I don't see any reason why Jay Cutler can't win four, five, or even six Olympias, putting him in the same category as Dorian, Ronnie, et al. He was only born in '74 which makes him 35 or 36 at the moment and he won't even have reached forty if he eclipses Dorian's number of Sandow wins. Ronnie was still winning his Olympia's at 40+.
If not Jay, then possibly Phil Heath is another guy who can mature and has time on his side. I don't mind Kai Greene, but I don't think he'll ever win the Olympia.