Take Jack after the unforgivable losses to Flynn and Meehan, then throw him in against the following in succession: Trevor Berbick 31-4, 6-2, 80" Reach, 218 pounds James Bonecrusher Smith 19-5, 6-4, 82" reach, 233 pounds Tony Tucker 34-0 6-5 82" reach, 221 pounds Pinklon Thomas 29-1. 6-3, 77" reach, 217 pounds Tyrell Biggs 15-0, 6-5, 81" reach, 229 pounds Larry Holmes (pretty much same age as the Willard Dempsey beat with a lot more good fighting ahead of him) 48 and a very disputable 2, 6-3, 225 pounds Tony Tubbs, 24-1, 6-3, 80" reach, 238 pounds Mike Spinks 31-0, 6-2, 79" reach, 213 pounds Frank Bruno 32-2, 6-3, 82" reach, 228 pounds How does he fare?
How many rounds. Glove size? Modern ruling, or knock em down once they rise contest? Right away I suspect he'd lose to Tucker and Holmes. He would probably be able to out-work Tubbs and Smith. Biggs might be too inexperienced and I'm not sure about Thomas. Spinks is interesting but maybe too immobile and old at this point to win but could surely last a hell of a lot longer than he did against Tyson. Bruno is tough because he'll surely gas in the later rounds but would be pasting Dempsey with the jab and he has neutralizing power. He's a hell of a lot better than say Firpo.
One of these big punchers might catch him...there are a couple of puncher's chances in that lot. But on a case by case basis i'd pick Jack.
I think a decent boxer with a solid chin would give him problems...of those, Spinks, Tubbs, Tucker and Holmes fill that requirement. Yeah, I think Larry at that stage was still an effective fighter with great ring smarts. Spinks is often disregarded because of his blowout loss to Tyson, but he was a capable heavyweight and actually bigger than Dempsey. These guys I think would be the ones most likely to upset Dempsey. Biggs...not sure. I don't think he was really tough enough or experienced enough but he had lovely movement and a beautiful jab. I think he lacks staying power though. Bruno probably gets mashed...but Frank would be huge compared to Jack in terms of bodyweight and would not go down quickly. I just think Dempsey is too quick and savage for Bruno. I'm a bit up in the air about Berbick, Thomas and Smith. A prime Pink would be a great pick for me, but the one that faced Tyson was faded. But, for all we know, they could all beat him. Scandalous to say I know, but who can say?
When did Demspey face anywhere near a succession of this calibre of fighter who at the same time had the physical tools that these did? Not just on old Willard, or a string bean Fred Fulton or a Carl Morris on a losing streak, but large, long highly-skilled heavyweights on sustained winning streaks or at least who were former champs? I don't think anyone can say with any degree of veracity that Dempsey even goes .500 against this line-up were he to fight them in succession.
You must be kidding. Dempsey took great shot, if hit. He had defense,and was a fighter Tyson admits copying some moves from. He had great punch, and most of those guys on list are joke. Spinks vs Dempsey? atsch
There is no comparison between any of those listed and the fighters Dempsey fought. Most of his opponents were smaller, shorter, less rangy and possessed less impressive records. Remember that Mike Spinks as a heavyweight was basically the same size as Firpo, 6-2 1/2 and 210+. Firpo, the "giant" from the Pampas. And Mike Spinks was the midget in the line-up presented above. Now, if Dempsey had fought Wills, my argument would have slightly less than it's impressive credence.
I'll post Janitor's response- " Anyone who believes that this line of opponents would stand even a remote chance against Dempsey, should be covered in treacle and rolled in feathers. There is a great descrepency between the talent pool of Dempsey's period and that of Tysons. "