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Oleksandr Usyk picks a winner in prime Sugar Ray Leonard vs Terence Crawford

Tom Eaton

20th July, 2026

Oleksandr Usyk picks a winner in prime Sugar Ray Leonard vs Terence Crawford
Image credit: Getty

Terence Crawford cemented his place amongst the pound-for-pound greats when he dethroned Canelo Alvarez last year, and now fellow modern boxing legend Oleksandr Usyk has revealed how he believes ‘Bud’ would have fared against the iconic Sugar Ray Leonard.

Crawford became boxing’s sixth five-division world champion when he got the better of super-middleweight poster boy Canelo back in September.

There, he also became the only post-war fighter to have captured the undisputed crown in three different weight-classes – having already achieved the feat at both super-lightweight and welterweight.

Shortly after that history-making triumph, Crawford made the decision to walk away from the sport with his undefeated record intact, content with a career that finished with a record of 42-0.

Meanwhile, Sugar Ray Leonard is hailed for his efforts in the 1980s, when he battled with his fellow ‘Four Kings’ and got the better of each of Robert Duran, Thomas Hearns and Marvin Hagler. 

After Hearns became boxing’s first five-division champion on November 4, 1988, Leonard joined him as the sport’s second quintuple champion just three days later when Leonard got his hands on both the WBC super-middleweight and WBC light-heavyweight gold in a knockout win over Donny Lalonde.

Yet, despite the skill, will and legacy of Leonard, Usyk told Daily Mail Sport that he thinks Crawford would have got the better of the Wilmington-born sensation if they were to meet in their primes.

Usyk also predicted that Crawford would have overcome Pernell Whitaker, Floyd Mayweather and Sugar Ray Robinson – a testament to the regard in which the Ukrainian holds Crawford, who had been considered as his pound-for-pound rival before his retirement.

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