldorf, Fury’s well publicised mental health battles began.

Klitschko then turned his attention to Anthony Joshua, flooring AJ in the sixth before succumbing to an eleventh-round stoppage in front of 90,000 fans at Wembley. Aged 41 and with no more challenges left to face, Klitschko wisely called it a day.

As for Fury, his story has many chapters as yet unwritten. As it turned out, that night in Germany was the end of the beginning, not the beginning of the end.

Was it a huge upset? It was certainly an upset.

Perhaps the last word should go to the late, great trainer of champions, Emmanuel Steward. Some years previously, Steward had called Fury “the next dominant heavyweight champion” and “the heir to Klitschko’s throne”. On pugilistic matters, Detroit’s wise old man of boxing rarely got it wrong.

Lennox Lewis v Hasim Rahman, April 22nd 2001, Brakpan, South Africa/h4>

Lennox won’t like it, but he appears on this list twice.

His first fight against Hasim Rahman turned out to be the classic cautionary tale of an over-confident champion underestimating a challenger who knew he was getting his one big shot, and grabbed it with both hands. Or more accurately, with one huge right hand.

By 2001, Lennox Lewis reigned supreme as the heavyweight division’s dominant fighter. His only serious rival to that claim was Evander Holyfield, who he beat by unanimous decision 18 months earlier after first fighting the ‘Real Deal’ to a controversial draw.

Over the previous decade, Lewis had dispatched a string of 90s notables including Holyfield, Michael Grant, Shannon Briggs, Andrew Golota, Henry Akinwande and Ray Mercer.

He’d stopped Frank Bruno in seven in 1993, shortly after announcing his arrival as a top line heavyweight with a stunning two-round demolition job on the feared Donovon ‘Razor’ Ruddock.

The heavy-hitting Ruddock had given a peak Mike Tyson all the trouble he could handle in two thunderous bouts, but Lewis just blasted him away.

His lone defeat to Oliver McCall – more on that later – had been avenged in some style, and he was unbeaten in seven years entering the ring against the respected but unheralded Hasim Rahman from Baltimore.

The names on Rahman’s resume were no match for Lewis’s.

Corrie Sanders – who would go on to knockout Wladimir Klitschko in another big upset – had been stopped in seven, but Rahman had losses against both Oleg Maskaev and David Tua. Lewis had beaten Tua easily in his fight prior to Rahman.

A glance at the two fighters’ amateur record neatly summed up the different levels they were operating on.

Lewis was a standout star, defeating future world champion Riddick Bowe to land super heavyweight gold at the 1988 Seoul Olympics.

Rahman had fought just 10 amateur bouts, first lacing up a pair of gloves aged 20 in an attempt to escape the Baltimore street life which had nearly killed him on several occasions.

And yet, the warning signs were there.

The fight was being staged at Carnival City, a short drive from Johannesburg, South Africa at an altitude of nearly 6,000 feet. To accommodate US TV networks, it was scheduled to begin at 5am local time.

Lewis had trained – poorly by most accounts – in Los Angeles, arriving in South Africa less than two weeks before the fight.

His arrival was delayed due to being on set for a cameo role in the Hollywood blockbuster Ocean’s Eleven, featuring an all-star cast including George Clooney, Brad Pitt and Julia Roberts.

Pre-fight talk centred on a planned showdown against Mike Tyson, a fading force at 35, after Lewis had taken care of Rahman.

The champ tipped the scales at a career high 18st 1lb. The impression was not one of a focused heavyweight champion with his mind on the job.

The chance to fight for the world heavyweight title was probably not something the young Hasim Rahman thought about much while he was getting shot and stabbed growing up in Baltimore. He’d also survived a fatal car accident, at a price of 500 stiches to his face and neck.

But ever since finding sanctuary in the boxing gym, he was totally dedicated to the sport, and he sensed that Lewis was not taking him seriously.

