Though the term gerrymander was coined following Massachusetts' state senate districting in 1812, many scholars have posited that it was actually Patrick Henry who first practiced this art, by designing an unnatural district that would ensure his rival James Madison's defeat in Virginia's first congressional elections in early 1789. Historians have ample evidence to buttress such claims, for numerous Founding Fathers bitterly complained that Henry was going out of his way to design a district for Madison's defeat. Through hard and smart campaigning, however, Madison managed to defeat his opponent, James Monroe—thus marking the only congressional election in American history pitting two future presidents against each other. This article closely examines Virginia's 1788 congressional districting and finds that, contrary to the accepted wisdom, ingenious and artificial combinations were not used to design Madison's district, for it was composed of a compact group of whole counties entirely within the Piedmont region, and bounded on all sides by natural geographic features; Madison's true problem was not the district's formulation, but that he lived in an area that was predominantly Anti-Federalist. In fact, Virginia's entire 1788 districting scheme shows no marks of partisan purpose, for it was both politically fair and one of the most geographically logical plans in all of American history.