My honest take !
Undefeated ? MAYBE if he retired at the right time. Tyson style was a young mans style and around 28-29 years of age his decline most likely would have begun, so he never would have had a very long career even if D'Amato was alive.
But if D'Amato was alive i don't think that Tyson would have lost to Buster Douglas.
He wouldn't have gone to prison.
He probably would have faced Holyfield in the late eighties which would have benefited Tyson because Holyfield had just moved up from cruiserweight and hadn't “matured” into a real heavyweight yet.
Tyson probably would have faced a pre Emanuel Steward trained Lewis in the early nineties which would have benifited Tyson, who then could take advantage of Lewis then often flawed defense.
Bowe fought 2 boxers that had similarities to Tyson in Tubbs and Mathis Jr and he didn't look good against either of them. I don't think Bowe could overcome Tysons speed and aggressiveness.
Tyson loved and respected everyone in the original Team Tyson, Kevin Rooney, Steve Lott and Matt Barinski.
Jim Jacobs and Bill Cayton.
Camille Ewald
Probably even Don King at some point.
But the one advantage that D'Amato had compared to all of them was that Tyson loved and respected him, BUT he also was scared to death of him.
And with Tysons mentality that probably was exactly what he needed to stay on track, at least for a much longer time.
Tyson was asked about D'Amato
-”Were you ever afraid ?”
-”I was always afraid of him, i'm afraid of him now and he's dead. He made sure you were afraid of him”.
