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Mike Tyson’s many eras: From ‘Iron Mike’ to prison to Holyfield to a Jake Paul bout

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Mike Tyson’s many eras: From ‘Iron Mike’ to prison to Holyfield to a Jake Paul bout

The many lives of Mike Tyson will add another chapter Friday.

At 58 years old, 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’s Tyson’s first sanctioned professional match since 2005.

The Tyson who will enter the ring at AT&T Stadium in Arlington, Texas, on Friday is a far cry from the Tyson whose pro career ended 19 years ago, when he quit on his stool before the start of the seventh round in a loss to Kevin McBride. He’s an even further cry from the Tyson who infamously bit Evander Holyfield’s ear, the Tyson who spent three years in prison or the “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 competitor: “I’m not gonna lose,” he said this week.

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

The 1980s: The rise of ‘Iron Mike’

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

Tyson fought 15 times in a 10-month span in 1985, winning all by knockout. He fought 13 more times in 1986, becoming the youngest heavyweight champ in history (at 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 believe sincerely that Mike creates an aura of invincibility,” Tyson’s co-manager at the time, Jim Jacobs, said afterward. “I have watched Trevor Berbick on tapes. And this Trevor Berbick was nothing like the Trevor Berbick I have watched. He fought as if he was in slow motion.”

By Tyson’s 21st birthday, he was 30-0 with the unified WBA and WBC heavyweight titles. In fight No. 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 by 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 peak of Tyson’s career.

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

The early 1990s: An upset, and a conviction

Tyson was a 42-to-1 favorite and seemingly a safe bet to go to 38-0 when he took on Buster Douglas in February 1990. Instead, the Tokyo Dome was treated to one of the largest upsets in sports history when Douglas knocked 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 crumbling leading up to the upset. His first wife, actress Robin Givens, said in a televised 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 ahead of the bout.

After the loss, Tyson rebounded with four wins in 12 months to re-establish his standing and set up a match with heavyweight champ Evander Holyfield, but that fight wouldn’t 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 would serve three before his release on parole in March 1995.

The late 1990s: Tyson vs. Holyfield

Tyson returned to the ring in August 1995 to much fanfare and won 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 by 1996, produced a stunning TKO of Tyson in the eleventh round.

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Rewatching the Classics: Mike Tyson vs. Evander Holyfield 1

A rematch was quickly arranged for 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 bewildering moments in professional sports history. As the third round drew to a close, Tyson grabbed Holyfield multiple times and bit both of Holyfield’s ears, severing part of Holyfield’s right ear and ending the bout with a Tyson disqualification.


Holyfield touching his right ear after being bit by Tyson in their 1997 match. (Photo: Jeff Haynes / AFP via Getty Images)

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

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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 an incident from 1998, before coming back to fight Orlin Norris in October 1999. That bout was ruled a no contest.

The 2000s: Boxing retirement, pop culture emergence

At 33 years old, Tyson tried to mount a late-career resurgence. After knocking out Lou Savarese in June 2000, Tyson called out heavyweight champ Lennox Lewis, infamously stating, “I want your heart, I want to eat your children.”

His opportunity versus Lewis finally came in June 2002. Lewis largely controlled the fight, as the champion survived Tyson’s round one onslaught and controlled the pace with strong 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 accelerated the end of Tyson’s professional career. His last pro win came against Clifford Etienne in 2003.

His final professional bout — until Friday’s against Paul — came against McBride in 2005. Tyson, who struggled mightily with his stamina and the height difference, managed to keep the fight close on the scorecards, but then was issued a two-point penalty for head butting. The sixth round ended with Tyson slumped on the mat after a slip, and the match ended without Tyson ever getting off his stool to answer the seventh round.

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“I do not have the guts to be in this sport anymore,” Tyson said afterward. “I don’t want to disrespect the sport that I love. My heart is not into this anymore. I’m sorry 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 versus McBride. Tyson would quit the bout before the start of the seventh. (Photo: Paul J. Richards / AFP via Getty Images)

Within a few years, Tyson found a second career — through movies, television and entertainment.

He made an appearance in the movie “Rocky Balboa” in 2006, but his breakout moment came in “The Hangover” in 2009, when he air drummed to 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.

The 2020s: A return to the ring

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

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

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

In late May, Tyson suffered an ulcer flareup while flying from Miami to Los Angeles, forcing the fight to be delayed. According to Tyson, the ulcer was over two inches large 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 we have options, though. That’s when I got nervous.”

Required reading

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

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Why the Pistons at -3.5 is the play as the NBA Playoffs second round gets underway in Detroit

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Why the Pistons at -3.5 is the play as the NBA Playoffs second round gets underway in Detroit

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The NBA Playoffs had their second round begin Monday. We were treated to two games, and one was significantly better than the other. That probably should be the expectation for Tuesday’s slate as well. Regardless of how the game goes, if we can cash some betting slips, that’s really the main goal here. I expect the Cavaliers vs. Pistons to be a more entertaining game tonight, and I have a bet for us on the game.

