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How would Oleksandr Usyk fare against past greats of the division?

Luke G

21st June, 2025

How would Oleksandr Usyk fare against past greats of the division?

Luke G. Williams ponders some mythical match-ups involving the Ukrainian, with expert insights from Usyk cornerman Russ Anber along the way…

WHEN Oleksandr Usyk moved up to heavyweight having cleaned out the cruiserweight division, the conventional wisdom – borne of the old adage that ‘a good big ‘un always beats a good little ‘un’ – was that he would be unable to take the scalps of the likes of Anthony Joshua and Tyson Fury.

Post-Lennox Lewis and Wladimir Klitschko, and with the towering Fury ensconced as lineal champion, the presumption was that a blown-up cruiserweight would prove too small to rule what seemed to now be a ‘super-size’ heavyweight division. Recent boxing history apparently supported such a contention. Exhibit A? How easily a 242lbs Wlad handled the 212lbs David Haye in an eagerly awaited 2011 showdown in Hamburg that proved a damp squib. Exhibit B? The way Fury bullied and bludgeoned the murderous punching but smaller man Deontay Wilder across three fights from 2018 until 2021.

Seven fights at heavyweight later, however, and Usyk has turned prevailing wisdom about how big a heavyweight needs to be in the modern era completely on its head, beating Joshua and Fury twice apiece, despite ceding significant height, weight and reach advantages. He’s also notched a victory against another bigger man, 233lbs Daniel Dubois, into the bargain.

Usyk

Russ Anber – Usyk’s valued and expert cornerman for the most recent 13 bouts of his 23-fight pro career – sees these successes as evidence that the Ukrainian – who turns 38 on 17 January – could compete with any heavyweight in history.

“I don’t know what number you would rank Usyk at among the great heavyweights, but you could put him in with anybody in history and he would have the skill set to compete,” Anber argues. “Size makes a difference but in Usyk’s case when you compare him to most of the other great heavyweights in history he’s a similar size or even bigger than the guys who are often considered the quintessential heavyweights – guys of around 220lbs, such as Ali, Frazier and Foreman. As for the likes of Rocky Marciano and Jack Dempsey, they were shorter than Usyk and, in their prime, fought at about 185lbs. Significantly smaller than a full-fledged modern-day heavyweight like Usyk. 

“Until Lennox and the Klitschkos came along, that sort of size was the norm for top heavyweights. Guys bigger than that – Primo Carnera, Jess Willard and so on – didn’t have the same level of success as the likes of Ali or Joe Louis. The fact that Usyk has had success against Joshua and Fury shows that size isn’t an impediment if you’re highly skilled. Usyk could have fought, succeeded and competed in any era – including against super-sized heavyweights such as Lennox and Wlad.”

With this in mind, let’s consider how Usyk might fare in mythical match-ups against some of the great heavyweights of yesteryear.

In each case examined below, the final verdict is my own opinion, but I’ve also included the thoughts of Anber along the way.

Usyk vs Jack Johnson

Anber’s insight: “Jack Johnson was brilliant. He was a true ring scientist. He had great footwork, excellent hand-speed and knockout power, as well as fantastic defence. He wouldn’t have been an easy target for Usyk though because he wouldn’t have stuck around to be hit. Johnson was just as fleet of foot as Usyk and this would have been a very exciting chess match. The southpaw factor would play a role here though.”

My verdict: Usyk versus Johnson over 12 or 15 rounds? I’d take Johnson to outfox Usyk and tie him up – but only if the referee was applying the standards of Johnson’s time as opposed to today in terms of how much grappling and holding were allowed. Usyk versus Johnson over the insane distance of, say, 45 rounds? The outcome is anyone’s guess.

Usyk vs Jack Dempsey

Anber’s insight: “To be honest, I think if he was fighting today Dempsey probably would have fought at light-heavyweight. I don’t think he ever weighed more than 194lbs, which is below the modern-day cruiserweight limit. Sure, Dempsey fought a much bigger man in Jess Willard when he won the title, but Willard didn’t have the skills of a Lennox Lewis.

If Dempsey fought Usyk then Usyk’s size would have been a real issue for him. Jack was certainly vicious and came to fight but he had limitations. If you look in detail at Dempsey’s career, there’s the fact he never fought a black fighter when he was champion and he never beat a truly great heavyweight either, so I’m left wondering how he would have handled a guy like Usyk who’s 6ft 3ins, 225lbs, moves like a middleweight and brings such intensity. Dempsey found Tunney too swift of foot and I think he would have been totally baffled by the footwork and southpaw style of Usyk.”

