Hutchings was designated a distinguished military student and was thereafter commissioned into the U.S. Army as an infantry officer. During his subsequent 23-year tenure in the military, he served overseas tours in Korea, Germany and Italy. Hutchings' career in the Army was defined by his numerous Special Operations assignments, including command of a Special Forces Scuba detachment and four separate tours in Ranger units.In the Rangers, Hutchings commanded at the platoon, company and battalion level, and in his final tour on active duty, served as Deputy Commander for the Army's 75th Ranger Regiment. He has been awarded the Ranger and Special Forces tabs, as well as the Scuba, Master Parachutist, Military Free Fall, Air Assault, and Expert Infantry badges. Hutchings is a graduate of the Army's Command and General Staff College, the Joint Professional Military Education Program, the School of Advanced Military Studies and holds two advanced degrees. During the summer of 2000, Hutchings was selected for promotion to full Colonel in the regular Army as well as attendance for schooling at the Air Force War College; he instead declined these advancements to retire and assume duties as the Commandant of Virginia Military Institute.