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Holyfield Names the One Active Fighter Who'd Have Given Him Trouble

The only four-time heavyweight king says a 25-0 southpaw would've been a nightmare — and his reasoning is all about style, not power.

By FightSplit Editorial Team · Published Aug 26, 2026

Oleksandr Usyk celebrating a heavyweight title victory in the ring
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Evander Holyfield beat Mike Tyson, Riddick Bowe, George Foreman and Larry Holmes. He's the only man in history to win the heavyweight title four times, and one of just two fighters — Oleksandr Usyk being the other — to go undisputed at both cruiserweight and heavyweight. So when Holyfield says there's a current fighter he isn't sure he could have handled, it's worth stopping to listen.

That fighter is Usyk, the 25-0 Ukrainian who sits atop the division as lineal champion with 16 knockouts on his ledger. Speaking to Boxing Social, 'The Real Deal' admitted a fight with Usyk would probably have been a difficult one — and his reasoning had nothing to do with punch power.

Holyfield explained that the opponents he thrived against were bullies and aggressors, the come-forward types he could read and counter. His rule of thumb for spotting a bad matchup: find a fighter built like yourself. The awkward, non-aggressive stylists were the ones who gave him headaches — and that's exactly the box Usyk ticks.

It's a candid self-assessment from a man who spent his career solving problems most heavyweights couldn't. Usyk isn't a wrecking ball. He's a movement-first southpaw who wins on angles, feints and volume, and that's precisely the profile Holyfield says he never fully cracked.

The Résumé Behind the Praise

Usyk has earned every word of it. After his own undisputed run at cruiserweight, he moved up and beat Tyson Fury, Anthony Joshua and Daniel Dubois twice each, becoming a two-time undisputed heavyweight champion. Fury (36-2-1) has since drifted to the fringes of the top three; Joshua (29-4) and Dubois — now WBO titleholder at 23-3 with 22 KOs — both rebuilt after losing to him.

The picture gets more interesting from here. Usyk looked underwhelming last time out in a TKO win over kickboxing star Rico Verhoeven, and he's since announced he'll fight just once more before retiring. A surprise name has reportedly emerged as his potential farewell opponent. Whoever it is, they'll be sharing a ring with a fighter a genuine great just told the world he'd rather have avoided.

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