By John Hively (photo by Richie Maldonado)

Many months ago it was reported that Floyd “Pretty Boy” Mayweather had bragged to Sugar Ray Leonard that if the two had ever met in the squared circle during their primes Leonard would have been a sure loser. Trash talking Floyd must have imbibed way too much of some stimulating elixir to have reached such heights of delusional madness. Had the two ever engaged in ring combat during their respective primes, it is likely that Leonard would have beaten Mayweather silly and knocked him out in the process.

There are a few categories of pugilistic merit that a prime Leonard and today’s Mayweather share. For example, Leonard was as fundamentally sound in the science of boxing as Mayweather, more or less. Sugar Ray was arguably as fast of hand and foot as Floyd, but it is at this point where the skills and experience of the two can be distinguished much more clearly, and Sugar Ray appears to have all of the advantages.

Leonard was the harder puncher of the two and by more than a fair margin. The evidence is in the number of higher quality boxers the great Leonard stopped during his legendary career, especially when compared to the more modest accomplishments of the trash talking—and carefully managed—Mayweather.

From 1978 to 1981, Sugar Ray fought in an era when the welterweight division was at one of its historical peaks in terms of fistic talent, featuring several great boxers at or near their primes: Thomas Hearns, Wilfred Benitez, Roberto Duran and Pepino Cuevas. With the exception of Cuevas whom he did not fight, Leonard defeated all of them convincingly. All of these fighters would likely make most lists of the top fifty welterweights of all time. It’s difficult to believe that a carefully managed pugilist like Mayweather would have faired as well against them as did Leonard.

In Leonard’s welterweight days, Thomas “Hitman” Hearns was a pure fighting machine. Standing six foot one inches tall, the Hitman possessed considerable height advantages over his opponents. He was a highly skilled boxer with two extremely quick hands that were both loaded with sleep inducing dynamite. His fists were so swift and powerful that even the iron jawed Cuevas and the steel chinned Duran fell before the Hitman’s thunderous barrages in less than two rounds each. Leonard the Great rallied to gun down the Hitman in the fourteenth round of a scintillating contest. Given what he has shown thus far in his career, it is difficult to imagine that Pretty Boy could have defeated such a formidable opponent as Hearns, much less last the distance. Edge: Leonard

From 1978 to 1980, Roberto “Hands of Stone” Duran was a great welterweight. After giving up the lightweight title, in addition to several other pugilists, Duran ran roughshod over former champion Carlos Palomino. Duran then won the welterweight title when he handed Leonard the only defeat he was ever to suffer during his prime years in their historic clash in Montreal.

In their second confrontation in New Orleans, Leonard rolled to a close, but clear, lead, before compelling the ferocious Panamanian to quit during the eighth round. It was only the second loss of Duran’s legendary career.

A vicious puncher and an outstanding boxer at his peak, the prime Panamanian tiger would have overwhelmed a peak Mayweather right from the beginning as a lightweight or as a welterweight. Pretty Boy would have been hard pressed to survive the distance against the controlled, but furious, assaults of this all time great, and nobody would have called him “pretty” at the end of the battle. Edge: Leonard

Wilfred Benitez was a brilliant boxer with a fair punch at welterweight. He was adept at avoiding the blows of his adversaries and then countering them at will. Benitez won his first world title before most people attend their senior prom. At the age of seventeen, the young wizard of the ring out-thought and out-fought the great Antonio Cervantes to win the junior welterweight title. He then moved up in weight to capture the welterweight belt from the highly competent Carlos Palomino. Sugar Ray handed the great Benitez his first defeat to win the welterweight title, and he did it by stoppage!

In terms of skill, any battle between Floyd and Benitez would have rated a toss-up, but in terms of who they defeated it is possible to give the advantage to Benitez because of his victories over Cervantes and Roberto Duran. Edge: Leonard

Pepino Cuevas was a tremendous left-hooker. Bones broke and flesh tore apart when he landed that left hook of thunder. After winning his WBA welterweight title by a second round kayo over capable Angel Espada, the ultra-left-hooker defended it eleven times, ten by kayo; And then Tommy Hearns ruined him for the remainder of his career when he blew Pepino away in two heats. For all of his greatness, it is highly unlikely a prime Cuevas could have defeated a peak Sugar Ray.

