Sugar Ray Leonard vs Roberto Duran IV (1996 / '97)?

Great question. Some might find it hard to believe that Duran could still be competitive but the Camacho fight is one piece of evidence that he could be and that he could actually win. Leonard said he had injured his shin before the Camacho bout but, who's to know how severe it was?

The Leonard who lost to Camacho would have his hands full against the Duran who nearly out-pointed Camacho. Duran actually looked better in the rematch, at age 50. Duran was still beautiful in slipping, blocking and countering at close range. He would have been more successful in closing off the ring on Leonard. Duran looked flat against Leoanrd in fight 3 but Leonard didn't look so great either. Duran's fighting heart certainly out-lasted Leonard's and I think he would have beaten the version of Ray who lost to Camacho.

The fight would have been dull, as both were well past their primes.

If Leonard tried to stand and trade with Duran, he'd get stopped. Leonard was knocked out by the relatively soft-punching Hector Camacho at middleweight, can you imagine him fighting Duran the way he fought Camacho? It would not be pretty.

Also, Leonard's legs were gone and his hand speed was that of a sundial. Duran still had plenty of fight left in him and would win this by decision or KO. Duran ws much more competitive against Camacho than Leonard was, that's why I pick him.

So it looks like this would be a fight between the more washed out versions of great fighters so it would be a matter of who had lost the most between them. It would still be Leonard vs Duran and would have drawn a large audience despite skill erosion. I believe that Duran at that stage was probably a little better than Leonard and would have quite possibly taken a split decision victory.

NO MAS!!!