Well pfp in their primes Calzaghe isnt even in Leonards league... But at SM Leonard had lost a step , still very very good but could be taken... Im thinking about the SRL that fought Heans II,LAlonde... I think that version of Leonard and Calzaghe would have been a very close fight ,,,, Im thinking Leonard has some big moments but in the end Calzaghes natural size and non stop punching and youth(his prime weight) give him the edge here.. 114-112 115-113 type decision for Calzaghe. Could see both hurting or maybe dropping eachother at one point (joe had decent power at SM) but neither in danger of being kod. Would be an exciting back and forth fight though.
I'm not sure Leonard had the size (and was close enough to his prime at that stage in his career) to beat an excellent 168 lb. fighter like Joe. The fight against Lalonde (a LHW) was at 168, and Lalonde hurt Leonard a few times, and Leonard looked sluggish. The Hearns rematch was at a catchweight of 163, and Leonard looked bad in that fight too. Of course, this is Ray Leonard we are talking about, one of the most versatile and adaptable fighters you'll see. He was an amazing fighter. So it wouldn't surprise me if he would've pulled it off. But when you take a very good fighter who spent his whole career at 168 and up, against a guy who peaked at 147 and was declined and didn't look good above 160, it's hard to pick Leonard.
Leonard was exceptional, Joe was average. If Ray can decision Hagler at 160, he runs rings around Joe at 168.
Srl is ahead of Calz on the pol, but still no good agurment why he would win! Well, guess its just another normal day on esb:smoke
Well IMO that version of Leonard that beat Hagler at 160 is definitely the bettter fighter..... But he slipped in just the next couple years and thats when he made his move to SM. Thats the version i picked that Joe would edge.