Gentry played college football at the University of Southern California where he was also a member of Phi Kappa Tau fraternity. At USC, he played on the 1931 and 1932 Rose Bowl championship teams.[4] He was a decorated soldier, rising to the rank of Capitan,[5] and serving as an intelligence officer in World War II. He later was a state and national commander of the Veterans of Foreign Wars.[6][7] Gentry's post-football career was in the law and he was city attorney of Pasadena, California for sixteen years. He was also a published writer and poet.[8]