Rahman based his training camp in New York’s Catskill Mountains to prepare for the altitude, and arrived a month before the fight to further acclimatise. In short, he was preparing like a champion.

Billed as ‘Thunder in Africa ’, at stake were Lewis’s WBC & IBF heavyweight titles. Both men looked calm as they entered the ring, Lewis relaxed as always, Rahman confident.

They each enjoyed reasonable success early on, but it was Lewis who led 39-37 (three rounds to one) on all three judges’ scorecards after four rounds. But the champion was looking laboured, breathing heavily on his stool between the fourth and fifth.

Certainly, Rahman was in the contest and didn’t look like the 20/1 outsider the bookies had made him. He had some swelling around his left eye after an accidental clash of heads, but all that was about to prove irrelevant.

Lewis started the fifth well but was tagged by a solid Rahman right in the second minute of the round. The challenger followed up with a series of jabs, none of which seemed to trouble the champion as he leant back off the ropes, smirking.

But he wasn’t smiling for long as Rahman came again and detonated a huge straight right, landing flush on the champion’s jaw with 40 seconds to go in round five. Lewis wasn’t close to beating the count and for the second time in his career, had suffered a stunning upset knockout defeat.

The outcome is often put down to Lewis’ lack of preparation, but that does a disservice to Rahman.

Lewis’s trainer Emmanuel Steward claimed that it wasn’t lack of fitness but more a lack of “mental focus and intensity”, and the boxing ring is the wrong place to be doing without either of those.

“I would have expected Lennox Lewis to win that fight seven days a week, 24 hours a day”, exclaimed George Foreman, as the dazed, dethroned Lewis was left asking his corner, “what happened?”.

It seemed strange that Lewis, a consummate professional and one of the smartest fighters in the game, would fall into the trap of under-estimating his opponent – especially as he’d already done similar with such dire consequences earlier in his career.

The fall out was unseemly, Lewis claiming that Rahman got lucky, Rahman demanding his respect. With Rahman joining Don King after becoming champ, Lewis had to go through the courts to get his contractually obliged rematch.

Seven months later in Vegas, a much sharper Lewis delivered emphatically. Landing a massive right hand every bit as devastating as Rahman’s in the first fight, it was all over in four rounds. Lewis had his belts back.

A sore loser after the first fight, Lewis was not exactly a gracious winner second time round. That was out of character for one of history’s more thoughtful and level-headed champions.

It just goes to demonstrate the extreme mental and physical demands that boxing at this level places on its combatants. But Rahman, an essentially decent man despite his wayward past, deserved better treatment from Lewis. It ended 1-1 between them, after all.

By now 36 years old, Lennox Lewis, self-proclaimed ‘pugilist-specialist’ and one of Britain’s greatest ever, was approaching the end of the line. After two more wins over Mike Tyson and Vitali Klitschko, the big man was done.

Hasim Rahman, still in his twenties, would go on to have another 24 contests, eventually calling it quits at the age of 41.

But those two fights with Lewis set him up for life. Still in the game as a mentor to young boxers, it turned out to be a happy ending for the man from Baltimore, who came from the very bottom, and made it right to the very top.

Lennox Lewis v Oliver McCall, September 24th 1994, London, UK

Long before his catastrophe against Hasim Rahman in South Africa, Lennox Lewis had to endure another nightmare against a maverick puncher from Chicago named Oliver McCall.

To describe McCall as a volatile character would be playing it down, and then some. He had a long history of substance abuse, would often make his way to the ring in tears, and his bizarre moniker the ‘Atomic Bull’ was entirely apt.

In the post-Mike Tyson heavyweight landscape, a trio of outstanding fighters emerged to stake their claim as top dog in the division following Tyson’s incarceration in 1992: Lennox Lewis, Evander Holyfield and Riddick Bowe.

Holyfield had made short work of Tyson conqueror Buster Douglas, but lost his undisputed title in the first fight of a classic trilogy against the exceptional Riddick Bowe, a former classmate of Tyson from Brownsville, Brooklyn.

