This month’s heavyweight clash between Oleksandr Usyk and Tyson Fury is shaping up to be a defining moment, not just for the two fighters, but for the future of the heavyweight division. For Usyk, the reigning unified champion, it’s a chance to cement his legacy as one of the sport’s all-time greats, having already conquered two weight divisions. Meanwhile, Fury, the self-proclaimed “Gypsy King,” is fighting to reclaim his throne after suffering the first professional loss of his career earlier this year to Usyk. There is no love lost between the two following an exciting bout back in May, and the rematch in Saudi Arabia is increasingly tough to call, with little separating the Tyson Fury betting ahead of December 21. Frank Warren believes that Fury can be considered “the best of his generation” if he defeats Usyk, and while the Brit appears confident, he knows there is much to do, having almost been bested by MMA fighter Francis Ngannou before the first loss of his career to Usyk seven months ago. “I think a lot of the journalists, and what you read after [the first fight], they said whoever won it would be the best heavyweight of the twenty-first century,” he told DAZN’s Face-Off. “[The winner] the first unified champion [of the era] and they go up there with all the greats of the past. I’m glad they’ve said that. “Oleksandr got the result by split decision. If Tyson wins it, that’s where that mantle goes, that he is the best of his generation.” That said, this fight is more than just about belts—it’s a battle for supremacy in an era stacked with heavyweight talent. Both men have already etched their names into history, but this rematch provides a unique opportunity for one to emerge as the definitive heavyweight of this generation. As anticipation builds, it’s worth reflecting on the greatest heavyweight boxers of the 21st century and comparing how Fury and Usyk have left their own marks on the division.
Oleksandr Usyk
Usyk has redefined the boundaries of what’s possible for a smaller heavyweight. After becoming the undisputed cruiserweight champion, he seamlessly transitioned to heavyweight, where he outclassed Anthony Joshua twice and handed Fury his first defeat. Usyk’s versatility, technical brilliance, and unparalleled footwork make him a nightmare for any opponent. A second win over Fury could solidify his status as the finest heavyweight of his generation.
Tyson Fury
Few fighters in boxing history can match Fury’s blend of size, agility, and ring presence – it’s almost uncanny a man that big can move as quickly as he can. The Gypsy King stunned Wladimir Klitschko in 2015 to claim the heavyweight crown and then cemented his legacy with a trilogy against Deontay Wilder, including two emphatic wins. While his first defeat against Usyk in 2024 left some questioning his place in the heavyweight pantheon, a victory in the rematch could restore his claim as the greatest of the era.
Deontay Wilder
Aside from the two opponents in Saudi, there have been plenty of great heavyweights that have dominated boxing odds odds since the turn of the millennium. Deontay Wilder’s knockout power is the stuff of legend, with 42 of his 44 wins coming by way of stoppage. The former WBC champion terrorised the division for years, with his one-punch power capable of ending fights in an instant. Though he fell short against Fury in their trilogy, his performances against Luis Ortiz and Bermane Stiverne showcased his ability to rise to the occasion. Wilder’s explosiveness ensures he remains a defining figure in modern heavyweight boxing, capable of shifting the fight with one massive shot.
Wladimir Klitschko
For over a decade, Wladimir Klitschko dominated the heavyweight division with his jab, clinical right hand, and impeccable discipline. From 2006 to 2015, Klitschko reigned as the unified champion, racking up wins over the likes of David Haye, Alexander Povetkin, and Kubrat Pulev. Although his loss to Fury marked the end of his reign, his sustained dominance and incredible longevity make him one of the greatest heavyweights of all time.
Anthony Joshua
Anthony Joshua’s meteoric rise from Olympian to heavyweight glory was marked by a series of high-profile victories. His dramatic win over Klitschko in 2017 cemented his place as a global superstar, and subsequent triumphs over Alexander Povetkin, Dillian Whyte, and Joseph Parker showcased his consistency at the highest level.
While his losses to Usyk and Andy Ruiz Jr. exposed vulnerabilities, his ability to bounce back and reclaim titles speaks to his resilience. That said, it’s hard to see where AJ goes from here, having been destroyed by Daniel Dubois which set him a long way down in the pecking order ahead of what could have been a dream match with Fury at Wembley.
