That's an interesting question, because while he was clearly regressing, he could still beat a lot of guys just with sheer power and the intimidation factor. Many will say Holyfield, but Evander hadn't done much in the division yet, save for the war with an inspired, but past his prime, Michael Dokes. I think 1990 Tyson had enough left to beat the Holyfield who warred with Dokes. There weren't many good contenders around. If I'm pressed, I'd say possibly Holyfield and, interestingly, George Foreman. Without the defense he showed from 1985-1988, Tyson would have a tough time with post-comeback Foreman.
I hadn't read you post but I see we came up with the same two names. I really can't think of anyone else who contended at that time who would have a good shot at beating Tyson.
I always felt the Tyson who fought Ruddock was a bit underrated. People seem to focus on the fact that he was slipping a bit skill wise but when you watch those fights he still looks pretty devastating at times. In fact I wonder how many heavyweights at that time could stand up to the punishment Ruddock took in that rematch, I'd even question Evander at that time surviving. Tyson was still fast and powerful, he also had stamina to last a long fight, something he didn't have against Holy in 96. Tyson was a lot less easy to discourage pre prison, I actually look at the Ruddock fight as a measure of Tyson's own grit, according to many he folds when put under pressure, but he didn't that fight. Ruddock's famous smash punch landed more that once and even had Tyson stunned. I don't even know if the Holyfied of 91 could have hurt Tyson of 91 like that. I couldn't say 100% but I think he would have got past Holyfield by being too powerful, fast and having the stamina to carry this on later in the fight. I think Bowe could have been a big threat in 92 and Lewis later around 96, by which time Tyson would be near the end of his career. So yeah, maybe a prime trained Bowe could be his undoing, but Rid**** would need to be like he was in that first Holy fight. I still sway on the Holyfield match up though, sometimes I can easily imagine Evander using his will to combination Tyson to death in the championship rounds. I see Lewis as a different era, I think he was too raw in the early 90's if Tyson was around.
I actually think that it would have enhanced Tyson’s legacy significantly, if he had avoided the Douglas fight, and met his match at the hands of Holyfield. Holyfield would have been a much more credible conqueror. That aside, it was only a matter of time before somebody beat him. When a champion loses focus, and turns up to fights unprepared, nature is going to cash the cheque eventually.
I see the reverse. His loss to Douglas was viewed as a fluke because of Douglas' spotty history . Holyfield was full grown and likely at his peak and he would have been at his most motivated against Iron Mike.
Holyfield, Bowe and Lennox had serious chances, yes. Foreman was too slow to beat Mike IMO. Mercer gets beaten by Mike for the same reason. Others mentioned names Tyson would have destroyed.