None. Not one. Greb gave him fits in sparring -but it was only a few rounds. I can't see that happening in a fight that's scheduled for 12. Dempsey, like any fighter, is brought to a peak in conditioning and mental readiness on fight night -not in sparring. Those who pick a Charles or a Jones to beat him should forget about the Tunney fights and consider the 1919 version that destroyed Willard. Dempsey's style, more than anyone -even Tyson- was designed for a young man -it relied on maximum agility, flexibility, stamina, aggression, speed, and long-term power. Dempsey's style required more energy than most anyone this side of Armstrong and Greb. The natural deterioration that comes with age, combined with his Hollywood existence as champ, combined with his inactivity, gave Dempsey a very short prime. However, from about 1919 to about '22 or '23 tops. He dissoluted more rapidly over the next three years and then stepped in against Tunney a different fighter completely. You can't compare the Hollywood version of Dempsey to the Hobo version of Dempsey. It's a simple matter of ferocity! Max Baer said it best back in 1934: "Ive been around twenty-five years, and Ive met only one guy who could get in a room with me, lock the door, turn out the lights, and work his way out. Jack Dempsey. The day he licked Willard, Id have been lucky to last a round with him. I think that pretty much explains why no MW or SMW would go far with this creature. That Jack Dempsey, who was fresh off the rails, who remembered how it was to [literally] fight to eat, who bathed his face and hands in brine to toughen them up and chewed resin from pine trees, was the fighter most likely to take you to hell and leave you there. No smaller man would stand a prayer.
Greb, if Dempsey could have beaten Greb he would have fought him when promoters from Buffalo, Milwaukee, Philadelphia, Pittsburgh, Denver, South Bend, Benton Harbor, and other places were fighting each other for the chance to stage the match. Dempsey was several times wired offers for the fight and Kearns refused to match them. He knew that at the very least Dempsey would have to struggle greatly to beat Greb if he could in fact beat him which was a question that begged answering.
This is amusing. You can't be serious about Joe Calzaghe vs Dempsey? There is absolutely no way Joe Calzaghe even on his best day lasts 3 rounds with Dempsey. 160 pound Toney, Roy Jones, and maybe Carlos Monzon could give Dempsey a challenge.
None, although if I had to pick one he wasn't really a SMW but weighed very near the amount in his prime so I guess Conn would have a outside chance.
Harry Greb has to be mentioned in this context because he gave Dempsey a lot of problems in sparring and beat many of Dempseys best opponents. Of course just because Greb gave Dempsey trouble in sparring and Kearns didnt want the match dosnt mean that Dempsey wouldnt have got to Greb inside the distance. As champion Dempsey would have been able to dictate terms likley to make this happen. Bob Fitzsimmons should probably be mentioned also because of his effectivness as a heavyweight finisher. Beyond that anybody is a bit of a stretch really. They might be able to do it in theory but you have to make two or more leaps of faith to see it happen.
Dempsey at his peak was quick and a composite puncher on a level with Louis and Langford. The HW Sam could have beaten him but the 168 Sam would not. Jones and Toney??? Great fighters but come on? This is becoming something of a running sore...