On the other hand, in a clash against Pretty Boy, a prime Cuevas would come forward, and if Jose Luis Castillo proved effective in the first of his two fights against Mayweather, it’s a sure bet that Pepino would do just as well, and most probably better. Until we’re sure just how much punishment Mayweather is willing to take, and what adjustments he can make during a fight in which he is hard pressed and hurt, it would be difficult to pick him as a likely winner over the great left-hooker of yesteryear—not just yet anyway. Edge: Leonard

All of which brings us to the main problem in evaluating the greatness of Mayweather. Either because he has fought in weight divisions that were devoid of truly great fighters, or because he has been a carefully managed boxer, Floyd has yet to defeat any pugilist that might eventually prove to be an all-time great.

Jose Luis Castillo, Diego Corrales, Jesus Chavez and Zab Judah are arguably the best fighters Floyd has fought. They are very talented gladiators, and there are no questions about their high level skills, yet none of them rate close to Leonard, Hearns, Duran, Benitez and perhaps Cuevas in abilities. Corrales was suffering from weight and legal problems and was an easy mark for Pretty Boy. Castillo took Floyd to the wire in their first encounter, and some people thought Jose deserved the decision. In their rematch, Mayweather won by a fair margin. Pretty Boy also beat Chavez by a comfortable edge.

Zab Judah is the best welterweight Mayweather has encountered just yet. Zab’s heart and jaw aren’t the best, and sometimes his mind isn’t even on the fight at hand, as evidenced by his dismal performance when heavy underdog Carlos Baldomir out-hustled the then champion.

Judah is a good fighter, and certainly of championship caliber, that is, of course, when a great warrior isn’t the title holder standing in his way. Kostya Tszyu bounced Zab off the canvas as if he were a rubber ball a few years ago, and put an end to his title aspirations in less than two rounds, which is something Pretty Boy could not do.

Did anybody notice that Mayweather never fought Kostya Tszyu? The Russian Assassin possessed a hammer for a right fist, and a war between the two might have made for a great fight, but such a fistic endeavor would have been exceedingly dangerous for the American.

When taking an opponent seriously, Tszyu possessed an uncanny ability to make minor adjustments to his game during a fight and ensure victory against all comers for seven long years. Ring combat between the two would have been a chess match, and it’s easy to envision a Tszyu win by kayo or perhaps a Mayweather triumph via close decision.

Should Floyd climb into the ring against the past-his-prime Oscar De La Hoya, we might have a better idea as to his true class. Like Leonard, Oscar fought as a welterweight when the division was at a fairly high peak in terms of fistic talent. However, it wasn’t nearly as great of an era as during the years when Leonard fought in the division, but it was reasonably close. Although Oscar had the talent to be the next Sugar Ray Leonard, the difference is that Leonard reigned supreme over a stronger division, but with un-avenged losses to Felix Trinidad and Shane Mosley, De La Hoya did not dominate his somewhat lesser era. That’s a big difference between Ray and Oscar.

If Oscar and Floyd duke it out, Pretty Boy had better win by a comfortable margin if he really wants to be considered as an all time great. It’s not all together clear that Floyd would defeat the speedy and harder hitting De La Hoya. There is significant risk involved for both fighters, and risk is something that Mayweather does not appear to relish.

It isn’t likely that Pretty Boy will be able to match the accomplishments of Sugar Ray, even if he had the desire to do so. The welterweights of today aren’t a bad bunch of fighters at all, but there doesn’t appear to be a great pugilist in the bunch. Don’t look for Floyd to go up in weight to challenge Jermain Taylor for the middleweight title, or to demand a match with the light heavyweight champion, Antonio Tarver. Those feats are reserved for ultra-talented legendary fighters, guys like Harry Greb, Mickey Walker, Sugar Ray Robinson, Archie Moore, Tommy Hearns and Sugar Ray Leonard.

Given that Sugar Ray fought and defeated the greatest fighters of a great era, while Floyd has been a carefully managed boxer in a significantly lesser period, it shouldn’t be too difficult to determine that Leonard would have prevailed in any battle against Mayweather should those two have ever had the opportunity to duke it out while in their respective primes.

I think this article is too biased for Sugar ray. although I do agree that had the two met, leonard would have came out on top.