CAPT Bailey entered the Navy through Recruit Training Command Orlando, FL, in 1990.  He attained the rank of Petty Officer First Class until his commissioning in 2001 as a Lieutenant Junior Grade. He served in various enlisted leadership positions in both operational and shore-based commands.

CAPT Bailey graduated from Officer Indoctrination School in Newport, RI in 2001 and reported onboard USS TARAWA (LHA-1) as the medical Division Officer where he directly assisted in the initial and follow on stages of Operation Iraqi Freedom and Task Force Tarawa.  In 2003, he reported to Naval Medical Center San Diego as the Assistant Department Head of Patient Administration.  In 2005 he reported to 1st Medical Battalion and served as Charlie and Alpha Surgical Company Commander as well as the Battalion Operations Officer.  CAPT Bailey served in multiple combat tours in Al Anbar province to include Al Taqaddum, Fallujah, Ramadi and Rahwa as a Surgical Company Executive Officer where he led over 600 Navy and Marine Corps personnel.  CAPT Bailey led all efforts in the design, planning and implementation of Operation Defeat Al Qaeda in the North.

In 2008 he was assigned to U.S. Fourth Fleet, Naval Forces Southern Command, Mayport, FL., as Fleet Surgeon.  He developed the Concept of Operations and employment of relief efforts in support of Joint Task Force Haiti (Operation Unified Response), the largest maritime humanitarian and disaster response effort in the history of the U.S. Military totaling over 17,000 personnel.  

In 2010 he attended the U.S. Naval War College in Newport, Rhode Island. Upon graduation, he reported to U.S. Marine Forces Pacific as the Deputy Branch Head and Program Director for Theater Security Cooperation for Health Services Support, where he received the Association of Military Surgeons of the United States 2012 Humanitarian Assistance Award.  

In July of 2014 CAPT Bailey was screened and selected to serve as the Executive Officer, 2D Medical Battalion, Camp Lejeune, NC., where he led the daily operations, training and development of over 1,300 Sailors and Marines in support of Operation Enduring Freedom, Inherent Resolve, Freedom Sentinel, 22nd, 24th and 26th Marine Expeditionary Units, Theater Security Operations, Global Health and Contingency Operations. 
 
In 2016 CAPT Bailey reported to U.S. INDO-PACIFIC Command where he was selected to be the Chief of Staff for the Office of the Command Surgeon (J07) as well as the Director of Medical Operations and Plans where he was responsible for the day to day medical operations for the world’s largest Geographical Combatant Command spanning 100 million miles, 52 percent of the Earth’s surface, 36 countries and half of the world’s population.  He owned and managed all Operational Plans at the highest security classification levels to include Major Combat Operations, Homeland Defense and Support to Civil Defense Authorities.  He was the senior team lead for Legislative Affairs and direct medical advisor to the INDO-PACOM Commander for House and Senate Armed Services Committee Testimony.

In June of 2019 CAPT Bailey reported to US Marine Corps Forces Pacific as the Senior Medical Operational Advisor for I and III MEF forces which comprise over 87,000 Marines and Sailors throughout the Pacific Theater where he directed the execution of multilateral collaborative planning efforts with adjacent, subordinate, and higher commands as well as provided Commander’s intent for all plans/exercises for over 56,000 personnel in joint, bilateral, and multilateral capacity.

In May of 2020, CAPT Bailey assumed Command of Field Medical Training Battalion West at Camp Pendleton, CA. where he led a staff of 57 Officers, Sailors and Marines, and produced over 2,700 Corpsmen to the Fleet Marine Force.  CAPT Bailey completely restructured the curriculum to include methods of course delivery and the introduction of various medical procedures and processes to include prolonged casualty care, which will enable FMF Corpsmen to provide lifesaving care in distributed and isolated wartime environments across the globe.

In June of 2022 CAPT Bailey reported as the Deputy Commander of Naval Medical Forces Pacific where he assisted in the oversight of 102 senior staff at an Echelon three Headquarters.  He executed command and control for ten Navy Medicine Readiness and Training Commands, two Naval Dental Centers and eight global research labs for 19,500 military/civilian and contract staff providing healthcare delivery.  CAPT Bailey was instrumental in establishing the Pacific Rim Network where he managed a budget of $800M in a TRICARE eligible area of 597,941.  Additionally, he was a plank owner in establishing and serving as the Deputy Commander of forward deployable Task Group 504.4 in support of Operational contingencies in the INDOPACIFIC area of operation.  He is the first Plans, Operations and Medical Intelligence Officer to hold either of these senior executive positions within the Navy Medicine Enterprise. 

On 02 April 2024 CAPT Bailey detached Naval Medical Forces Pacific to serve as the Senior Executive Assistant for the Navy Surgeon General at the Bureau of Medicine and Surgery, Falls Church, VA where he led all coordination with SECNAV, CNO, VCNO, OSD (HA), OHA, White House Medical Unit and TMO staffs to tackle the most complex HHS issues and provided world class healthcare to sailors, Marines, and beneficiaries.  in February 2026 he reported as the Executive Officer to the Director of the Defense Health Agency, Fall Church, VA. 

In May 2026 he reported as the Director, Naval Medical Center San Diego, Commander, Navy Medicine Readiness and Training Command San Diego.

He holds a Bachelor’s degree, an M.S. in Health Services Management and an M.A. in National Security and Strategic Studies.  CAPT Bailey is the only two-time selectee as Navy Medicine’s POMI of the Year (2009/2013) and the only senior medical operations officer to serve as the Senior Executive Assistant to the Navy Surgeon General.  CAPT Bailey has served in multiple combat tours dating back to 1992 (officer and enlisted tours).

His awards include:  Legion of Merit (two stars), Defense Meritorious Service Medal (two stars), Meritorious Service Medal (Gold star), Joint Service Commendation Medal (cluster), Navy and Marine Corps Commendation Medal (three gold stars), Joint Service Achievement Medal, Navy and Marine Corps Achievement Medal (four gold stars), Combat Action Ribbon and various campaign medals, awards and warfare devices.