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Almost 20 years after his last professional fight, Iron Mike Tyson is returning to the ring in this Saturday’s hyped showdown against American crossover star Jake Paul. At age 58, plenty have dubbed the decision mad. But the maddest moment of his career? Not even close.
So on the eve of his return to the squared circle, Fox Sports Australia casts an eye of the 30 most controversial moments of a heavyweight Hall of Famer whose life has been a swirl of cash, KO's and crazy Bengal tiger attacks which cost him $250,000. They are ..
.. 30.
Tyson tries to fight gorilla It is sometime in the late 1980s, and Mike Tyson is being led around New York zoo on a private tour with his wife Robin Givens. Nearing the gorilla enclosure, the champ notices that one particular silverback is bullying the others. An incident he takes such an exception to, Tyson immediately offers the zookeeper $10,000 to open the cage so he can “smash that silverback’s snot box”.
Thankfully for all concerned, the employee declines. 29. Pigeon thief bashed Apart from his signature fists, Tyson has also long been famed for his love of pigeons, and has tended to them all his life.
In fact, it was one said birds that led to the champ’s first fight. The story goes that a local thug not only stole one of Tyson’s beloved pets, but when called on it killed the pigeon in front of him. “When I confronted him to get it back,” Tyson recounted later, “he pulled it out of his coat, twisted its neck off and rubbed the blood on me”.
While furious, Tyson was scared to fight but remembers a friend saying he had to. “So I hit the guy with a right and he went down. I was stunned .
.. it was my first taste of applause”.
28. Death threat to Lennox Lewis In the build-up to a 2002 fight with Lennox Lewis, Tyson declared his goal was not only to fight professionally “but to kill him”. Unsurprisingly, this wasn’t the only death threat issued by Iron Mike, who also said of Donovan Ruddock before their 1991 bout: “If he doesn’t die, it doesn’t count .
..”.
27. Dapper Dan’s street fight Mitch “Blood” Green was a notorious New York criminal, and boxer, who first fought Mike Tyson in 1986, with the latter winning over 10 rounds at Madison Square Garden. Yet it was two years later when a second fight between the pair made real headlines.
This time however, it was in a Harlem clothing store, wonderfully named Dapper Dan’s. According to eyewitness accounts, Tyson completely destroyed his rival, with pictures released later showing Green’s left eye swollen shut. 26.
Tupac gets shot For almost 30 years, it remained one of the greatest mysteries in American pop culture. After sitting ringside for close friend Tyson’s title win over Bruce Seldon in 1996, rap star Tupac Shakur would that same night be shot and killed in a Las Vegas drive by. For years, mystery surrounded exactly who fired from the white Cadillac, fatally wounding 2Pac in the chest, arms and thigh.
Finally last year, Crips gang legend Duane ‘Keffe D’ Davis was arrested and charged over the famed cold case, for which he now awaits trial. While not directly involved, Tyson has long admitted to feelings of guilt about the tragic event, explaining how he had encouraged his friend to the fight and was initially supposed to meet him out afterwards, before changing plans to be with family. 25.
Staredown If ringside officials judged staredowns, Iron Mike would have started most fights up 10-7. For proof, Google his eyeballing Peter McNeely before their 1995 headliner. 24.
The plane incident Back in April 2022, Tyson was captured on a Jetblue flight leaning over his business class seat and punching seven shades from a fellow passenger who, apparently intoxicated, had been harassing the Hall Of Famer. Eyewitnesses would later say that Tyson had become increasingly agitated by the harassment and banter from his fellow passenger, which eventually included having water thrown at him. Little surprise then for what Iron Mike threw back.
23. Tyson KO's garbo Another pigeon story, another brutal right hand. Only a few years after bashing that wannabe bird thief in his first stink, Tyson also went and belted a garbo who inadvertently threw out one of his prized coops.
After the death of another favoured bird, Julius (this time, apparently, to natural causes) young Mike had intended to honour the pet by using a piece of its wooden coop as a stickball bat in his next game. None of which, of course, his local sanitation man knew when he went and hurled said coop into the crusher. For which, Iron Mike rushed him, caught him flush with a right hand and left him out cold, convulsing on the pavement.
