If Tyson had beaten Douglas then fought Holyfield I really don't know who to pick. He didn't stick to boxing as much as he could have when he was drawn into a brawl back then and I don't know if he'd had been content to counter punch Mike like he did as he got older, he was a much smarter fighter when he fought Mike late in both their careers, a younger Holyfield was a lot more reckless and thats something that got him in trouble against Bowe.

I'll say if Tyson came in looking to throw his combos and looking to go to the body and head and use defense, yes he could beat Holyfield. But he hadn't been that fighter for a whole before Buster beat him, but he got through it because of his one punch power.

Tyson was already on the decline on that point and the only way he'd beat holyfield was if he came in fighting like he used to. But Don King killed that guys career, so as long as Don King is involved Tyson wouldn't have beaten Holyfield. Got rid of all his good trainers and people that would make him work his butt off, he'd be around promoting the fight and not training and with Don King while Holyfield trained like a demon from heck. So given the realistic circumstances it's hard to see Tyson winning, but it's not out of the question. It's just unlikely considering the way his career was going. Then again if Tyson had trained hard for douglas prior and beat him then I'd have a little more faith in him. If he got up for Douglas he'd do it maximumly for Holyfield.