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Although irregular warfare occurred throughout the occupied South during the Civil War, a band of Missouri guerrillas, led by William Clarke Quantrill, engaged in a series of especially vicious, effective, and notable exploits. Organized in December 1861, Quantrill's Raiders included such notorious characters as George Todd, Frank and Jesse James, Cole Younger, and “Bloody Bill” Anderson. Until the death of Quantrill in 1865, the pro-Confederate band engaged in a series of bloody raids and exploits intended to terrorize Missourians loyal to the Union and Union forces.

A combination of factors contributed to the formation of Quantrill's Raiders. First, a deep bitterness, resulting from the struggle over the status of slavery in Kansas during the 1850s, existed along the Kansas–Missouri border. Although the controversy had been resolved by 1861, many free-soil Kansans (who opposed the extension of slavery into the western territories) viewed the outbreak of the Civil War as an opportunity to exact revenge on pro-slavery Missourians who had plagued Kansas's territorial phase. In late 1861, Kansas “jayhawkers” conducted a series of raids into western Missouri that inflamed the local population and created a sympathetic region for pro-South guerrillas to operate in.

Another factor that fueled Quantrill's operations was that by early 1862 Union military authorities had managed to expel Confederate armies from Missouri. Consequently, pro-Confederate Missourians had no other way to act on their fury against the often heavy-handed federal authorities other than by supporting or joining the guerrilla bands that popped up throughout the state at the start of the war. Moreover, Missouri was nominally a loyal state, thus the federal authorities tended to devote their finite manpower elsewhere. This made Missouri, especially the still raw frontier region along the Kansas border, a fertile field for guerrilla operations.

Quantrill actually began the war as a Kansas jayhawker but, sensing a better opportunity, switched sides during the summer of 1861 and joined the pro-South Missouri State Guard. When the State Guard retreated from Missouri that fall, Quantrill deserted and organized a guerrilla band in December. In Quantrill, the guerrillas of western Missouri found a ruthless, charismatic, and talented leader. He quickly attracted a vicious set of followers. It is impossible to determine how many of those who followed Quantrill were merely psychopaths for whom the war provided a convenient outlet for their violent urges, how many were sincerely committed to the cause of Confederate independence, and how many were simply provoked by Unionist outrages. Regardless of the motivation of its members, the band was exceedingly effective. For the most part, their operations consisted of low-level raids and ambushes in which small units employed hit-and-run tactics based on the horse and revolver. When their actions provoked a strong Union response, Quantrill's men would scatter into squads of two or three and find sanctuary in the thicketed Sni-a-Bar region of Jackson County, Missouri. Another popular tactic was to wear the uniforms of captured Union soldiers, ride up to unsuspecting members of the Union Army, and shoot them at point-blank range.

Quantrill's first significant operation was the sack of the village of Aubry, Kansas, in March 1862. In August, his band participated in an attack on a Union garrison at Independence, Missouri, and in the battle of Lone Jack. That same month, Quantrill's operations received official sanction from the Confederate government in Richmond, Virginia, under the new Partisan Ranger Act (1862). After receiving a commission as a captain in the Confederate Army, Quantrill led bloody raids on Olathe and Shawneetown in Kansas before leading his band south to Arkansas for the winter. Quantrill then traveled to Richmond to petition for a commission as a colonel. Although his application was rejected in November 1862 by a government that preferred to deal with partisans and guerrillas at arm's length, Quantrill began signing his orders as “Colonel Quantrill.”

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