1. Are we using a prime Dempsey here or the rusty shell of himself who fought Tunney? 2. Tunney and Holyfield fought literally nothing alike. Polar opposites.
The Real Deal would make Jack reel, hurt him so bad he won’t know what to feel, send him to a hospital to heal after choking on that Real Deal meal.
I go with the pre Tunney version of Dempsey to win this one---KO or stoppage 8-10 rounds. Harder puncher and would swarm Holyfield until he eventually caved!
What helps me when it's hard to decide is to make two scenarios, one for each fighter winning and how I think they'd win it.
I don't know if people realise how interesting this really is. When Holyfield was twelve years old, he called Dempsey to tell him he'd one day get revenge for him over Gene Tunney. In late 1978, Evander Holyfield snuck into Tunney's room and asphyxiated him with a throw pillow. I don't know what throw pillows are exactly but it's apparently some kind of pillow that you would be capable of smothering a man to death with. A hitman's tool, presumably, if this story is to be believed. I don't claim to know and it's possibly very Natalie Wood and we'll never really know. But with that interpersonal dynamic, either way, it adds a dimension of interest and intrigue to this match-up.