well bruce lee never fought professionally, so if this is assuming on the basis that bruce lee the movie star vs professional boxer then it would be obvious that jack dempsey would win however in a kickboxing ruled and sanctioned fight i think it would be a closer fight.
Speed would go to Bruce Power (hands) i would say Jack Head movement i would give to Jack Experience goes to Jack without a doubt Kicks goes to Bruce The best at being on a stamp is Jack I would say on the Jack would use head movement to dodge Bruces punches and bring back some hooks to Bruces face as he didnt have much of a guard and boom good night my good sir Bruce
Bruce wasn't that great of a grappler even for his size. Dempsey had a legit black belt in judo and was pretty good catch as catch can wrestling. Also he his pull up regiment was freakish, as impressive as any thing Bruce did, and he was doing it with 180-195 pounds and not 140 pounds. Simply put dempsey could grab him up and **** him. Bruces only shot would be a kick that dempsey isn't use to defending...but I ****ing doubt that turns the tricks.
Seriously, this isn't fair to Bruce Lee. You are trying to put him in a sporting situation, the likes of which he'd never expressed an interest in being involved with. Lee was trying to find truth in self defense techniques, and developed a philosophy based on using what ever proves to be effective. Martial Arts styles were more like religious sects and denominations in his day, with numerous fundamentalist whack jobs running them. Lee was only 33 when he died, and that was like 20 years before the first UFC. Had Bruce Lee visited Brazil beforehand, he may have become a BJJ practitioner. Lee's approach would have been completely different than what we know as mma. Lee viewed a fight as life or death. Lee's first targets were the opponent's lead knee, groin, and eyes. Jack Dempsey didn't fight that way. Sure, you could argue Dempsey would have the same tools available in a real fight. Yes, he would. Howerver, Dempsey would be a rule abiding fighter trying to fight a fight with no rules. Lee would be a person whose entire philosophy was based on fighting without rules. Lee's primary attacks would be the eyes and groin, and he would look to resort to other techniques he had learned only if his initial acts failed. Dempsey would be a guy used to winning a sporting contest being given the option of using techniques that he'd never previously been allowed.
your a troll by your posts numbers and you never ever explain or justify your assumptions so go back to sherdog.
Dempseys knowledge of wrestling/judo coupled with his world class boxing would be devastating, especially in his era when MMA would be in its infancy and we wouldn't know what we know today. I could imagine someone like Dempsey being a tornado of pure and utter destruction.