If you only know Mike Tyson from his bout with Jake Paul last year, don’t let that performance define his legacy. Sure, a quick Wiki search might show his recent losses, but questioning the credibility of one of boxing’s most iconic figures would be a mistake. From avenging Muhammad Ali’s loss to Larry Holmes at just 21 years old, to becoming the youngest heavyweight champion in history at age 20 by knocking out Trevor Berbick on November 22, 1986, Mike Tyson’s impact on the sport is undeniable. With four decades in the game, “Iron Mike” still commands attention, and not too long ago, he opened up about the toughest fight of his storied career.
Following his 2024 bout against Jake Paul, Tyson made his presence felt again—this time ringside as an analyst for the Rolando Romero vs. Ryan Garcia fight. Before the Fatal Fury event kicked off, Mike Tyson sat down with iFL TV for a candid interview. Among the topics? His surprise decision to fight Paul, a cheeky reference to the ongoing “100 gorillas vs. Mike Tyson” debate, and most notably, a question about the hardest fight of his career.
While Mike Tyson has previously cited one opponent, he offered a new answer this time. “Probably had to be [Evander] Holyfield,” he admitted candidly, pointing to the man who handed him one of his most devastating losses.
Fresh off a 1st-round TKO victory against Bruce Seldon, Mike Tyson went to fight Evander Holyfield only to be stopped by The Real Deal via 11th-round TKO. Believing he could even the score, Tyson returned the following year—same venue, same opponent—but with an outcome no one saw coming. Instead of redemption, the night became infamous. The 50-7 boxer was disqualified in the third round for biting off Evander Holyfield’s ears, later claiming it was retaliation for head-butts. The DQ loss didn’t just stain his record, it also carved a permanent chapter in boxing folklore.
Despite the controversy, Mike Tyson and Holyfield eventually buried the hatchet. With Holyfield retiring in 2014 and the Brooklyn native still active, their once-heated rivalry has cooled. Yet, even after 28 years, ‘The Baddest Man on the Planet,’ still considers Holyfield the toughest man he’s ever faced in the ring. However, he did add some names alongside Holyfield when the ifltv reporter asked him the question. “And (Donovan)Ruddock and those guys,” he continued, before adding, “But I always say Pinklon Thomas was. Why was he the toughest? Because he took like eighteen punches before he went down. I just commend him on that.” But this is not the first time, Tyson has credited the lesser-known Thomas for giving him a tough fight.
Seventeen punches later, Mike Tyson finally drops his toughest opponent
Mike Tyson has stepped into the ring with some of boxing’s most iconic names—Evander Holyfield, Lennox Lewis, Larry Holmes, Frank Bruno, and Michael Spinks, to name a few. Each brought their own challenge, style, and legacy to the squared circle. Yet, when it comes to pinpointing the toughest opponent of his storied career, Tyson doesn’t name any of those legendary foes, even the ones who bested him easily.
Instead, he singles out Pinklon “Pink” Thomas. Why? In a conversation with History Bites, Mike Tyson reflected on his May 1987 fight with Thomas—a bout he won via sixth-round TKO. But what stood out to Tyson wasn’t just the victory, it was the something else.
“I thought it was Pinklon Thomas, he was my toughest opponent,” Tyson had admitted in the show. “I never thought him, but two years ago I watched the tape of him… I hit him with seventeen punches, flat on the face, he went down but it was seventeen punches! Seventeen punches, flush, all of them were as hard as they could be and the last one he just passed out. I thought, ‘God, that is my toughest fight, he took seventeen on the chin,” he admitted. For a man who built his reputation on early knockouts, the fact that it took such a relentless barrage to finish Thomas left a lasting impression on him.
And what makes Thomas’s toughness even more extraordinary? It’s the fact that ‘Pink’ not only racked up wins over elite names like Tim Witherspoon and Mike Weaver, but did so while fighting a much quieter, internal battle—drug addiction. So, all things considered, who do you think truly stood out as Mike Tyson’s toughest opponent? What do you think?
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