A native of Detroit, Michigan, CAPT Bailey is a graduate of the U.S. Naval Academy with a degree in general science, a graduate of the U.S. Naval War College with a master's in national security and strategic studies, as well as a master's degree in Government Information Leadership (CIO Specialty) from the National Defense University. He is a National Security Telecommunications and Information Systems Security 4011 Certification and is certified as an Information Systems Security Professional and Federal Chief Information Officer.
CAPT Bailey's career includes over 14 years of sea duty assignments including USS Flatley (FFG 21) as Auxiliaries Officer and Operations Officer, USS Wasp (LHD 1) as Combat Information Center Officer and Auxiliaries Officer, USS Deyo (DD 989) as Operations Officer and Commander, Destroyer Squadron EIGHTEEN as Operations and Plans Officer, and served as the Executive Officer on the USS Carr (FFG 52).
CAPT Bailey's deployed assignments include the U.S. Southern Command, Central Command And European Command theatres, as well as Assistant Chief of Staff for C5I for Expeditionary Strike Group TWO.
CAPT Bailey's shore assignments include Surface Warfare Officer School as a Steam Engineering Instructor, The U.S. Naval War College, the Joint Staff as Action Officer in Information Assurance, and Commanding Officer of Naval Computer and Telecommunications Station San Diego.
CAPT Bailey's awards include the Defense Meritorious Service Medal, Meritorious Service Medal (2), Navy Commendation Medal (6), and Navy Achievement Medal (2).