Goood one. Gene Tunney gave the older Jack Dempsey troubles mainly because of his footwork. Jack had difficulty catching him. A prime Dempsey certainly would have no problems catching Gene. As for Joe Louis, Walcott would have given him trouble at any stage of his career. I read that Walcott used to spar with Joe and gave him fits even back then. To cut it short, my money would be on Dempsey. The reason is because Jack would go right to Louis and the fireworks would begin immedieatly. Joe wouldn't be darting around the ring like Tunney did. But by the same token, Joe Louis might catch Jack with a combination the same way he did Walcott. Could go either way, but I would bet on Jack. Dempsey's main trouble with Tunney was chasing him around the ring all night.
Joe Louis. Don't forget Louis was stepping into the ring with Walcott at a solid 213lb. He had a good 20lb on Jack by this point. Combine that with superior punching abilities and better fundamentals and Louis takes it.
Louis by tko. Prime for prime,it'd be very close with Louis coming out on top. With these versions,it would be Louis more emphaticlally,as at this respective points in their careers,he had n't declined as much as Dempsey had.
Louis beats Dempsey by a close UD.Neither would be able to stop the other, but it would be a helluva fight for two over-the-hill fighters.
Joe Louis by early descruction. Faster hands, sharper shorter punches. On the outside Dempsey has to deal with not a pesky jab but a jab that Billy Conn described as somebody busting a light bulb in your face. Both guys could still hit after their primes but Louis had the better boxing skills to get his power to the target which is what matters the most. Not who hit the hardest which would probably also be Louis.
Another interesting matchup would be Walcott from the Louis fights vs Dempsey from the Tunney fights. I think Walcott could box his way to a decision and score a sneaky knockdown or two in the process, not really hurting Dempsey but surprising him with a pin-point counter.
This is one of the tougher problems that I have been posed on this site. Both were great fighters whose reflexes were shot. Both came from behind to beat a star of the next genaration, e.g Sharkey for Dempsey, Walcott for Louis. This is the difficult part, because it makes it hard to diffarentiate who was further gone (always the getout clause in these type of fantasy matches). I will say Louis because, there are less gaps in what he was doing at this time. He was competitive on the cards vs Walcott, and got a decisive stoppage in the rematch.
Except Louis actually cleanly knocked the crap out of Walcott, while Dempsey beat Sharkey because of a andrew golota to the nutsack.