My picks would be
Tommy Lucchese: Machiavellian mobster, relatively successful thanks to rackets in clothing, construction, etc., made strong alliance with Gambino
Carlo Gambino: obvious reasons, very wealthy thanks to mob connections, forger better relations with Lucchese.
Benny Squint Lombardo; very low key, preferred to delegate authority to high-ranking grunts like Funzi Tieri, Chin Gigante, or Fat Tony. Died a free man.

Would have chosen Tony Accardo and Paul Ricca, but they're non-NYC mafiosi.