I'd pick Jack Dempsey. Holyfield was great: fast but Dempsey was faster: powerful but again Dempsey hit harder. Dempsey's swarming style plus Holyfield's willingness to trade in this fight would cost him and he'd either lose by decision or a late stoppage in an entertainig hard fought contests.
Holyfield v Dempsey two determined warriors. Dempsey would have the edge in speed and power. Holyfield would fight all night but he never had genuine KO power even as a cruiserweight. Dempsey puts the heat on Evander early and the Georgian has to starting jabbing and moving or get KO'd. At 190lbs Evander doesn't know how to run so he trades and Dempsey bowls him over by the 8th.
I don't see 190 lbs. Holyfield being overwhelmed by anybody but a large heavyweight. What made Holy special from the beginning, was a ring intellect that most young fighters don't have. He would know to hold Dempsey, to keep moving laterally. Sure, he'd stand and trade sometimes, but nobody is going to just carve that chin up. Holyfield had a solid punch at cruiserweight, a great chin and incredible stamina. He's one of the few modern fighters who wouldn't get rattled going into the championship rounds, beyond the 12th. Yes, Dempsey is a handful at 190, but Holy was at his perfect weight there. Qawi was no Dempsey, but Holy did very well dealing with the pressure - the kind of pressure few fighters in history could handle in their 12th pro fight. Holyfield possesses some of the intangibles and boxing acumen that Tunney used successfully against Dempsey - not a peak Dempsey, I know, but the style still gave him problems - and Holy would know what to do in the ring with Dempsey. Plus, this idea that Holy would get too caught up in standing and trading with Dempsey.... that was HW Evander, the guy with the Napoleon complex, who wanted to prove he could bang with anyone. At CW, Evander boxed; he moved. He didn't get left hook happy or flat footed all the time. This is a pick em', to me, because Holy has the necessary physical and mental skills necessary to give Dempsey fits.
I think it's too close to call a winner on this fight. I believe Dempsey at his absolute peak might be devastating enough to be favoured over, or at least 50-50, with virtually ANYONE. But Holyfield's style has always thrived against the most aggressive high-energy type fighters. Holyfield is the ultimate counter-fighter A match-up of these two is guaranteed to be exciting. And there will be no quitting or faking in this one. Two warriors making war. What more can you ask for ?
I say we give Dempsey some time to get on Roids also and then catcup to Holy in that category then lettem fight.