The Many Eras of Mike Tyson: From ‘Iron Mike’ to Prison to Holyfield to a Jake Paul Fight

On By Littum

Mike Tyson’s many lives add another chapter Friday.

At 58, Tyson will fight Jake Paul, the 27-year-old YouTube star turned boxer who wasn’t even born when Tyson’s career was in its prime. It is Tyson’s first sanctioned professional fight since 2005.

The Tyson who steps into the ring on Friday at AT&T Stadium in Arlington, Texas, is a far cry from the Tyson whose pro career ended 19 years ago when he stopped on his stool before the start of the seventh round in a loss to Kevin McBride. He’s a far cry from Tyson, who infamously bit Evander Holyfield’s ear, Tyson, who spent three years in prison, or “Iron Mike,” who dominated the sport in the 1980s.

This Tyson is a shell of the fighter he once was — though he retains the confidence of a championship contender: “I don’t want to lose,” he said this week.

As Tyson prepares his comeback against boxing’s viral star today, his career beckons for a rewind. Here’s a look at Tyson’s evolution over the decade.

1980s: The Rise of ‘Iron Mike’

At 18, Tyson won his professional debut with a first round TKO against Hector Mercedes on March 6, 1985 in Albany, NY. From there, his rise was meteoric.

Tyson fought 15 times in 10 months in 1985, winning all by knockout. He fought 13 more times in 1986 and became the youngest heavyweight champion in history (20 years, 145 days old) with a second round full of vicious left hooks that sent Trevor Berbick – the last fighter to defeat Muhammad Ali – stumbling around the ring .

“I truly believe that Mike creates an aura of invincibility,” Tyson’s co-manager at the time, Jim Jacobs, said afterward. “I’ve seen Trevor Berbick on tape. And this Trevor Berbick was nothing like the Trevor Berbick I’ve seen. He wrestled like he was in slow motion.”

By Tyson’s 21st birthday, he was 30-0 with the combined WBA and WBC heavyweight titles. In fight #31, Tyson defeated Tony Tucker to win the IBF title and become the first heavyweight to hold all three major belts. He went on to defend those belts six more times at the end of the decade – all via knockout. His finish of Michael Spinks, 91 seconds into the first round, is considered by many to be the pinnacle of Tyson’s career.

The numbers for Tyson’s 37 fights in the 1980s were staggering: He won 33 by knockout and 17 of them in the first round.

The early 1990s: An upset and a conviction

Tyson was a 42-to-1 favorite and seemingly a sure bet to go 38-0 when he took on Buster Douglas in February 1990. Instead, the Tokyo Dome was treated to one of the biggest upsets in sports history when Douglas hit him. out in the 10th round. Douglas had just been TKOed by Tucker three years earlier and was relegated to the undercard the same night Tyson dominated Spinks.

Behind the scenes, Tyson’s personal life had begun to crumble, leading to the disruption. His first wife, actress Robin Givens, said in a TV interview that being married to Tyson was “torture, pure hell” and filed for divorce, citing spousal abuse. Tyson also split with his manager and trainer prior to the fight.

After the loss, Tyson bounced back with four wins in 12 months to re-establish his status and set up a fight with heavyweight champion Evander Holyfield, but that fight would not happen for five years. In 1992, Tyson was convicted of raping an 18-year-old woman and was sentenced to six years in prison. He was to serve three before his release on parole in March 1995.

Late 1990s: Tyson vs. Holyfield

Tyson returned to the ring in August 1995 to great fanfare, winning back the WBC and WBA titles within 13 months to finally set up the heavyweight clash with Holyfield. But Holyfield, seen as over the hill in 1996, produced a stunning TKO of Tyson in the eleventh round.

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A rematch was quickly arranged in June 1997. The highly anticipated Tyson-Holyfield II set a then PPV record of 1.99 million buys.

