If the fight came off and shortly afterwards Mike went to prison as Champ. History would have been kinder to Mike. Again, I'm one to believe that Holyfield matured better and never let his fading reflexes limit his game. He made adjustments. Tyson on the other had didn't make adjustments and attempted to fight the same way he did when he was younger but instead of pulling the 3-4 punch combos that he was capable of doing earlier in his career. He'd throw one punch at a time because that was all he was capable of doing. In 1991 this wouldnt have been an issue. Mike was still Mike. Sure he wasnt under Rooney but IMO he was good enough, quick enough, and young enough to beat his contemporaries.
Yeah that to me is why a 91 fight would have been so compelling - you can make great arguments for either fighter. Also, practically speaking, 91 would have been the best time for the 2 guys to fight each other. Holyfield was prime, and Tyson was still close to his. I still say that 91 Tyson was better than 89-90 Tyson and that is why the fight would have been best in 91. Unfortunately it is impossible to imagine a scenario where a prime Tyson would fight a prime Holyfield since Tyson's prime ended in 88, and Holyfield was just starting.
I think the 96 Holyfield is the toughest match up for Tyson. I think the 91 Holyfield was too aggressive and undisciplined to beat Tyson. However, the 96 Holyfield was more of a war of attrition, fouling, counter puncher who proved to frustrate Tyson and really did not take too much punishment. My opinion is that in 91 Holyfield tries to brawl Tyson and gets knocked out in the 5-7th round.
Tyson. I think the fight would resemble Ruddock fights, with Tyson surprised by the shots Holy takes. Tyson TKO 5. Tyson eats a lot of power shots but isnt hurt at all. Holy sticks to Boxing but gets dropped in the first round. Holy comes out Boxing on his toes for round 2 and wins it. 3 and 4 are close but Tyson was too strong and still had enough agression,speed And body work to finsh the show. Right hook to the body right uppercut left hook, TKO5 by Tyson. I love Holy by the way but post douglass pre prison Tyson was still a beast and Holy would not be able to hurt him. This isnt slow Foreman who was too slow too finish Holy this was Mike on the comeback trail.