Ruby may have been the smartest and cagiest of the three Obert brothers inducted into the Handball Hall of Fame. Relying on his court sense and skill, Ruby won doubles titles in all three versions of the game. Despite his dominance of the doubles scene, Ruby had the distinction of being both the youngest (age 19) and oldest (41) to win the Open singles division of the AAU National one-wall competition. In all, he captured 36 national AAU, USHA and YMCA titles.
Off the court, Ruby served on the national one-wall committee and conducted clinics at high schools throughout New York.