In most every sport, there is always that question of how the best of one era would fare against the best of another.

In boxing, fans indulge in this practice perhaps more than in any other sport.

After receiving a bronze medal at the 1996 Olympics, Floyd Mayweather, also known “Pretty Boy” Floyd and “Money” Mayweather, has been compared to many of the all-time greats before him, particularly those competing in the ’80s and ’90s.

Floyd has been compared to many former great champions, and rightfully so as he is arguably one of, if not the smartest and most naturally gifted fighter to ever lace up a pair of gloves. There is one name that we hear and see often when comparing Floyd to greats from other eras, “Sugar” Ray Leonard.

Leonard, who holds a stoppage win over Mayweather’s father Floyd Sr., was part of “The Fabulous Four” during the 1980s. The group included the likes of Tommy Hearns, Roberto Duran, and Marvin Hagler. He also competed in the 1976 Olympics where he claimed a gold medal.

With the skills Ray Leonard possessed, it’s very easy to see why many believed he would have been the ultimate challenge for the Grand Rapids native.

So how would Floyd match up with “Sugar” Ray at welterweight?

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We will break down their fantasy fight using these categories

Speed: I think Leonard holds the edge in this category, handily. Mayweather is undoubtedly a fast fighter with both his hands and feet. However, Leonard had that “blazing” speed. When you combine that kind of quickness with the combination punching Leonard would display, it makes it very difficult to defend no matter how great you are defensively.

Advantage: Leonard

Power: In his younger days, Mayweather was a savage. He would use accuracy, speed and explosive power to embarrass his opponents. Victims included the likes of Genaro Hernandez, Angel Manfredy, Diego Corrales and Arturo Gatti. The same could not be said once he jumped to welterweight. Mayweather became more defensive and used more pot-shots and counters to frustrate his opponents. On the other hand, Leonard came to fight and carried his power better at the higher weight classes. This was never more evident than when he stopped the great Tommy Hearns, who was undefeated at the time, in the 14th round, with his left eye practically shut.

Advantage: Leonard

Defense: The undefeated former champion takes this one and quite easily. Not many can say they are a master of the “sweet science.” The name of the game is hit and not get hit. No one mastered that better than Mayweather. Floyd, who was groomed by his father and two uncles, was a boxing genius. The way he would stand in front of his opponents, hit them and then make them miss by inches was a treat to watch for true fight fans. I can’t recall a time when Floyd was down on all three cards, trying to go all out for a knockout, with his eye shut. In Leonard’s defense, Mayweather never fought a Tommy Hearns. Floyd gets the nod here.

Advantage: Mayweather

IQ: I give this one to Mayweather as well. While I understand that a true test of your IQ is based on the level of competition you face, and clearly Leonard faced much better competition, however, Floyd did fight the best fighters of his era and made the majority look like they didn’t belong. I can’t recall many fighters, if any, that could adapt on the fly the way Mayweather could. He was a true master inside that squared circle. He rarely got hit with the same punch later in a fight or multiple punches consecutively. This is credit to his mastery of distance, reflexes, and boxing smarts.

Advantage: Mayweather

Prediction: While I had it even in terms of categories, I’m not too sure the fight itself would be that close.

Both guys are extraordinary boxers with a tremendous amount of talent and skill. However, while I feel Mayweather is the more “skilled” boxer of the two, I think the speed, power and combination punching of Leonard would have made Mayweather gun-shy. The Mayweather at welterweight was much different than the one who fought at 130-140. Older Floyd was more single shots with combinations here and there. Not to mention, would he have the power to make Leonard respect him? I’d have to say no. Yes, I do think Floyd would box well early and use his great timing to make it competitive for a while. I just think Leonard eventually gets to Floyd and starts landing hard to the body and head before eventually stopping the younger Mayweather between the 8th-10th round.