James Madison, Patrick Henry's chief opponent in the Virginia ratification battle, is among the Virginia delegation to the House.

In retaliation for Madison's victory in that battle at Virginia's ratification convention, Henry and other Anti-Federalists, who control the Virginia House of Delegates, had gerrymandered a hostile district for Madison's planned congressional run and recruited Madison's future presidential successor, James Monroe, to oppose him.

Madison had defeated Monroe after offering a campaign pledge that he would introduce constitutional amendments comprising a Bill of Rights at the First Congress.

Originally opposed to the inclusion of a bill of rights in the Constitution, he had gradually come to understand the importance of doing so during the often contentious ratification debates.

By taking the initiative to propose amendments himself through the Congress, he hopes to preempt a second constitutional convention that might, it is feared, undo the difficult compromises of 1787, and open the entire Constitution to reconsideration, thus risking the dissolution of the new federal government.

Writing to Jefferson, he states, "The friends of the Constitution, some from an approbation of particular amendments, others from a spirit of conciliation, are generally agreed that the System should be revised. But they wish the revisal to be carried no farther than to supply additional guards for liberty."

He also feels that amendments guaranteeing personal liberties would "give to the Government its due popularity and stability".

Finally, he hopes that the amendments "would acquire by degrees the character of fundamental maxims of free government, and as they become incorporated with the national sentiment, counteract the impulses of interest and passion".

Historians continue to debate the degree to which Madison considered the amendments of the Bill of Rights necessary, and to what degree he considered them politically expedient; in the outline of his address, he wrote, "Bill of Rights—useful—not essential—".

George Washington, on the occasion of his April 30, 1789 inauguration as the nation's first president, addresses the subject of amending the Constitution.

He urges the legislators,

    whilst you carefully avoid every alteration which might endanger the benefits of an united and effective government, or which ought to await the future lessons of experience; a reverence for the characteristic rights of freemen, and a regard for public harmony, will sufficiently influence your deliberations on the question, how far the former can be impregnably fortified or the latter be safely and advantageously promoted.