My verdict: As much as I love Dempsey, I’m with Russ on this – Usyk would have been too big and too skilful for the ‘Manassa Mauler’. Tunney befuddled him, and Usyk would have done the same.

Usyk vs Gene Tunney

Anber’s insight: “This is a problematic fight for Usyk. Tunney’s skill-set separates him from other boxers of the last century of a similar size. I think Gene was incredibly underrated. The way he toyed with Dempsey showed how good Tunney was, as well as perhaps exposing just how one-dimensional Dempsey was. Dealing with Tunney’s movement and skills would have been very difficult from a cerebral perspective for Usyk.”

My verdict: A fight for the connoisseurs – Tunney and Usyk are too of the most single-minded pugilists to ever rule the division. Usyk’s size would give him an edge, but if Gene was able to use modern training methods to bulk up, then over a three-fight series, I’d back his incredible boxing brain to figure out a way to shade a trilogy 2-1.

Usyk vs Joe Louis

Anber’s insight: “Wow – what a fight this would have been! If Usyk was to have any success against Joe Louis he would have had to use his movement. As great as Joe Louis was, and as much as I love him, I think it’s a fair statement – as well as a consensus opinion among boxing observers – that movers gave Joe Louis problems.

Billy Conn and Jersey Joe Walcott gave him issues, for example, and I think Usyk could have caused him major problems too. Certainly, if Joe had one flaw it’s that he was a bit slow of foot. Another thing that could have been decisive – and I’m wracking my brains here to be sure – but I don’t think Joe Louis ever fought a southpaw.”

My verdict: Anber is 100 per cent correct – Louis never fought a southpaw, indeed it’s often claimed that after suffering sparring fits against Melio Bettina he vowed never to fight a left-hander. With this in mind, Usyk’s style seems tailor-made to give Joe nightmares. I’d take Usyk to upset the man most view as the second greatest heavyweight who ever lived.

Usyk vs Rocky Marciano

Anber’s insight: “The night Rocky won the title, let’s remember that Jersey Joe Walcott was ahead and beating him. If it had been a 12-round fight Marciano would have lost. That fight gives us an indication of the problems Usyk could have given Rocky. However, let’s also not forget that Marciano knew how to put an opponent under pressure, and you could never write him off until the final bell. Usyk would have to box circles around him to win. From a coaching perspective, Rocky’s style of constantly crouching to his right would not have played out well against the slick southpaw.” 

My verdict: Marciano seems to be overrated or underrated depending on who’s assessing him – what cannot be denied is that the ‘Rock’ was one of the toughest hombres to ever pull on a pair of gloves. Could Usyk have succeeded where 45 other men failed across 49 fights? On balance, I’d say yes, but the Ukrainian would have had to go through fistic hell to prevail.

Usyk vs Liston

Anber’s insight: “This fight would depend on which Liston showed up. Usyk has an incredible ability to find a way to win though and I think he could have done just that against LIston, in a similar way to how Ali did. Usyk couldn’t have just stood there and traded with Liston, but if he followed the Ali recipe to perfection and avoided a war he could have prevailed. I certainly wouldn’t expect Usyk to stand there and let Liston bomb away the way he did against Patterson”

My verdict: A truly unpredictable fight – the fearsome Sonny of 1960 that wrecked Cleveland Williams, Roy Harris and Zora Folley would have had a chance of stopping Usyk, but I get the feeling the Ukrainian’s superior stamina and mindset would have proved crucial.

Usyk vs Muhammad Ali

Anber’s insight: “Stylistically, I think Ali would have been a nightmare for Usyk. The movement, the speed and the defensive ability of Ali would have made life very difficult. Mind you, bear in mind I’m talking here about the peak Ali of the mid-1960s, who was gone by the time he came back from his ban and fought Frazier. The Ali of 1965 or 1966?

I don’t think there’s any heavyweight in history who would come out on top against him. I just don’t see who could beat him – I love Louis, I love Usyk, but Ali at his best when he was dancing, moving and hitting guys at will, well, you couldn’t touch him with a handful of rice. The real Ali, the prime Ali – no one would beat him, probably even if they fought the fight of their lives.”

My verdict: Peak Ali to best Usyk on points, the faded Ali of the early to mid-1970s to eke out a potentially debatable points win, depending on how seriously he had trained.

