In border states where the issue of to secede or not to secede had never been definitively settled, the Civil War was a precarious time. With territory claimed by both the Union and the Confederacy, and citizens themselves at odds, guerrilla warfare was commonplace, and citizens were often harrassed by both the side they opposed and the side with which they sympathized.
Of the bushwhackers who fought to gain control of border states, none were as notorious or feared as Quantrill’s Raiders, who supported the Confederacy by terrorizing Union sympathizers on both sides of the Missouri-Kansas border for the duration of the war, and gave birth to the gang led by Frank and Jesse James.
Missouri was one of the mostly hotly contested border states. Missouri had entered the Union in 1821 as slave state under the Missouri Compromise, which held that no state north of Missouri’s southern Arkansas border could enter as a slave state. The compromise was stricken down with the 1854 Kansas-Nebraska Act, which allowed those states to decide their own status as slaveholding or free. The complication in the Kansas-Nebraska Act for Missouri slaveholders was the fact that Federal law allowed slaves who entered free states their freedom; what resulted was outright war between Missouri slaveholders who wanted a slaveholding Kansas, and Kansans who wanted a free state.
By 1860 Missouri was divided almost equally between slaveholders and non-slaveholders; as a result, the decision was made to remain with the Union but to also remain neutral, not supplying soldiers or supplies to either region. This neutrality was hardly peaceful; by 1862 guerrilla warfare was rampant throughout the state as both Union and Confederate sympathizers fought to gain control both of Missouri and Kansas.
Of these guerrilla warriors, none was more feared than those led by William Clarke Quantrill.
Quantrill’s renown was due to his impartiality; he attacked both Union officials and soldiers and civilians alike. While Quantrill and his men fought Union installations in Missouri by attacking patrol regiments and supply trains, they directed as much of their ire at civilians with Union sympathies.
Although he was not sanctioned by the Confederacy, Confederate generals turned a blind eye to Quantrill and his band, who made their work easier with their deliberate and coordinated efforts to destroy the Union presence in Missouri and Kansas; Quantrill and his men were organized not unlike a military regiment, and relied on military strategies like assigning rank to members of the group, planing attacks and escapes when going to battle with their foes, even up to taking prisoners, which Quantrill did until the Union Army began shooting guerrillas rather than arresting them, at which point Quantrill began to do the same for both Union soldiers and civilians alike.
In an attempt to drive these pro-Union citizens from Missouri and Kansas, Quantrill and his followers would attack towns and farms known to be Union. Their most infamous attack came to be known as the “Lawrence Massacre.” Leading as many as 450 guerrillas, Quantrill descended on Lawrence on August 21, 1863, and before he was done, almost 200 men and boys lay dead. Many of these men and boys were very young or very aged, and were executed in front of their families.
The executions and armed skirmish were not enough; Quantrill and his men burned nearly the entire town to the ground, after robbing and looting the bank and other businesses. Leaving a path of devastation behind, Quantrill and his followers went to Texas, where they joined Confederate forces there.
By the spring of 1865, Quantrill’s band of guerrillas had dwindled to less than twenty, but nonetheless, they made their way to western Kentucky, raiding Union sympathizers there. On May 10, Quantrill and his men were ambushed by Union soldiers, and Quantrill received a gunshot wound to the chest. He died on June 6.
Quantrill and his Raiders, as they came to be known in the years after the war, were reviled as bloodthirsty madmen by those who supported the Union and beloved by Confederates as brave and heroic warriors.
One of Quantrill’s lasting contributions to history was the James-Younger Gang, led by brothers Frank and Jesse James and Cole and Jim Younger, who used their training as guerrillas in Quantrill’s Raiders to rob banks and trains throughout the west in the years after the war.