Dempsey’s style plays into Fitz’s game much more than Corbett did, as Fitzsimmons was a trap setter who seemed uncomfortable pursuing on the front foot. Jack would essentially be coming to Bob, which is like suicide. Fitzsimmons KO/TKO around round 8
I'm not sure where the links are, but there was a newspaper in Dempsey (hvywt)'s time that had fantasy fights pitting Dempsey against Jeffries (who came back to KO Jack) and Fitzsimmons. They had Fitzsimmon's putting Jack Down hard, but Jack just pulling through and recuperating to KO Fitzsimmons.
super interesting match-up. I take Dempsey on the basis of a good big man beats a good little man. Dempsey was 15 to 20 lbs. heavier. I agree with the poster who disputed Dempsey having the style advantage. A come forward, bob and weaver, is more likely to play to Fitz's strengths than a jab and mover. On balance I pick Dempsey as the more likely winner, but Fitz as a very live underdog. If I were placing a bet, it would be on Fitz as I would probably like the odds. And I would really be surprised if this one went to a decision.