Very hard to say, both incredibly skilled albeit i think Crawford is the more dangerous fighter. Leonard was very very slick and is way more proven at the highest level. I lean towards him on points, either a UD or SD. Crawford has simply not fought at the level Leonard did consistently.
Ray, easily. I never liked the guy, just like I never liked Roger Clemens in baseball even before the steroids, but greatness cannot be denied.
How I feel,Fergy. Crawford's an excellent fighter but Ray was something else. Simply a level above everyone else at 147lbs except for a certain Walker Smith Jr and even that would be very competitive.
Leonard W via UD. It's a tactical bout with spurts of action. He beats Crawford to the punch more times than not. Crawford doesnt do anything better than Leonard IMO (other than switch-hitting). Leonard is quicker (of hand & foot), hits just as hard, has a solid chin & a high Ring IQ. Leonard won't have any weaknesses for Crawford to exploit.