Madison's political experience before becoming governor consisted of a twenty-year tenure as state auditor.

Although his military service made him extremely popular in Kentucky, he sought no higher office until the citizens insisted he run for governor in 1816.

[3][4] It is not known when Madison moved to Kentucky, but land records in Lincoln County indicate he and his brother Gabriel were there by at least 1784.

On November 5, 1792, Adair's men were encamped near Fort St. Clair when they were ambushed by an Indian force under the command of Little Turtle.

[7] In Adair's report to Brigadier General James Wilkinson, he wrote: "Madison's bravery and conduct need no comment; they are well-known.

"[8] Governor Isaac Shelby appointed Madison as Auditor of Public Accounts on March 7, 1796.

[5] On December 5, 1806, he served on a grand jury in the case of Aaron Burr's conduct; they did not find grounds for treason charges.

[4][8] Winchester was captured by General Henry Procter, but about four hundred men under Madison repelled several charges by the British.

[11] Shortly after the battle, the Indians looted the American provisions, which included a large quantity of whiskey.

[15] James Johnson, the other candidate for office, withdrew from the race due to Madison's popularity, thus the latter was elected without opposition.

[3] Madison traveled to Blue Lick Springs for his health soon after the election, but was too weak to return to Frankfort for the inauguration.

[15] Madison's only official act of office was the appointment of Colonel Charles S. Todd as secretary of state.

[3] A measure calling for a special gubernatorial election easily passed the state House of Representatives, but failed in the senate by a vote of 18–14.

[16] ^[a] Powell, Encyclopedia of Kentucky, and NGA give Madison's birthplace as Augusta County.