The Mike Tyson story: From ‘Baddest Man on the Planet’ to prison and psychedelics

Telegraph Sport chronicles the turbulent life of the 58-year-old, who will fight his first competitive bout for 21 years against Jake Paul

Almost half a century ago, a petty criminal named Gary Flowers lit the touchpaper on the most explosive career in modern boxing history – a career that will enter its strangest chapter yet when Mike Tyson fights Jake Paul in Texas on Friday.
Tyson was probably 10 years old at the time of the incident, a truant child in a crime-ridden suburb of Brooklyn who shied away from physical confrontation. Then Flowers and his pals messed with the one thing he really loved: his pigeons.
Short for his age and burdened by a lisp which earned him the nickname ‘Little Fairy Boy’, Tyson was hardly an obvious candidate for glory in the ring. But when Flowers grabbed one of those pigeons and twisted its head off, the first glimmerings of “Iron Mike, the baddest man on the planet” were born.
“I didn’t know what I was doing,” Tyson wrote in his soul-baring autobiography, The Undisputed Truth. “But I threw some wild punches and one connected and Gary went down.” Flowers would be the first of many to fall in such unceremonious style, including such boxing luminaries as Larry Holmes, Michael Spinks and Donovan ‘Razor’ Ruddock.
The provocation by Flowers has the flavour of a comic-book origin story – a real-world echo of Bruce Wayne’s parents being shot down in a dark alley. And it begat a dark and twisted tale: a nightmarish version of the American dream in which Tyson emerged from the streets to become a unified world champion, then a convicted rapist, and finally a self-loathing addict, “snorting coke and drinking Hennessy while being hooked up to a morphine drip”.
His vivid history explains why Friday’s freak-show has generated such extraordinary interest, with front-row tickets selling for millions of dollars. Boxing fans are still hunting the adrenaline rush that the young Tyson supplied, in the days when he used to rage around the ring like a baby Tyrannosaurus.
Watch the video of his first world title fight against Trevor Berbick from 1986, and it still makes your hair stand on end. Modern heavyweight boxing is often cagey and strategic. But Tyson wanted to end his opponent from the first punch. Explosive and relentless, he deployed the “peek-a-boo” technique he had learnt from his mentor, Cus D’Amato. This meant keeping the elbows in tight, weaving up and down in a U-shaped pattern, and unleashing vicious counters and uppercuts from short range.
On this day in 1986, Mike Tyson TKO’d Trevor Berbick in Round 2 to win the WBC heavyweight title 🥊 #Boxing pic.twitter.com/eAoj9BLsJu
Of the many picaresque characters in Tyson’s story, D’Amato is the most important. The two men would never have crossed paths if Tyson had not been a juvenile delinquent, arrested an estimated 40 times by the age of 13. One of the counsellors at his young offenders’ centre was a boxer who spotted his talent during a sparring session, and then drove him to rural New York State for a trial. It took D’Amato only a couple of minutes to say the prescient words “future heavyweight champion of the world”.
Before long, Tyson had moved in with D’Amato. His time in the Catskill Mountains was occupied by running, sparring, reading boxing encyclopaedias and watching videos of vintage fights. Despite the brutal nature of the training, it was the nearest he ever came to peace.
For a glimpse of Tyson at his most serene, look at the film he recorded with BBC boxing correspondent Harry Carpenter in 1988 (available in full on YouTube). Together, they cued up videos of past champions such as Jack Johnson, Jack Dempsey and Joe Louis, and discussed their place in history. Tyson’s deeply informed commentary showed off his natural intelligence, which belied a lack of formal education. But Carpenter also told friends: “There was something chilling in his eyes.”
You would not have known it from the film, or from his results – which at that stage stood at 34 straight wins – but Tyson was already losing his focus. Another big twist in his life had come in 1985, when D’Amato died of pneumonia at the age of 78. From that moment, the wild and reckless ghetto boy began to push the disciplined athlete to one side. It was not long before Dr Jekyll had given way to Mr Hyde.
Temptations were everywhere. Until the mid-1980s, Tyson had had just a small number of girlfriends. After he became a celebrity, he was having a selection most nights. He was also drinking and snorting coke like a rock star. And he was hanging out with his old gangster buddies from Brownsville. Without the father figure of D’Amato to rein him in, the decline began long before Buster Douglas scored the most famous upset in boxing history: a 10th-round knockout in Tokyo, on Feb 11, 1990. According to Tyson’s own account, “It was obvious to anyone that I didn’t really want to be there.”
At just 23, Tyson was already closer to the end of his elite boxing career than the beginning – a fact unchanged by this latest escapade in Dallas. He rebounded well enough from the Douglas setback, extending his win-loss record to 41-1 with victories over Henry Tillman, Alex Stewart and Ruddock. But he was about to lose three of his prime years, after a contestant in the Miss Black America pageant – Desiree Washington — accused him of raping her in his Indianapolis hotel.
