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Who would win a fight between Sugar Ray Leonard and Floyd Mayweather?

It’s a different era that Sugar Ray was in entirely, something Ray probably considers when thinking about why he’d beat Floyd Mayweather, as he told the world recently.  Photo by Patrick Smith/Getty Images

The way I look at it, during the late 70’s and the early 80’s the sport of boxing was arguably the #1 sport on the planet. It was that big of a deal and all over the free networks. Something its been attempting to do as Floyd was leaving. More kids who now routinely choose Football, Baseball or Basketball, were lacing up the gloves.

The competition was a lot better for Ray, and the fighters overall were tougher, more skilled and far hungrier than the modern fighter of today. All of which means that Sugar Ray’s generational experience in the ring was more seasoned and deeper than the one Floyd fought in– and that would hurt him against Ray.

Leonard was a more solid and active ring general who fought all 3:00 minutes of every round. He was also the kind of fast black fighter that would’ve given Floyd far more problems than a Zab Judah or Demarcus Corley did, and he’s also the kind of “A” fighter who would’ve definitely struck Floyd the way Shane Mosley did in the 2nd round that nearly got him KTFO. Sugar Ray Leonard was one of the greatest finishers of all-time, and its hard to imagine Floyd recovering too many times after being hurt by Leonard.

Then there’s the issue of greatness.

Both are undeniably that, but Ray Leonard’s was indeed at 147, while Floyd was really an all-time great 130 lb guy. Most of what he’s done at 147 pales to a guy like Sugar Ray when you really take a look at it, which goes a long way in determining the outcome of a fight like this.

We saw him bring the great Juan Manuel Marquez up two weight classes to put a clinic on what became a bloated counter-puncher. He didn’t face what many believe was a PED tainted and “Incredible Hulk” version of Marquez that Manny Pacquiao saw in December 2012.

He had problems with what he thought was a “shot” Miguel Cotto in May 2012; and if you look closely at his encounters with glorified club fighters Luiz Ortiz and Marcos Maidana (especially Maidana), you can see how volume punching with calibrated forward aggression bothers Floyd. A lot of critics will tell you this is why he avoided Antonio Margarito and Kostya Tszyu. In Sugar Ray Leonard’s time it would have been tough for him to avoid those same challenges in the prideful 80’s, where all the great fighters fought everyone.

Today, “TBE”, is trying to make another Brink’s truck robbery attempt on the public by facing the crude Conor McGregor in a boxing match, while he could be making some true legacy making history with “GGG”, aka Gennady Golokin. That, would be his version of Sugar Ray Leonard vs. Marvin Hagler.

From this view, this fight would be like Donald Curry facing Sugar Ray. It would be a good fight for awhile- with Curry holding his own, until Ray smashed him with something nice. If you’re someone who thinks Floyd would’ve beaten Ray Leonard, ask yourself a few questions.

What if a guy like Jose Luis Castillo had Ray’s speed? What if Judah had Ray’s conditioning, stamina and supreme confidence? What if a not-so-39-year-old Mosley landed that powerful overhand right? What if Oscar De La Hoya – an older one at that – hadn’t abandoned his damn jab? Hell, what if Pacquiao was maybe his 2010 version when he struck Mayweather with that ill straight left in round 4?

Think about that.

We saw Floyd was stay away from solid, speedy black fighters after his April 2006 experience with Judah at age 29, and he was leery enough of Mosley to bring Floyd Sr. back to camp after their infamous blow-up on HBO. We all know he never wanted it with Timothy Bradley- or a Keith Thurman if we’re being real, and because of modern training and a different approach to how boxing is these days, Floyd is a very preserved fighter at nearly 40. He’s probably now, physically, what Sugar Ray was when he was 30 against Marvin Hagler.

Just look at him, or compare them if you like. Look at footage from Floyd against Berto and take a look at Leonard against Hagler. They are the same fighters physically despite 10 years in age between them, because Ray built a career full of serious stylistic risks. Floyd Mayweather avoided fights that Leonard would’ve taken. Not because he couldn’t win them: Please believe Floyd could’ve wound up giving Margarito, better versions of Cotto, Mosley and Tszyu a serious spanking.

But he chose not to.

Floyd Mayweather has never truly demonstrated enough greatness in the welterweight division to make me believe he’d beat Sugar Ray Leonard. He’d probably give the Sugar Ray Leonard who dismissed Thomas Hearns in their 1981 classic, the same problems Kevin Howard gave a not-so-great Leonard in his 1984 comeback bout.

Floyd’s speed, iron-clad desire not to lose and his all-world defense would bother Ray for awhile. Not to mention Floyd’s sharp, pot-shot offense would allow “Money” to drop a few rounds in the basket. But once Floyd got nailed by any lightning-quick power shot from Sugar Ray’s lethal arsenal- IT’S OVER. Sugar Ray Leonard would KO Floyd Mayweather in the 9th round out of nowhere.

***

And totally random here but, Floyd, at welterweight folks, started picking and choosing carefully to avoid optimal competition, something else I believe hurts him in a match-up with Leonard.

Now, he’s picking what would be a complete tomato can in the ring with him in the beer room brawling Conor McGregor (<---click on how he's trying to convince himself this is more than a bullsh*t fight). Notice how he's not talking about a level playing field or PED testing with Conor (Remember, Nate Diaz insinuated such about a possibly filthy McGregor), because he also knows that he'd have a much more difficult fight with say, an Adrien Broner (who sounded like he'd fight Floyd for free).

Floyd, do yourself a favor for your own good, and at least give the public something worthy of your talent when you decide to comeback. If you’re going to trademark #TBE50, at least do it against somebody who, as you say, ‘there’s no blueprint to beating’, like GGG.

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