CDR Todd "BUG" Bailey entered the Navy in 1987 after graduating from the Georgia institute: of Technology with a Bachelor's degree in Aerospace Engineering He entered Flight School in 1987 and received his Naval Aviator’s wings in 1989.

After completing en-route training at NTSU Waco. Texas. CDR Bailey reported to the "IRONMEN" of VQ-3 at NAS Barbers Point. Hawaii, in April 1990 to fly the E-6A "Mercury." He made the homeport change to Tinker AFB. Oklahoma, with the squadron in 1992.

In 1994, CDR Bailey reported to the VT-28 "RANGERS" as an instructor pilot in the T-34C Mentor. After a successful instructor tour, CDR Bailey was selected to serve as a "Super JO", and returned to fly the Mercury in 1996. He reported to the Q-4 "SHADOWS in 1997 and served as an Instructor Pilot, Mission Commander - Evaluator and Assistant Administration and Operations Department Head.

In July 1998. CDR Bailey reported for duty to the Commander. Strategic Communications Wing ONE. and served as the Current Operations Officer. In October 1999, CDR Bailey returned to VQ-4 for his third operational tour. During this tour, he was assigned as the Admin Officer and the Operations Officer. He continued to serve as an E-6A/B Aircraft Commander. Instructor Pilot, and Mission Commander - Evaluator.

In October 2001, CDR Bailey reported back to Strategic Communications Wing ONE and in April 2002 was sent TAD to Commander. FIFTH Fleet, where he served in the STRIKE planning division and as the Liaison Officer to Commander, Joint Task Force 180 in Bagram AB, Afghanistan until October 2002.

After the completion of his tour at CSCW-1. he was assigned to Commander Naval Forces Central Command as the Exercise Director responsible for overseeing 44 military exercises with 13 countries, Commander Bailey assumed the duties as the Officer-in-charge, Center for Naval Aviation Technical Training Detachment Tinker AFB, Oklahoma, in September 2005,
Commander Bailey's personal awards include the Meritorious Service Medal, Joint Commendation Medal, Navy and Marine Corps Commendation Medal (five awards) and numerous personal, unit and campaign awards.