What if Tyson beat Douglas?

Do you mean he keeps the same habits as he did before Douglas?

Tyson goes on to lose to Holyfield.

 

He’d lose and maybe retire around 93. Die of drug overdose around 95.

 

Not a whole lot changes honestly. Cus and Jacobs died, Rooney was already fired, and the incident with Robin Givens still happens. Tyson still probably doesn't beat Holyfield because his life was becoming a mess and the people who helped manage his chaotic behavior were gone. I'm not even sure a 100% focused Tyson beats Holyfield anyways. Win or lose, the time line continues with him probably beating Stewart and Ruddock then going to jail. I would imagine the rest of his career plays out the same.

However, if Tyson does lose to Holyfield, he'd probably be an even bigger emotional wreck than when he came back in the 90's. He might even retire permanently after 2 devastating losses when he had built up an image of being invincible.

 

Holyfield would've always beaten him IMO, so he would've lost to him the next fight.

 

So he gets away with his bad habits that led to that loss and continues them? Ok then. He loses to Holyfield in a spectacular fashion, far worse than he lost their first fight in real life, because he was actually trained and focused for that fight.

 

Why? Realistically, far less embarrassing to lose to Holyfield than to Douglas.

 

I think Tyson has a chance against Holyfield during 1991 period, Tyson to me still looked good against Ruddock, and had the engine to go a full 12 rounds in a tough fight. Where as Holyfield was getting rocked and having wars vs the likes of Alex Stewart, Bert Cooper, Michael Dokes.

Remember the Holyfield during this period, wasn't as smart as Holyfield that fought Tyson in 96. That Holyfield fought a smart tactical fight tying up Tyson and what have you, the Holyfield of the early 90s opted to go to war too much. And that for me would be his downfall against that version of Tyson in 91.

 

Of course. But Tyson was a lot less mellow in the 80's than the 90's, less mentally and emotionally mature. Having two devastating losses at the peak of his fighting prowess might've permanently ruined him.

At least post prison he can take comfort knowing he was no longer at his best. People forget even back in the 80's Tyson was considering retirement and had lost passion for the sport. If he not only lost to a 42-1 underdog but also lost to the best opponent available, it's reasonable to think all the motivation would be zapped out of him completely.

 

Evander Holyfield shocks the world - years prior to when he actually did.

 

If Moran counts out Douglas in the 8th round assuming the fight went exactly as it did. He'd go on to beat Holyfield who, at the time, wasn't nearly the tactician he became when they met in 96.

However, this isn't to say he goes undefeated. Part of the problems that plagued Tyson post Rooney was his consistency and discipline. While both Holyfield and Lewis stand out in retrospect as his biggest challenges, the timelines simply don't favor them. Lewis under Correa wasn't the phenom that we saw dig deep against Ray Mercer or tactfully neutralize David Tua years later. Lewis improved over time, and when he did he became the great fighter we know today.

I'd say the only active fighter between 1990-1992 who would have the best chance to defeat the Tyson of the Ruddock fights is probably Riddick Bowe, assuming his chin can withstand the punishment. Mike would be a spot on favorite over any one else during that time.

 

I guess in that case they would have watched the Holfield Vs Tyson fight a few years earlier (when both fighters were in better shape than when that fight happened).
And whatever the outcome of the fight, that match would be historic.

 

This is the truth.

 

He’d already fallen apart in ‘88. He had a genuine suicide attempt, driving into a large tree head on at immense speed with the intention of killing himself.