BoxRec

What if Tyson had knocked Douglas out in Tokyo in 1990, setting up a superfight with Holyfield? Who would have won?

Same thing as 1996. Holyfield too tough, too strong willed, too hard headed. Holyfield was Tyson's kryptonite.

I always felt that Holyfield would beat Tyson, even back in 1991 when they were slated to meet before Tyson pulled out with a bogus injury.
I believed that Holyfield's mental toughness (combined with his skills, of course) would be too much for the fragile minded "Catskill Thunder."

I see it the same way as the guys above. Evander is just all around the better fighter.

Like so many others, I waited for what seemed like forever for this fight to happen, and of course it didn't ( when it was supposed to. ) Evander Holyfield was in the peak of his prime and had his focus 100% set on winning the title. He was doing everything that a top contender needed to do, ie. staying in top shape, keeping active, and fighting the best contenders he could get fights with. He had a solid team in his corner and handling his career as well. Tyson was still a force to be reckoned with, but seemed to have lost a step after Rooney left his camp. Not totally sure one way or the other as to who would have won, but my inclination is to lean slightly towards Evander for the reasons given above.