Lieutenant Cheshire was the pilot of a F9F-2 Pantherjet fighter with Fighter Squadron 51, aboard the aircraft carrier USS Essex (CV-9). On 26 January 1952, his aircraft was struck by anti-aircraft fire. During the ditching process in Wosan Harbor, North Korea, he ejected at about 150 feet and was killed. His remains were not recovered. His name is inscribed on the Courts of the Missing at the Honolulu Memorial.

Cheshire was awarded the Air Medal with 3 Gold Stars, the Purple Heart, the Combat Action Ribbon, the Korean Service Medal, the United Nations Service Medal, the National Defense Service Medal, the Korean Presidential Unit Citation and the Republic of Korea War Service Medal.