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That is the mostly likely scenario. Dempsey could certainly hurt him if he catches him with something big but we saw Ali comeback when hurt time and again. Unless Dempsey gets to stand over him when he`s down he wont be finishing Ali. A classy problem Jack probably wont have. Just comparing their levels of opponents its questionable whether Dempsey could even be competitive with Ali at his best.
I think Dempsey gives him some problems early but eventually Ali takes over and there is no turning back. Ali was bigger, taller, stronger, faster, had a longer reach, a better jab, better footwork, better defense, better overall skills, better chin, better stamina, he made more money, he banged more women, he was champ longer, he won more HW world title fights, he beat more hall of famers. Unlike Dempsey he was never counted out and he was never knocked out of the ring... well, he never crawled back in the ring to knock somebody out... but he never had to. He did stop Liston x2, Frazier, and Foreman though.
Don't be silly Burt, Ali all the way. Quick question for you:- If you had appeared in a pantomime with Dempsey, would it have been " Jack and the Bienstock "?.........i'll get me coat.
Dempsey and Frazier were similar stylistically. Great left hook and bob and weave skills. Dempsey was a little bit of a more complete fighter though. I would say it is about even with maybe a nudge toward Ali.
I don't think Ali beats any all time great easily. Henry Cooper gave prime Ali a competitive fight, until his haemophilia struck.
I would give Dempsey a real shot against the 70s version of Ali that planted his feet and traded more, but a prime Ali convincingly outpoints him.
Ali was not stronger, and did NOT have a better defense by any stretch of the imagination. I don't think he had better stamina either.