In 1926, the Alaska Department of the American Legion held a contest for Alaska students from grades seven through twelve. The students were to design a flag that would represent the state. Benny's flag was the winner of the contest. He designed an all dark blue flag, with the big dipper on it and the North Star at the top. For his simple and creative design, Benny won a gold watch engraved with the Alaska flag, and a $1,000 trip to Washington, D.C. to present the flag to President Coolidge. Benny didn't go because his father was ill, and then because the President was out of the country, so the money was put towards his education.