Floyd Mayweather Hit With Blunt Verdict From Roy Jones Jr. on Sugar Ray Leonard Fight

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.

Floyd Mayweather is arguably the most perfect boxer ever. However, Sugar Ray Leonard is one of the greatest boxers in history. And let’s not forget, he’s the only one of the “Four Kings” of boxing (Leonard, Hagler, Hearns, and Duran) to have defeated all three of the others. Both Floyd Mayweather and Sugar Ray Leonard are 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 if Floyd Mayweather had started boxing a few years earlier and Sugar Ray Leonard had delayed his retirement by a few years. 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 once and for all.

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 presented 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, Jones explained, “To me, people don’t give him enough credit. People always say, ‘Well, Floyd beats Sugar.’ No, baby, Floyd is not nearly 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?

“How?” Jones asked. “How you gonna keep him off on him?” ‘Money’ Mayweather was known for his defensive prowess and his ability to make adjustments mid-fight, which often left his opponents punching the air. 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 nothing. Sugar is a dog. People don’t give him enough credit for that,” Jones continued.

Jones recalled Leonard’s 1981 fight against Thomas Hearns, and Leonard’s trainer, Angelo Dundee, telling him between rounds 12 and 13 that he was losing the fight. The iconic line – “You’re blowing it now, son! You’re blowing it!” is almost boxing lore today. Fired by his trainer’s damning declaration, Leonard went out there and knocked Hearns through the ropes in the 13th. A round later, Sugar Ray Leonard destroyed Tommy Hearns with his relentless combinations, ending the fight in the 14th round.

“For Sugar to go out there and do that, they don’t give Sugar enough credit,” Jones recounted passionately. “For me, I like Floyd. Floyd’s cool… But just the way he been doing with normal people. That’s not going to work. With what I saw in his prime, that’s not going to work with Sugar. Sugar’s got a third element right here (smacks his chest). We think Floyd got one but we don’t know. We’ve never seen it challenged.”

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 Floyd 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 for sure what would have happened if these two boxing legends had met inside the ring. Do you agree with Jones?