Charles D'Olive was born on July 10, 1896, in Suggsville, Alabama. He enlisted in the Aviation Section of the U.S. Army Signal Corps for flight training on April 28, 1917, after after completing flying school, was assigned to the 3rd Aviation Instruction Center at Issoudon, France. He joined the 93rd Aero Squadron at Vaucouleurs, France, in August 1918, and was credited with the destruction of 5 enemy aircraft in aerial combat before transferring to the 141st Aero Squadron in October 1918. After returning to the U.S. he was discharged from the Army Air Service in February 1919. Charles D'Olive died on July 20, 1974, and was buried at the Vine Street Hills Cemetery in Cincinnati, Ohio.

His Distinguished Service Cross Citation reads:

The Distinguished Service Cross is presented to Charles Rudolph d'Olive, First Lieutenant (Air Service), U.S. Army, for extraordinary heroism in action near St. Benoit, France, September 12, 1918, First Lieutenant D'Olive, in conjunction with another American pilot, engaged and fought five enemy planes. Outnumbered and fighting against tremendous odds, he shot down three enemy planes and outfought the entire enemy formation.