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via Imago

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via Imago

Remember when Floyd Mayweather Sr. said—“Floyd would have whooped his a**, ’cause I would have whooped his a**. I fought his a** — we did 10 rounds — and when they stopped the fight, hey, I was still right there, ready for more.” Yeah, well, that was just one of the many exchanges Sugar Ray Leonard and the 28-6 boxer have made in their grueling feud spread across forty-seven years! It took one technical knockout loss from Sugar for the Mayweathers to continue a family rivalry with him to date.

You see, although Floyd Mayweather Jr. never fought Leonard (the undefeated champ was just 10 years old when the 36-3 boxer enjoyed his prime), a hypothetical matchup between the two has always been on the minds of fans. So much to the point that during the 2000s, when the 50-0 was defeating present-day blockbusters like Canelo Alvarez, all interviewers would ask the father-son duo and the Wilmington native, was—”Who would win if Pretty Boy and Leonard ever were to fight?”

“Look here — me and you can go do a charity right now, and I’ll whoop your a**. It’s on the video, and he can see it himself. And if he don’t like what I’m saying, bring your a** on. I’ll whoop it,” Sr. has continued to threaten Leonard in March 2015 on The Mayweather Channel. Adding fuel to the fire, the latter had returned the jab. In an interview with Boxing Hub TV five days later, he answered the reporter’s question. If Mayweather Jr. fought the Fab Four—Sugar Ray Leonard, Marvin Hagler, Roberto Duran, and Tommy Hearns—the four dominant fighters during the 1980s, could he beat them?

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Not holding back, Leonard replied, I think Mayweather can compete with the four of us in my era. But it’s a little more firepower that would come his way.” He respected Jr. as a fighter, but when it came to his lot? There was no chance that Pretty Boy could stay standing against the aggression these four elites brought to the ring. Could he beat me? No,” the 1976 Montreal Olympic gold medalist said, holding his chin high.

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Continuing to answer about the other three boxers, Leonard declared, Could he beat Tommy? I don’t think so. Could he beat Hagler? No. Could he beat Duran? No.” Straight-up facts? Maybe. Because while Mayweather Jr. retired without a scratch on his face in 2017, all three of them fought more than 60 fights individually. Could the now 48-year-old overpower Hagler’s granite chin? Or Duran, the aggressive brawler-turned-technician? Not to mention Hearns’ lethal right hand at all. Though understanding a fighter’s mindset, Leonard softened his statements. In all due respect to Mayweather—who is an incredible technician—you ask him, he would say the same thing: that he could beat us, that he would beat our guys in my era. Fighters say that. Fighters believe that. Fighters believe they can beat anyone. And if you don’t say you can beat anyone, you’re not a fighter,” he said.

Still, hypothetically speaking, if Sugar Ray Leonard and Floyd Mayweather Jr. were to clash in their primes, which is only possible theoretically because Leonard is 69 years old, who would win? Let’s take it from the fans themselves.

Sugar Ray Leonard vs. Floyd Mayweather Jr.

While there are plenty of forums where the matchup has been debated upon, what is better than Reddit to argue with fellow fanatics and defend your favorite boxers? An year ago, a user posted this very same question, which rivered in nearly five-hundred comments and takes on the matter!

One of the comments read, “Ray Leonard beat Hearns, avenged his loss to Duran twice and beat Hagler, as well as Benitez. Anyone one of those guys would be the best fighter Floyd has ever faced..Leonard beat them ALL, like I said in a previous comment. Leonard was too fast, sharp, smart, with GREAT footwork on the back-foot, could come forward and could cut off the ring masterfully, nightmare matchup for Floyd…” 

And that one user’s opinion seemed to sum it all up because the ones that followed were no different. Most of the boxing community is sided with Leonard on this one. But what are your thoughts? Could Floyd Mayweather Jr.’s prime overshadow Sugar Ray Leonard’s? Or is it a one-sided matchup in favor of Money Mayweather?

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