Not an easy one Fergy but I pick Leonard. More gifted all round than Roy. And a far better rogue's gallery of opponents.
Sugar Ray Leonard by far had the better wins, but Roy Jones Jr at his best looked unbeatable although against lesser opposition. Both fighters had incredible speed and power but Leonard showed he could dig really deep in tough fights, where as Jones never really showed that in his career, which was down to how good he was and maybe not always fighting the best available opposition. Overall i'd say Leonard even though Jones was more dominant Leonard showed his mettle more in tough situations.
Leonard, without reservation. He was willing to fight Duran, Benitez, Hearns, etc. Jones wanted less risk and was willing to let people wonder "what if?" Of course, not as many transcendent stars in Jones' time either, that plays into it.
Sugar Ray Leonard without any hesitation or reservation Fergy. Leonard is an Olympic Gold Medalist and holds titles in 5 weight classes with a CV that has some serious competitive bouts. To be fair to him Roy Jones Jr did get robbed at The Olympic Games in Seoul 1988 but didn't have the same standard of competitors or fights that captured the publics attention beyond serious boxing fans.
Leonard, he not only had the talent, but he had more dance partners to show that talent. May be a different story if Jones lived in a different era or if things could have worked out differently.
I mean, those 2 belts Leonard won against Lalonde was kind of bs, Jones 4th title at HW was much better/historic. In terms of achievements both are about even, but Leonard does have those big 4 big wins against Hearns, Benítez, Duran and Hagler that propels him above Jones Jr.
Roy was so gifted he made fights turn into exhibition s. blowing out his opponents in virtuoso type of style. He wasn't in any really dog fights till end of his career when he was a shell of his former self. SRl on the other hand fought murderers row: Hagler, Hearns, and Duran. Just the mere mention he won against all three. Sugar was fighting somebody in Hagler who was bigger and meaner. Duran was a Looney sunhovabitch, and Tommy, TOMMY!, If I had to pick 2 guys in history who a prize fighter should not be able to sleep before the night of the fight against would be Tua and Hearns. That right hand was from hell. Leonard had to dig deep during those wins, gutcheck time! I remember hearing rays wife saw something in his eyes after defeating tommy Hearns that she never saw before, heck he probably never ever imagined being the conqueror of such a difficult fight, he was beaming with pride perhaps even astonishment. Sugar Ray had the better opposition in his resume, was a complete offensive genius (before Manny Pacquiao s time) but Roy was the far superior athlete. Heck people were saying "yeah but he never fought noone" despite being pound for pound #1. I'm still trying to envision a pound for pound sense of how ray Leonard would do at light heavyweight had he been faced with those same foes, if he was myrhically bigger, also head to head I would favour Roy Jones junior at whatever weight class (pick one) and then again: Roy was fighting somebodys, he just made them look like they were nobodies! Better fighter and atg ranking : sugar, superiorly athletic and h2h: Jones
I would go with Ray. Ray was more of a traditional fighter that was athletically blessed where Roy did a lot of things wrong but got away with it because of his incredible releflexes and speed. Both were in huge fights but pound for pound I would say SRL.
Both great fighters, both multi weight champions, and both exceptionally gifted. I have to admit to a preference for RJJ…the man’s physical skills were out of this world. The reflexes were just insane. But SRL was no slouch either, quick as a whip and one of the greatest boxer punchers I’ve ever seen. But Leonard’s resumé gives him the edge if comparing on an all round basis. Hardly RJJ’s fault that monsters like Hearns, Hagler and Duran weren’t around on or near their prime in his day, though a fight with Michael Nunn at 168 in the mid 90s would have gone a long way to beefing up his resume. Providing he won of course.