I usually hate these mythical matchups and don't bother with most any of them because debating is pointless since we will never know but this one I actually like. Leonard is one of the most versatile and resiliant fighters in boxing history so I don't think Mayweather would be able to overwhelm him with anything. I think it could be one of those fights where both fighters give each other different looks throughout the fight. As much as people dislike both of them, they were flat out good. The paralels are amazing. I mean, both are two of the best cerebral fighters of their generation. Both have pinpoint accuracy with a fair amount of pop. Both have footwork second to none, moving inside to outside and side to side. Look at the first five or so rounds of the Leonard - Hearns fight, the side to side movement had Hearns completely off his game. Both are perfect fundamentally, and both have athletic ability to go on top of it. The parallels really are mindblowing and thats as much of a testement to Leonard then anything, the guy was 25 years ahead of his time and maybe more.

So really I think picking a winner would be splitting hairs if you don't beleive in the boxing evolutionary theory then it's a toss up. I mean I think when you break it down to the basics, they're even.

I would be inclined to give Mayweather the advantage because of how just technically perfect he is. I mean, antics aside, the guy is this generations all time great fighter.

However, Leonard is one of the more resiliant fighters of all time. I mean he had the odds stacked against him behind on the cards versus some all time great fighters and always found ways to win. It's hard to argue against a fighter who ALWAYS wins, whether the decision is disputed or not. So that's something to bear in mind. There is no way Leonard would be in any way overwhelmed thats for certain.