He was repeatedly elected to the New Hampshire General Court, but failed in his 1916 bid to become the member of the United States House of Representatives for New Hampshire's 1st congressional district, losing to Republican Cyrus A. Sulloway.
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In 1920, Franklin D. Roosevelt resigned as Assistant Secretary of the Navy in order to run for Vice President in the 1920 presidential election.
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President of the United States Woodrow Wilson named Woodbury as Roosevelt's successor and he subsequently served as Assistant Secretary of the Navy from August 27, 1920 until March 9, 1921.
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