Angelo Dundee handled both Napoles and Leonard, and I don't know if he ever stated who he thought would win between the two. At pure welter, Napoles was probably at his best in the two Curtis Cokes title fights, while SRL was best in his victory over Tommy Hearns (throw out Duran No mas). Doubtful if Napoles could beat Hearns due to size difference, and lack of foot speed. Therefore, if SRL "fights" Napoles, Ray gets beat up like Cokes did......but SRL would demand a rematch and just dance around Napoles and outpoint Jose over 15 rds in the second fight.
This is easier for Leonard than some would think. Napoles was great in his own way. However, as boxing evolved from that time, the welterweight division was one of the most prosperous. Napoles slips further down the list as time progresses. He's not like Louis, who remains near the top. "Mantiquilla" is slippery and has his moments, but don't mistake him for Benitez. He's not THAT hard to hit and Leonard would clearly be stronger. After a few rounds of a chess match, Leonard sneeks in a solid left hook and sends Napoles to the canvas. Jose is up and visits the canvas two rounds later. Ray is a bit more aggressive now and Napoles is growing desparate as the cut above his eye grows. In round 9, a left-right-left-left-right combination sends Napoles to the mat again. Leonard is simply a class above Napoles, who has never faced anyone like Ray before. Leonard by KO in 9