Sergeant Bailey was a member of the 9th Infantry Regiment, 2nd Infantry Division. He was seriously wounded by the enemy in South Korea on 22 September 1950 and returned to duty two days later. He was taken Prisoner of War while fighting the enemy in Korea on 26 November 1950 and died while a prisoner on 12 April 1951.

Bailey was awarded the Purple Heart, the Combat Infantryman's Badge, the Prisoner of War Medal, the Korean Service Medal, the United Nations Service Medal, the National Defense Service Medal and the Korean War Service Medal.