Jack Dempsey vs. Joe Louis would be my pick as THE fight to determine who the GREATEST boxer is! The winner? It's a toss-up in my opinion.
yeah, Jack could have beaten Mike Tyson easily. They have the same fighting style, so they'll meet each other head on. But Mike's toughness isn't very good when compared to the other pro HW boxers who have been champion. Dempsey's punching technique that maximized his ability to hit as hard as he possibly could would overwhelm Tyson!
Rocky...I dunno. I think it would be a great fight. But Dempsey is like Rocky with a nastier attitude and way better technique. That's why he'd win.
Foreman wouldn't win because he'd get tired and he doesn't have the explosive speed.
Ali would try to rope-a-dope on a relentless Dempsey who just won't stop coming after him despite his footwork, and he'd get KOed. Dempsey won't stop punching, unlike a tired and heavy Foreman, and Ali isn't going to rope-a-dope THAT kind of power and speed!
Lewis. Too tall for his own good. Dempsey would bob-and-weave inside and butcher his torso. Then hit him with that hellacious jolting haymaker to the jaw when those hands drop and the tall man's footwork is gone, and knock him out, and send his mouthpiece into the audience.
Jeffries!? That would be a very brutal fight. Jeffries would lose by a close decision. He's just too damn tough, strong, pain tolerant, and cardio conditioned to get work out and finished/KOed by Dempsey. Dempsey would actually knock him down at least once, despite all of the opponents Jeffries had before he retired (and that includes Bobby Fritz; he sure as hell had the power and accuracy with his punches...pound-4-pound I think he's the most powerful hitter in the past 300 years...but he lacked the technique and size of Dempsey). But he's slower and can't mix it up with his technique like Dempsey. Dempsey would find himself getting up quite a bit but he wouldn't quit. Both would have to go to the hospital for something in the end.
Dempsey would fight you, it didn't matter who you were. He wanted to fight one of the absolute best heavyweight catch/submission wrestlers in history when the guy challenged him (Ed "Strangler" Lewis) but his manager didn't let him. Dempsey has streetfighting expertise and he knows SOME catch wrestling and the guts to fight someone like the Strangler. He wasn't a racist asshole either. The only reason he didn't get to fight someone of another ethinc group was his manager. he refused to let him. dempsey said he would have fought anybody. I see certain boxers, grapplers, and MMA fighters of the past and present time and I really respect the fact that they had a "switch" they could turn on or turn off. They could go from average-Joe nice guy sitting on a bench in the park saying hello to people walking by and then blast off into a killing spree when they need to defend themselves. Fedor, the current Pride FC heavyweight champion is an unstoppable brutal force in the ring, but he's so nice outside of the ring it's almost scarrier than his fighting persona. These are true warriors!
haha...the part about the tiger and gorilla is quite possible. If Mas Oyama, a VERY heavy-handed karate master who beat all kinds of opponents from all around the world in streetfights and could even chopthe horns off of bulls and punch them to death could do what he did, then yeah a less powerful man can KO a gorilla or a tiger which isn't as big or as hard-headed as a bull! I'm sure the toughest of the ancient Greek boxers and no-holds-barred fighters who were as tough as a human being can possibly become could do this stuff quite easily.