H2H Duran would throw in the towel himself as he gets frustrated from being unable to pull his hair out with the boxing gloves on
In terms of pure skills, it's so close you can slice it with a thin paper. Whenever I run into a situation like this I decide the question based on a h2h match up. At LW, Duran would be bigger, as fast and he would be able to push and handle Whitaker on the inside while being as hard to hit as Whitaker himself. On the outside is where Whitaker could win it, but being purely a counter puncher usually and with Duran not leading that much but usually waiting to counter or slip a jab etc himself before using that to get inside, it's a really hard one. I think with wins over guys like Marcel, Buchanan, Mamby and Leonard the very least that shows is that Duran handles slickness, speed and a solid jab from great counters punchers very easily and at LW he was much more able to take advantage of his strength and speed, whereas against Leonard (which everyone relates to too much for this fight) he was towered over and Leonard threw better combinations and was faster than Pea. Although everyone brings up the myth he had trouble with boxers, he never really did until he was past thirty, slow, unmotivated and small compared to his opponents. It was only trouble against boxers at 154 when he was slow and fat or against Leonard at 147 in the rematch. Leonard would have won that second fight just as easily if he fought the same fight as he did in the first anyway. Duran was just not going to win that second fight. At his weight, he had no trouble against Buchanan, who was easily one of the slickest, craftiest boxers of the day. Viruet and Marcel too were incredibly slick. Fought exactly like Mayweather and Mamby was also very crafty. He had no trouble with any of them because at LW he was as fast, as big and as crafty himself and when started to slow just that little bit, he always came on like a steam train. The good pressure fighter Pea fought was Chavez, who at that stage of his career was slow compared to Duran and didn't have nearly the defensive and boxing/countering skill either. It was also at WW, where Chavez was never that good anyway so it makes it difficult to compare. The best southpaw Duran faced was Hagler and he handled him rather brilliantly though Hagler doesn't fight at all like Pea, so it's very hard to answer. Also, on the frustration thing which everyone harps on about, at LW that would not happen. Pea engaged more than Leonard did in that second fight and I think Duran was really past his fire by that stage after the first win. I remember Freddie Brown saying he lost the fire after that first Leonard win. He had nothing left to be angry about and had made a strange peace with himself. He had attained the highest peak of the mountain and there is nowhere to go but down from there, and down he went in a big way. After that there were only ever flashes of the once great form that he showed from 1968 to 1980. He had guys like Viruet and Fernandez clown on him as much, and more in Viruets case, as Leonard did and he never got frustrated. Just more fired up. They were not as good as Leonard or Pea of course but it was a different story at LW in his peak years. It was an aberration and it would have happened against Viruet or Fernandez on that night too. Highly skilled, defensive counter puncher vs the highly skilled aggressive counter puncher. The final conclusion is .. Roberto Duran wins a very close fight. But Clear victory for Duran. So the answer: Duran.
Duran got trolled into quitting by Leonard. I don't understand where all this vocal confidence about Duran beating Whitaker comes from. Whitaker would continuously BobNWeave™ behind Duran, slap his ass, and run the other way to turn him. Duran gets trolled into embarrassment and a no mas.
Two of the best fighters ever seen on film. Both are superb ring generals, versatile/adaptable, seamlessly incorporate offense and defense, can put punches together, great in-fighters and body-punchers (Duran better in that regard), can fight at distance (Whitaker with the superior jab and backfoot boxing), and they're both extremely fluid and creative. Tested against all-time great opposition, as well.
A push. The offensive fighter with the best defense vs the defensive fighter with the best offense? Yeah, probably.