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

Oscar Pick

22nd July, 2026

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

Oleksandr Usyk has considered how Terence Crawford, his fellow modern great, would fare against a prime Sugar Ray Robinson.

When it comes to fantasy matchups, Crawford is perhaps most often paired with Floyd Mayweather, who likewise retired as an unbeaten five-division world champion.

Unlike ‘Bud’, though, Mayweather never fought higher than 151lbs, whereas Robinson won world titles at welterweight and middleweight during his remarkable 199-fight career.

Down at 147lbs, two of the American’s signature wins came against fellow Hall of Famer Kid Gavilan, who he unanimously outpointed in 1948 before winning their rematch by the same verdict in 1949.

Prior to that, Robinson had five iconic encounters with Jake LaMotta, losing just one of them, before ending their fierce rivalry with a brutal 13th-round stoppage in 1951.

As for Crawford, he did not quite match Robinson’s level of competition but, even so, there was no denying his greatness by the time he retired last December.

He did, after all, manage to unanimously outpoint Canelo Alvarez last September, just over two years removed from his ninth-round stoppage over welterweight rival Errol Spence Jr.

Usyk has therefore told Daily Mail Sport that he would back a prime version of the three-weight undisputed king to defeat Sugar Ray Leonard, Mayweather, Pernell Whitaker and Robinson.

While the first three matches would likely deliver competitive affairs, the majority of fans may struggle to give Crawford much of a chance against Robinson.

Not only is Robinson widely regarded as the greatest fighter who ever lived but he was also a natural middleweight, whereas Crawford only moved up to 168lbs to dethrone Alvarez in his last outing.

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