The Cleveland Cavaliers had a bit of a makeover this season, but the first round of the playoffs was essentially the same outcome they’ve always had. They exchanged Darius Garland for James Harden and Dennis Schroder. That didn’t happen in the same trade, but it did give the team a new look after starting the year with Garland, Lonzo Ball, and DeAndre Hunter. This team will only go as far as Harden and Donovan Mitchell will take it.

Cleveland Cavaliers All-Stars Donovan Mitchell and James Harden talk during Game 2 in the first round of the 2026 NBA Playoffs vs. the Toronto Raptors at Rocket Mortgage FieldHouse in Ohio. (David Dermer/Imagn Images)

In the first round, the Cavaliers looked like a really bad team. They won four games at home and lost all three road games. In fairness to them, they had at least two of those games in Toronto that were winnable. While they won games at home, they didn’t exactly dominate the Raptors. Game 7 was fairly sweat free, with a 12-point win, but they were fortunate not to have Brandon Ingram suit up for Toronto. I see both Evan Mobley and Harden as the keys to winning this series for the Cavaliers.

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The Detroit Pistons were given a bit of a wake-up call. They came into the playoffs as the No. 1 seed in the Eastern Conference, but they looked anything but the part of a dominant team in the opening round. They hosted the Magic and lost the opener. Then they lost two of the next three games, going down 3-1 in the series. They won, as expected in Game 5 at home, but Game 6 was wild. They were down and looked out of it in the second half. The Magic scored just 19 points in the second half, and Detroit forced Game 7.

Detroit Pistons guard Cade Cunningham dribbles the ball while Indiana Pacers guard Ethan Thompson defends during the second half at Gainbridge Fieldhouse in Indianapolis, Ind., on April 12, 2026. (Trevor Ruszkowski/Imagn Images)

In Game 7, the Pistons locked in and were in control from the tip. It was an epic collapse from the Magic, and probably a disaster that cost their coach his job. The Pistons ended up winning by 22. They extended their coach as a result. Interestingly enough, JB Bickerstaff, the coach, was fired by Cleveland in part due to a lack of playoff success. He should be very familiar with the Cavs players and their strengths and weaknesses. I’d expect him to be an X-factor if he can exploit the weaknesses.

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In this series, you have to expect that Mitchell and Cade Cunningham will cancel each other out from a scoring perspective. Jarrett Allen and Mobley will provide a great variety of defense for Jalen Duren. The Pistons’ advantage will be Tobias Harris. For the Cavaliers, Mobley will be a tough matchup. Harden is also a guy who might be able to get some mismatches.

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Cade Cunningham of the Detroit Pistons smiles after the game against the Toronto Raptors at Little Caesars Arena in Detroit, Mich., on Dec. 30, 2023. (Chris Schwegler/NBAE)

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This is the tightest series in terms of pricing, with the Pistons being slight favorites. Three of the four games were very tight in the regular season, with all three being decided by four or fewer points. They both won two games, one on the road and one at home. I don’t expect this to be a defensive series. It isn’t the game either of them really wants to play. I think the Pistons are locked in, though. I haven’t seen much that’s great from the Cavaliers on the road in the playoffs. Give me the Pistons -3.5 here.

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For more sports betting information and plays, follow David on X/Twitter: @futureprez2024 

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Prep talk: Verbum Dei set to honor football grads Kenechi Udeze, Hardy Nickerson

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Prep talk: Verbum Dei set to honor football grads Kenechi Udeze, Hardy Nickerson

Two of the best football players in Verbum Dei history, Hardy Nickerson and Kenechi Udeze, are set to return to the Watts campus on Thursday night for a ceremony honoring their contributions.

Nickerson, from the class of 1983, played linebacker at California, then 16 years in the NFL. Udeze, from the class of 2000, was an All-American defensive lineman at USC and later first-round draft choice. Both have since gone into coaching.

Nickerson is in his first year as head coach at JSerra. Udeze is an assistant coach at Florida International.

There also will be a celebrity basketball game at 6 p.m.

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Nickerson said, “Verbum Dei helped shape me in so many different ways. Every day I think of something I learned from high school.”

This is a daily look at the positive happenings in high school sports. To submit any news, please email eric.sondheimer@latimes.com

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Joe Girardi remembers John Sterling’s passion, humor in emotional tribute to Yankees legend: ‘I miss him’

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Joe Girardi remembers John Sterling’s passion, humor in emotional tribute to Yankees legend: ‘I miss him’

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The Yankee Stadium crowd altered its usual roll call on Monday night in the series finale against the Baltimore Orioles to honor a legendary man synonymous with the team’s long history.

Chants for John Sterling, the longtime radio announcer for the New York Yankees, roared from the bleachers and seats in the Bronx on a somber Monday for baseball fans in the tri-state, and even across the country.

Joe Girardi was among those mourning the loss of an iconic voice that he had the pleasure of knowing as a player, manager and media colleague throughout his own career in baseball. Like many, Sterling’s impact was one Girardi felt immediately, which is why there was only one feeling when he heard the news.

