Major General Charles Evans Kilbourne (b. 1872 d. 1963), an 1894 VMI graduate, had a distinguished career in the U. S. Army before returning to his alma mater to serve as the sixth Superintendent. He entered the volunteer Signal Corps as a 2nd Lieutenant at the outbreak of the Spanish-American War in 1898, and received the Medal of Honor for gallantry in action in the Philippines in 1899. He received his regular Army commission in 1899 and served in China during the Boxer Rebellion. During World War I he was Chief of Staff of the 89th Division and was wounded in action in France. General Kilbourne served multiple tours of duty in the Philippines and was instrumental in the development of the military installations on the island of Corregidor, including the initiation of the tunnel system used during World War II by General MacArthur's troop. He also served in the War Plans Division in Washington DC from 1932-1938.

Kilbourne was promoted to Brigadier General in 1928. He received his promotion to Major General in 1935 and retired from active duty the following year. He was the first person in American history to hold simultaneously the nation's three highest military awards: The Medal of Honor, the Distinguished Service Cross, and the Distinguished Service Medal. Kilbourne became Superintendent of VMI on October 1, 1937 and guided the Institute through the challenging years of World War II. He retired on June 20, 1946 and was named Superintendent Emeritus. He died on November 12, 1963 and is buried in Arlington National Cemetery.