Virginia was the tenth state to ratify the Constitution, and all thirteen states eventually ratified the document.[29]

Senator
Henry and other anti-federalists hoped to elect a Congress that would amend the Constitution to take away most of the powers it had been granted ("commit suicide on [its] own authority", as Madison put it). Henry recruited Monroe to run against Madison for a House seat in the First Congress, and he had the Virginia legislature draw a congressional district designed to elect Monroe. During the campaign, Madison and Monroe often traveled together, and the election did not destroy their friendship. In the election for Virginia's Fifth District, Madison prevailed over Monroe, taking 1,308 votes compared to Monroe's 972 votes. Following his defeat, Monroe returned to his legal duties and developed his farm in Charlottesville. After the death of Senator William Grayson in 1790, Virginia legislators elected Monroe to serve the remainder of Grayson's term.[30]
During the presidency of George Washington, U.S. politics became increasingly polarized between the supporters of Secretary of State Jefferson and
the Federalists, led by Secretary of the Treasury Alexander Hamilton. Monroe stood firmly with Jefferson in opposing Hamilton's strong central government and strong executive. 