Bowe had lost to Lewis in the super-heavyweight final of the 1988 Seoul Olympics, and their rivalry grew more bitter and nasty as they made their way through the paid ranks.

In late 1992, Lewis faced off against the hard-hitting Canadian Donovan ‘Razor’ Ruddock in a final eliminator to challenge for Bowe’s undisputed crown.

Lennox delivered perhaps his finest ever performance in a ruthless two-round destruction of the fearsome Ruddock, and Lewis v Bowe was on.

Or was it? Rather than face Lewis, and attempt to gain revenge for his defeat at the Olympics, Bowe went back on the agreement.

Objecting to Bowe’s volte-face, the WBC stripped him of their title. Bowe’s response? To literally throw his WBC belt in the bin . It was an act of extreme petulance and a cheap PR stunt devised by Bowe’s obnoxious promoter, Rock Newman.

Awarded the WBC belt by default, Lewis made three successful title defences – the second of which was a seventh-round stoppage of Frank Bruno – before facing McCall at the Wembley Arena.

Lewis entered the ring as a heavy betting favourite with an unblemished record of 25-0.

McCall, a former Tyson sparring partner and under the guidance of future Lewis trainer Manny Steward, had five defeats on his record but was still considered a dangerous and unpredictable fighter.

That assessment was proved absolutely correct. After just 20 seconds of round two, the Atomic Bull connected with an overhand right which sent Lewis crashing to the canvas.

He clambered to his feet, but still clearly dazed, the referee decided to stop the fight. Lewis, arms outstretched in protest, had suffered his first career defeat and McCall had pulled off a huge upset win.

The McCall camp celebrated wildly, no-one more so than promoter Don King, cavorting around the ring ecstatic to be back as a player once more in the heavyweight division.

McCall made one successful defence of his title before returning to London a year later, losing on points as big Frank Bruno finally realised his world heavyweight dream on a memorable night at Wembley Stadium.

Bruno’s dream quickly turned sour as he was viciously stopped in three by Mike Tyson in his first title defence.

Lennox Lewis, now under the tutelage of Manny Steward – the man who masterminded his defeat to McCall – rebuilt steadily with four straight wins before facing McCall again in 1997.

Things got weird in the rematch.

McCall’s chaotic personal life had once more got the better of him. Out of the ring for almost a year, he was in rehab just before entering camp.

On fight night itself, he literally ran into the ring, and tried for a couple of rounds before appearing to decide that he didn’t want to be there.

From the third round on, and to the bewilderment of spectators, commentators and Lewis alike, McCall refused to throw punches or even try to defend himself. Referee Mills Lane had no choice but to call a halt less than a minute into the fifth.

Veteran US announcer Larry Merchant surmised, “I’ve seen some strange things in boxing. That is surely one of the strangest”. The Lewis camp knew they’d just witnessed a man having a nervous breakdown, and their celebrations were subdued.

Lewis would avenge his only other defeat to Hasim Rahman, and is thus able to proudly state that he beat every man he ever fought.

Against all the odds, McCall, now 54, fights on, holding a record of 59 wins and 14 losses. His only defeat inside the distance remains that bizarre rematch against Lewis in Las Vegas.

What is a man still doing fighting at 54 you might ask? For the Atomic Bull, it seems like the ring is the safest place to be.

Sonny Liston v Cassius Clay, February 25th, 1964 – Miami, USA/h4>

In 1964, the world – or America at any rate – was not yet ready for Cassius Marcellus Clay.

The man who would go on to achieve sporting immortality, and, as Muhammad Ali, become one of the most famous people of all time, was at this time simply a fleet-footed, fast-talking, precociously talented 22-year-old boxer.

Ali would of course go on to become, in his own words, “The Greatest”, and one of the most iconic figures of the 20th century, gaining a cultural significance beyond that of any mere sportsman.

