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Harry Stewart joined the U.S. Army Air Corps in 1942. After taking and passing the Pilot Cadet exam, Stewart would go on to train as a combat pilot with the famed Tuskegee Airmen in Alabama. Stewart would serve in Europe with the 332nd Fighter Group, better known as the "Red Tails", providing escort cover to bombers. On one occasion he would earn the Distinguished Flying Cross for downing three German fighters in one day.

After the war Stewart was selected to compete in the U.S. Air Force's inaugural gunnery meet team competition in 1949. Known today as the Red Flag, it is remembered by history as the military's first 'Top Gun' style competition. The all-Tuskegee team dominated the competition, but were not officially recognized as the winners until 1995.

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