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Monroe was elected to the Virginia legislature in 1782 and served (1783–86) in the Continental Congress under the Articles of Confederation. He was not a delegate to the Constitutional Convention, and in his own state he supported Patrick Henry in opposing the Constitution, which seemed to him to create a government so centralized that it encroached on states' rights.
Under the new government, he served (1790–94) in the U.S. Senate, where he proved himself an outstanding lieutenant of Jefferson and a vigorous opponent of George Washington, Alexander Hamilton, and the Federalists. Appointed (1794) minister to France in the hope that his Francophile sympathies would smooth the ruffled relations between the two nations, he did nothing to lessen French resentment over Jay's Treaty, and he was recalled in 1796.
Governor of Virginia from 1799 to 1802, he was sent (1802) by President Jefferson to France as a special envoy. There he assisted Robert R. Livingston (1746–1813; see Livingston, family) during negotiations (1803) for the Louisiana Purchase. The next year, in Spain, he aided Charles Pinckney in the unsuccessful negotiations with the Spanish government. A later mission, to England, was even more disastrous. Monroe and William Pinkney struggled to arrive at a commercial treaty to end the disputes between Great Britain and the United States over shipping, but they could get no concessions, and Jefferson did not even submit the treaty they drafted (1806) to the Senate for approval.
In 1808, Monroe made a bid for the presidential nomination. He thus alienated James Madison, but the estrangement did not last long, and Monroe, after serving again as governor of Virginia, was Madison's Secretary of State (1811–17). For a time he was also Secretary of War (1814–15), after the dismissal of John Armstrong.
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