High Quality Content by WIKIPEDIA articles! Woodruff was the first captain of the corps of cadets and a 1915 graduate of the United States Military Academy. His classmates included future World War II generals and his commanding officers, Dwight Eisenhower and Omar N. Bradley. After graduation, he served on the Mexican border and with the 2nd Infantry Division (United States) in World War I. Major Woodruff attended various Service Schools and served as an instructor in the Department of Tactics at the U.S. Military Academy. In 1938, Lieutenant Colonel Woodruff served in the War Department General Staff operations and tactics section.