But all that lay a long way away when Clay, as he then was, made his first challenge for the world heavyweight championship.

Many ring observers felt he was in for a painful beating at the hands of the frighteningly powerful and downright terrifying champion, Charles “Sonny” Liston.

The brooding, sullen Liston was everything the effervescent Clay was not.

Born into abject poverty, the second youngest of 25 children on farm in rural Arkansas, confusion surrounds Liston’s exact date of birth. Most accounts put it at either 1930 or 1932, but it’s possibly much earlier than that.

Unable to read or write, Liston endured a violent, miserable childhood, running away from home aged 13. He would eventually serve time for robbery, and it was in jail where he first began to box. Liston would later say that the food in the Missouri State Penitentiary was the best he ever ate.

Leaving jail in 1952, Liston embarked on a brief but successful amateur career before going pro under the management of the mob, who effectively controlled boxing in the post-war era.

Liston’s criminal background and mob ties led to repeated run-ins with the law. He swapped St. Louis for Philadelphia but only found more trouble, and more serious underworld figures who took an interest in his career.

Despite this chaotic, semi-legal existence, by 1962 Sonny Liston had risen to #1 contender for Floyd Patterson’s heavyweight title.

The amiable Patterson was seen as the acceptable face of the civil rights movement and had the support of community leaders, the public at large and even President John F. Kennedy. Nobody wanted Liston as the champion.

The President urged Patterson not to fight Liston, but Floyd was a fair man and insisted that Sonny had earned his chance. He would come to regret that generosity.

Making his way into the ring to face Liston, Patterson looked, as memorably put by one scribe, “like a man being led to his execution”. He couldn’t even look at Liston as the referee gave the two men their pre-fight instructions. Patterson, a fine champion, didn’t last a round.

History has been much kinder to Liston the man than his contemporaries ever were. Upon claiming the most prestigious title in all of sports, he received no recognition, no respect, no welcome home parade. It hurt him bitterly and made him even more resentful.

Floyd Patterson, willed on by those who wished to be rid of the champ nobody wanted, was put up to try and beat Liston in an immediate rematch. It ended in another first-round knockout.

So this was the man Cassius Clay was stepping into the ring against in February 1964.

Returning from the 1960 Rome Olympics with light-heavyweight gold, the 18-year-old Clay was possessed of an easy charm, a winning smile and he was not what you’d call short on self-confidence.

But by the time he faced Liston, the act was starting to wear a little thin. Clay was expected to “know his place”, but he was his own man right from the very start. He didn’t conform, he didn’t play by the rules and he didn’t follow orders.

With razor sharp reflexes and hands and feet almost as fast as his mouth, Clay was considered a promising talent. But good enough to beat Liston? He’d already been decked twice, once by a famous Henry Cooper left hook, much to the delight of the UK fans.

In fact it was only down to some mischief from his cornerman, Angelo Dundee, that bought Clay precious time to recover from ‘Our Enry’s’ sledgehammer left.

Eight months after that narrow escape in London, Liston v Clay was on. Clay had done so much talking in the build-up that he actually managed to make the reviled Liston a more popular winner in many fans’ eyes.

His nascent support for Malcolm X and the militant Nation of Islam hadn’t much helped his public image either.

Come the weigh-in, in those days held on the morning of the fight, Clay went into overdrive. His hyperactive performance convinced many he was scared witless and might not even turn up to fight. Liston, as usual, sat in silence, exuding menace.

But once the first bell sounded, Clay went about stripping away that menacing aura, layer by layer.

Dancing, slashing, jabbing and moving, Clay used all of his advantages in speed and height to lead the old warrior a merry dance. It was an utterly unexpected one-sided beating.

In the previous three years, Liston had been so dominant that no-one wanted to face him. The three fights he did have (including those two against Patterson) all ended within one round.

Not viewing Clay as a serious threat, he cut corners in training too. Thus, as early as the fourth round, Liston was exhausted, frustrated and demoralised, barely able to lay a glove on the quicksilver Clay.

