Colonel Drake graduated from the United States Military Academy in June 1912 and was promoted to second lieutenant in the 7th Infantry Division. He participated in the United States occupation of Veracruz May 29 to October 20, 1914. He was promoted to first lieutenant on July 1, 1916.
Colonel Drake was promoted to captain and transferred to the 58th Infantry Regiment on May 15, 1917 at Gettysburg, Pennsylvania. The unit was sent to France in May 1918 and he was promoted to Major in June and subsequently participated in the Aisne-Marne Offensive, the St. Mihiel Offensive, and the Meuse-Argonne Offensive.
Colonel Drake commanded the Quartermaster Corps in the Philippines during the Japanese invasion. He was third in command during the Battle of Corregidor in May 1942.