No he didn't. Holyfield's a superior fundemental boxer to Dempsey, though Dempsey probably has the edge at mid-range, but it's a negligible edge at best. Gene Tunney proved that if you can box Jack and nullify his offence with good counterpunching/combinations and footwork (plus a strong jab), you have him beat. Easier said than done but Holyfield has all the tools to get the job done. Impressively so.
Has Dempsey ever been Koed? Dempsey fought several big men, much bigger than Holyfield. But you think he gets Koed in the first 3 rounds?
Right, but Tunney is smaller than Dempsey and probably had equal speed. I think Holyfield is one of the better skilled heavyweights of recent times, but I disagree that he was as skilled as Demspey. Demspey had the best aggressive defense at heavyweight of all time in my opinion, and was an adept counterpuncher. Holyfield is a solid boxer, but he's definetely not a better boxer than Tunney, but he does have size, which Tunney didn't. You're talking about one of the best boxers in history in Tunney. Holyfield is versatile and good at everything, but Demspey is faster and more intelligent than Qawi, and a much bigger puncher. I will say that Holyfield may have been more versatile than Dempsey because Dempsey's goal was to knock you out, but Dempsey is better at his style than Holyfield is at his when he's boxing.
From the clips I've watched of Dempsey he was a vicious and relentless puncher, build him up a bit to circa 220 with "modern methods", like Holyfield used, and he'd be sticking Holly on his ass like Toney did.
1 KO loss only, but it's rumoured to have been a fix. He KO1'd the same guy the same year, 1917, so go figure.
I should not have give any rounds but Holyfield destroys him early. I honestly dont think Evander would respects Dempsey much and would rough him up inside and slug him out of there. Holyfield took bombs from much bigger opponents whom definitely punched much harder than small Dempsey.
Firstly the Holyfield from Qawi 1 wasn't a prime Holyfield. He was still green and inexperienced, not to mention physically smaller. Holyfield has a better jab that Dempsey, he has the edge in handspeed (though its close), he punches straighter and has better combinations (again close), he's stronger on the inside and he's physically stronger too. He also has the the chin to survive Dempsey's (mostly) wild rushes. As soon as Dempsey gets close Holyfield would just tie him up and push him back. Holyfield certainly isn't that far behind Tunney in skillset, like you're making out. If at all.
The only guys I can think of that Holyfield faced that have punching power on par with Dempsey are Lewis, Bowe, and Tyson. The only one with speed was Tyson, who was past his best. But Tyson and Demspey had very different styles, and honestly, Holyfield may rough Dempsey up with his head, but if anyone is going to be be landing punches, it will be Dempsey who throws more compact combinations and has the handspeed advantage. Holyfield's best bet would be to box Dempsey from the outside, get in uppercuts when he can, and then tie him up when he comes in close. If Holyfield chooses to trade with Demspey, I think he gets put down, regardless of how good his chin may be. Demspey was a serious puncher. He reminds me a little bit of Pacquaio with his movement and explosive punching power.
I disagree about Holyfield's jab. Demspey used a jolting jab that was very effective at initiating his inside swarming attack which consisted of tight, highly compact combinations. Considering he had the speed advantage, I think this would be the worst place for Holyfield to engage Dempsey. I think Holyfield has a great jab too, but in this case, they would be used differently. Holyfield would use his jab to stay on the outside, and Dempsey would use his to get inside. I can't really say who's is better, but I think Dempsey's speed advantage could play a pivotal role. Like I said, I think Holyfield's chin, toughness and skillset would make this a very difficult fight for Dempsey. And while I used Qawi as an example, Demspey has much better footwork, is much faster, and has better aggressive defense. Honestly, Demspey is a lot like a heavyweight Pacquaio.
The problem is Dempsey never used his jab much at all, and like Manny was often wild and reckless in his attacks. This wouldn't work against the Holyfield of say, the Foreman or Bowe 2 fights (where Holy outjabbed Bowe). He would physically get the better of him, push him back and wear him down with fast counters when Dempsey gets desperate in the later rounds. Still though I guess we'll never know, it's all subjective, ha
At the peak of his powers Dempsey was only about 190 pounds and a shade over 6 feet tall - I dont think he'd have enough to beat one of the greatest heavyweight warriors of all time in ring under modern boxing rules. in a box car or back of a saloon Jack would murder him though - thats just how he rolled.
I don't think his size is that big of a factor except in the sense that he may not be as durable as bigger men. He certainly could hit as hard, but he had the speed of a small man, and he had an iron chin. I think it would be a great fight. Holyfield would have to respect his speed and power, and box him from the outside, and rough him up when he can, but be very careful of Dempsey's quick hands and power. Honestly, I would just tie him up when he got inside and headbutt like Holyfield tends to do.