But in the challenger’s corner before the start of the fifth, there was panic. His eyes were burning and he could hardly see. The suspicion at the time, and for a long time after, was that Liston’s corner had tried some nefarious trick to temporarily blind Clay by spreading liniment on Sonny’s gloves.

Yet Clay’s trainer Dundee, who knew every trick in the book, dismissed that suggestion some years later.

Whatever it was, Clay got on his bike in the fifth and managed to avoid serious punishment as an increasingly desperate Liston launched one final assault. The danger having passed, Clay re-asserted his dominance in the sixth. Liston had had enough.

As the bell rang for the start of the seventh, the champ remained seated. Clay, arms aloft, shuffled to mid-ring as a disbelieving crowd looked on. The referee raised Clay’s hand – cue pandemonium.

Clay cavorted around the ring, barely able to contain himself. This was the occasion of his famous “I shook up the world! I shook up the world! I must be the greatest!” outburst.

The great Joe Louis, a friend of Liston’s and working for TV that night, called it the biggest upset in the history of heavyweight boxing.

If you ever wanted an exact definition of talking the talk, and walking the walk, Clay’s performance that night was it.

The infamous re-match, in May 1965, ended in even greater controversy. Liston was felled in the first round by the so-called ‘phantom punch’ – a chopping right hand so fast that most people didn’t see it.

This was the punch that gave us that iconic photograph of Ali stood over his fallen foe, berating him to get up. Ali wouldn’t retreat to a neutral corner and so the count started late. Liston rose to his feet after around 20 seconds.

Referee Jersey Joe Walcott let the fighters continue, but was then ordered by the officials to stop it on account of Liston failing to beat the count.

Debate as to whether or not Liston took a dive continues to this day. Rumours persisted of threats made to Liston by the mafia and the Nation of Islam. Those who think Liston suffered a genuine knockdown are in the minority, but he was certainly hit by a hard shot.

For Ali, his incredible journey was entering its next stage. A deeply unpopular, divisive figure in 1965, he was later stripped of his world title and banned from boxing for refusing to fight in the American war in Vietnam.

By the time he was cleared to fight again, Ali was revered as a man who stood up to the establishment and fought for what was right, no matter the personal cost. Later battles against Joe Frazier, George Foreman and Ken Norton cemented the Ali legend.

For Sonny Liston there was, perhaps inevitably, no fairy-tale ending. He was found dead at his Las Vegas home in 1971, amid whispers of foul play and a mob hit.

A champion on the margins, Liston’s fate has been viewed in a slightly more sympathetic light in recent years. Musicians as diverse as Tom Petty, The Roots, The Animals and Wu-Tang Clan have all referenced this enigmatic man, while Mark Knopfler lamented “the king they cast aside”, in his 2004 “Song for Sonny Liston” .

The mythology built up around the sport of boxing sometimes makes it hard to locate the truth. This can be said of Muhammad Ali more than perhaps any other fighter, but there is no less mystique surrounding the complex and ultimately tragic figure of Charles “Sonny” Liston.

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 the biggest shock in boxing history, indeed arguably the biggest shock in all sporting history, bar none.

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

In February 1990, the 23-year-old 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 Trevor Berbick in two-rounds.

He added the WBA title in his next fight against James ‘Bonecrusher’ Smith, before winning the IBF belt from Tony Tucker to become undisputed heavyweight champion just a month after his 21st birthday.

Tyson’s path from New York street thug to the 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, he was to discover boxing while serving time in a youth detention centre.


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

D’Amato and his wife legally adopted the orphaned Mike Tyson. Ironically enough, D’Amato’s new charge would go on to become the most feared heavyweight champion since Liston, the scourge of his previous protégé Patterson.

In the mid to late 80s, Tyson laid waste to an entire generation of heavyweights, a human wrecking ball leaving a trail of destruction in his wake.

