Sugar Ray Leonard
Floyd Mayweather
I give the advantage to Leonard in this fight.
Leonard was naturally bigger, I doubt Mayweather would be able to hang with middleweights and super middleweights like Leonard did. Leonard was powerful at 147, that power along with the speed made him very dangerous offensively.
Leonard was flashier, Sugar Ray scored points with his late rounds flurries, flashy moves and power punching. Floyd's style isn't as appreciated by the judges.
Most importantly Leonard could handle defensive fighters like Floyd's father Mayweather Sr. and Wilfred Benitez. Leonard's ring intelligence is almost unmatched, he picked his spots, didn't let anyone make him look bad and won over the judges.
He could adapt during fights like almost no one else could. Floyd is known for this too.
Sugar Ray fought the better competition and beat great fighters like Hearns, Hagler, Benitez and Duran.
Leonard would win by a decision. I wouldn't bet on a stoppage because Floyd's defense is very good, he is well-conditioned and his toughness is underrated.
Here is Leonard's fight with Floyd Sr, very entertaining.
Floyd Sr was a pretty good fighter but he couldn't dedicate himself to the sport like Floyd Jr did. Sr. wasn't as mobile as Jr. but his technique was very good.
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