You might ask: Which Sugar Ray? Well, since there were two truly elite fighters with the Sugar Ray moniker, let’s speculate on both — one at a time.
First, Sugar Ray Robinson. As a welterweight, Robinson was virtually unbeatable, with a perfect balance of power punching and ring generalship. As a middleweight, Robinson was superb, but less than perfect and, frankly, more interesting. In Robinson vs. Pacquiao in their primes as welterweights, I’ve got to think Sugar Ray would use his superior reach and foot speed to eke out a tactcial, hard-fought decision.
Now, what about Sugar Ray Leonard? If it’s the Leonard who decided to stand toe-to-toe in his first fight against Roberto Duran, then I see Pacman, more willing to adapt, moving and sticking and landing enough meaningful blows to win, maybe even stop Leonard in the later rounds. If it’s the Leonard who so frustrated Duran in their second fight that it elicited the infamous “No mas” from Duran, then Pacquiao might have a problem. Or not. As long as Manny didn’t succumb to the same sort of frustration that Duran did, it’s within reason to visualize his relentless pursuit of Leonard eventually wearing down Sugar Ray. My guess: Pacman by a late TKO.