Duran beat him but Hearns always gave him problems with his jab even outboxing him in the first fight until he got tired.
This is a tough one to answer. And then you put Benitez in there, which was also tough. He couldn't even go to the post fight party he was so sore. I think each fight taught him more and more. I think Benitez,Duran and Hearns wore him out where he needed and early retirement.
Thomas Hearns. Duran beat Leonard in a close fight. But Leonard outclassed him the other two times. Hearns outboxed Leonard both times (8 years apart). So overall, I'd have to say Hearns was the tougher matchup.
Montreal was so close. Duran's victory was celebrated so much people forget that Leonard fought well in that fight.
Duran was in fantastic shape in Montreal - Best conditioned for him ever at 147 lbs - that was Leonards hardest fight because he lost and was hurt badly in the fight. Hearns in fight one boxed well and very competitive until Ray came back to stop Tommy- 2nd fight at a higher weight -I thought Tommy won - think they called it a draw but Ray hit the floor 2x- I have never watched fight 2 since their fight so may be off on details. Still Duran of Montreal - a beast
toughest opponent, not toughest fight. Duran was most definatley a much tougher guy that Hearns could ever hope to be. Hearns was almost delicate, hit him hard and he's on ***** street, homosexual ave. Duran was one of the toughest fighters ever!!!!
Wow a real tough question! But I'd lean towards Duran. Here's why and its real simple. Without the hell Duran put Leonard through in Montreal he probably don't beat Hearns their 1st fight. Duran made Leonard a much better and determined fighter. He learned something about himself. Duran brought out the best of Leonard like Lomatta brought out the best of Robinson, Schmeling created the best Louis, Frazier created the toughest version of Ali. So the Duran in Montreal fight set up the come from behind win against Hearns in fight #1. It also set up the Kalule win when he fought pretty much flat footed and determined for the Ko against him. And the Hagler fight when Hagler started getting to Leonard during the later stages of that Fight. Duran made Leonard a much better fighter.
Yet Hearns dumped Duran face first on the canvas in a way he'd never been left before, or since. It was a completely one sided massacre. Per the question one can look at it so many ways. Duran put a fair beating on Leonard in their first fight even if it is reasonable close when scored on the basis it was fought under. Leonard however made him quit in the rematch and may not have even conceded a round in the rubber match. So we have one extremely tough outing and basically two walks in the park truth be told. Hearns outboxed him for the majority of rounds they fought. He dropped him twice and probably caused the need for eye surgery. Leonard however did eventually stop him and did have him in trouble in the rematch where as Duran was never really in trouble. Leonard improved a bit post Duran, thanks to Duran, and was peak for Hearns. You can argue every which way depending on personal criteria. With Duran you've got the first fight only where as with Hearns you have two of them. Over the duration Hearns was for sure the tougher opponent but in a single outing the first Duran fight would be trumps.
Leonard's face after the first Hearns fight holds the answer. Benitez and Duran were tough in a different way but Hearns made Leonard dig deep in a way nobody else would have.