After passing the bar exam, FDR went to work for a law firm in New York City that represented some of the most powerful big businesses in the country, including Standard Oil. However, he had no intention of remaining a lawyer for long. In 1907, he mapped out a path to the presidency that closely mirrored what actually happened over the next 25 years of life. As a Harvard classmate who worked with Roosevelt remembered, "he described very accurately the steps which he thought could lead to this goal. They were: first, a seat in the State Assembly, then an appointment as Assistant Secretary of the Navy…and finally the governorship of New York. 'Anyone who is governor of New York has a good chance to be President with any luck,' are about his words…"12
Franklin's prediction proved to be uncannily close to reality, although his first stop was the New York State Senate, not the State Assembly. During the 1910 campaign for State Senate, Roosevelt portrayed himself as a man of the people running against an out-of-touch Republican incumbent. He barnstormed around the district in a bright red car, sometimes giving speeches from the back seat. And in the villages and farms of rural New York, he began to develop the conversational (no, not like Facebook conversational) style of public speaking that he later brought to the White House.13
Roosevelt spent less than three years in the New York Senate. He had been an avid supporter of Woodrow Wilson during the presidential election of 1912, so it was no big surprise when Wilson offered him the job of Assistant Secretary of the Navy—the same job that Uncle Teddy had held on his path to the presidency.
Before he went to Washington, the public side of FDR's persona was well established. FDR was often featured in the media during his time in the Senate. For the next twenty years, his opponents often criticized him as more style than substance; "Franklin D. Roosevelt," journalist Walter Lippman wrote in 1932, "is no crusader. He is no tribune of the people. He is no enemy of entrenched privilege. He is a pleasant man who, without any important qualifications for the office, would very much like to be president."14
The press didn't know it yet, but FDR was becoming less of a lightweight during his time at the Navy. For one thing, his boss and mentor Josephus Daniels, the Secretary of the Navy, was a skilled government insider. Daniels knew how to play the game of Washington politics, and during his seven years at the Navy, FDR learned how to play it, too. Roosevelt learned the importance of giving small favors to other power players, like helping out when a Senator's nephew wanted a promotion. He learned how to deal with the many factions vying for a voice in the Democratic Party.15
And he learned how to deal with labor. On the advice of Louis Howe, his secretary, FDR handled all discussions with labor leaders personally. In the process, he developed a better understanding of the problems that working men faced.16 Twenty years later, as Howe had hoped, this blue-collar constituency also became a key component in FDR's political base.
Officially FDR's secretary, Louis Howe was much more than an assistant to the future president. In addition to advising Roosevelt on labor, Louis Howe played a central role in his political career. In essence, Louis Howe was FDR's Karl Rove. Karl Rove was Karl Rove's Karl Rove, if you know what I'm saying. They were an odd couple: Roosevelt was tall, handsome, and from one of the most elite families in the country. Howe was short, unattractive, and from an unimpressive family background. Howe, however, loved power and was a master of the political game. Over the course of FDR's political life, Howe orchestrated the behind-the-scenes machinations and strategy, becoming very close to the Roosevelt family in the process: at one point he even moved into the Roosevelts' house!17