H2H is close could go either way. But legacy wise Holyfield is higher beat better names, beat more top 10 ranked fighters, considerably more world title wins. Usyk edges Holyfield at Cruiserweight for resume but overall resume its clearly Holyfield for me.
Cruiserweight: I think its pretty clear Usyk is better. Breidis and Hunter are better than any of Holyfield's cruiserweight opponents IMO. Glowacki is another good win that is comparable to Holyfield's best wins at cruiser while Breidis is way superior to any of Holyfield's cruiserweight opponents. And while Huck was past it, Bellew was also past it despite his wins over a past it Haye, and Gassiev just hasn't accomplished much despite the hype, these are still all solid wins. Heavyweight: I think Holyfield has the edge here due to the quality of competition he beat. Yes, Foreman was 42 but i will gladly take that version of Foreman over Chisora and perhaps even Dubois. 93 Bowe is a fantastic win, and then the rematch win over Moorer. Tyson in 96 was past it but still a good win over a unique style. Mercer is an excellent win. All of these guys have very different styles. Usyk has two very good wins over Joshua and two over Fury where he overcame significant physical disadvantages. The Dubois win is aging nicely. But in terms of stylistic variety, its hard to make a case here. Usyk will need to beat both Parker and Kabayel and maybe 1-2 other guys before surpassing Holyfield. H2H: I like both fighters but assuming you have a ref who won't allow head butting, i think Usyk wins a close decision over Holyfield. Usyk's jab would bother Holy the way Moorer's did and Usyk is quicker and smarter with a better left hand. On the other hand, Holyfield has an excellent left hook that will cause Usyk some issues as well as the cross. Holyfield has the speed and work rate to keep up with Usyk the way that giants like Fury and Joshua just can't do. Still, i think Usyk is a smarter boxer whose stance gives him an advantage. If they fight 3 times, Holyfield would likely win 1 but i favour Usyk to beat him 2 out of 3 times. All round ability Usyk has better defense, better footwork, and overall better boxing ability as he rarely gets caught in unnecessary brawls with more powerful fighters like Holyfield did. I also give the edge in jabbing to the Ukranian. Holyfield has a better lead hook, can absorb more punishment, is a slightly better combination puncher, can manhandle fighters a bit more. Usyk is physically strong and does not allow fighters to physically bully him but Holyfield used his physical strength to bully other fighters. All round ability is close but i do think Usyk having the better defense and footwork gives him slightly more of a shot at beating other ATG's.
Usyk is a better boxer, smoother, more efficient, better footwork, quicker hands. He beats Holyfield by almost every metric. But Evander beats him. And beats him up. Why? Hey, I don't have all the answers.
Usyk is the more skilled and consistent fighter. You see it in how cleanly he boxed through top-tier opposition without ever being outclassed. At cruiserweight, Usyk clearly stands above—he beat more quality opponents and became undisputed by winning every belt on the road. Holyfield was also unified, but his best wins there were just Qawi and De León. Usyk beat Briedis, Gassiev, Hunter, Glowacki all undefeated and prime fighters. His cruiser run was simply much deeper in a stacked Crusierweight era. At heavyweight, Holyfield's got more wins but also more losses and inconsistency. Usyk's resume is shorter, but beating Joshua twice, Chisora, Dubois, and Fury twice shows he's adapted his style and kept his form even against much bigger men. So while Holyfield was the better heavyweight, Usyk proved more across two divisions, and did it with fewer blemishes. Legacy-wise, I rate Usyk higher.
Holy Holy He's the better fighter. Usyk is quite overrated at this point. The giant glaring issue with me is he can't fight on the inside. He also doesn't take it to the body well. A smart pressure fighter will always give him problems
That's what I was thinking. H2H is close. Flip a coin (voted for Holy because he's my 4th favorite fighter) but legacy wise, Holy runs away with it (for now).
If Usyk finishes undefeated he has a much higher legacy. Almost all of Holy's good wins, outside of Bowe, were guys over 40 (Foreman, Holmes), morbidly obese (Dougals), or drug-addicted (Tyson).
Quicker hands? No. Here's Holyfield half-assing it again.. because he needs more comp. But so fast, he cuts Stewart to shreds This content is protected
Bull****, about asterik on all of Holyfield wins. Douglas-Tyson version would have got the same thing against that Holyfield.. maybe two more rounds.. which you didn't know then/now.. which is why you still picked/pick Tyson over him in 96'. Holyfield was definitley faster than Usyk. Like, Cassius Clay fast.
From what I have seen, including their records, I am going with Evander Holyfield for Head to Head and Legacy.