At the risk of picking the low hanging fruit,I gotta go with either Carlo Gambino or Tony Accardo. Each achieved absolute power in their respective Families,had all the money they could ever want,were both feared and respected by pretty much everyone in their world,avoided any significant jail time (Gambino-22 months,Accardo-0),and died in a manner that was not ruled a homicide.All in all,Mob life doesn't get much better.