Master Chief Bailey was born on December 3, 1974 in Claremont, NH and enlisted into the Navy on November 1, 1995. After graduating Recruit Training in Chicago, IL, he attended the Aviation Structural Mechanics A-School in Millington, Tn. Upon completion in June of 1996, he was stationed at VS-32, homeported out of Naval Air Station Cecil Field, Jacksonville, FL. While assigned to VS-32 he completed two 6 month deployments in support of Operation Southern Watch onboard the USS George Washington (CVN 73) from September 97 - March 98, and USS John F. Kennedy CV (67) from October 99 – April 00. He was promoted to Petty Officer Third Class and Petty Officer Second Class during this tour.
In November of 2000, Petty Officer Bailey was assigned to Naval Submarine School, Groton, CT. working as the Leading Petty Officer for the Commanding Officer, and as a Military Training Instructor for Electronic Technician A- School. While assigned to Sub School he completed his Master Training Specialist. He also served as a Security Force Augmentee for the Installation Security Department. In September 2001 Petty Officer Bailey submitted his Master-at-Arms conversion Package and was approved for conversion. He was promoted to Petty Officer First Class during this tour.
In October 2003, Petty Officer Bailey reported to Master-at-Arms A-School in Little Creek, Va. Upon completion of A-School in January 2004, he was assigned to Naval Submarine Base New London, Groton, CT. While assigned he served as the Harbor Security Division Leading Petty Officer, Training Officer and Watch Commander.
In January 2006, Petty Officer Bailey was assigned Naval Air Station Sigonella, Italy, where he completed the duties of Watch Commander, Training Officer and Admin Officer. He was promoted to Chief Petty Officer during this tour. While assigned he completed Military Police Investigation and Protective Service Schools before deploying to Law and Order Task Force, Iraq in support of Multi-National Forces Iraq.
In December 2008, Chief Bailey reported to Naval Expeditionary Guard Battalion, Guantanamo Bay, Cuba. His duties included Camp 2/3 Watch Commander, Camp Leading Chief Petty Officer and Camp Iguana Officer in Charge. Chief Bailey was promoted to Senior Chief Petty Officer during this tour.
In April 2010, he reported Naval Air Station Jacksonville, Jacksonville, FL., where he completed the duties of Security Senior Enlisted Advisor and Security Manager.
In March 2011, Senior Chief Bailey reported to Naval Submarine Base Kings Bay, Kings Bay GA, and completed the assignments as Police Operations Officer, Military Working Dogs Senior Enlisted, Anti-Terrorism Officer, Security Senior Enlisted Advisor, and Deputy Security Officer.
In March of 2013, Senior Chief Bailey was assigned to Marine Corps Security Forces Battalion Bangor, assigned as Alpha Company Senior Enlisted Advisor, Battalion Senior Enlisted Advisor, Charlie Company Senior Enlisted Advisor, Guard Officer, and Orientation Officer and was promoted to Master Chief Petty Officer.
In September of 2016, Master Chief Bailey reported to Naval Security Forces Bahrain, were he served as the Senior Enlisted Advisor and Acting Command Master Chief.
In November of 2017, Master Chief Bailey reported to the USS Dwight D. Eisenhower (CVN69), were he serve as the Security Department Leading Chief Petty Officer.
In November, 2019, Master Chief Bailey reported to Naval District Washington (NDW), were he served as the Senior Enlisted Leader for NDW Naval Security Forces.
In May 2021, Master Chief Bailey reported to Naval Support Activity Souda Bay, Greece, were he served as the Security Department Leading Chief Petty Officer.
In December 2021, Master Chief Bailey reported to Marine Corps Security Forces Battalion-Bangor, currently serving as the Battalion Master Chief.