Former Heavyweight Contender Reveals Surprising Reason for Challenging Mike Tyson: "I Wasn't Thinking Straight"

George Fields March 28, 2025, 8:10 a.m.
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Chris Eubank Sr, a former two-weight world champion, has opened up about a moment he's not proud of. The boxer admits he made a mistake when he asked Mike Tyson for an exhibition match in the early 2000s.

Eubank Sr hung up his gloves in 1998 after his second loss to Carl Thompson in a WBO cruiserweight title rematch. But retirement didn't mean the end of his boxing dreams. A few years later, he found himself chasing money and made a decision he now regrets.

On his YouTube channel, Eubank Sr shared the story of how he approached Tyson for a fight. The response he got from 'Iron Mike' left him feeling ashamed.

"Come on man, you're my friend,"
Tyson told him.

Eubank Sr now sees this moment as a wake-up call. He said it put him in his place and reminded him of the respect he has for Tyson, whom he considers a hero.

Mike Tyson's reputation in boxing is legendary. He burst onto the scene with a string of knockouts, winning his first 19 professional fights. Twelve of those wins came in the first round.

In 1986, at just 20 years old, Tyson became the youngest fighter in heavyweight boxing history to win a world title. He knocked out Trevor Berbick for the WBC heavyweight championship. Tyson didn't stop there. He went on to add the WBA and IBF titles to his collection, becoming the undisputed champion.

Tyson's reign at the top came to a shocking end in 1990. James 'Buster' Douglas pulled off one of the biggest upsets in boxing history, handing Tyson his first defeat.

Fast forward to 2022, and Tyson was back in the ring. This time, he faced YouTuber-turned-boxer Jake Paul. The comeback fight didn't go Tyson's way, with Paul winning by unanimous decision.

Eubank Sr's story shows that even boxing legends can make mistakes. He's not shy about admitting his regrets, including the infamous Michael Watson incident. But by sharing these stories, he's showing that it's never too late to learn and grow from past errors.

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