Satterfield's career began in 1896 when, after having studied art as a part-time student in Pittsburgh, he moved to Youngstown, Ohio for work and began sending unsolicited cartoons (most of which were based on the William Jennings Bryan presidential campaign) to the Cleveland Press;[9] the Press's editor eventually bought one, and hired Satterfield as a regular artist. In 1898, Satterfield was transferred to the Kansas City World, where he functioned as that paper's entire art department for four years until 1902, when Mark Hanna hired him to be a full-time cartoonist for the Cleveland News.[9] By 1917, Editor and Publisher said that his work had "the largest circulation of any syndicated cartoons" in the United States.[10]
In 1924, Satterfield signed an exclusive contract with Publishers Autocaster Service;[11] later, he worked for the Newspaper Enterprise Association.[2] In 1928, he produced Picture Life of a Great American: Pictorial Life of Herbert Hoover, a prototype of a comic book, in association with the Herbert Hoover presidential campaign.[12][13][14] In 1934, he left the Cleveland News and joined the Green Bay Press-Gazette.[15]