I don’t think it is a case of who lands first, because both these guys were tough to stop, tough I still don’t see it going past the mid rounds. I would favour Louis because Dempsey will be coming forward, and Louis liked nothing better than to set up a killing ground for come forward fighters.
It would be a great fight, but I lean towards Louis. Dempsey had great hand speed, but as Louis demonstrated in the Schmeling rematch, he was no slouch in hand speed either. They're about even in punching power I'd say, but Louis probably had a wider array of attacks. The only clear advantage I'd say Dempsey has is in chin, which could give him an early KO, but if Louis is well-trained and prepared, I think that he would likely adjust to Dempsey's aggressive style and prevent Jack from getting the KO in the early rounds. Dempsey's stamina problems might get to him in the later rounds, giving Louis an advantage.
Here's a link to an interesting read on the subject: http://coxscorner.tripod.com/dempsey_louis.html A bit lengthy, but a very thorough analysis. Whether or not you agree with the conclusion, there is plenty of food for thought.
former Jack Dempsey trainer Teddy Hayes describes how a Dempsey-Louis encounter would develop. Hayes was the trainer of Dempsey for eight years during the period when the Manassa Mauler pounded Fulton, Willard, Brennan, Carpentier, and Firpo. Hayes declared, Jan 18, 1936 New York Amsterdam News, "Why Kearns and I would never have thought of matching Dempsey with a boxer. We kept putting him in there with those big, slow bums and Dempsey made us all look good. We didn't want any part of that Tommy Gibbons fight, but gave Jack his way. And what happened? The first time Dempsey met a good boxer he was shown up. You know how Gibbons cuffed him around at Shelby: That was the tip-off on Dempsey." "Dempsey at his best wouldn't last four rounds with Joe Louis", insisted Hayes, "He'd let Dempsey force all the fighting and cut him to ribbons. He'd be stalking Dempsey from the opening bell, backing away, catching Dempsey's shots on his arms and elbows and waiting for the opening to put across that sleep producer. it is the most realistic opinion
I understand that Hayes had a falling out with Dempsey, though essentially he is thinking along the right lines. Either way, we are matching two of the best finishers in history, and anything could happen.
Well, Jack Sharkey was the only man to fight them both, and he said, "If Jack Dempsey and Joe Louis were to meet in a phone booth, I'd bet my very last dollar that it would be Dempsey walking out." Maybe he was just trying to embellish the fact that he was getting the better of Dempsey before getting careless, whereas he got trashed by Louis, but worth remembering all the same. That said, I've got to go with Louis here. I think Dempsey would have to win it very early. Louis could be a little bit of a slow starter now and then, and Dempsey of course was one of the most explosive four round fighters in history, so Dempsey getting Joe out of there early doors is a possibility. But Louis by mid rounds KO would probably be the percentage call. As others have said, Dempsey would probably just end up being way too brave for his own good. Louis was the more accurate and quicker puncher and I think he'd time Dempsey's raids eventually. Dempsey tried his hand at boxing against Gibbons but he's not going to win a battle of the jabs against Louis, either. I struggle to see Dempsey beating Louis more than say, once out of four or so attempts.
dempsey by ko in a great great fight while it lasts- style and chin to his advantage- if braddock and b baer could put louis down the explosive dempsey would win. baer, sharkey, schemling all of whom were in the ring with these two picked dempsey. two best heavys ever
Louis would win. He is by far the more refined, well schooled fighter. He has every conceivable advantage over Dempsey.
This may be an over simplification but I like Dempsey early in round one or two after that all Louis.
I agree with this for most part, I do think Dempsey's unbridled aggression, athleticism and big punch give him a chance very early to overwhelm Joe but if he fails to that, he will be jabbed, crossed, and countered in clinical fashion.