22. Catching Brad Pitt in bed with his wife No list of crazy Mike Tyson tales would be complete without that yarn about the fighter catching Hollywood heartthrob Brad Pitt in bed with his wife Robin Givens -- including the actor apparently pleading “dude, don’t hit me”. While Tyson and Givens married in 1998, their tumultuous marriage lasted only a year before the actress filed for divorce.
Yet in his memoir Undisputed Truth, Tyson claims he went to visit his ex and discovered the pair in bed together. “You had to see the look on his face,” Tyson recounted of Pitt. “He looked like he was ready to receive his last rites”.
While Givens has long denied the encounter ever took place, Tyson doubled down in a TV interview stating: “I was due a divorce but every day would go to her house to have sex. This particular day, someone beat me to the punch.” 21.
Marijuana Mike So heavily was Mike Tyson addicted to alcohol, marijuana and cocaine during his fight career, he disappeared for days on benders, fought while under the influence, and even beat drug testers with a contraption dubbed the ‘Whizinator’ -- a fake penis filled with someone else’s urine. So how ironic now that the same man is reportedly earning $1 million-per-month through his new marijuana empire, dubbed Tyson 2.0, which offers premium strains, edibles and extracts.
20. Meeting Cus D’Amato Craziest part of this one? Well, without Cus D’Amato, there is no Mike Tyson. It’s that simple.
The legendary trainer was working out of New York’s Catskill Boxing Club when he initially met a wayward young kid from a nearby reform school. And from there? Well, Cus went and created a heavyweight king. More than simply teaching Tyson that famed peek-a-boo style, D’Amato morphed into an undeniable father figure, and spiritual centre for the fighter who would never quite be the same following his death – which occurred just a year before Tyson became boxing’s youngest heavyweight king.
19. Jailed for road rage Midway through 1998, Tyson was jailed for nine months following a road rage incident in which the fighter, following a three-car collision, and according to District Judge Stephen Johnson, “lashed out at two innocent people” using “the hands and feet of a professional fighter”. Which was far different to a separate fender bender Tyson endured only a year earlier, and on the night before his famed rematch with Evander Holyfield.
On that occasion, a punter reversed straight into his new Lamborghini in a Las Vegas parking lot. Yet rather than get enraged, Tyson considered the whole thing bad juju -- so gifted his keys to a valet before walking away. 18.
Larry Holmes KO When it comes to crazy fight tales, there are few better than when a 14-year-old Mike Tyson told his idol, Muhammad Ali, how one day he would avenge the champ’s loss against Larry Holmes. Which within eight years, incredibly, he did. Facing Holmes in a 1988 Atlantic City headliner, Tyson was approached by Ali just before the fight and told: “Remember what you said, get him for me”.
He finished Holmes within four rounds. 17. Undisputed Amid all the madness that was Mike Tyson’s fight career, special mention must be made of that night in 1987 when, with WBC and WBA titles already in his possession, he went and bested reigning IBF champ Tony Tucker to become undisputed heavyweight king.
At the time, Tucker was himself undefeated in 34 outings and went all 12 rounds against the man who would stay undisputed for almost three years and six defences. 16. Marvis Frazier KO Put simply, this one was the quickest knockout of Mike Tyson’s career – with the big unit needing just 30 seconds to end Marvin Frazier, the son of former heavyweight king Joe Frazier.
Arriving four fights before Tyson would become history’s youngest heavyweight champ, the brutal finish went right uppercut, big left hand, then another right uppercut before a right-left combo ended it. 15. Tyson bites Lennox Lewis’s leg Back in 2002, Tyson’s hyped press conference with Lennox Lewis descended into all sorts of chaos during the face off, including allegations Tyson bit his rival during a melee involving some 20 hangers on.
The drama started when, with the pair standing across stage from each other, Tyson stormed over to confront Lewis, whose team quickly moved in as support. As a result, Tyson threw a wild left hand toward a minder, with Lewis then responding with a right aimed at his rival. And from there, chaos ensued as the stage was rushed by bodyguards, corners and at least one bloke wearing a Hells Angels jacket.
