USMA Class of 1945, Captain Middleton was the pilot of a F-51D Mustang night fighter with the 12th Fighter Bomber Squadron, 18th Fighter Bomber Wing. On April 30, 1951, while on a combat mission, his aircraft was hit by anti-aircraft fire, spun in from 2,000 feet and crashed near Miudong, Korea. His remains were not recovered. His name is inscribed on the Courts of the Missing at the Honolulu Memorial.