Hard to say. I might have to go with the Benitez fight just based on how highly Benitez was thought of yet SRL beat him clearly. He's probably my fav sugar of the three(SRR.SRL.SSM) but I love them all. Even when he lost he usually gave a great account of himself(Hearns rematch, Duran 1). He looked arguably his best against Green too so check that out. I don't get people saying the Hearns 1 fight because he looked pretty bad early on. Much credit for him for turning the tide and eventually stopping Hearns but I thought he looked better beating Benitez & Green.
I don't know about the first Hearns fight being his best, after he rattled Hearns in the 6th he just switched off and failed to go in for the king
Benitez. I've got the feeling that his perfomances against Kalule gets a bit forgotten, though. It wasn't that pretty, but still very impressive to walk through a good JMW like that.
There was a ray leonard knockout vid on youtube with the song "supreme beings of leisure - never the same" playing but I can't find that vid. Too bad, that was my favorite Leonard vid.....*weeping*
Hearns and Benitez. In both instances he was facing something he never thought he'd have to deal with in his career and he overcame them. In the case of Hearns, someone who completely neutralized his boxing skills with reach, speed and power. So SRL was forced to improvise and did so admirably. In the case of Benitez, someone who could make this blazing speedster MISS. SRL said after the bout "Nobody can make me miss punches like that!" It was disconcerting to say the least, but Leonard kept his head and stuck to his gameplan. I was never a Leonard fan. Paying him compliments is about as pleasant to me as a bad prostate exam. But you have to say this about the guy- from a mental standpoint, he was hard to rattle. And when he was rattled he pulled himself together pretty quick.
The 1976 Olympics. I believe Ray Leonard stated that those fights at 139 lbs. were tougher than any of his Professional Bouts. And his 3-bouts with Bruce Curry at the Olympic Box-Offs.
First thought would be Green, but like someone stated earlier, quality of opponent is a consideration... Green wasn't on Leonard's plain. So that being said Leonard's greatest victory has to be Duran II. Facing the man who just defeated him. and put on such an exhibition, to make a great Champion virtually quit. is just amazing!