I personally think Duran is outdone in every department. If he tries mauling him like he did Leonard in Montreal, he’s in for a hell of a shock, he’s eating a check left hook and going supine, Leonard can’t time power punches the way Robinson can time guys on the way in, so Leonard had to use elite movement to beat him, whereas Robinson wouldn’t need to, he could box him, but if Duran tries to close the distance and maul Robinson, Robinson will inevitably be able to time devastating punches. Robinson either knocks him out when Duran tries closing the distance, or he lands some hard punches, puts Duran into survival mode where he can keep the fight at arms length due to Duran’s respect, rather than Robinson having to use a lot of movement, although I feel like, if Robinson had to box and move and couldn’t gain Duran’s respect for whatever reason, he could do so, but there’s no situation where that would be necessary unless he broke his hand or something.
RD has a chance if he traps Robinson in a corner and uses his infighting prowess, him being the (arguably) best inside fighter in the history of the sport And we all know what Robinson's biggest weakness was That being said, if they were to fight 10 times, i don't see RD winning more than 4 of those bouts at best.
As much as it pains me to say it, this is all Sugar Ray. Montreal Duran was an amazing fighter but he was helped by Leonard's desire to match Roberto's machismo. SRR would not be goaded into making the same mistake. Robby was too big and too long for Duran and I just can't see Roberto really hurting Robinson. For me, lightweight Duran and welterweight Robinson are two of the five best fighters at a single weight class of all time. Robinson wins 145-140.
If this was held in Robinson's era where guys fought 3 and four times in a short span Duran would get at least one win. But taking on a prime Robinson at his natural weight class is a monstrous task even for Roberto Duran. The real Sugar Ray wins a close decision ,
Robinson was in his absolute prime as a welterweight. In 1946...as a welterweight...he had 75 fights...and his record was 73-1-1. He had beaten every top contender in the 147 division. He had refused to play ball with the Mafia...who controlled much of boxing during that time...and was denied a shot at the title. Finally...he was given a chance at the title against Tommy Bell. SRR held the welterweight crown from 1946 to 1951. The best fighter of all time.
Genuinely, and this pains me to say, I think the very best of SRR likely KOs Duran. Robbi hits just as hard as Tommy IMO, has even more tools to his belt and more experience. In the same vein that Tommy caught Duran with the same right hand snapped in behind the jab, I can envisage Robbi doing the same, knowing that he, too, like Tommy, can hook off the jab, use the jab to disguise his excellent right hand and we know that Robbi has KO power in both hands. Robbi doesn't have the same reach discrepancy that Tommy had, but he's got better feet, excellent reflex and is so experienced in landing the big punch against a shorter fighter. In a series of 10, I would put money on Duran raising his level for one night like he did in Montreal, but I would also put money on SRR to adapt quickly, dominate the series and find the KO in 2 - 4 fights.
