During the Civil War, Missouri rapidly descended into a self-destructive spiral. The struggle in the late 1850s over whether neighboring Kansas would become a slave or free state had mobilized both proslavery extremists and Unionists within Missouri. When war broke out, secessionists along the Missouri River in particular (the center of slaveholding) turned against their Unionist neighbors; at the end of 1861, Union forces, made up primarily of Missouri's own militia, took steps to reassert control. The very success of these Union efforts forced pro-Confederate groups to break up into small cells of "bushwhackers." Fierce guerrilla warfare ensued, as both sides focused much of their efforts on civilians in an attempt to ferret out and eliminate supporters of the enemy.

The most notorious bushwhacker was William C. Quantrill, who operated in Jackson County, just across the Missouri River from Clay County. On August 21, 1863, Quantrill led Frank James and scores, perhaps hundreds, of other guerrillas on a raid against Lawrence, Kansas, a center of abolitionism. The bushwhackers burned the town and killed every male they could find, men and boys alike, totalling at least 200. In retaliation, General Thomas Ewing, the Union commander for the section of Missouri that included Jackson County, issued General Order No. 11. He banished all civilians from most of four counties that bordered Kansas. The area became so devastated through fire and plundering that it became known as the Burnt District. This engraving, based on a famous painting by conservative Unionist George Caleb Bingham (a notable figure in Jesse James's later life), offers a melodramatic version of this mass expulsion, vividly capturing the secessionist image of the Unionist war effort.