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William Howard Taft Campaign Buttons. Welcome to the William Howard Taft campaign buttons section on campaignbuttons-etc.com. William Howard Taft was elected 27th President of the United States in November of 1908. Taft's vice presidential running mate was Congressman James Sherman of New York. Taft a Republican, lost re-election in 1912 in a three way race between himself, Progressive/Bull Moose candidate Theodore Roosevelt and the winner Democrat Woodrow Wilson. President Taft later went onto to serve as Chief Justice of the Supreme Court in the 1920's. Pictured here are William Howard Taft campaign buttons from those campaigns of 100 years ago.