This dissertation examines the secession crisis and the Civil War as a watershed moment in the Jackson Purchase region of Kentucky. In 1819, following the acquisition of land from the Chickasaw, the Purchase became the last area added to Kentucky. It was settled by small farmers who migrated from the Bluegrass and Green River areas of the state, as well as other parts of the south, particularly Tennessee and North Carolina. During the antebellum period, the Purchase became a Democratic Party stronghold in a state dominated by the Whig Party. During the 1850s the area experienced an economic boom through river trade with the south and railroad construction. The improved cultivation of tobacco during the same period greatly increased the number of slaves and slaveholders at a time when the institution declined in the rest of the state.;During the secession crisis, the Purchase was the only area of the state to overwhelmingly support John C. Breckinridge and agitate for separation from the Union. After Kentucky voted for neutrality, Purchase secessionists threatened to secede from Kentucky and join west Tennessee. In addition, the area contributed more soldiers to the Confederate Army than any other region of Kentucky. Yet from late 1861 to 1865, the Federal army occupied the Jackson Purchase. The area was overrun with guerrilla warfare and irregular activity. The 1864 so-called "reign of terror" instituted by Union General Eleazor A. Paine had a particularly profound effect on Purchase citizens. Federal occupation continued through Reconstruction as the area became one of the few regions of Kentucky to host a branch of the Freedman's Bureau.;In the decades following the Civil War the area increasingly celebrated its Confederate roots through veterans and memorial groups. Residents increasingly defined themselves through their wartime experiences. They added to their regional distinctiveness by emphasizing their southern roots and highlighting their devotion to the Confederacy. As such, they reinforced their "separate" identity from the rest of Kentucky.