Give it to Tyson. Totally different head space and training than the version that did fight Holyfield post-prison.
Still Holyfield. He knew how to beat Tyson and would've been able to execute that gameplan even more effectively than he did in actuality. Tyson would make the earlier rounds more competitive but as the fight went on it would start to look more and more like their actual fight. I'd even argue that the Holyfield that Tyson did actually fight would still beat 88 Tyson, albeit in a tougher fight.
Tyson by TKO. Peak Tyson (1988) vs Peak Holyfield (1993) and we're getting a far different outcome than their actual fights. Yep, Mike Tyson was actually that good in 1988. Unfortunately he would never get better, which was a shame but also a good thing that Holyfield got him when he did. Both men would've been active in this one meaning no prison stint and no semi-retirement from steroid abuse.
Mike at his absolute best, regardless of how short that period was, was better than Holyfield at his. Mike's legacy as one of top HWs of all time is based on what he achieved at such a young age and in such a short period. Holyfield never got that kind of legacy until having to fight many years.
Tyson annihilates him. Not a man alive considered Holyfield a dominant heavyweight at that time. He was saved by Fan Man. He was a guy who could win or lose anytime out. 88 Tyson was the devil incarnate.
The fact Holyfield was almost floored by the first punch of a post prison Tyson will never not be funny to me. Peak Tyson beats any version of Evander, doesn't matter what gameplan he has or how juiced up he is.
Close fight, but Holyfield was older and also past prime in the Tyson fight. Holyfield that beat Bower would beat any version of Tyson, he is just all wrong for him like Foreman was all wrong for Frazier.
Tyson was never the same fighter after 10 unprepared rounds with Tokyo Douglas, 19 rounds against Ruddock and 4 years in the pen. Mike was a midget running a division of giants. That required catching lightning in a bottle every night. Even without all the coke, booze, mayhem and the above beatings that is not sustainable for very long. But for 3 years and ten fights he did this, and laid waste to the division. If you can't see the drop off that came with his resumption in 95, then perhaps boxing isn't the sport for you to follow.
I think it mattered that he might have perceived him that way. On the other hand, isn't it strange that Holyfield was seriously ill in 1996 and in 1997 outclassed the younger Moorer, whom he lost to in 1994? Did this illness somehow help him? Getting back to the topic, I think Holyfield himself once said that the 1987 Tyson was unbeatable, but I think Evander will always be a code name for him. Regardless, I think Tyson will take him on points after a fierce battle.
Evander was better equipped for Tyson post prime. Holyfield had changed his fighting style. He was heavier and stronger than he was in the early 90s. Evander was not wasting punches like he once did. Holyfield started fighting like a heavyweight. That extra strength served him well to forced Mike back and also absorb Tyson's punches. EH also learned a few new tactics that come with hard won experiance. Using his shoulders, elbows and head. The smaller, younger Evander couldn't keep Bert Cooper off him.