While boxing continues to deliver thrilling matchups, some dream fights remain locked in the realm of ‘what if.’ One such fantasy clash that has long ignited passionate debates among fans is a hypothetical showdown between Floyd Mayweather and Sugar Ray Leonard. Though the bout could never happen in reality, it hasn’t stopped enthusiasts from arguing over who would emerge victorious. Now, boxing legend Roy Jones Jr. has weighed in—and his take might finally settle the debate.
Both Floyd Mayweather and Sugar Ray Leonard were five-division world champions who competed in overlapping weight classes, most notably welterweight and light middleweight. This means that, hypothetically, they could have met in the ring under fair conditions. According to four-division world champion Roy Jones Jr., who is widely respected for his fight IQ and analysis, such a matchup wouldn’t just have a clear winner—it would be one-sided. But the real question is: who does Jones believe would dominate the fantasy fight?
Speaking to Andre Ward in an interview with All The Smoke Fight, ‘Captain Hook’ described Sugar Ray Leonard as a mean fighter. When Ward pressed him for more detail, Jones explained, “To me, people don’t give him enough credit. People always say, ‘Well, Floyd beats Sugar.’ No, baby, Floyd is not as mean as Sugar was.” Ward, clearly surprised by the bold take, asked again to confirm if he had heard correctly—did Jones believe Leonard would beat Mayweather?
NBA, Basketball Herren, USA Playoffs-Toronto Raptors at Philadelphia 76ers, Apr 16, 2022 Philadelphia, Pennsylvania, USA Professional boxer Floyd Mayweather looks on before game one of the first round for the 2022 NBA playoffs between the Philadelphia 76ers and the Toronto Raptors at Wells Fargo Center. Mandatory Credit: Bill Streicher-USA TODAY Sports, 16.04.2022 18:16:03, 18102832, NPStrans, Floyd Mayweather Jr, Toronto Raptors, NBA, TopPic, Wells Fargo Center PUBLICATIONxINxGERxSUIxAUTxONLY Copyright: xBillxStreicherx 18102832
“How?” Jones asked. “How you gonna keep him off on him?” ‘Money’ Mayweather was known for his defensive boxing style, which often left his opponents puzzled. Despite that, Jones claimed Leonard’s aggression would prove too much for the undefeated Mayweather. “Sugar is a dog. Just cause his name is Sugar doesn’t mean anything. Sugar is a dog. People don’t give him enough credit for that,” Jones continued.
Jones recalled Leonard’s 1981 fight against Thomas Hearns, claiming Leonard’s trainer, Angelo Dundee, told him between rounds 13 and 14 that he was losing the fight. So, Leonard went out there and knocked out Hearns in the 14th round. “For Sugar to go out there and do that, they don’t give Sugar enough credit,” Jones claimed. Regardless of who would have come out on top, there’s no denying that both Mayweather and Leonard are legends of the sport—icons whose brilliance may never be replicated in boxing again.
However, who do the boxers themselves think would win the fight?
Sugar Ray Leonard once told Floyd Mayweather he would have defeated him
Interestingly, some history buffs would know Leonard actually had a connection with the Mayweather family. He had dropped and stopped Floyd Mayweather Sr. in 1978. According to a May 2016 report from Boxing Scene, Sugar Ray Leonard admitted, “Floyd is a very precise fighter, he’s a technician in the ring.”
However, that doesn’t mean that he thought Mayweather was better than him. Leonard believed his skill set and era of competition would have given him the edge over Mayweather. “I told Floyd that I would have beat him–if he was in my era,” Leonard said. “And he told me the same thing, that he would beat me if I was in his era,” he continued.
“I did tell him that [I beat his father] – like father, like son.”
That being said, even though Roy Jones Jr. seems confident in his prediction that Sugar Ray Leonard would have defeated Floyd Mayweather, nobody can really know what would have happened if these two boxing legends had met inside the ring. Do you agree with Jones?
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