By Steve Kim

On May 3, Floyd Mayweather makes his bi-annual appearance in the ring. Once again, to the perpetual disappointment of boxing fans, it will not come against Manny Pacquiao. Truth be told, the sell-by date on that fight expired at least a year ago. But years from now, when you look back at Mayweather's Hall of Fame career -- regardless of where you assign blame for this fight never coming to fruition -- there will be a gaping hole in his resume.

Compare that to Sugar Ray Leonard, who fought during the vaunted 'Four Horsemen' era of the 1980s alongside and against Thomas Hearns, Roberto Duran and Marvin Hagler. All three are members of the International Boxing Hall of Fame; Leonard had a composite record of 3-1-1 against the legendary trio.

Leonard, now 57 (and still very close to fighting weight), couldn't have lived with a clear conscience if he didn't take on the very best of his contemporaries. "Listen, man, what about Marvin Hagler? That's why I came back," said Leonard about returning from a 35-month hiatus in 1987 to famously upset the reigning middleweight champion of the world as a prohibitive underdog. It was a fight that sent the embittered Hagler into retirement.

"I could not see myself not fighting Tommy Hearns. I could not see myself not fighting Roberto Duran twice -- I excuse the third one," continued Leonard, laughing, understanding that their third encounter was akin to The Karate Kid, Part III, something that went on one chapter too long. "The rematches usually work themselves out. Even with Hagler, he didn't want a rematch. He went away. That was a normal rematch because the fight was so close and the fight they say was 'controversial'. That was a natural rematch. But no, I could never see myself never fighting those guys. No question."

When asked if not having fought each other hurts the legacy or reputation of either Mayweather or Pacquiao, Leonard answered, "I don't think it'll hurt Mayweather or Pacquiao. It's a fight that the world wanted to see but it didn't happen. I think Mayweather has done so much and he's been unbeatable, if that's the word to use, and now he's really coming to where he's fighting up and coming stars as well as fighters we thought had a chance because of the youth. Mayweather's an anomaly. He truly is, I mean, I look at him and say, 'Holy s---, this guy is so focused,' and there's no way I could've been that focused at that point in my career."

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Thanks to the contracts and politics that rule boxing, Floyd Mayweather, Jr. will likely never fight Manny Pacquiao. (Getty Images)

Mayweather is ensconced with Showtime and closely aligned with Golden Boy Promotions, meaning that in the 'Cold War' era of the boxing business, where two universes exist and never intertwine, certain match-ups will never come to fruition. If you are under the Top Rank promotional banner or fight underneath the bright lights of HBO, you simply aren't in position to fight Mayweather or his Showtime colleagues at the moment. It's the reason why the likes of Victor Ortiz and Robert Guerrero were able to land assignments versus Mayweather, but the much more accomplished Tim Bradley (who faces Pacquiao for the second time on April 12) may never get that shot.

"I think it's disappointing to all boxing fans who want to see that rare or special fight," said Leonard, who is well aware of the pugilistic politics involved."This is business, but highly anticipated fights are what made boxing what it was and when these fights don't take place it hurts the fans. No question. It bothers me. There are certain fights I want to see."

During his heyday, Leonard was able to participate in fights promoted by the likes of archi-rivals Don King and Bob Arum by having a certain leverage that most boxers simply didn't have, given his cache from winning the 1976 Olympic gold medal and being anointed the heir apparent to Muhammad Ali by ABC's kingmaker, Howard Cosell. From the beginning of his career, with the guidance of Mike Trainer, a shrewd and hard-bargaining lawyer, Leonard was steered away from long-term promotional pacts and essentially engaged in one-offs. No promotional entanglements were ever going to get in the way of the fights Leonard yearned for.

"The thing with Mike and I," explained Leonard, who had a career mark of 36-3-1 (25 knockouts), "I didn't care who I fought. I didn't make suggestions, I didn't say anything. That was on J.D. Brown, Angelo Dundee and Janks (Morton). I didn't care -- bring'em on. I just think it's a different mindset because back then if you lost a fight it's no big deal. It's not THAT significant. I mean, it's great if you could stay undefeated but it wasn't that big of a deal.

"But with Mayweather, I think it's a big deal."

There is a theory that Mayweather, whose record stands at a perfect 45-0 (26 knockouts), has an unnatural obsession about losing his undefeated mark, and therefore, his claim of being the greatest ever.

"Y'know, I can't agree with that. I've been hearing that, I catch hell from my boys, all my friends, 'He's afraid to fight so-and-so' -- he's not scared to fight anybody," said Leonard, coming to Mayweather's defense. "He's proven he could beat these guys. He has every tool in the book and some extra stuff in his trunk. First of all, he knows how to be in the right state of mind. He's always in incredible shape and he calls the shots."

Just like Ray did.

But c'mon, he would've beat Mayweather back in his day, right?

"There is no one way to fight Floyd. Floyd reminds me a little bit of his father with that kind of defense," said Leonard, who defeated Mayweather Sr. in September of 1978 by stopping him in the 10th and final round in Providence, R.I. "Y'know... I don't know, am I confident I could beat him? Yes, And he would feel the same way but that would've been a huge fight. I don't even want to go there."

By now he's chuckling, perhaps not only thinking about the daunting task it would have been inside the ring but the astronomical payday that would come with it.

"I don't even want to think about that. But it would be a challenging fight."

***

Steve Kim began covering boxing in 1996 and has been writing for Maxboxing.com since 2001. He is also a regular contributor for Boxing News. He can be reached at k9kim@yahoo.com and he tweets (a lot).