Legend of Mike Tyson: Five most memorable fights of the former heavyweight champion’s storied career


In one of the more unlikely occurrences in an already unprecedented 2020, former heavyweight champion Mike Tyson will return to the ring on Saturday at the age of 54. Tyson (50-6, 44 KOs) hasn’t fought an officially sanctioned bout since 2005 when he refused to continue against journeyman Kevin McBride and called an end to his tumultuous 20-year career. 

This weekend, however, Tyson will take part in an eight-round exhibition match against fellow retired legend Roy Jones Jr. (66-9, 47 KOs) on pay-per-view from the Staples Center in Los Angeles. 

Considering Tyson’s unquestioned worldwide fame and the nostalgic feelings his unexpected return to the ring has produced, let’s take a look back at the five most memorable fights in which “Iron Mike” has taken part. 

Youngest heavyweight champion in history

It’s almost insane to believe this actually happened, but it did. At just 20 years of age and a mere 20 months into his pro career, Tyson made good on his then-deceased trainer Cus D’Amato’s prophecy with a two-round execution of WBC champion Trevor Berbick. The savage nature in which the dynamically quick and powerful Tyson sent his taller foe staggering around the ring was, in part, payback for Berbick having retired Tyson’s hero, Muhammad Ali, just five years earlier. 

The victory on Nov. 22, 1986, was Tyson’s 13th of the calendar year, which was mind-boggling enough. But more importantly, it announced a new era in heavyweight boxing and began a meteoric two-year journey in which Tyson became the biggest star in American sports as well as one of the most recognized names across the globe. 

The 91-second destruction of Michael Spinks

In the two years after beating Berbick, Tyson went on to unify all three recognized heavyweight titles. But there were some who still felt that Michael Spinks was the world’s best heavyweight given his status as lineal champion thanks to a pair of victories over Larry Holmes years earlier. The showdown titled “Once and For All” was among the most anticipated fights of the decade and earned Tyson a then-record purse of $22 million. Luckily for the promoters, he wasn’t paid by the second. 

On June 27, 1988, Tyson scored a pair of knockdowns and rolled back the eyes in Spinks’ head before some in attendance had even taken their seats. Sadly, given the rising chaos in Tyson’s personal life, this would be his mountaintop moment as a professional. Even so, it’s hard to imagine any heavyweight in history having their way with this version of such a devastating force. 

Biggest upset in boxing history

Where were you on Feb. 11, 1990? Most will likely remember the exact moment they became aware of 42-1 underdog James “Buster” Douglas doing what had felt like an impossibility to that point. Given what we know now about Douglas’ hidden skill set and Tyson’s imploding personal life, the outcome of this classic fight held inside the Tokyo Dome in Japan makes a lot more sense. At the time, however, it was the equivalent of David having his way with Goliath in the Old Testament. 

Despite a career mired in underachievement, the 6-foot-4 Douglas channeled the grief of his recently deceased mother and refused to back down despite being dropped in Round 8 on a vicious uppercut. Douglas got off the canvas to dramatically finish off an undertrained and bewildered Tyson in Round 10. One year later, Tyson was arrested on rape charges and would go on to serve less than three years of a six-year sentence. 

Bite Fight: Evander Holyfield Part II

Holyfield, who five years earlier missed out on a shot at facing “Iron Mike” due to injury and Tyson’s eventual jail term, finally had his day in 1996 when, considered washed up at age 34, he pulled a monster upset via 11th-round TKO. Just seven months later on June 28, 1997, the rematch billed as “The Sound and the Fury” took place inside the MGM Grand Garden Arena in Las Vegas. It was there that Tyson, on the tail-end of a post-jail rejuvenation as a viable pay-per-view brand, took a major step forward into the third and final chapter of his unique career. 

This was the first of what would become a sad trend of in-ring meltdowns as Tyson, upset at the headbutts he felt Holyfield was delivering without any penalty, was disqualified for biting off a piece of Holyfield’s right ear. The unprecedented result sparked a wild melee inside the ring and netted both a one-year suspension of his boxing license in Nevada and a $3 million fine.

Record-setting beatdown from Lennox Lewis

Although Tyson, one week shy of his 36th birthday, was well past his prime and now an elite fighter in name only, there was still one more massive payday to be had against reigning unified champion Lennox Lewis. Given Tyson’s dramatic decline, the fight played out to very much be the mismatch insiders had predicted. But given his own personal debt at the time financially, it was a payday Tyson needed. 

In order to draw interest, Tyson provided plenty of outright insane moments throughout the promotion, including attacking and biting the leg of Lewis during a press conference in New York. The incident made finding a venue tricky. Eventually, the fight landed in Memphis at The Pyramid on June 8, 2002, and would become a rare PPV event co-produced by rival American premier cable networks HBO and Showtime. Tyson went on to take a hellacious beating before Lewis finished him off in Round 8. In the end, though, the fight proved to be the highest grossing in history up to that point in producing 1.95 million PPV buys and a live gate of $106.9 million. 





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