He was commissioned a second lieutenant on March 13, 1902, and assigned duty at the Presidio of San Francisco. He served in the Philippines and later Alaska, and took part in the expedition into Mexico with the 16th Infantry Regiment in 1916. During World War I, he served on the general staff of the 1st Division and as assistant chief of staff for the 3rd Army. After the war, Short became a member of the War Department General staff and served with the Far Eastern section of the Military Intelligence Division until 1924. He then attended the Army War College and after graduation served as a staff school instructor. He commanded 1st Infantry Division from 1938 to 1940 and I Corps from January 1940 to January 1941. General George Marshall appointed him to the Hawaiian command on February 8, 1941. He earned the Distinguished Service Medal and was considered to have had a successful career at that time, especially in light of his promotions during peacetime.