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It depends on which Ali and which Tyson we’re talking about. If we take them both in their primes for Ali that would be just before his exile and Tyson, right around the Spinks fight. This may be an unpopular opinion but pre-Spinks Mike Tyson would’ve given Ali trouble. Ali struggled his entire career with compactly built swarmers with unorthodox styles that threw punches in bunches and bobbed and weaved. Tyson was ALL those things at his peak. People also forget that peak Tyson was also very difficult to hit squarely due to his underrated defense. That said peak Ali was like no other heavyweight we’d ever seen in the ring. Ali toyed with a dangerous Ernie Terrell drawing out a fight he could’ve finished early to an easy unanimous decision but to see a heavyweight at the peak of his powers just look at Ali’s 1966 bout with Cleveland Williams.





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Ali would’ve beaten any heavyweight in history that night. He was blindingly fast, devastating with his power, reflexes perfect at a level no other heavyweight has ever attained. If both are at their peak Tyson gives Ali Trouble for maybe 3 rounds and then lights out by around 5 or 6 after Tyson grows frustrated with his inability to catch Ali squarely. Freakin’ boxing, what else? He could go through the Michael Moorer or Holyfield route of going up from cruiser- or light-heavyweight, dominate the division, and then move onto heavyweight and flaunt his tremendous prowess against the likes. Cooper had a great left hook but wasn't that big a heavyweight. I think he'd struggle over a long fight with such a strong guy as Chuvalo. Also Cooper was knocked out cleanly by Floyd Patterson whereas Chuvalo was never even off his feet let alone knocked out in a fight.