Hard to pick a definitive winner, would be a damn good fight. This is a match up where Holyfield's instincts to go to war would actually benefit him rather than work against him as you don't out box Usyk, not even Holyfield with his speed of hand and foot beats Usyk on the outside he has to pressure, throw in volume, make it a war. If he can do that he can win, but if he finds himself unable to force exchanges he'll get out boxed. I'm leaning towards Usyk. His movement and ring IQ are special even among great fighters and he's always found a way to win even when physically massively out matched and we've never seen Usyk even come close to losing. I think he can adjust to whatever Holyfield brings, the head butts, the speed, the volume doesn't matter what problem he's presented he can figure a way to overcome it. Usyk in a close decision fight perhaps a split decision.
I like Usyk in this. Forgetting about their physical attributes and styles for a minute, I simply think Usyk is the smarter fighter. Holyfield had a tendency to get sucked into fighting the opponent's fight. He insisted on brawling with Bowe and Foreman when he could have had a much easier time outboxing them. Holyfield just couldn't help himself. Against Czyz he tried to turn Bobby into a bloodstain by loading up on every punch and thus giving Czyz the opportunity to slip and counter. His trainer was telling him "Stop loading up. You don't need to load up for this guy. Whatchu loading up for?" and Holy was like "I know I know" and ... the next round he did exactly the same thing. Usyk is more like water. He's trying to avoid the opponent's strength while picking his punches. He's downloading the opponent's style and measuring his timing in the first half of the fight. Invariably, when he feels he has a handle on what the other guy is up to, he shifts a gear and starts picking the dude apart. If the other guy has a good rally, Usyk uses that analysis to have an even better rally and shifts up another notch. Holyfield never had that many layers to his game, and while superlative, his tactics were fairly straightforward. Usyk is one cerebral, tricky SOB in addition to having a great boxing level.