Depends when they fought. Earlier it's a harder fight for Jack to win later it's an easier fight for Dempsey to win. Either way most would expect Dempsey to win.
Dempsey both at their best...Dempsey said he "loved" to fight the tall straight up big guys as Harry Wills was...Why, Sam Langford himself declared when Dempsey and Wills signed for a bout which was aborted, "my money is on Dempsey for he is the greatest heavyweight I ever saw". Dempsey at his best was a ***** to tangle with prior to his getting rich, going Hollywood, and his law suits against his larcenous manager Jack Kearns...And three years without a fight or tuneup, found a rusty, slow Dempsey being outboxed by a trigger minded boxer Gene Tunney...But Dempsey came close to winning back his title in the famous "long count" bout in 1927 with that terrific 7 punch onslaught that landed on Tunney in the 7th round...Dempsey, whatever you thought of his career, never moaned, never whined and never derided his opponents EVER...Dempsey and my man Louis were my heavyweights, along with Marciano and Joe Frazier...Yessir...
55-45 Dempsey. I believe the fight ends in a knockout. I give Dempsey the slight edge but I could see wills winning on points or by KO..very evenly matched Wills was not like the big lugs Dempsey fought. Wills had skills speed athleticism and punching skills. He clinched really well and thew a mean right uppercut Dempsey at his best I think might breakdown wills first and land a tremendous left hook to finish things..Dempsey behind on points in the 12th
No clue but it would have had to take place in 1919 right post Toledo .. that being said I am not one of these folks that conveniently dismiss Wills as a big, slow, strong heavyweight based on a few minutes of footage of him at age 35 .. I'm more inclined to view him as a guy that massacred Langford multiple times, iced Norfolk in two rounds ( two men Dempsey would never , ever fight ) and so on ..
Norfolk's record during Dempsey's prime did not warrant a shot at Jack.The best heavyweight scalp on his record during Dempsey's reign is John Lester Johnson.
I would take Dempsey. Wills's style seems made for Jack. However without seeing footage of him it's impossible to know for sure. I do know that of the footage we have of Wills I would easily pick Jack. Not just on ability but the way Wills folds up against Uzcudun to me is alarming. I couldn't see Jack going out like that.
I would favour Dempsey, but Wills chances shouldn't be dismissed. He was a harder puncher than given credit today, and he was a trap setter.
Good points.It is an old Wills but he doesn't seem to have much appetite for it when the going gets tough. Dempsey took a real hiding fromTunney ,but never stopped trying to win.
Having seen an older Harry Wills fight against Paolino Uzcudun on film. he reminds me of a modern heavyweight Ernie Terrell in size and style...His style would be I believe catnip to a Jack Dempsey both at their best....Jack loved the big guys as did Joe Louis...As the song says "slow and easy-----"...
I don't know who would win prime for prime, but I believe Dempsey would have won if he had defended against Wills any time 1922 to 1926, and probably 1920 onwards. I think one of the biggest mistakes ever made by a fighter was when Dempsey agreed to fight "#2 contender" Tunney instead of "#1 contender" Wills.
Wills was 38 at the time, in about his 100th fight. I'm amazed anyone could be confident of a Dempsey victory when he never faced anything close to Wills' combination of size, ability and pedigree, and wouldn't go near the only guy who matched that description.
