To answer the question, the 1940s Robinson is the only welterweight in history to favor over Leonard. In a vacuum, Leonard is the favorite over any other welter.
Only Duran, Robinson, and Hearns with a better strategy (clinching when necessary) would I consider. I think Leonard beats all the 90s guys with Trinidad and Mosley being the most dangerous but still huge underdogs. Ray would school Oscar badly and probably stops him in a 15 rounder. At 154, there’s Hearns. I’m a big McCallum fan but he gets outboxed and Norris would get KO’d.
Trinidad is the only guy in the last 30 years who's a dangerous fight for Leonard at 147, but like I said, Tito gets stopped in the end.
Leonard vs Mosley would be interesting early due to both guys being so quick handed but I think Leonard would have tamed Mosley early and make him gun shy.
I think Gavilan is about a 50/50 shout tbh and I'd give Rodriguez a similar shout. Both very tough fights for Ray imo though he might be given the edge. Rodriguez's style would make for an interesting fight. I'd give Griffith a really good chance too, not far off 50/50 if he was at his best and determined to grind, maul and make things ugly in between clean punching and dictating the pace. I'd lean towards Leonard though. I'd pick Napoles if he was a big welter/small middle and not a natural lightweight. He had a lot of the necessary tools and was a tad better at his peak than Ray a but would be at a notable size and speed disadvantage.
Emille Griffith and Luis Manuel Rodriguez are good shouts, I think they have a chance to beat SRL. Napoles, for all his skills, is at a disadvantage in size and speed.
With Leonard's speed, Napoles tendency to cut; Leonard might literally blind him. Which is a shame, as a fight as good as that shouldn't ever come down to cuts. Leonard should be favoured regardless, due to the speed and size advantages as Tin says, but if Napoles was the same size; I'd make him the favourite.
Gavilan, yes, I see him as a legit threat to beat Leonard. He has the all the necessary tools to do so. Rodriguez? Hmmm, I'm thinking Rodriguez experiences the same issues Benitez had; meaning he struggles with Leonard's range and handspeed. Rodriguez typically had the quickness edge on his opponents, but it wouldn't be the case versus Leonard. I think it's gonna be EXTREMELY EXTREMELY difficult to outbox Leonard, and I can't see a Rodriguez, nor a Whitaker or Mayweather, accomplishing it. Griffith? I think he's a touch too slow. Duran had the extreme quickness to close the gap on Leonard, and his defensive head movement made him a hard target to find. You kind of lose those attributes in Griffith, but I do think Griffith is competitive. In the end, I reckon Leonard is just a step ahead. Napoles? It's already been said. Too small, and cuts too easily.
Really wouldn't call Griffith slow, if anything he's underrated in the speed department. As inconsistent as Griffith can be when he's at his A-game he can be a very hard fighter to beat.
