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Charles Clarence Robert Orville "Bob" Cummings (June 9, 1910 – December 2, 1990), Captain, United States Air Force. Bob Cummings was issued flight instructor certificate No. 1, making him the first official flight instructor in the United States. In November 1942, Cummings joined the United States Army Air Corps and during World War II served as a flight instructor. After the war, Cummings served as a pilot in the United States Air Force Reserve, where he achieved the rank of Captain.