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Mike Tyson doesn’t have many regrets from his legendary boxing career. He went 50-6 as a professional, held the heavyweight title for four years, and is considered today one of the greatest pound-for-pound fighters in boxing history. But one aspect of his career that “Iron Mike” will always regret is failing to defeat Evander Holyfield.

Holyfield shocked the boxing world in 1996 by beating Tyson with an 11th-round TKO. Then, a year later, Holyfield won by disqualification after Tyson infamously bit a piece of his ear off in the ring.

Tyson was recently offered $25 million for a rematch and a chance to exact some long-awaited revenge on his longtime rival, but he reportedly turned the offer down.

Mike Tyson and Evander Holyfield have negotiated a trilogy fight

After Mike Tyson made his much-anticipated boxing comeback against Roy Jones Jr. last year, boxing fans from around the world started to call for a trilogy fight against Evander Holyfield. Holyfield was immediately interested, but he claimed Tyson backed out of a deal.

“My side tried to make the fight happen and we got nothing but excuses,” Holyfield said in a December press release. “Now I can see why he wanted a tune-up fight before thinking about fighting me. Roy Jones was a good local opponent for Mike. But a fight with me would be a global event and the only fight that anyone wants to see is a fight between us.

“There is absolutely no reason why we shouldn’t make it happen. No more excuses. This is the fight that must happen for both our legacies. Saturday night you said you were ready to fight me, so sign the contract and get in the ring, Tyson. The world is waiting and it’s on you now. I’m ready.”

Since Holyfield’s comments, the two sides have engaged in negotiations regarding a rematch, but no dice yet.

Evander Holyfield’s team claims Mike Tyson turned down $25 million for a rematch

According to an ESPN report, Mike Tyson recently rejected a $25 million guarantee to fight Evander Holyfield in a rematch on May 29 at Hard Rock Stadium in Miami Gardens, Florida. Holyfield’s team said they’ve been trying their best to make a trilogy happen, but that Tyson refuses to agree to a deal.

“We thought this was a done deal but it quickly fell apart when Tyson’s people declined all offers,” Kris Lawrence, Holyfield’s manager, said in a statement on Monday. “We were negotiating in good faith all along and it appears we just ended up wasting our time.”

If true, it’s a puzzling decision for Tyson to decline the offer. A chance at some long-awaited revenge and a $25 million bonus? Seems like a no-brainer.

A Tyson-Holyfield trilogy is still a possibility

Don’t give up on a Tyson-Holyfield rematch just yet. After the $25 million report surfaced, Tyson spoke with Haute Living during an Instagram Live broadcast and claimed the May 29 fight against Holyfield is on.

“I just want everybody to know the fight is on with me and Holyfield,” Tyson said. “Holyfield’s a humble man I know that and he’s a man of God but I’m God’s man. Listen, I’m going to be successful May 29.”

But a few hours later, Tyson’s rep told TMZ that the boxer spoke too soon, and the two sides are still far apart in their negotiations. A trilogy might not be officially scheduled quite yet, but at least it sounds as if Tyson is interested.

Let’s just get the deal done, shall we?


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