How Mike Tyson’s improbable life and redemption arc has led to a major main event at 58 years old

For Mike Tyson, the idea of having nine lives has never been enough. 

Throughout nearly six decades on this earth, Tyson has already lived the lives of at least 10 different people. He has shapeshifted so consistently from unknown to legend, pariah to boxing ambassador, and from being the youngest heavyweight champion in history to retiring amid a cloud of shame in 2005 after nearly a decade of selling in-ring meltdowns on the pay-per-view level. 

If you want to talk about highs and lows, the native of the crime-ridden and unforgiving Brownsville section of Brooklyn, New York, has done and seen it all. 

Tyson was on the wrong end of the biggest upset in the sport’s history against James “Buster” Douglas in 1990, just a few years after the death of his mentor/trainer Cus D’Amato and a bitter public divorce to actress Robin Givens saw him attempt to take his own life in 1988. By 1992, he was convicted of rape and jailed for nearly three years at the age of 25, thus forfeiting the peak of his athletic career after becoming the biggest star, not just in sports, but in pop culture in the late 1980s. 

The fact that Tyson was released from prison in 1995 and went on to win back a piece of the heavyweight title shouldn’t come as a surprise at this point in his chaotic life journey. Yet, what did Tyson do next to top that? He left the boxing world in complete shock just two years later when, after losing his title to Evander Holyfield, he bit off a piece of his longtime rival’s ear during their rematch and nearly ran himself out of the sport for good. 

Tyson’s post-boxing career hasn’t been anything less of a soap opera, either. 

There were years of extreme drug abuse and more brushes with the law, including jail time, and the tragedy of losing his four-year-old daughter in a 2009 treadmill accident. There was also a shocking and meteoric star rebirth, including the rehabbing of his public image, which began with a comedic acting performance in the 2009 film “The Hangover” and introduced “Iron Mike” to a new generation. That led to a one-man show on Broadway (including a 2013 special on HBO) that saw Tyson come to terms with his inner demons and make peace with many of his life’s greatest regrets. 

So, should it come as any bit of a surprise to anyone that this Friday, at 58, Tyson (50-6, 44 KOs) will return to the sport that gave him his name and rescued him from a life of poverty and countless arrests before the age of 18 when he boxes 27-year-old YouTube star and professional fighter Jake Paul (10-1, 7 KOs) inside AT&T Stadium in Arlington, Texas?

As absurd as that notion really is, the answer is no.

Tyson, who returned in 2020 to outbox Roy Jones Jr. in an eight-round exhibition match that did monster numbers on PPV, was originally scheduled to fight Paul — using modified rules of eight, two-minute rounds and 14-ounce gloves — on July 20 until a bleeding ulcer led to Tyson throwing up blood and having a medical emergency on a cross-country flight to Los Angeles. 

That development doesn’t necessarily lend confidence to the idea Tyson should be doing this at his advanced age nor that the Texas State Athletic Commission should want to have anything to do with sanctioning it. But the more one listens to Tyson speak ahead of this fight and begins to understand just how far he has come to this point of relative peace in his life after decades upon decades of chaos and commotion, the more one realizes that Tyson wouldn’t be interested in such a challenge if not for that same level of daunting risk. 

Look no further than a few candid moments Tyson provided Netflix cameras for the pre-fight documentary series titled “Countdown: Paul vs. Tyson,” which did well to get inside the mind of the power-punching assassin with the iconic tattoo above his left eye. 

“I want to achieve so much, I’d rather die a short life of glory than a long life of obscurity,” Tyson said. He would later, while referencing the mid-air health setback that caused him to delay the Paul fight, lament how scared he was of dying on the airplane and how much he would prefer to die inside the boxing ring. 

Make no mistake, anytime a fighter talks openly about the romanticized notion of dying within combat and going out like a warrior rings as nothing short of alarming to the ears, especially considering how many in-ring deaths actually take place in this sport. Add in the fact that Tyson is now just days away from taking punches from a man some 31 years his junior and his words leave an even more harrowing resonance to what he’s trying to say. 

But Tyson isn’t just unlike nearly every other 58-year-old you have ever come across (complete with training camp videos that show just how frighteningly explosive he still appears to be), he’s also at a point of self-reflective happiness in his life where an argument can be made that him accepting this fight — in a long line of ill-advised former champions coming back for one more payday — might have nothing to do at all with the money. 

