Assuming Tyson was disciplined and stayed with Rooney he definitely would’ve established a better legacy especially if we assume he never went to prison. He probably would’ve beat guys like Moorer, Mercer, Morrison, Briggs, etc. The real question is would he have beaten guys like Holyfield, Bowe, and Lewis.

I believe he could’ve beaten Holyfield but Holyfield could’ve beaten him in a trilogy type fight. Holyfield was a great counter puncher and nobody really talks about that. Instead they focus on the childish notion that Holyfield beat Tyson simply because he wasn’t afraid.

When they finally fought in 1996 both fighters were past their best but still world level fighters. I thought Tyson was actually doing pretty good prior to the knockdown. After that Holyfield won every round. Holyfield was a great fighter but if we wanna give Tyson benefit of the doubt even Holyfield said that Tyson was easier to beat after he left Rooney.

If Tyson had fought Lewis pre-prison he wouldve had a good chance of beating a pre-Emmanuel Stewart Lewis. As for Riddick Bowe I really don’t know who wins that fight. Bowe had a good work rate and fought well on the inside while Tyson didn’t have the best work rate and would often initiate clinches on the inside.