Would Tyson have retired undefeated if Damado lasted his whole career?

Cusa's influence is probably overestimated. It's hard to say what would happen. The truth is that in 1988 Tyson fired his trainer because he required him to focus on discipline and Mike had already stopped doing it. since then, the regression in form has been visible. Rooney wasn't a great coach, he was just demanding, nothing more. If Tyson had maintained discipline, he would probably have developed his skills in a natural way and I think that around 1991-1993/1994 he had his peak... Then he would have lost his parameters, becoming an increasingly worse player, unless he would have somehow evolved by modifying his style, but this is probably not the type . Of course, he could have had weaker fights, but I think that he might not have found a defeater until 1997/1998, I don't see anyone who would have been better at that time, but he could have caught Mike on a bad day. However, I do not think that Tyson, after 30, would fend off the attacks of players such as Tua, Byrd, Ike, and the Klitschko brothers.
Tyson's possible wins over Holyfield 1990, Bowe 1992, Lewis 1993 would not be as appreciated as Ali's wins over Foreman or Frazier's wins over Ali. I think it would be considered that Tyson reigned in a weak era and Bowe, Holy, Lewis were not very strong. However, if he lost on a bad day to someone like the 40-year-old Foreman or Mercer, whose style did not suit him, it would only confirm the opinion that he was not a player like Joe Louis or Ali. However, this is just speculation because I don't believe that Tyson was mentally able to maintain discipline for over 10 years, with Cus or not.

 

I'm pretty sure him firing Rooney was more him speaking in public about Tyson then-wife than him demanding discipline lmao. Also blud was -and maybe still his- a gambler and alcoholist.
Tyson keeping his prime longer is a fascinating what-if honestly, and as much as overblown and overfantasied it is, I like read opinions on it, but I agree with most of y'all, even if the fall-off was delayed.

 

NO, HE WAS ALWAYS GOING TO IMPLODE.AT SOME POINT.

 

Preparation would've been completely different. Very possible for Tyson to win those fights. Most fighters are advised to fight someone who's on the slide. This may be the case for Mike. From 88 to 89, was a HUGE difference.

 

Yeahh, Mike was a wild boy back then, even before his apex.

 

I don’t think it would have mattered one iota. Mike would have probably left Cus same as he left Cayton and Rooney, same as Floyd left Cus.

Mike Tyson was no longer a 16-year-old impressionable street urchin given a second lease on life while living a monastic existence at the foot of an ‘all-knowing’ guru who would preach mumbo-jumbo and show him old fight films.

He was a super rich young man, married, the toast of NYC, partying and spending like there was no tomorrow with all-night jewelry sprees where they opened the stores just for him. He was the heavyweight champion of the world and the biggest star in sport. He was untouchable and indestructable (or so he thought).

The dynamic had completely changed. He was the cash cow and these people were getting rich off him now, not the other way around. They worked for him, not the other way around. He was aware of this and wasn’t going to subjugate himself to them as he came into his own as a young man ill-equipped to deal with the fame, much less with real relationships and such.

Cus wasn’t going to discipline him. He couldn’t. And hell, even when Tyson was still an amateur he didn’t do the right thing and make Mike act right and go to school (which surely would have been in his best interest to get enough education to at least read a contract and comprehend it). If Cus couldn’t keep Tyson from getting in trouble as a teen, what the heck makes anyone think he could control him as an adult withi all the power and all the money he could ever dream of having?

 

Lewis always would've beaten him, Holyfield and Bowe have very good chances themselves.

 

Not.
If Tyson (even without prison) went through the "labyrinth" of the 90s in which there are: Bowe, Foreman, Moorer, Holyfield, Lewis... and fought with all of them - he would be defeated.
I also think that everyone I listed would be defeated as well.
One can refer to Lewis, who even if he had beaten Bowe, would have won fights with better versions of Tyson and Holyfield, and instead of McCall he would have been defeated "somewhere along the way".
The 90s are too high quality and too deep for any boxer to go through them undefeated, and to be "thrown into the fire" at the same time.
I hope I explained it well.