Theodore Roosevelt and Woodrow Wilson are frequently mentioned together, because they ran against one another during the presidential election of 1912. Although there are many facts on Woodrow Wilson, his ties to Roosevelt are notable, especially considering how the election turned out.
Although he had previously announced his 'retirement' from politics, following his departure from office in 1909, by 1912, Roosevelt had decided to run for president again. When he left office, he had 'hand-picked' William Howard Taft as his successor. Believing they shared similar views on important policies, he felt he was leaving the country in capable hands. Yet, he was rudely awakened by their disparate views on October 27, 1911 when Taft ordered his administration to file an antitrust suit naming U.S. Steel as defendant. During Roosevelt's time in office, he had been a progressive advocate for the 'busting' (or dissolution) of monopolistic trusts. But he had also taken the time to investigate any alleged trusts, and determine whether they were 'good' or 'bad' trusts. During his investigations, he determined U.S. Steel to be one of the 'good' trusts, encouraging healthy competition and growth in the marketplace.
With the filing of the U.S. Steel antitrust suit, Taft had guaranteed his position as Roosevelt's newest enemy. Armed with a very successful career in politics – and a laudable performance as president – Roosevelt decided to try his hand at re-election. However, the Republican Party as a whole did not support his bid for re-election, due to his delay and Taft having already won their vote. As a result, Teddy was denied the nomination. Not one to be discouraged, he broke with the Republican Party and established his own branch – the Progressive Party. Later nicknamed the 'Bull Moose Party' it served as a platform for Teddy's continued bid to resume presidential office.
In effect, what would normally have been a contest of Theodore Roosevelt vs. Woodrow Wilson became a four-way fight, resulting in an unprecedented outcome. Although there was a fourth, 'socialist' candidate (Eugene V. Debs), he only secured 6% of the popular vote and none of the electoral votes. After extensive campaigning – complete with an attempted assassination of Teddy in Milwaukee on October 27, 2012 – the results were in. Roosevelt's charm and political record garnered him 88 electoral votes and 27.4% of the popular vote, with Taft only receiving 8 electoral votes and 23.2% of the popular vote. With these unprecedented, surprising results, Teddy became the first candidate who was not part of the traditional parties to come in second.
Yet, despite the unprecedented success of Theodore Roosevelt Woodrow Wilson secured the highest electoral votes (435) along with a majority of the popular vote (41.8%). Many analysts note that Roosevelt and Taft running in the same campaign most likely 'split' the Republican vote, essentially guaranteeing Wilson's victory. Although he made a valiant effort to secure a second elected term for himself, with their resulting loss, Roosevelt and his Progressive Party slowly faded into the background of politics for many years thereafter.