Dempsey was a green middleweight when Sudenberg beat him. Firpo hit hard enough to drop anyone. Dempsey walked through Carpentier's punch which on making contact with his chin promptly broke his hand. Fitz had the capacity to take Dempsey out, that is not the issue ,the question is would he be likely to do so before Dempsey got the fists on him? I say Dempsey should be a warm favourite here, he was a better mover ,had a more evasive defence, was significantly bigger, and hit just as hard, if not harder.
For being a somewhat smaller guy and having an awkward build, Bob Fitzsimmons was truly a remarkable fighter.. Lineal titles in three weight classes. Wins over some pretty big men. Giving a prime Jeffries the fights of his life. And sticking around in boxing to the near age of 50 which back then was about the equivalent of fighting to 100. He definitely makes my top 10 p4p all time.
Gibbons lasted just fine. Dempsey's reckless style might dovetail perfectly with Fitzsimmons' surgical trapsetting.
Fitz > Gibbons...But Fitz wouldn't fight a negative fight like Gibbons did...He would be coming to fight. I think it plays more into the hands of the bigger and very fast man in Dempsey...Who is a puncher.
I don't mean to...it's mainly just the styles for me, and the size. Fitz did KO heavys, and his physicality puts him near the top of the heap at middleweight...but I don't think he could beat a heavyweight as good as Dempsey.
Boxing evolved a fair bit from Fitz's time to Dempsey's with Jack being one of the innovators. Watching Fitz's footage is a bit like watching fencing on stilts. Dempsey just offered so many angles, had that uncoiled spring thing with defense mixed up with attack. I think he would bamboozle Fitz.
Fitz with those short hard counters inside Dempsey's lunging swings. Fitz loved to catch guys as they punched their way toward him, and he was pretty good at rolling shots to minimize the damage he took back.
Both hit like hell but I think Jack being the faster man gets the ko. But this a dicey fight for Jack.