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Mike Tyson says one man stands alone as his toughest ever opponent

Shaun Brown

6th December, 2025

Mike Tyson says one man stands alone as his toughest ever opponent
Image credit: Getty

Mike Tyson would feature on many opponents’ lists if they were asked to name the toughest foe they ever faced.

“Iron” Mike flattened his first 19 opponents before stepping up in class and finding sturdier resistance from the likes of James “Quick” Tillis, Mitch “Blood” Green, Jose “El Nino” Ribalta and James “Bonecrusher” Smith — the first men to take the heavyweight phenom the distance.

That run brings us to 1987, when Tyson was approaching his 21st birthday and already the unified heavyweight champion. More belts were on the horizon, but not before he confronted the man he now describes as his own toughest opponent. In a clip uploaded by Calfkicker Clips, the notorious New Yorker explained that the fighter who earned that distinction was Pinklon Thomas.

“He was my toughest opponent…

I hit him with 17 punches flat on the face and he went down but it was 17 punches flush –– all of them hard as can be. And the last one he just passed out. I thought ‘God, that is my toughest fight. He took 17 on the chin.’”

Tyson vs Thomas took place on May 30, 1987, as part of HBO’s troubled heavyweight unification series to crown an undisputed champion. Only a few years earlier, Thomas had been one of the world’s leading heavyweights, holding the WBC title and positioning himself for a major showdown. Confident in the build-up, he even told Tyson he would have to “replace the gold in his mouth.”

With Angelo Dundee in his corner, Thomas insisted he would not be another statistic on Tyson’s growing résumé. But from the opening bell, the young champion unleashed a torrent of punches on the former belt-holder. Cut in the first round, Thomas tried to adopt a more evasive approach as the fight progressed, yet a sustained barrage of hooks and uppercuts finally ended his challenge in the sixth.

The Mike Tyson machine simply rolled on to the next man in line.

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