Command Sergeant Major Bailey enlisted into the active Army in June of 1984, and attended basic combat training and advanced individual training at Fort Sill, OK. Upon completion of training, he was awarded the military occupational specialty Fire Support Specialist (13F), with follow-on duty assignment in Germany. He is currently employed as a counter transnational organized crime (CTOC) and counter threat finance (CTF) contractor for United States Special Operations Command (USSOCOM) at MacDill Air Force Base in Tampa, FL.
Command Sergeant Major Bailey has held leadership positions from Squad Leader to Command Sergeant Major. His assignments include Forward Observer assigned to 2nd Armored Division (FWD) in Germany; Drill Sergeant assigned to the 91st Infantry Division, Modesto, CA; Special Operation Team – Alpha (SOT-A) Team Sergeant attached to 1st BN, 19th Special Forces Group (Airborne) in Kuwait for Operation Desert Spring, then OPCON to 5th SFG(A) for Operation Iraqi Freedom in Iraq; Group SIGINT Chief for Group Support Company (GSC), 19th SFG(A), Draper, UT; SOT-A Team Sergeant attached to 2nd BN, 19th SFG(A) at Advanced Operations Base 3220 in Wardak, Afghanistan for Operation Enduring Freedom; First Sergeant of GSC, 19th SFG(A) and Company Sergeant Major of Group Special Troops Company, 19th SFG(A), Camp Williams, UT; Command Sergeant Major of Group Support Battalion, 19th SFG(A), Ogden, UT; Senior Enlisted Advisor for USCENTCOM Army Reserve Element (ARE), Tampa, FL; Command Sergeant Major of the 505th Military Intelligence Brigade (Theater), Camp Bullis, TX, and currently serves as the Command Sergeant Major of the Military Intelligence Readiness Command at Fort Belvoir, VA.
Command Sergeant Major Bailey has a Master of Business Administration (MBA) degree in Project Management. His military education and training includes all levels of NCOES to include the United States Army Sergeants Major Academy, Brigade Pre-Command/CSM Course, Joint SOF Battalion Pre-Command/CSM Course, Senior Enlisted Joint Professional Military Education (SEJPME) Course, Defense Support of Civil Authorities, Airborne School, USASOC Static-line Jumpmaster Course, Air Assault School, Drill Sergeant School, Summer and Winter Mountain Warfare Schools, Signals Intelligence (SIGINT) Collector Course (35P MOS), Basic Infantryman Course (11B MOS), and Telecommunications Operator Course (74C MOS).
Command Sergeant Major Bailey’s awards and decorations include the Bronze Star Medal, Meritorious Service Medal (3 OLC), Army Commendation Medal (4 OLC), Army Achievement Medal (silver OLC), Good Conduct Medal, Army Reserve Component Achievement Medal (silver OLC and 4 bronze OLC), National Defense Service Medal with bronze service star, Armed Forces Expeditionary Medal, Afghanistan Campaign Medal with 2 campaign stars, Iraq Campaign Medal with 2 campaign stars, Global War on Terrorism Expeditionary Medal with bronze service star, Global War on Terrorism Service Medal, Korean Defense Service Medal, the Joint Meritorious Unit Award, Combat Action Badge, Master Parachutist Badge, Air Assault Badge, Drill Sergeant Identification Badge, German Armed Forces Marksmanship Badge (silver), and several foreign military parachutist badges.
Command Sergeant Major Bailey lives in St. Petersburg, FL with his wife Beth and their two hound dogs. He has two incredible daughters, Sierra and Maia, who reside in Utah