This political cartoon, originally published in Puck Magazine is entitled, 'Teddy Doodle: The Spirit of 1908'. It depicts Theodore Roosevelt's popularity in 1908 with the general public and fellow Republicans who wanted him to run for re-election in 1909.
Although he served two terms as President, one of which by succession through President McKinley's assassination, technically he was elected for only one term. In 1908, talk of presidential term limits had not yet been discussed, and Theodore could legally run for another term. The 22nd Amendment to the U.S. Constitution banning Presidents from serving more than two terms did not pass Congressional vote until 1947 and was not ratified until 1951.
Despite public support, Teddy Roosevelt decided against a re-election bid as he did not want to break tradition. Instead, he nominated his friend and political ally, William Howard Taft.