Holyfields main problem was he liked to brawl. He would box, get hit and wing ten or eleven punches back at the guy. Usyk would eat that strategy alive.
I I'm not saying that Usyk has no chance of winning. But, i have never seen a fighter in my life that would "eat Holyfield alive" at cruiserweight. Evander was a beast at cruiser. And, an exceptionally skilled one.
I'll still take The Real Deal; he fought far better opposition by far though he lost to some of them. Head to head prime it's a fantastic fantasy fight.
Holy struggled with an aging Qawi in their first fight at cruiser. He got a lot better and buried Qawi next time out (I have to ask...PEDS?) and took out other good guys like De Leon, but even in his prime, he sometime struggled with smaller fighters who also came up, like Moorer and Cooper. Not sure if Byrd and Toney are worth mentioning, as that was late career, but there seems to be some notable pattern of success against him from smaller guys. I voted for Usyk, but I am real curious that Holyfield has so few supporters in this thread.
It was only Holyfield's 12th professional fight when he fought Qawi the 1st time. Also Usyk's toughest fight was against a smaller opponent in Briedis at Cruiserweight aswell.
It might depend on when and where, but I'd probably back Usyk. In the here and now, Usyk overwhelmingly likely to win - a prerequisite for the hypothetical is they both make it to the ring, which means Evander is off the PED's. In the 90's, with Holy on PED's? Probably depends where it is - I think Usyk would do enough to shade it on honest cards, but it'd be close enough for a Vegas robbery to be plausible.
Holyfield More proven against better opposition. I voted by decision, but I could also see Holyfield stopping Usyk.
I think stylistically Usyk does a bit better than Holyfield does against Super Heavyweights. Usyk's boxing ability, southpaw style, movement, is a perfect combination to take down the bigger guys. But in regards to great Heavyweights of similar size I don't think there's much between Usyk/Holyfield IMO.
Holyfield was dirty with headbutts, but he wouldn't turn up throwing lots of deliberate low blows like Dubois did (including the one that dropped Usyk).