A native of Garfield Heights, Ohio, Capt. James "Beetle" Bailey graduated from Embry-Riddle Aeronautical University in 2004. He was commissioned through Officer Candidate School in Pensacola, Florida, and was designated as an aerospace engineer (maintenance) duty officer in 2006.

He earned a master's degree in project management from Northeastern University in Boston and holds a master's in defense and strategic studies from the U.S. Naval War College. He is a graduate of the Advanced Logtech Program from the University of North Carolina’s Kenan-Flagler Business School.

Operationally, Bailey completed six deployments to the Western Pacific, South China Sea, Mediterranean and Middle East, supporting Operations Iraqi Freedom, Enduring Freedom, New Dawn, Atlas Guardian and Inherent Resolve. His assignments include the “Tophatters” of Strike Fighter Squadron (VFA) 14 and the “Seaknights” of Helicopter Sea Combat Squadron (HSC) 22.

His ship company tours include serving as the IM-2 and IM-4 division officer aboard the USS Enterprise, making its final deployment in 2012. He performed his O-4 milestone tour aboard the USS Harry S. Truman during the first Dynamic Force Employment deployment, operating above the Arctic Circle for the first time in over 30 years. He later served as the 13th aircraft intermediate maintenance department officer aboard the USS Harry S. Truman and was deployed for 285 days in response to Russia’s invasion of Ukraine.

His shore and acquisition assignments include the Center for Naval Aviation Technical Training Detachment at Whiting Field, where he served as an instructor and the director of maintenance training for all Navy and Marine Corps aviation maintenance officers, earning recognition as the 2015 domain Officer Instructor of the Year.

While assigned to NAVAIR, he supported the Maritime Patrol and Reconnaissance Aircraft Program Office (PMA-290) and PMA-260 in both logistics and program management roles. He performed duties as the N423 Carrier Strike Group readiness officer on the staff of the commander of Naval Air Force Atlantic and most recently served as the PMA-260 Level 1 integrated product team lead for common ground support equipment. Capt. Bailey assumed command of PMA-260 June 17, 2026.

His awards include the Meritorious Service Medal with a gold star, the Navy Commendation Medal (seven awards), the Navy Achievement Medal and the Battle Efficiency Award (three awards). He is authorized to wear the Professional Aviation Maintenance Officer warfare insignia.