Who'd Have Stood More Of Chance of Beating Prime Ali?

What do you mean? Holyfield an Bowe are not intelligent? Sure Bowe weren’t the sharpest tool outside the ring but he knew how to fight. So did Holyfield. Besides they had good cornermen in Futch an Benton for advice if they needed it

 

Riddick Bowe, providing he came motivated and in shape (though not too skinny like the second Golota fight).
He could out jab Ali at a distance, and maul and bully him in up close.

Don't put a few dirty tactics behind Bowe either. He was just that kind of guy.
He wouldnt at all be intimidated or in awe of any of Alis tactics. He especially wouldn't put up with any nonsense from Ali at any of the press conference.

Bowe was a street hood at heart. He would go in to those press conferences WISHING Ali would pop off at the mouth.

Of course, to be fair, "prime " Ali was best known for his footwork, so it is entirely conceivable that got up on his bicycle and ran the whole fight .

Anyways, both guys were legends, it would be entertaining while it lasted

 

I rarely comment on H2H fights involving fighters from different eras, as there are too many unknown variables for me, but I really can't see Bowe out-jabbing Ali at long distance.

Holyfield mostly out-boxed Bowe when they fought at long range. Bowe used his extra size & strength to get the better of Evander on the inside. Ali was taller, rangier, lighter on his feet and had faster straight punches thrown from long range, than Evander. Hell, even Herbie Hide was getting the better of Bowe at long range, until Bowe walked through his shots & took it to the inside.

Bowe is tall and rangy, and his jab was good against bigger, slower HWs, but if he beats Ali, it's by outmuscling him on the inside. No way he outboxes him at long range, imo.

 

I think both guys have a shot, I would say Holyfield is the more likely to beat him.

 

Ali retired in the 80s- Bowe debuted in the 80s this isn’t Langford vs AJ here.

 

OP specified 66 Ali vs 91/92 Bowe. I.e. different eras.

I suspect PEDs weren't widely used in boxing in 1966, but were in the 1990s, for one thing.

I've no problem with people speculating on the outcome of this fight or any other cross-era contest. The further apart the eras the more unknown variables, though I take your point this instance isn't from vastly different eras, relatively speaking.

 

Holmes

 

Bowe looked shifty against Biggs and Tubbs. The answer is Evander.

 

Holyfield. He was very flexible. That took him a long way.