James Montgomery Flagg was married twice, first in 1899 to Nellie McCormick, whom he met at Biddeford Pool. After she died in 1923, he married Dorothy Wadman, with whom he had a daughter, Faith.
During World War II, Flagg once again illustrated patriotic posters, and received a letter of commendation from President Franklin Roosevelt. In addition to his work as an artist and writer, he also found time to become involved in theater, both as an actor and as a writer for "motion pictures."
