I don't rate old timers head to head. But even if you did, you'd have to take the styles into comparison here and you'd see that Ray's style would be troubled by Calzaghe's, unless you overrate the older era's on purpose. Not to even mention, Ray was at his best at 147, he did very well at 160, 168 is yet another jump and you're talking about one of the best ever at that weight. It's the same how I'd pick Hearns over Robinson stylistically at 154, how I'd take Monzon over him at 160, how I'd take Roy over him at any weight... this is even doing an era/era consideration.
I have too agree on this and also some of the assessment. But SRR is still the most talented and gifted fighter of all time, hence why he would beat JC very clearly in a p4p match up. Picking Roy over SRR is dary. In a p4p fight Roy would get KO'ed.
Maybe Klitschko vs Peter II depending on how Peter fares against what's Maskaev. And IF he has to fight and manages to get past Vitali.
Cotto-Mosley is the only big fight coming up that I think is truly close to 50/50.. Pavlik-Taylor comes next and Calzaghe-Kessler / Floyd-Hatton aren't close at all.. at least 80/20. Next year, the third Marquez-Vazquez match should have very close to even odds also.
Pavlik/ Taylor for me. I will be wishing with all the good mojo i can muster for Pavlik to blast JT, I just wouldn't bet my house on it. 50/50 for sure.
Calzaghe is a big 168 pounder, I'm not sure how Robinson could defend himself in such a physical mismatch against a very brilliantly skilled fighter.