President William McKinley needed a new running mate for his re-election campaign in 1900 because his first vice president, Garret Hobart, had died in office. Theodore Roosevelt, governor of New York, was widely expected to get the job. Initially unsure he really wanted it, Roosevelt was convinced by his political friends that the vice presidency was his avenue to the White House. No one could have anticipated how quickly that would come to pass. Just six months into his term, President William McKinley was assassinated and Vice President Theodore Roosevelt ascended to the presidency in 1901, a job he would hold until 1909.
Roosevelt had pledged not to seek a third term as president but his disillusionment with his handpicked successor, William Howard Taft, led political observers to believe he would try to take the 1912 Republican nomination from the incumbent. At a speaking engagement in Cleveland, Ohio in February, Roosevelt finally made the official announcement that “my hat is in the ring.” When the Republican National Convention selected Taft instead, Roosevelt took his ambition and this campaign slogan to his newly formed Progressive Party. Hats and references to hats appeared on a variety of campaign items. Roosevelt lost the 1912 election to Democratic candidate Woodrow Wilson but the Progressive Party stunned the Republican establishment by finishing second with over 27% of the popular vote and 88 electoral votes from six states. President Taft who received 23% of the popular vote became the only sitting president to finish third in a re-election bid. Socialist Eugene V. Debs, running for the fourth time, finished fourth with 6% of the vote.