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Former New York Yankees player and manager Joe Girardi reflected on his relationship with the late John Sterling, the legendary radio announcer who passed away at 87. (GETTY)

“Just sadness because I know how much he meant to the organization, to the Yankees, to me, [and] to people,” Girardi, who serves as a YES Yankees analyst, told Fox News Digital in a phone interview on Monday.

“I’ve always loved to be around people that have such a great passion for what they do. John truly had that. He had a gift, but he truly had a passion. For that, his example was great. I miss him. I miss hearing him on the radio because there’s a lot of times I’m traveling and I’ll put the game on the radio. I have SiriusXM radio and listen to games. I miss it. I miss hearing him and Suzyn [Waldman].”

Waldman, Sterling’s long-time partner on WFAN Sports Radio, was one of those Girardi spoke with on Monday after hearing the news.

YANKEES RADIO ICON JOHN STERLING DEAD AT 87

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“She said something that really resonated with me about John. She goes, ‘John only did what he wanted to do and never did anything he didn’t want to do.’ You think about living your life – that’s a good life,” Girardi explained. “I think of things I do that I don’t want to do, but I do them anyway. That wasn’t John Sterling. He lived his life to the fullest. He enjoyed it, enjoyed being around people, and was ready to go and do his job. He brought life into your family room, or into your car, or wherever he was at and whatever he was doing.”

For 64 years, Sterling was in the broadcast industry, but he left his mark on one of the most iconic organizations in all of sports when he joined the Yankees in 1989 and didn’t leave his post until April 2024.

Even then, Sterling returned to the radio booth for the Yankees’ postseason broadcasts as they made their way back to the World Series for the first time since Girardi’s 2009 team won it all over the Philadelphia Phillies.

It was during his time as a manager that Girardi said he remembers his favorite interaction with Sterling that rang true to the exceptional character and man he was.

New York Yankees radio broadcaster John Sterling emcees the Old Timers Day ceremony before a game between the Kansas City Royals and New York Yankees at Yankee Stadium in New York City on July 30, 2022. (Rich Schultz/Getty Images)

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“I think the interactions that I remember the most, and it was well into my career obviously. I was the Yankees manager and John was doing the pre-game,” Girardi began. “We do it every day and John would have his old tape recorder, and have his phone with him. We were in the middle of the interview and he stops the tape. He takes his phone out of his pocket, flips it open because then they were flip phones. He says, ‘Darling, I’m doing the manager’s show. I’ll call you back in three minutes.’ I ‘m thinking, ‘Who does that?’ He beats his own drum so much, he stopped right in the middle of the show, and I believe we started over. But obviously that call was very important to him. When I think about it today, and this was many years ago, I still laugh today. This was early in my career as a manager because Suzyn took over, and I just sit laughing. That was John Sterling.”

Sterling was also known for his signature home run calls, something Girardi and many others waited with anticipation to hear when a player would hit it over the fences.

They always began with, “It is high, it is far, it is gone!” before breaking out into a catchphrase, or even a song. For Alex Rodriguez, “It’s an A-bomb from A-Rod,” or most recently with “Here comes the Judge!” when Aaron Judge hits a blast.

“Always curious what that was going to be,” Girardi added. “And I was thinking, ‘How do you come up with that?’ He was so creative – I wasn’t given that gene. He was so creative, I always wondered how he thought of it, how long it took him to think of it, and he never missed a beat. A guy got called up and hit a home run the second day? He had it. It was there.”

FILE – In this Sept. 25, 2009, file photo, New York Yankees broadcaster John Sterling sits in the booth before the Yankees’ baseball game against the Boston Red Sox at Yankee Stadium in New York. Sterling was helped out of his flooding car by Spanish radio play-by-play man Rickie Ricardo on Wednesday night, Sept. 1, 2021, after Sterling got stuck trying to drive home after a game. Sterling and Ricardo both called New York’s game at the Los Angeles Angels from Yankee Stadium because the radio crews have not resumed traveling with the team as part of COVID-19 protocols. (AP Photo/Bill Kostroun, File)

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Girardi admitted that being older now he appreciates more and more how gifted and talented Sterling was, as well as the grind he went through for so many years calling 162 games with spring training and many postseasons as well.

But even more precious to Girardi than the accolades, signature calls and a consecutive 5,060 games called was the care he had for everyone he ran into.

“What you saw was how much he cared about you as an individual and how much he cared you had success,” Girardi said. “That was the amazing thing about John: he wanted you to have success and for the Yankees to win. It meant something to him. It wasn’t him just doing a job. This was a huge part of his life, and the enjoyment it brought him, you could see it.”

The old cliché is do something you love and you’ll never work a day in your life.

For Girardi, Sterling did more than just that.

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New York Yankees radio broadcaster John Sterling speaks with Aaron Judge before the game against the Tampa Bay Rays at Yankee Stadium in New York on April 20, 2024. (New York Yankees/Getty Images)

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“He was an example of how you were supposed to live,” he said. “Find your passion and do it as long as you can. Joe Torre used to always say, ‘Don’t ever take your uniform off until they take it off you.’ That was John Sterling.

“That’s the sign of a man who truly loves what he does. That’s an example that we all need to look forward.”

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