Dempsey fights: Douglas Bert Cooper Old Foreman Old Holmes Riddick Bowe Holyfield fights: Willard Brennan Miske Carpentier Firpo Tunney Does Dempsey sweep the Holyfield competition? Does Holyfield sweep the Dempsey competition?
Holyfield sweeps. Dempsey loses the lot. Different eras. Different skill set. People may say he beats Douglas but Douglas ain’t no Willard.
I see Holyfield sweeping, but he might lose to Tunney. Dempsey will win the first 2 but has a very good chance of losing against older Foreman. He beats Holmes, but I think Bowe beats the brakes off of him.
I know one thing, Evander Holyfield, at Dempsey's age then, absolutely destroys Gene Tunney! ...IF Gene Tunney agrees to fight Evander Holyfield.
Very interesting post. Agree with other posters, I can't see Holy having too much problems with any of those guys. He took punches from modern giants Lewis, Bowe and Foreman so I feel most of these guys punches bounce of him like peashooter. True he had a bit of trouble with Foreman and Holmes but even grandfather versions of these guys are far better than Willard or Firpo. Only Tunney may have the smarts but Holy could box as well and don't feel there is that huge gulf in skill. Dempsey would lose to Tokyo Douglas but beat every other version. Cooper was very underrated IMO and could give him trouble in a classic fight. Bowe wins a wide decision. I feel Foreman is simply too big but of course if Alex Stewart could batter him imagine Dempsey having a go and I feel it is more of a pick 'em. Old Larry could outpoint him simply because he is light years ahead of anyone from that era as far as ring smarts. If Tunney could bamboozle Jack even old Larry would box rings round him.
Dempsey would beat Douglas. Douglas who fought Holyfield. And Cooper. Old Foreman, Old Holmes, and Bowe would beat Dempsey. Those issues of the fighters who fought Holyfield. Because Peak Bowe (first fight) and Peak "Old Foreman" fought Holyfield. Holyfield would beat all of Dempsey's opponents except Tunney, who he would lose to on points. If Holyfield didn't knock out Willard in 15 rounds, and the fight lasted 45, then Holyfield would lose.