Bailey attended Athens High School and then enrolled in the University of Georgia where he was a member of Sigma Chi fraternity.
He paused his education to serve in the U.S. Air Force during World War II for three years and graduated from the University of Georgia in 1947 with a business degree.
He married Margaret (Peggy) Bassing in Augusta, Georgia in 1948; they lived in Winter Park, Florida until 1954 when they moved to St. Augustine.
[5] The St. Augustine Junior Chamber of Commerce presented Bailey with the Man of the Year Distinguished Service Award in 1956.
[4] In 1977, Bailey was awarded the Order of La Florida for distinguished service to the city, contributing to St. Augustine's cultural and historic preservation.