The federal Alien and Sedition Acts of 1798 had met vigorous opposition in Kentucky, led in part by the young politician Henry Clay (who two decades later will become known on the state and national scenes as the “great compromiser”).

Events leading to a second state constitution in 1800 reveal an internal division (that will continue to characterize the state).

Farmers, who float their grain, hides, and other products on flatboats down the Mississippi to Spanish-held New Orleans, ally themselves with other antislavery forces to oppose slaveholders and businessmen.

Lieutenant Colonel James Wilkinson, a central figure in Kentucky politics, had in 1787 taken a secret oath of allegiance to Spain and had begun intrigues to bring the western settlements of Kentucky under the influence of the Louisiana authorities.

Officially known as “Number Thirteen”, Wilkinson receives a Spanish pension until October 1800, when Napoleon induces Spain to restore Louisiana to France.

With this agreement, confirmed in March 1801 as the Treaty of San Ildefonso, go not only the growing and commercially significant port of New Orleans but also the strategic mouth of the Mississippi River.

This treaty of supposed retrocession creates much uneasiness in the United States.