After his clash with the bosses of Tammany Hall, FDR knew that his political career in New York was temporarily halted. He therefore threw his energies into supporting Woodrow Wilson for the next presidential election, hoping that his support would bear fruit in the form of an appointment. It was in his efforts to campaign for Wilson in early 1912 that he gave a speech in Troy that hinted at the political beliefs that would resurface as the New Deal. According to one biographer, Nathan Miller, FDR's speech was a "carefully worded assault" on private property when its use conflicted with public welfare. Although naïve and superficial, the speech was the first inkling of the impulses that would guide the first years of FDR's presidency, and challenges the claims of critics that he had no real political beliefs or agenda. In June of 1912, Teddy Roosevelt lost to William Howard Taft for the Republican nomination for president. Outraged supporters returned to Chicago and created the Progressive Party, under which Teddy Roosevelt ran. FDR also jumped on the Progressive bandwagon and created the short-lived Empire State Democracy, meant to be a permanent Progressive organization.

It was at this time that FDR cemented his relationship with Louis Howe, a partnership that would lead to the White House. Howe might have remained perpetually unlucky had he not seen in FDR the potential for substantial political success. Howe, a dwarf whose face had been scarred by a bicycle accident, was unable to attend college because his father had run up debts from the operation of the Saratoga Sun, the Democratic mouthpiece of the nation. Howe then took over running the paper, but was forced out of a job in September of 1901. He then became the assistant to the Herald's correspondent in Albany, but was forced to work for a man who was running an organization that tried to wrest control from Tammany Hall to make money. Howe would have remained in this peripheral role in the New York political scene had he not met FDR and become his most trusted political advisor.

Howe ran FDR's second political campaign while Roosevelt was in the hospital wrestling with typhoid. He took out full-page ads in the papers extolling his candidate's virtues and distributed $5 bills to campaign workers on Election Day. He proposed a bill designed to protect NY farmers from New York City commission merchants, and circulated copies of the proposed bill with a letter from FDR requesting their comments and promising his support to all the farmers of New York, all while his candidate was slowly recovering.

While Howe ran a campaign with a missing candidate, Woodrow Wilson and Teddy Roosevelt fought for the country, with Wilson's New Freedom pitted against Roosevelt's New Nationalism. While Wilson's focus on destroying trusts and monopolies gave him the edge over Teddy Roosevelt, their progressive agendas and commitment to social justice were the same. Teddy Roosevelt ran his campaign heartily, although he suspected he would not win. Because the country had voted for Taft in the last election thanks to Teddy's support, his opposition to Taft now only served to split the Republican vote and pave the way to Wilson's win. However, the split in the votes that led to Wilson's win showed the country's true reformist leanings: both of the leading candidates were progressive, revealing that the American people were ready for substantial reform long before the Depression made reform a necessity.

FDR returned to the New York State Legislature in 1913, but this time avoided conflict and waited instead for a call from Woodrow Wilson, for whom he had campaigned so keenly. On the morning of Wilson's inauguration, FDR met with Joseph Daniels, Wilson's appointee for Secretary of the Navy. Daniels asked FDR to be his Assistant Secretary, thinking that he and Roosevelt would complement each other nicely. Daniels was not nautical, whereas Roosevelt had been an avid sailor since his youth and loved ships. Daniels was a Southerner, FDR a blueblood Yankee. Thus, on March 17, 1913, FDR found himself at Teddy Roosevelt's old desk in the Navy department after having been active in politics for less than three years. It was due to a combination of luck, charm, and political know-how that Roosevelt had achieved his position in such a short time. The path to the presidency that he had boldly outlined for himself as a law clerk now seemed all the more attainable.

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