I think AJ times Dempsey again and again with his uppercut and knocks him out early. Dempsey's ferocity and willingness to engage is his undoing here. AJ isn't Jess Willard, he's mobile, good jab and big, big power and he finishes fights.
AJ is no Willard, not even close. I doubt Joshua can even rope a steer. Jack takes takes him out shortly after the introductions. There was never aboxer born or who will be born who can beat Dempsey at any part of his career.
Toledo Dempsey by murder! AJ couldn't take the punches of Andy Ruiz!...Boxing writer Reg Guttridge said that Dempsey was "Once...the most powerful...ruthless...and dangerous unarmed man in the world!" Yeah...the perfect opponent for AJ...
Unfortunately, after meeting middling John Lester Johnson, Jack's world inside the ring did not involve fighters "of color." Tunney was taking notes apparently.
I’d take AJ to beat Dempsey as well but this is completely disingenuous. Dempsey was clearly rusty and hadn’t fought in 3 years by the time he fought Tunney. I put just as much stock in those losses as I do in Holmes’ losses to Tyson. Less actually considering Holmes went on to be a force in the division where as Dempsey never fought again.
Probably Joshua. Even though he’s lacking in some areas I think his size and power would overwhelm Dempsey. And using Jess Willard to bolster an argument for Dempsey won’t work here
My trademarked Boxing Prognosticators Algorithm (BAP) sees the following: Dempsey KO AJ within 3 rounds, 55% chance of occurring. AJ wins 12 round UD, 45% chance of occurring.
The combatants never come to blows. Nobody in Dempsey's era will make a fight that crosses the Color Line. When AJ tries to arrange the fight in 2025 instead, he learns that the sanctioning bodies won't allow him to fight a small lightheavyweight.