For the record, there will be plenty of money at stake for both, with most pre-fight whispers about the fight purses circling around $40 million for Paul (based on comments he made at their August press conference) and $20 million for Tyson (which was the number his friend, and former UFC champion, Henry Cejudo recently shared on his podcast).

Tyson, who currently has multiple successful business ventures including a marijuana empire near his home in Las Vegas, spoke freely on the topic of money during an interview this week with SPORTbible.

“This fight is not going to change my life financially,” said Tyson, a father of seven children who has been married to his third wife, the former Lakiha “Kiki” Spicer, since 2009. “If I did it for free, it’s not going to change my life. My wife is constantly telling me, ‘You do not need to do this fight.’ 

“This is what I want to do; this is me. I’m seeking my glory.”

There would probably be more uproar surrounding Tyson boxing again at his age if it wasn’t for how good he looked against Jones four years ago and if it wasn’t for how many viewers are expected to tune in who legitimately believe, even at his age, that he can rely on his experience and power to knock Paul out. 

In fact, it’s almost insane to realize that most betting lines have Tyson as just a small underdog in this fight at +170 to the -210 Paul, mostly because Tyson’s opponent has largely feasted on novice and aging opponents (from retired MMA stars to NBA players and fellow YouTubers) while relying on huge size advantages. In fact, the lone time Paul squared off with someone his size and with the same level of ability and experience, he suffered his lone pro defeat by split decision in 2023 to Tommy Fury, the reality TV star and half-brother of former heavyweight champion Tyson Fury (who just so happens to have been named after “The Baddest Man on the Planet”). 

When Tyson says this isn’t about the money, it’s not difficult to believe him considering how much guilt and regret he lived with for so many years after sabotaging most of his professional career following a meteoric and historically scintillating start (which was still enough to get him voted into the International Boxing Hall of Fame in 2011). 

In 1988, when Tyson became the undisputed champion by knocking out unbeaten, lineal heavyweight king Michael Spinks in just 91 seconds, it wasn’t so much of an opinion but more of an inevitable fact that Tyson could one day retire undefeated as the greatest heavyweight in boxing history. Yes, Tyson went on to tack on a small handful of quality wins to his resumé both before the Douglas upset and after his return from prison, but he never came close to living up to the expectations of who he was in the Spinks fight, which boggles the mind once you remember the 35-0 Tyson was still just 21 at the time of that breakthrough performance. 

Tyson may have come to terms with the years and years of regrets he carried for what could have been in his boxing career but there’s something oddly romantic to the idea of him coming back after all these years to right the wrong of how he previously left his career when, in his final sanctioned bout in 2005, Tyson refused to get up off the canvas and was counted out while sitting on his bottom in a disgraceful sixth-round TKO loss to journeyman Kevin McBride. 

Yes, the comeback bout against Jones exorcised a good deal of those demons, even though the fight was officially an exhibition, featured far more body shots than head punches and ended with a split-draw result that didn’t reflect the dominance Tyson showed throughout. 

FanDuel has odds for every aspect of Tyson vs. Paul as well as the undercard on Friday. Check out the latest FanDuel promo to get in on the action.

For Tyson to truly be at peace with boxing, however, and be able to let it go for good after decades of saying he would never return to the ring again (or take on that intimidating “Iron Mike” persona another time), it almost has to come in a setting like this, with extreme danger, where Tyson is the underdog, for once, and not the overwhelming favorite tasked with only not defeating himself. 

Should Tyson, in fact, do the unthinkable and knock Paul out, forget about breaking the internet, it’s the kind of result — akin to George Foreman’s shocking knockout at 45 of Michael Moorer to claim the heavyweight title in 1994 — that would elevate Tyson even further to the level of beloved hero and light years away from the dark shadow of demons that have haunted him for the majority of his career and much of his post-boxing life. 

Yes, there are many ways this fight can end badly for Tyson and all of us who can’t help but tune in on Friday to the ultimate “car wreck that you just can’t turn away from watching” would, in many ways, become accomplices if such an unhappy ending were to take place. 

But if you’ve followed Tyson’s life and career in the public eye closely over the past four decades, it’s almost a wonder that an event like this hasn’t taken place any sooner. 

The only thing Tyson has never truly known is how to live the many different lives he has lived to the fullest of extremes. Win, lose, draw or potentially catastrophic outcome notwithstanding, this is what keeps Tyson alive, fulfilled and, maybe for the first sustained period in his adult life, happy.