The Tyson fight was one of circumstances , styles, timing and more importantly mental toughness. Holyfield was past prime when he won but his roided strength and mental toughness was too much for Tyson at that stage of his career. I recall when the Holyfield and Tyson fight was first mentioned I thought Tyson would mop the floor with him as Evander would be there to be hit. And if they had fought before the Douglas fight I still say Mikey would have detonated him. But after the Douglas fight and his prison term Mike was never the same fighter. I've always compared his fall with Duran, after Roberto was proclaimed King of New York by beating Leonard he stayed drunk for months and gained weight like it was gold, by his own admission, he was never the same. Though he got motivated again and redeemed himself Tyson never had the versatility and mental toughness of Roberto. If I had to say what was the single most detrimental episode in young Mikes career it would be listening to Don Kings prison jail house mind games about how his white management was using him, the MAN was keeping him down and you need to come with your brother who will look out for you. Second was marrying the consummate gold digger Robin Givins, though my record on marriages is worse than Tysons, but due to this experience I recognized what was going on . Ciao!
Holyfield was physically very strong AND he could also absorb an inhuman amount of punishment. This made him the perfect foe for Tyson who would naturally get frustrated when someone could take his punches and bully him in clinches + head butt him. I don't think 96 Holyfield beats many great heavyweights. I think the 90-93 version is the best version for taking on quicker heavyweights. The physical strength that he gained works on short swarmer's like Tyson but would have very little effect vs the likes of Holmes, Ali, Liston etc.
Frazier probably wouldn't let him work on the inside and would bully him around and have the power to knock him out.
Holyfield would have a better time with not many now that I think of it… Mike murks a lot of guys, I’d even say he’d do much better against Bowe, Lennox, Foreman, Liston, Ali, Holmes etc - Vitali? I think Mike might find Vitali a whacky puzzle, probably beats him but it’s “odd” I’m thinking…
I’m thinking Frazier gets decimated by Tyson personally… that’s a very unfair fight IMO, Frazier has fair odds IMO for beating Holyfield.