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Theodore Roosevelt Campaign Buttons. Welcome to the Theodore Roosevelt campaign buttons section on campaignbuttons-etc.com. Theodore Roosevelt won his first political office when he was elected as a Republican to the New York State Assembly in 1881. Roosevelt's next attempt at office was when he ran for Mayor of New York City in 1896 but was not elected. Following his service in the Spanish American War, Roosevelt was elected the Governor of the State of New York in 1898. Roosevelt was then elected Vice President of the United States in November of 1900 on the Republican ticket with President William McKinley. Roosevelt became President of the United States in September of 1901 upon the assassination of McKinley. President Roosevelt also known as Teddy Roosevelt was elected President in his own right in November of 1904. Roosevelt's 1904 vice presidential running mate was Charles Fairbanks Pictured here are Theodore Roosevelt campaign buttons from those campaigns of more than a century past. Also featured here are Roosevelt Fairbanks campaign buttons.