Usyk vs Joe Frazier

Anber’s insight: “An interesting fight, and a dangerous fight for both men. This would have been a fight where Usyk would have to somehow find a way to win against the relentless pressure of Frazier. If Usyk could use his feet and movement, I think he could do so.

Let’s remember that Frazier never fought the Ali that fought Sonny Liston – had Joe fought that Ali I don’t think he would have been as competitive as he ended up being across their trilogy. I don’t think Frazier would have caught up with that Ali. It would be a very tough fight for Usyk and he would have to make sure he didn’t walk into Joe’s left hook.”

My verdict: Usyk to prevail in a classic war, with his movement proving the key.

Usyk vs George Foreman

Anber’s insight: “This is one champion who didn’t seem bothered by the southpaw stance. Ask Michael Moorer! Nonetheless a very tough night for Usyk here. On any given night, the best of George Foreman could beat any heavyweight who ever lived. I remember talking to [trainer] Marc Ramsay about this once.

We decided that if boxing was like ice hockey and had a draft system whereby you could pick fighters for your promotional stable and, if you could pick fighters from any era, then our first pick would be George Foreman. With the power he had, George could beat anyone.

Some people have said that if Foreman fought Ali 10 times he would win nine of them and I might well agree with that. However, then I think of the great Jimmy Young, and what his skill set did to George, and I think Usyk could emulate that blueprint.”

My verdict: Although Foreman’s power is to be respected, I think that Usyk could tire Big George out with his superior feet and relentless feints and pressure to take a decision victory.

Usyk vs Larry Holmes

Anber’s insight: “This would be a terrifically difficult fight for Usyk and every fighter who ever lived! If you look at Holmes’s skill-set, his longevity, his heart and his chin, there’s not a lot of guys who would beat him on his best night.”

My verdict: The best Holmes would edge the best Usyk – courtesy of that jab and his incredible powers of stamina and recovery.

Usyk vs Evander Holyfield

Anber’s insight: “This is a pick ‘em fight, between the two greatest cruiserweights of all-time, but I think I would go with the overall skill set and defence of Usyk proving decisive.”  

My verdict: Holyfield is that rarity among modern heavyweights – namely, a fighter against whom Usyk would have had a size advantage. For his cruiserweight classic against Dwight Muhammad Qawi in 1986, the ‘Real Deal’ weighed just 186lbs (4 lbs under the then cruiserweight limit) and even against Mike Tyson a decade later he still only scaled 215 lbs. A peak Holyfield would give Usyk problems, but I’d take the Ukrainian to edge a barnstormer.

Usyk vs Tyson

Anber’s insight: “A tough fight and Mike certainly had the style and power to bother Usyk, particularly with the pressure of his inside fighting, where he would have tried to get right on Usyk’s chest. It would have taken great footwork from Usyk to stay away from Mike over 12 rounds, he certainly wouldn’t have wanted to stand in front of him.

Tyson would have been tenacious and maybe dirty at times, but I think he would have been surprised by how strong Usyk was. Question here is, what would happen if the fight didn’t go as Tyson wanted. How would he overcome that?”

My verdict: If Usyk could weather the early storm he could have demoralised and stopped Tyson late on. Mind you, the Tyson who iced Michael Spinks could have done the same to any heavyweight in history, Usyk included.

Usyk vs Lennox Lewis

Anber’s insight: “Believe it or not, I think this would have been a very competitive and hard fight, in the same way that Lennox’s fights against the smaller Evander Holyfield were. I like this fight a lot. Usyk would have given Lennox some problems. I see this as a very competitive fight – not an easy fight for either man. Lennox’s size wouldn’t have been decisive here – it would have been a case of who applied their skill-set better on the night.”

My verdict: Lewis to prevail in a 12-round classic, with his jab and moments of success for his fearsome right uppercut proving decisive.

Usyk vs Wladimir Klitschko

Usyk and Klitschko

Anber’s insight: “I really like Usyk in this fight and I tip him without any hesitation. As much as I like Wladimir, he essentially was able to do a couple of things very well and very simply: namely, bounce on his toes, probe with the left hand and hit you with the right.

And that’s not enough to beat Usyk. Klitschko’s style would work against him against Usyk, the ability and speed he has and the variety of his combinations leaves me in no doubt that he beats Wladimir.”

My verdict: Usyk to outwork and exhaust Wlad and stop him late on.

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