I'll pick Dempsey. Better hand and foot speed...at least he seems to be faster based on the footage of both of them and his bob and weave style would be problematic for the stand up straight hands down style that Bob employed. I've read how Fitz was a trapsmith and liked to trap an opponent into a big shot but I think that wouldn't work against Dempsey. He might catch Jack coming in because Dempsey would be on him from the opening bell but could he stop him? Or catch him cleanly enough times to do the trick? The best footage of a young..or younger Fitz is the Corbett fight and barring the solar plexus punch, Corbett was winning and putting it to Bob...and Jim was a mobile tho stand up straight fighter as well. I just think Jack's style, combined with his own speed of hand and 2 fisted power might be a little too much for Fitz. Dempsey by mid round KO.
Dempsey. He had more than a right hand and some semblance of defense. Unless Dempsey walks into a right (which is possible, considering he got beat from pillar to post by Firpo), he whips his ass.
Although Fitz was a freak for his size I don't think any blown up middleweight beats Dempsey. Another extremely hard punching smaller man in Carpentier made no impression on Dempsey and as much as i'm a big admirer of Ruby Rob I can only see one outcome here.
Carpentier did make an impression on Dempsey, and Carpentier was a bit of a sham, whereas Fitz was the real deal. Quicker, shifty fighters caused more problems for Dempsey. Fitz was lauded for his quickness and timing and was a two fisted puncher. I'll take Dempsey to walk through and beat him down though.
There's various opinions.Some say he really shook Dempsey up he certainly lands a lot of leather on Dempsey in the footage. Others say Dempsey carried him for a few rounds. I agree though Fitz was probably much more of a proposition than Carpentier.
Prime Dempsey with his bobbing and weaving style...and heavy two-fisted attack would be too much for Fitz...
Fitz wasn’t easy to stop by any means. From February 1890 to November 1905, only Jeffries stopped him in a near 15 year period. Durability is best judged when a fighter is hit, and during this time the likes of Choysnki, Sharkey, and Maher landed on Fitz. Many who lived in the times felt Fitzsimons was a better puncher than Dempsey and rated him higher than Dempsey. A cunning strategist in the ring, Fitz combined tremendous leverage on his blows with uncanny accuracy. I like Dempsey in the first third of the fight, and Fitz beyond round 9. 60/40 in favor of Dempsey.
I'd favor Dempsey, but not to walk through Fitzsimmons. Fitzsimmons would have a chance, but I think he'd need to get through quickly. I question the notion that Corbett was winning against Fitzsimmons because he was having the better of the rounds. It was a finish fight, so there wasn't going to be any decision or scoring. Corbett was chalky and seeming to be weakening in the rounds leading up to the KO, and it doesn't sound like many in attendance were looking for him to last.
Choynski had him down and nearly out, Fitz survived and dropped Choynski 4 times in the 4th and twice in the 5th to end it. Sharkey had him on the floor early in their 2nd fight. Maher floored him in their first fight and had him ready to go when Choynski ,who was in Fitz's corner entered the ring claiming he had heard the gong, picked up Fitz and steered him to his corner. Corbett had him down in the 6th rd Dempsey would probably keep him there.
It's actually a fight Fitz could win, think Firpo or dare I mention it, Jim Flynn? Fitz was very sneaky and a counter-puncher. As McVey said he was dropped by some really good punchers, Maher and Choynski were in Dempseys bracket as punchers but he showed Holmes-like recuperative powers. Nobody hit Jack like a trap-setting Ruby Rob so who knows?
This just proves that Fitz was a hard man to stop. Dempsey was floored by lesser punchers than Sharkey and Maher, and has a ugly KO1 loss on his resume. It could go either way.