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The presidential election of 1912 was the most Progressive in US history, with the two frontrunners, Theodore Roosevelt and Woodrow Wilson, both espousing Progressive philosophies. Although both Wilson and Roosevelt were Progressive, their attitudes toward Progressivism differed, at least in theory. This paper will provide an opportunity to review the complex nature of Progressivism, and to explore how presidents’ policies while in office often differ from their rhetoric on the campaign trail.