14. The Hangover movie Of all the Mike Tyson knockouts seared into our subconscious – and, geez, there’s been a few – one of the most wonderful, and rewatched, has to be that thunderous right hand which dropped Zach Galifianakis in The Hangover movie. While Tyson has since admitted to being “high on cocaine” during filming, said cameo breathed new life into his aura while also introducing the Hall of Famer to a whole new audience – many of whom will now be tuning in to his latest showdown against Jake Paul.
13. Barbara Walters interview Mike Tyson was only seven months into his incredibly tumultuous marriage with American actress Robin Givens when the pair, somewhat incredibly, went and laid their issues bare on national TV. During an extraordinary interview with Barbara Walters, Givens accused the reigning heavyweight champ of domestic abuse and described being married to him as “torture, pure hell, worse than anything I could possibly imagine”.
Unsurprisingly, the couple would be divorced within a year. 12. “I’m Back” video Mike Tyson melted the internet four years ago when, seemingly out of the blue, he uploaded a brief YouTube clip that showed him not only back in the gym, or muscled up, but throwing hands like somehow we were all still in the 80s wearing Stubbies and desert boots.
Despite being aged 53, Tyson’s brief clip – which lasted 47 seconds – not only sent fight fans delirious, but ignited a range of talks that eventually culminated in a shock exhibition bout months later against Roy Jones Jnr. 11. Ring walk The fight game is filled with memorable ring walks.
Think Tyson Fury atop his golden throne. Or Conor McGregor teaming with Sinéad O’Connor. Special mention too for that night Prince Nassem danced through a faux graveyard to Michael Jackson’s Thriller.
But Iron Mike? All he needed was a white towel cut up as a makeshift robe. That, and black trunks, black boots, black heart. Truly, to understand just how sinister a Tyson ring walk was, recall his ‘98 entrance against Michael Spinks.
Where with the coldest eyes outside a Jaws rerun, the fighter emerged bare chested, flanked by State troopers and with no music -- just a sinister collection of metallic clanging and banging. Tellingly, his walk out would eventually take longer than the 91 seconds he needed to finish Spinks. 10.
The Original Tiger King Nothing screams Baddest Man on the Planet quite like standing poolside, clad only in white underwear, while holding your prized Bengal tiger via an oversized metal chain. Long before Joe Exotic was setting Netflix ablaze, Mike Tyson was undeniably the world’s most infamous big cat owner. After his early release from prison in 1995, the fighter went and bought three Bengal tigers – Boris, Storm and Kenya, the latter of which he kept for almost 16 years.
Yet in true Tyson style, he eventually had to remove the animal from his home after it attacked a trespasser. “But I had a lot of money back then,” the fighter once explained of the incident, “so I gave her $250,000” . And as for how bad it was? “She was f---ked up,” he said of the trespasser who apparently jumped his compound fence and was attacked.
“You couldn’t believe what they can do to a person’s flesh. I had no idea”. 9.
Comeback fight against Peter McNeeley It was billed, quite simply, as ‘He’s Back’. Some four years after being charged, convicted and imprisoned for rape, Mike Tyson emerged from jail for a $150 million Las Vegas blockbuster that would set new pay-per-view records. During the hyped build, McNeeley promised to wrap his rival in a “cocoon of horror”.
It never happened. Instead, McNeeley was dropped twice within the first two minutes -- with his manager Vinnie Vecchione eventually rushing the ring to save his man from further punishment. All up, just 89 seconds of carnage.
8. $160M fight purse Mike Tyson’s ability to make, and lose, money is the stuff of legend. Earning around US$30 million for many fights, Tyson’s biggest bag came against Lennox Lewis in 2002, pocketing $160M.
Unfortunately though, the cash rarely stayed long in the account of a fella who famously paid $125,000 to a Siberian tiger trainer, bought a $7 million diamond necklace and $2.3 million solid gold bathtub. Then, of course, came his highly controversial partnership with promoter Don King, who at one point was reportedly charging the champ $8000 a week for towels alone.
7. Desiree Washington Beauty pageant queen Desiree Washington was only 18 when, in 1991, she created international headlines by claiming Mike Tyson had raped her inside an Indianapolis hotel room. Within eight months, the heavyweight superstar, still only 25, and in his fighting prime, was found guilty and sentenced to prison, where he would eventually serve three years.
