1920-Billy Miske 1921- Tommy Gibbons 1922-Harry Wills 1923-Luis Angel Firpo 1924- Firpo rematch /George Godfrey 1925 Gene Tunney If Jack had fought those men,on that time line, fighting every year ?
Would beat everyone except Tunney still wins decision and Wills and Godfrey are questionable. I think Wills was older by then so Dempsey might beat him. Godfrey served as sparring partner and decked Dempsey in training then bragged to everyone about it. Next day Dempsey confronted him and then decked him in sparring. This could be a pickem.
Word of mouth says Wills declined considerably by time of filmed footage of him. However if he fought anything similar to the filmed footage I have no doubt Dempsey sparks him. Had Dempsey simply fought him and won instead of taking 3 years off, he’d be a lock top 5-10 heavy to this day imo.
He could lose to 21 Wills. 21 Wills should be better then the Wills Dempsey ducked. Maybe considerably so. But otherwise Dempsey should be running that table.
Hard to say since he lost his motivation when he won the title. I think he beats all of them but they were going to be tough fights. Gibbons he beats in a tough 15 rounder. Wills - there is no good prime footage of him. He was supposedly slow but i have no idea. Obviously beats Fripo both times. 50-50 vs Tunney without the 3 year lay off.
Dempsey had trouble with boxers and Tunney dominated him so thoroughly that even a slightly younger Jack without the layoff isn’t going to knock him out and not going to do enough to get a decision. It’s closer but still Tunney by UD.