Those watching on PPV and inside the MGM Grand saw one of the most confusing moments in professional sports history. As the third round drew to a close, Tyson grabbed Holyfield several times and bit both of Holyfield’s ears, cutting off part of Holyfield’s right ear and ending the fight with a Tyson disqualification.


Holyfield touches his right ear after being bitten by Tyson in their 1997 fight. (Photo: Jeff Haynes/AFP via Getty Images)

Tyson’s boxing license in Nevada was later suspended, a decision followed by other state athletic commissions. It would be over 18 months before the license was reinstated, and it was during that period that Tyson first dipped his toe into pop culture, appearing at WrestleMania XIV.

The decade ended with Tyson returning to the ring to knock out Francois Botha in January 1999 and then serving three and a half months in prison for assaulting two drivers in a 1998 incident before returning to fight Orlin Norris in October 1999. That match was ruled a no contest.

2000s: Boxing retirement, rise of pop culture

At 33, Tyson was trying to rekindle his career. After knocking out Lou Savarese in June 2000, Tyson called out heavyweight champion Lennox Lewis, infamously saying, “I want your heart, I want to eat your children.”

His opportunity against Lewis finally came in June 2002. Lewis largely controlled the fight as the champion survived Tyson’s first round onslaught and controlled the pace with powerful jabs. With less than a minute left in the eighth round, a Lewis right cross landed flush and put Tyson on his back for the count.

The loss hastened the end of Tyson’s professional career. His last pro win came against Clifford Etienne in 2003.

His last professional fight – until Friday against Paul – came against McBride in 2005. Tyson, struggling mightily with his stamina and the height difference, managed to keep the fight close on the scorecards, but was then issued a two-point penalty for the headbutt. The sixth round ended with Tyson falling to the mat after a slip, and the fight ended without Tyson ever recovering from the embarrassment of answering in the seventh round.

“I don’t have the guts to be in this sport anymore,” Tyson said afterward. “I don’t want to disrespect the sport I love. My heart isn’t in this anymore. I feel bad for the fans who paid for this. I wish I could have done better.”


Tyson on the mat after slipping at the end of the sixth round against McBride. Tyson would stop the fight before the start of the seventh. (Photo: Paul J. Richards / AFP via Getty Images)

Within a few years, Tyson found another career – through film, television and entertainment.

He appeared in the 2006 film “Rocky Balboa,” but his breakout moment came in 2009’s “The Hangover,” when he air-drummed Phil Collins’ “In the Air Tonight” before knocking out Zach Galifianakis’ character, Alan . . He later made cameos on “How I Met Your Mother,” “Dancing with the Stars” and in a Foot Locker commercial in which he apologizes to Holyfield for biting his ear and embraces his old rival.

2020s: A return to the ring

In 2020, Tyson agreed to fight Roy Jones Jr. in an eight-round exhibition, a bout sanctioned in California. Both boxers were over 50, and the bout was contested under specific instructions that it should not go beyond “the limits of a competitive boxing exhibition”, meaning that neither opponent should try to knock the other out.

The fight was scored a draw despite Tyson significantly outscoring Jones. On the same card, Paul appeared in his second boxing match, knocking out former NBA player Nate Robinson.

Netflix announced Friday’s Tyson-Paul fight in March 2024. It was originally supposed to take place in July. In April, the bout was sanctioned by the Texas Department of Licensing and Regulations to be a professional bout consisting of eight two-minute rounds fought with 14-ounce gloves.

In late May, Tyson suffered a stomach ulcer while flying from Miami to Los Angeles, forcing the fight to be delayed. According to Tyson, the wound was over two centimeters in size in his stomach and resulted in him losing 26 pounds. On the flight he said he threw up blood.

“I asked the doctor, ‘Am I going to die?'” Tyson said in the preview series, “Countdown: Paul vs. Tyson.” “And she didn’t say no. She said that we do have options. That’s when I got nervous.”

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(Photo: Timothy A. Clary/AFP via Getty Images)