Dempsey's filmed fights are, and in order of occurrence: Jess Willard Bill Brennan II Georges Carpentier Tommy Gibbons Luis Firpo Gene Tunney I Jack Sharkey Gene Tunney II ranked worst to best: 8. Gene Tunney II. It may seem surprising, but in the Long Count fight, Dempsey really was not doing much of anything before he put Tunney on the floor, and actually looked worse afterwards, which seems to defy logic. However, Dempsey did at least show his vaunted power. 7. Gene Tunney I. I know it's controversial for me to say it, but Dempsey was overall a better fighter here, even though he didn't show the kind of power against Tunney that he did in their rematch. But Dempsey put up a much busier, closer effort against Tunney, and I hope you can all agree with me the first fight was closer than the second. 6. Tommy Gibbons. Tbh, the only reason I rank this higher than the Tunney bouts is because Dempsey won, obviously. Other than that though, Dempsey looks just plain mediocre. He can't put away a seemingly mediocre light heavy, in an awful maul-and-brawl affair. 5. Jack Sharkey. I also think Dempsey looked bad here, and of course, it was controversial for me to say in the past, and probably no less now, but I believe Dempsey fought on even terms with a young Sharkey which was impressive, and did knock him out, although he probably low blowed Sharkey first, and then hit him when he wasn't looking. Not the most impressive knockout considering he was exploiting a vulnerable Sharkey. 4. Georges Carpentier. This is where I think the list seriously improves. Carpentier, though a light heavyweight, was very fast, strong, and overall a good athlete I'd say. The only reason I don't rank this one higher is because Carpentier was a light heavy. 3 & 2. Although most of these are hard to order, I had to tie these two because of how difficult they were. Luis Firpo and Bill Brennan. I have higher regard for Firpo as a heavyweight, and their both being heavies is what got them top spots on this list, but I am tied because of this: The Firpo win is a lot more impressive to watch, because Dempsey clearly showed a lot of power knocking Firpo down 9 times, and showed even more heart and chin climbing back in the ring after a knockdown to stop Firpo. On the other hand, after a thread on Brennan II a couple months ago, I want to rank it higher. It's not a glamorous win, but in all actuality, Brennan looked a better opponent than Firpo. Firpo was a little overweight imo and a wild, unskilled brawler. Brennan, however basic he was, showed some skill. 1. Willard. Imo his win over Willard cannot be matched. Dempsey was in decline from the beginning of his title reign. Willard was certainly not the greatest fighter ever, by no means, but Dempsey was a perfect fighting machine. Bobbing and weaving wonderfully, showing a good jab, and showing a helluva lot of power by battering Willard all over the ring as he dropped the giant 7 times in the first round. Unquestionably Dempsey's best. How do you guys have it? I would love to see how you guys order his fights and why. 1.