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Theodorus Bailey (October 12, 1758 – September 6, 1828) was an Americanmarker lawyer and politician from Poughkeepsie, New Yorkmarker. He represented New Yorkmarker in both the U.S. House and Senate. Served in the New York Militia during the American Revolution and postwar in the State Militia 1786-1805.

Bailey was born near Fishkill, New Yorkmarker on October 12, 1758 where he attended the rural schools and studied law. He was admitted to the bar in 1778 and commenced practice in Poughkeepsie, New York. He served with the New York Militia during the Revolutionary War. He also served in the State militia from 1786 until 1805 and attained the rank of Brigadier General

Bailey was first elected to the 3rd United States Congress as an Anti-Administration, and to the 4th United States Congress as a Democratic-Republican serving from March 4, 1793, to March 3, 1797. He was elected to the 6th United States Congress serving from March 4, 1799, to March 3, 1801. In April 1801, he was elected to the New York State Assembly, but vacated his seat before the State Legislature convened, because he was elected to the 7th United States Congress to fill the vacancy caused by the resignation of Thomas Tillotson, and served from December 7, 1801, to March 3, 1803.

In 1803, Bailey was elected a U.S. Senator from New York, and served from March 4, 1803, to January 16, 1804, when he resigned to accept the position of Postmaster of New York Citymarker, which he held until his death on September 6, 1828. He was interred in the Dutch Burying Ground and reinterred in the Rural Cemetery, Poughkeepsie, New York on January 8, 1864.

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