At the ensuing trial, the prosecution pointed to an incriminating pattern. Robin Givens, the sitcom actress Tyson was married to for a year, had filed divorce papers citing “unprovoked rages of violence and destruction”. Biographer José Torres had claimed that Tyson once told him: “I like to hear them [women] scream with pain, to see them bleed.” He received a six-year sentence, which would be halved on parole.
In an echo of the Catskills, the structure of prison life proved strangely calming, limiting the tumult and turbulence of Tyson’s manic lifestyle. With time to think and read, he devoured books by Alexandre Dumas and Leo Tolstoy. He had the faces of Chairman Mao and black tennis pioneer Arthur Ashe tattooed on his body. He also became a Muslim. But when he returned to the world in 1995, and especially to boxing, everything turned even weirder than before.
Post-prison Tyson is best remembered for the two Evander Holyfield fights of 1996 and 1997. They culminated in perhaps the single most memorable moment of his career: disqualification for biting off part of Holyfield’s ear.
“I felt Holyfield was using his head illegally,” he explained later. “I told the referee I wasn’t getting any help, so I went back to the streets. I cannot defend it, but it happened.”
With fight purses booming despite his growing notoriety, Tyson redefined the concept of celebrity excess. He bought the largest house in the state of Connecticut, and fantasised about filling each of the 19 bedrooms with a different girl. For 16 years, he lived with a white tiger, raised from a cub, until she eventually savaged an unwary intruder and had to be donated to a zoo.
He was a main draw at the WWE event WrestleMania. Not that any of it made him feel better about himself. At a press conference before his 2000 fight against Andrew Golota, he told reporters: “I’m on the Zoloft [a prescription antidepressant] to keep me from killing y’all.”
On the upside, Tyson did at least manage to win back the WBA and WBC world titles for a short time, and to peel himself away from exploitative promoter Don King. Despite earning around £250 million from boxing, Tyson’s shambolic finances often left him in debt.
But the substance abuse was so out of control that, by the time he came to Glasgow in 2000 to fight Lou Savarese, he was using a fake penis (“the whizzer”) to deliver clean urine sourced from a member of his management team. In that fight, Tyson knocked out both Savarese and the referee in the space of one crazy minute.
📅ON THIS DAY: Tyson & Savarese chaos🤯⏪Back in 2000 Mike Tyson stopped Lou Savarese in 38 seconds of the first round… and wanted to keep fighting😲 pic.twitter.com/kbOrui7gh5
Tyson’s last competitive fight, until this week at least, saw him suffer a dismal sixth-round stoppage against an Irish non-entity called Kevin McBride. On the eve of that 2005 contest, he called himself “a sad, pathetic case. My whole life has been a waste – I’ve been a failure”. Yet this would not be the view of the thousands flocking to AT&T Stadium in Arlington on Friday. Judging by the enthusiastic welcome he received in nearby Irving, during an open training session on Tuesday night, the vast majority want to see Tyson put YouTuber Jake Paul in his place.
Since the McBride fight, Tyson’s life has continued to throw up unscripted drama. A new generation discovered him through his cameo appearance in the smash-hit film The Hangover. He got married again, this time to Lakiha Spicer – the daughter of a Muslim minister whom he first met when he was 13. He joined Narcotics Anonymous and achieved intermittent control over his substance issues. In the last few years, he has been smoking the venom of the Sonoran Desert toad, described as the “Everest of psychedelics”, which has helped him give up other medications such as sleeping pills and anti-psychotics.
For all the many times when Tyson had endangered his own safety, his most traumatic and life-changing moment came out of the blue in 2009. He received a phone call telling him that his four-year-old daughter Exodus had died, having tangled her neck in the safety cord on her mother’s treadmill. Since that tragedy, he has devoted himself to his family – which includes eight surviving children – with the same passionate intensity he brought to every other part of his life. “I get to nurture my children and grow closer to my wife,” he wrote in The Undisputed Truth. “It feels good in my soul. That’s why I’m here.”
So why is Tyson going back in the ring on Friday? He is not broke any more, thanks partly to his successful Hotboxin’ podcast, but mainly to the industrial cannabis farms – branded under the name of Tyson 2.0 – which apparently pull in hundreds of millions of dollars per year. After everything he has survived, it seems quixotic to risk his health against a man 31 years his junior.
But then, Tyson’s has always been a fractured personality. The sensitive family man has never quite extinguished the embers of “Iron Mike, the baddest man on the planet”. After two decades of domesticity, it is time for his darker self – the one that Gary Flowers first let loose almost half a century ago – to return.