Porky Cragg was born on September 8, 1919, in Mount Vernon, New York. He enlisted in the Aviation Cadet Program of the U.S. Army Air Corps on November 25, 1940, and was commissioned a 2d Lt and awarded his pilot wings at Selma, Alabama, on July 11, 1941. His first assignment was as Assistant Squadron Engineering Officer with the 28th Pursuit Squadron of the 37th Pursuit Group at Albrook Field in the Panama Canal Zone. In the spring of 1942 he was assigned to the 80th Fighter Squadron of the 8th Fighter Group in the Southwest Pacific area, and became the commander of the 80th Fighter Squadron in April 1943. Major Cragg was credited with destroying 15 enemy aircraft in aerial combat between May and December 1943. He was declared Missing in Action when he did not return from a mission on December 26, 1943, and after the war ended, he was declared Killed in Action on January 16, 1946. His remains were never recovered.

His Distinguished Service Cross Citation reads:

For extraordinary heroism in action near Wewak, New Guinea, on 21 August 1943. Major Cragg, commanding his fighter squadron, escorted a bomber formation attacking an Airdrome. About twenty enemy interceptors were encountered. With all his squadron engaged, he observed ten additional enemy fighters about to deliver a coordinated attack on our bombers. With great daring, he throttled back, and using his plane as a decoy, diverted their concentrated attack upon himself. This action enabled our bombers to make an accurate and successful run unmolested. He then acted as sole fighter escort for the bombers on the return journey, shooting down one enemy plane and damaging another en route. In deliberately engaging ten enemy fighters single-handed, Major Cragg acted with conspicuous gallantry, and contributed greatly to the success of the mission.