Lieutenant Colonel Bailey graduated from Texas A&M University in 2000 with a degree in Aerospace Engineering and received a commission through NROTC. After completing flight training as an AH-1W pilot, he reported to the Warriors of HMLA-167 and was soon attached to HMM-266(REIN) for training and deployment with the 22d MEU. 1stLt Bailey served as the Assistant Future Operations Officer and a schedule writer throughout the MEU’s deployment to Afghanistan. Upon returning to HMLA-167, he served as the squadron’s Communications Officer and Family Readiness Officer through two deployments to Iraq. Captain Bailey departed the squadron in May 2007 and reported to 2d Marine Special Operations Battalion where he served one year as the battalion Air Officer, attended the MAWTS-1 Air Officer Course, and deployed to Afghanistan as the Air Officer and Operations Officer for Marine Special Operations Company India (MSOC I). Capt Bailey returned to HMLA-167 as the Director of Safety and Standardization and was promoted to Major in October 2010.
Major Bailey reported to 2d MAW (Fwd) in December 2010 as an individual augment to the G-3 Plans Division and deployed to Afghanistan until September 2011. Upon his return, he rejoined HMLA-167 as the Assistant Maintenance Officer and served briefly as the Maintenance Officer before reporting to the Marine Corps Command and Staff College in the summer of 2012. During Command and Staff, Major Bailey was selected to work on the Quadrennial Defense Review and reported to Headquarters Marine Corps in January 2013. He returned to Command and Staff and graduated in 2014.
Returning to the operational forces, Major Bailey reported to HMLA-367 in the summer of 2014 where he initially served as the Director of Safety and Standardization followed by one year as the Operations Officer. In November 2015, Major Bailey deployed to VMM-265(REIN) in support of 31st MEU as the H-1 Detachment OIC. During the deployment, he served as ACE Operations Officer as the squadron supported the MEU certification process and Exercise Ssang Yong in the Republic of Korea.
Lieutenant Colonel Bailey served as an Exercise Planner for United States Pacific Fleet from 2016-2018 where he also completed the DARPA Service Chiefs Fellowship Program in 2017.
In 2018, he moved to Camp Pendleton where he served as the Executive Officer for the 11th Marine Expeditionary Unit and deployed aboard the USS Boxer Amphibious Ready Group in 2019. Upon return from deployment, he completed conversion training in the AH-1Z Cobra and reported to MAG-39 where he currently serves as the Operations Officer.
His personal awards include the Meritorious Service Medal, Air Medal (with V), Navy and Marine Corps Commendation Medal (with V), and the Navy and Marine Corps Achievement Medal.