James Madison Federalist The first election for Virginia's 5th congressional district took place on February 2, 1789, for a two-year term to commence on March 4 of that year.

They put forward Monroe, a young but experienced politician who was a war hero wounded at the 1776 Battle of Trenton, as a candidate for the seat.

Although Madison had earlier stated that amendments to the Constitution were not necessary, during the campaign he took the position that they were, but should be proposed by Congress, rather than by an Article V Convention that Anti-Federalists such as Monroe and Henry supported.

After service on the Virginia Council of State, where he forged a lifelong friendship with Governor Thomas Jefferson, he was elected to the Second Continental Congress becoming its youngest member.

In the following years, he became a strong advocate of closer ties between the states, and when in 1784 he returned home and became a member of the Virginia House of Delegates (the lower house of the Virginia General Assembly, the state legislature), he helped defeat a plan by Patrick Henry to impose taxes to support the Christian religion.

After the war, Monroe studied law under Jefferson and was elected to the House of Delegates in 1782, and to the Congress of the Confederation in New York in 1783, where he sought to expand the powers of that body.

[8] Henry sought to avenge the Anti-Federalist defeat at the Ratifying Convention, and also believed Madison would not seek amendments, or would do so in a lukewarm fashion.

[9] On October 31, the General Assembly re-elected Madison to his seat in the lame-duck Confederation Congress, a body that would cease to exist with the coming of the new federal government.

Henry's motives in allowing this are uncertain, with some historians stating it was to keep Madison in New York, far from the elections for Congress taking place in Virginia.

[14] Henry told the General Assembly that Madison was "unworthy of the confidence of the people" and that his election "would terminate in producing rivulets of blood throughout the land".

"[17] Virginia's 5th congressional district consisted of the counties of Albemarle, Amherst, Culpeper, Fluvanna, Goochland, Louisa, Orange and Spotsylvania.

[22] A resident of Spotsylvania County,[23] Monroe was reluctant to run against his friend Madison, but was probably encouraged by Henry, George Mason and other Anti-Federalists, though discouraged by his uncle, Joseph Jones.

on its commencement; and that I might not lose an opportunity of contributing my feeble efforts, in forwarding an amendment of its defects, nor shrink from the station those who confided in me [would] wish to place me, I yielded.

"[24] Monroe's reluctance clashed with his ambition and desire for honorable public service, and as his biographer, Tim McGrath, put it, "He truly did not want to run against his friend, but who could refuse Patrick Henry?

"[26] The selection of Monroe was enough to worry Washington: "Sorry indeed should I be if Mr. Madison meets the same fate in the district of which Orange composes a part as he has done in the [General] Assembly and to me it seems not at all improbable.

[27] Federalist Henry Lee wrote to him, "I profess myself pleased with your exclusion from the senate & I wish it may so happen in the lower house [in which case] you will be left qualified to take part in the administration, which is the place proper for you".

But he felt it to be important that Congress proposed them, believing that route to be a quicker, easier, and safer means of passage than an Article V convention, which was favored by the Anti-Federalists such as Monroe.

Madison responded that were the Federal government unable to tax citizens directly, tariffs would be the major source of revenue, and this would disproportionately hurt the South, which had few manufactures and imported heavily from overseas.

[39] On December 8, 1788, he wrote to Jefferson (who was in Paris) that he would return to Virginia to campaign for his election,[40][41] a decision prompted in part by warnings from Virginians that he could not win without personally fighting for the seat.

He arrived at Washington's plantation, Mount Vernon, on December 18, for a visit that lasted until he returned home[42] to Orange County and his estate, Montpelier, just after Christmas.

[43] From the time Madison arrived in Virginia, the weather was unusually cold and snowy; the candidates often had to speak in freezing conditions, and the last weekend before the election saw 10 inches (250 mm) of snow.

[44] Aware he was not an orator of Henry's quality, Madison launched a letter-writing campaign, advocating for the new Constitution; though initially taken by surprise, Monroe also set out his positions in letters.

"[47] Strother wrote a letter in support of Monroe, calling him "a man who possesses great abilities integrity and a most amiable Character ...

Madison wrote to one of their clergymen, George Eve, on January 2, 1789, stating that "it is my sincere opinion that the Constitution ought to be revised, and that the first Congress meeting under it, ought to prepare and recommend to the states for ratification, the most satisfactory provisions for all essential rights, particularly the rights of conscience [religion] in the fullest latitude, the freedom of the press, trials by jury, security against general warrants, etc.

[56] These debates showed the physical contrast between the tall, athletic Monroe, who had a full head of brown hair, and the short, slender Madison and his receding hairline.

[60] Henry Lee wrote to Washington three days later, "Mr Madison is gaining ground fast but still he is involved in much doubt & difficulty.

"[61] The debate that DeRose deemed perhaps the most significant of the race took place one evening at the Hebron Lutheran Church in Culpeper (today in Madison County).

[62][63] White males who were 21 years of age or older and who owned 50 acres (20 ha) of unimproved land or half that with a house were eligible to vote in the Fifth District.

[65][66] There was no secret ballot in Virginia elections in 1789; voters entered the local courthouse and publicly declared their votes, to be recorded by a clerk.

"[74] Within ten weeks of the election, the two were exchanging friendly letters, and Monroe purchased for Madison four tickets in the Fredericksburg Academy lottery, one of which won.