Despite the verdict, Tyson long maintained his innocence. Writing in his 2013 autobiography, Tyson said: “I did not rape Desiree Washington. She knows it, God knows it, and the consequences of her actions are something that she’s got to live with for the rest of her life”.
6. Buster Douglas upset It was the insane result on which Mike Tyson’s career changed forever. And, unthinkably, at the hands of a rank outsider named James ‘Buster’ Douglas.
Walking into a heaving Tokyo Dome in 1990, Douglas represented one of the greatest underdogs in sporting history. So little chance was the title challenger, it’s understood only one Las Vegas casino even bothered offering odds – with the Mirage writing him up as a 42/1 underdog. None of which mattered to Buster however.
Driven by the memory of his late mother Lula Pearl, who had died just 23 days earlier, Douglas shocked the world, kayoing Iron Mike in the 10th round. The loss was the first of Tyson’s career. 5.
“I want to eat his children” Mike Tyson’s quotes adorn the walls of gyms the world over, including that of UFC boss and close friend Dana White. His craziest line though? That may just be the one that followed his devastating 38-second KO of Lou Savarese. After demolishing Savarese in a 2000 bout, Tyson then exploded into an unforgettable monologue that included comparing himself to Alexander the Great, then Sonny Liston, before also taking a big swing at Lennox Lewis.
“My style is impetuous,” he stated to Showtime’s Jim Gray. “My defence is impregnable. And I’m just ferocious.
I want your heart. I want to eat his children. Praise be to Allah”.
4. The face tattoo Incredibly, when Mike Tyson walked into a Las Vegas tattoo studio shortly before his 2003 fight with Clifford Etienne – his 50th and, we thought, final bout – he asked for a face full of hearts. Thankfully, the artist declined.
Instead, offering up that now signature Maori tribal design that makes Tyson one of the most recognisable human beings on the planet. When it comes to ink, the fighter also has three more notable tattoos of men he admires; tennis player Arthur Ashe, Marxist revolutionary Che Guevara, and Chinese communist leader Mao Zedong. 3.
World’s youngest heavyweight champ With apologies to Parramatta Eels premiership hero Mick Cronin, no athlete had a better time of things in 1986 than Mike Tyson – who became the world’s youngest ever heavyweight champ at just 20 years of age. In that single year, Iron Mike won a staggering 13 fights – including 11 by KO – which included demolishing Trevor Berbick. Of course, Berbick was some fighter himself, having beaten no less than Muhammad Ali.
He also went the distance with Larry Holmes. Yet in his world title blockbuster against Tyson, it was over for the champ within two rounds. 2.
Baddest Man on the Planet Here was the night Mike Tyson truly earned himself that Baddest Man on the Planet crown – and it took just 91 seconds. While his career may be littered with brutal finishes, Tyson’s first round KO over Michael Spinks – when aged only 20 – remains his greatest fight, finish, all of it. While already a world champion coming into this one, Tyson took his career, and aura, to a new level with his brutal stoppage of Spinks, who was himself undefeated in 31 fights and had already claimed both light heavyweight titles and the IBF heavyweight strap.
So anticipated was the contest, it grossed $70 million -- then the richest fight in boxing history. Yet so brutal was the finish, Spinks would never fight again. 1.
The Bite Here, truly, is the moment that sent Mike Tyson’s notoriety crash, bang, wallop into mainstream culture. After having already lost one blockbuster fight to Evander Holyfield, Tyson was battling through the early rounds of their hyped 1997 rematch when, late in the third ..
. well, the WBA champ would make what ranks among the most notorious decisions in global sporting history. Caught in a clinch with Holyfield, Tyson rolled his head above the challenger’s shoulder and – chomp -- bit a two centimetre chunk from his right ear, which he then promptly spat onto the ring apron.
Given the obvious pain, Holyfield leapt into the air, then spun in a circle, yet, incredibly, the fight continued. So Tyson, he bit the other ear. When the round ended, the fight was waved off, Tyson disqualified .
.. and his legend grew larger again.
.