No flashy dressing gown, no tassels, no gimmicks. Just his trademark black shorts, black ankle boots and simple cut-out towel. ‘Iron’ Mike Tyson. Even his name sounded vicious.

Thirty years ago, boxing was a more 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 promotional UK tour featured an appearance on prime-time TV chat show Wogan. It revealed a rather sweet, shy, effeminate, intelligent young man quite at odds with the violent force of nature who stepped through the ropes.

Tyson continued his relentless march. 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. That fight came to define Tyson at his most destructive, terrifying best.

Two more routine wins, including a fifth-round stoppage of Frank Bruno, meant that Tyson arrived in Tokyo boasting a perfect 37-0 record, with 33 knockouts.

The James ‘Buster’ Douglas story was altogether less dramatic and rather more wholesome than the narrative built up around Tyson.

Fortunate enough to enjoy the peace and quiet of a stable family upbringing in Columbus, Ohio, Buster’s childhood was nevertheless, like most people’s, not without a few bumps along the way.

As a bullied, 10-year-old boy returning home in tears one day, his mother demanded he go back out 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.

Douglas forged a solid if unspectacular pro career. In a 1987 fight 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 showdown in Tokyo with a 29-4 pro record.

But tragedy was to strike the Douglas camp just three weeks before the fight. Aged just 47, his mother, to whom he was extremely close, died suddenly. His handlers urged Buster to back out of the fight, but he was determined to see it through.

Douglas has since said that that grief helped to galvanise him, and from that moment on he felt no fear. That was crucial when facing a man like Tyson for whom intimidation was one of his principal weapons.

Another small but significant factor was the fact that Douglas had also fought on six Tyson undercards. 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 – long-time trainer and Cus D’Amato disciple Kevin Rooney had been ditched as Tyson came under the ever more malign influence of Don King.

Shortly before the fight, he’d been floored in sparring, with TV cameras there to witness it.

Despite the warning signs, 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 previously and was regarded as an easy warm up for a super fight with Evander Holyfield – ringside in Tokyo – already signed and sealed for later that year.

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

“Just another day at the office 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 it wasn’t long before Buster had Tyson’s attention. 6’4 to Tyson’s 5’10, he came out throwing jabs and right crosses, showing aggressive intent and taking the fight to Tyson right from the opening bell.

It was apparent from very early on that this was not going to be the quick blowout that had been predicted. 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 displaying none of his customary head movement out of his trademark peek-a-boo stance.

Tyson’s boxing skills are sometimes 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.

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.

Into the eighth, and both boxers dished out and received some telling blows, but after being forced back on to the ropes, Tyson connected with a signature uppercut to finally floor the gutsy challenger. Buster made it to his feet at the count of 9, when the bell sounded to end the round.

It looked like the writing was on the wall for Douglas, but instead that knockdown turned out to be Tyson’s 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, unsteady on his legs returning to his corner.

If that was shocking enough, what happened in the tenth was nothing short of seismic. 35 seconds in, Douglas unleashed a huge right uppercut stopping Tyson in his tracks.

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

Those pictures of a groggy Tyson on all fours, fumbling for his gumshield, trying in vain to beat the count, seem no less shocking today than they did for a 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 ferocious beating but still kept coming, defiantly searching for a way through.

He almost managed it with that knockdown in the eighth, but on this night, nothing and no-one was denying Buster Douglas. He put in an epic, punch perfect performance, and changed his life forever.

In the fight’s aftermath there were some shenanigans from 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.

The citizens of Columbus came out to salute their new, undisputed heavyweight champion.

But Douglas was not much one for the fame game, stating 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 ended up facing the man Tyson was supposed to fight, Evander Holyfield. But the edge had gone.

Fighting for the memory of his mother and for the opportunities his boxer father never got, Buster had put absolutely everything into dethroning Iron Mike and had nothing left 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 in jail, being released in 1995 to resume the second phase of his 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.

Odds are correct at the time of posting

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