A graduate of the United States Military Academy, he was one of the airmen who took part in the Doolittle Raid on Tokyo, Japan, during World War II, on April 18, 1942.

After bombing Japan during the raid and due to mechanical trouble with his bomber, he was forced to land in the Soviet Union, where he was interned with his crew for 14 months before escaping back to the United States.

[1] Following his enlistment in the United States Army in 1930, he was assigned to the 7th Infantry Division and was stationed at several posts including at Chillkoot Barracks in Alaska.

[1] Following graduation, he was commissioned as second lieutenant in the United States Army Air Corps and was assigned to Randolph Field in Texas for pilot training.

After earning his pilot wings, he was assigned to the 95th Bombardment Squadron at March Field in California where he flew Northrop A-17s and Douglas B-18 Bolos.

[2] In the immediate aftermath of the Japanese attack on Pearl Harbor on December 7, 1941, the 95th flew anti-submarine warfare patrols in the Pacific Northwest from December 22, 1941, to March 1942, before being assigned to Lexington County Airport, South Carolina, on February 9, 1942, in order to meet the greater threat from German submarines operating off the East Coast.

Departing earlier than planned due to concerns about Japanese detection on April 18, 1942, York's B-25, specifically aircraft No.

[7] Upon landing in the Soviet Union, the base commander of Vozdvizhenka asked York if he was a participant of the Tokyo Raid.

Several months later, they were relocated to Ashgabat (Ashkhabad), in what was then the Turkmen Soviet Socialist Republic, 20 miles (32 km) from the Soviet-Iran border.

[11] Following his return to the United States in late June 1943, York trained in B-25, Boeing B-17 Flying Fortress and Consolidated B-24 Liberators in preparation for his further combat service during World War II.

Following the end of war in Europe in May 1945, York was assigned as an air attaché in Warsaw, Poland, from July 1945 to January 1947.

Following his return from Poland in January 1947, he was appointed as commandant of the Air Force Officer Training School in San Antonio, Texas, from March 1947 to April 1948.

Prior to his death, York was interviewed in 1984 about his involvement in the Doolittle Raid and subsequent internment in the Soviet Union.