More than 30 years before Alaska was to become a state, the Alaska Department of the American Legion sponsored a territorial contest for Alaskan children in grades seven through twelve. Benny's design was chosen to represent the future of the Alaska Territory. Up to that time, Alaskans had flown only the U.S. flag since the territory was purchased from Russia in 1867. His design was chosen over roughly 700 other submissions from schoolchildren territory-wide in grades 7–12. Most other entries featured variations on the territorial seal, the midnight sun, the northern lights, polar bears, and/or gold pans. For his achievement, Benny was awarded $1,000, an engraved watch and a trip to Washington D.C.
Benny looked to the sky for the symbols he included in his design. Choosing the familiar constellation he looked for every night before going to sleep at the orphanage, submitted this description with it:
|“||The blue field is for the Alaska sky and the forget-me-not, an Alaskan flower. The North Star is for the future state of Alaska, the most northerly in the union. The Dipper is for the Great Bear—symbolizing strength.||”|
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