Bailey graduated from Madison Academy in Chatham Borough, enlisted in the Army Corps, and after finishing a tour of duty in Yokohama, Japan, joined the Class of 1949 on campus. He majored in economics, joined Campus Club, and belonged to the Rifle Club, the Advertising Club, and Whig-Clio.
After working in New York, he and Taz co-founded the Noe Pond Club. Along with his brother, they established swimming and tennis clubs in various locations near Noe Farm in Chatham, all offering recreational opportunities for nearby families.
Bailey kept in touch with Princeton in many ways. He attended every Yale football game but one, and served on Princeton’s National Schools Committee, the Alumni Council, and the Princeton Club of Northwestern New Jersey. He was also treasurer of the Concerned Alumni of Princeton.
Bailey was interested in antique firearms, with an extensive collection of Savage pistols and a definitive book on that gun. His own guns were given to the NRA National Firearm Museum in Virginia.