Holyfield vs Dempsey

I would give Dempsey a good chance against early 90s Holyfield. Holyfield was a great boxer but he liked to mix it up and I don't think his power/chin was much better than Dempseys. Can see it going either way, although Holyfield is capable of outboxing him if he fights the right fight.

Mid 90s Holyfield is just too strong, powerful and durable for Dempsey.

 

Two of the toughest, fiercest competitors in heavyweight boxing right here.
They're very similar in size, although Evander would outweigh Jack that would be more to do with muscle he bulked up on rather than natural size. Jack was bigger built then most seem to know.

Similarly to Marciano he was a well built guy and I think they could both have weighed upwards of 200lb, but 190 was a more optimum size for guys who have to go 15 rounds or more old school. Most don't realize this.

Another thing, Both "The Real Deal" and "The Manassa Mauler" love a fight even though they know how to box. Even when they're in with much bigger men both guys just can't resist going for broke when they smell blood, so this would be a great fight.

In terms of tools they both have hand speed although I think Dempsey's short punching was better, not much in it there and they both have solid jaws. Power goes with Dempsey. Holyfield could hit, make no mistake, and made great use of his power, but he lacked that natural club-handed beast trait that allowed Dempsey to floor the likes of Willard and Firpo with almost every punch. Holyfield has slightly better footwork and Dempsey has the better head movement. Aggresive and offensive.

I see both men charging out at the bell, Dempsey taking ring centre at first because that's how he was, few started as fast as Dempsey. He and Holyfield start s****ping and Holyfield gets caught by a left to the head along with some shorter shots to the body. The brawl for the first couple of rounds but Holyfield is taking more wear and tear. Dempsey's too quick toe to toe, one of the best inside fighters there ever was.
Holyfield starts going all "Bowe II" with his flurries of movement and boxing. Holyfield finds his rhythm and takes some rounds but the draining shots he took inside early limit his mobility. Jack finds him time and time again and Holyfield gets that Warrior blood boiling again and starts to fight. He and Dempsey both land well but brawling is Jack's world and his stamina stands up better than Evander's. His in and out head movement and bob and weaving also see him taking less damage. Holyfield doesn't have enough left in the tank to steal the remaining rounds and Jack goes to town, but Evander's heart and conditioning keep him in for the distance. Jack Dempsey WUD15

 

Holyfield bulked up over the course of the decade and by the time he fought Tyson, he was as strong as a bull. Tyson was surprised how strong he was.

He also hit harder, he sat on his punches more and IMO I thought his improvement in power by Bowe III was clearly noticeable in contrast to their first fight.

 

I'd pick Holyfield in a war.

 

I don't like to speculate. It is what it is.

 

You should just specify a version of Holyfield. Creating a mythical version of Dempsey is impossible. He could turn out to be a completely different fighter.

 

This could potentially be FOTY material. I'd also favour Holy slightly. For me, more well-rounded than Dempsey and as tough as old leather.