Charles was born in Fort Myer, Virginia, on the 23rd of December, 1872. His father was an Army officer stationed at Fort Myer and Charles went on to attend and graduate from the Virginia Military Institute in 1894. Four years later, he was commissioned as a Second Lieutenant on the 20th of May, 1898 and it wasn’t long after that Charles was deployed to the Philippines during the Philippine-American War. It was his actions here that would earn him the Medal of Honor. The citation reads:

Within a range of 250 yards of the enemy and in the face of a rapid fire climbed a telegraph pole at the east end of the bridge and in full view of the enemy coolly and carefully repaired a broken telegraph wire, thereby reestablishing telegraphic communication to the front.

After the Philippine-American War, Charles went on to serve in China during the Boxer Rebellion, as well as a total of five tours throughout the Philippines. He served on both the British and French fronts during World War 1, losing vision in his right eye after a mortar explosion. Charles was the commander of the 36th Heavy Artillery Brigade and the 3rd Infantry Brigade until October of 1918. After World War 1, he was the head of inspecting coastal defenses in Europe until May of 1919, when he then served on the faculty of the Army War College until 1924. By the time Charles retired from the Army in 1936, he had reached the rank of Major General and had commanded the Sixth Corps Area and the 2nd Army.

Charles returned to the Virginia Military Institute to serve as their sixth superintendent from the 1st of October, 1937 to the 11th of July, 1946. He was also the first American to receive the three highest US Army awards: the Medal of Honor, the Distinguished Service Cross, and the Distinguished Service Medal. Charles Evans Kilbourne Jr died on the 12th of November, 1963 at the age of 90 and he is buried with his wife Elizabeth and one of their two children in Arlington National Cemetery: Section 3, Grave 1705.