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Quantrill's Raiders were a group of Confederate bushwhackers who followed and fought under William Clarke Quantrill, an Ohio schoolteacher who relocated to Kansas and transformed a motley group of Southern-sympathizing farmers and townsmen living behind Union lines into one of the Confederacy's most effective and eclectic guerrilla units. The name "Quantrill's Raiders" seems to have been attached to the group long after the war; indeed, the members would later have reunions under that name. During the war, however, the name rarely, if ever, appeared (hardly a surprise given the chaotic nature of guerrilla warfare).

Quantrill himself remains, in many ways, a mystery. He seems to have been an opportunist, a man in search of an outlet for his capacity for both bloodshed and military leadership. His men, however, had some doubts about the fictitious tales he told of persecution at the hands of abolitionist "Jayhawkers" in pre-Civil War Kansas, and his desire for revenge.

The state of Missouri was uniquely fertile ground for the outbreak of guerrilla warfare in late 1861. Secessionists had already been organized and mobilized to some extent by the proslavery "Border Ruffian" movement of the 1850s, in which Missourians crossed the border into the Kansas Territory in an effort to make it a slave state, and battle with antislavery immigrants from the North. Unionists were perhaps less well organized, but more numerous overall within Missouri. The populace was deeply divided.

In 1861, the conventional campaign between Union and pro-Confederate forces rolled back and forth across the southern half of the state, until finally the secessionist governor, Claiborne F. Jackson, and his State Guard, under the command of General Sterling Price, were largely forced into Arkansas before the end of the year. Across the countryside, however, skirmishes erupted between Unionist and secessionist Missourians, and between secessionists and Union soldiers from Kansas, many of them bent on revenge for the warfare in their state in the 1850s.

It would later be claimed that the Confederate guerrillas, or "bushwhackers" as they came to be known, rose up against a tyrannical Union occupation. However, the insurgency flared with the greatest heat in those areas where Union forces were weakest. As Union soldiers concentrated to fight against Price's State Guard and regular Confederate forces under General Ben McCulloch, few were available to occupy the territory to the rear. It was only in late 1861, as garrisons were established in important towns, that the weaker and more poorly organized Confederate fighters were weeded out, and the stronger, more capable units came together. The most notorious of these was that led by William Clarke Quantrill.

Quantrill was far from the only Confederate guerrilla operating in Missouri, but he rapidly won the greatest renown. He and his men ambushed Union patrols and supply convoys, seized the mail, and occasionally struck at undefended towns on either side of the Kansas-Missouri border. Reflecting the internecine nature of the guerrilla conflict in Missouri, Quantrill directed much of his effort against Unionist civilians, attempting to drive them out of the territory where he operated.

Quantrill claimed sanction under the Confederate Partisan Ranger Act, which authorized certain guerrilla activities, and received a regular Confederate commission as an officer. However, like almost all of the Missouri bushwhackers, he operated outside of the Confederate chain of command. Some of his activities, most notably his massacre of some 200 men and boys in Lawrence, Kansas, in August 1863, appalled the Confederate authorities. In the winter of 1862-63, when Quantrill led his men behind Confederate lines into Texas, their often lawless presence proved an embarrassment to the Confederate command. Yet the Southern generals appreciated his effectiveness against Union forces, which never gained the upper hand over Quantrill.

During that winter, Quantrill lost his hold over his men. In early 1864, the guerrillas that he had led through the streets of Lawrence returned to Missouri from Texas in separate bands, none of them led by Quantrill himself. Though Quantrill would gather some of his men again at the very end of 1864, the days of Quantrill's Raiders were over.

Quantrill died at the hands of Union forces in Kentucky in 1865, but his legacy would live on. Many of his men, including Frank James, rode in 1864 under one of his former lieutenants, "Bloody Bill" Anderson, who was killed in October 1864. Much of that group remained together under the leadership of Archie Clement, who kept the gang together after the war, and harassed the Republican state government of Missouri during the tumultuous year of 1866. In December 1866, state militiamen killed Clement in Lexington, Missouri, but his men continued on as outlaws, emerging in time as the James-Younger Gang.