Benson was 14 years old when he won a contest in 1927 to design the flag for the Territory of Alaska, which became a U.S. state on January 3, 1959.

He was a Qawalangin (Fox Islander) Unangan born to a Swedish-American father, John Ben "Benny" Benson Sr., and Aleut-Russian mother, Tatiana Ioannovna Dediukhina, from a village near Unalaska.

Benson grew up at the Jesse Lee Home for Children in Unalaska and later in Seward.

[5] Shortly after that, in 1972, he met and married a former Jesse Lee Home resident, Anna Sophie Jenks.

Most other entries featured variations on the territorial seal, the midnight sun, the northern lights, polar bears, and/or gold pans.

Choosing the familiar asterism he looked for every night before going to sleep at the orphanage, he submitted this description with it: The blue field is for the Alaska sky and the forget-me-not, an Alaskan flower.