“A Most Cruel and Unjust War:” The Guerrilla Struggle along the Missouri-Kansas Border

An essay by ,
Missouri State University

Bursheba Fristoe Younger knew better than perhaps anyone the thorough devastation wrought by nearly a decade of guerrilla warfare along the Missouri-Kansas border. The Youngers, like many households, traced their hardships back to the partisan violence of the 1850s. A slaveholding family of southern descent, they owned a dry goods store in Cass County, Missouri, which was repeatedly robbed by antislavery bands of Kansas “jayhawkers.” At the outbreak of the national Civil War, Bursheba’s husband, Henry, remained an avowed Union man, but in July 1862, Unionist militia ambushed, robbed, and murdered the family patriarch as he traveled home from Westport.

Her son, Cole—the seventh of 14 children—took to the brush as a pro-Confederate guerrilla and eventually joined up with William C. Quantrill, the country’s most notorious “bushwhacker.” That association soon brought upon the Youngers even greater scrutiny from Union troops, who in February 1863 ordered the family home set ablaze. Bursheba’s resulting exile took her north to Clay County, where she lingered, her family broken and wealth gone, until the war finally burned itself out.

The Civil War touched the lives of virtually everyone who lived near the Missouri-Kansas border. The war in this part of the West blurred and often shattered the distinctions between home front and battlefield. Fierce differences over slavery and its expansion triggered the irregular violence that erupted in Kansas Territory in 1856, but this bloodshed often devolved into a vengeful cycle of retaliation. Such fighting was often deeply personal in nature; long before the Confederate attack on Fort Sumter, the border was consumed by a bitter civil war that pitted neighbor versus neighbor.

Political Conflict and Vengeance in Missouri

James Montgomery, a Kansas jayhawker. Photograph courtesy of the Kansas Historical Society.

James Montgomery captured the powerful ways that politics and vengeance transformed the factional struggle for Kansas into a conflict that gripped both sides of the state line. Proslavery gangs harassed and ejected most antislavery men from Linn County in 1855, but Montgomery clung to his claim, even after marauders destroyed the family’s cabin. As a wave of northern emigrants soon flooded the county, the Kentucky native emerged as the leader of a “Self Protective Association,” an outfit whose purpose was less defensive than its name suggested.

The triumph of the free-state movement calmed much of Kansas by 1858, but feuding continued to roil the southeastern counties. The plunder and theft carried out by Free-Soil bands came to be known as “jayhawking,” and as their campaign of intimidation drove many proslavery families back into Missouri, Montgomery seemed ready to unleash further terror upon slaveholders across the border.

Settlers in western Missouri braced themselves for violence. Anxieties grew in the winter of 1858-1859, when men under John Brown raided several Missouri farms, liberating nearly 20 slaves and killing one slaveholder. Over the next two years, citizens of Bates and Vernon counties repeatedly called upon Governor Robert Stewart for assistance, and in November 1860 he dispatched a brigade of state militia to the border. An attack by Montgomery’s men, however, did not materialize.

The secession crisis and the Confederate attack on Fort Sumter sharpened political divisions along the border. When the national Civil War broke out, most people in Kansas, which had finally been admitted as a free state, rallied behind the Union. Missouri, befitting its position as a border state, was bitterly divided in its loyalties. Most households, including the Youngers, hoped to preserve both the Union and slavery, but a substantial number identified with their native states of the South. The protracted struggle for Kansas had galvanized many Missourians, and in time the ranks of Confederate sympathizers grew, especially after emancipation and the Union army’s forceful policies alienated residents throughout the state.

Missouri, befitting its position as a border state, was bitterly divided in its loyalties.

The jayhawker invasion that finally came in September 1861 marked an even more destructive turn in the border war. Senator James Lane, having taken command of the volunteer brigade he had organized, dispatched Charles Jennison and his unit of “South Kansas Jay Hawkers” into the Osage Valley of western Missouri. The rest of the brigade, some 1,400 members strong, followed days later and raided Butler, Harrisonville, and other villages.

Determined to punish Missouri secessionists, Lane’s men plundered the farms of suspected rebels (and more than a few unoffending Unionists). On September 22, the Kansans sacked the town of Osceola, killing as many as a dozen Confederates and helping themselves to anything that might be of use to would-be rebels. Joseph Trego, like many comrades, rode home to Kansas on a horse seized from a Missouri farm. “It does me good,” he wrote his wife, “to use the luxuries of these fellows that have always been the enemies of Anti-slavery men.”

Union General Henry Halleck, commander of the Department of Missouri, condemned the jayhawkers’ wanton plunder and destruction. “The course pursued by those under Lane and Jennison has turned against us many thousands who were formerly Union men,” wrote Halleck. Federal troops gained control over Missouri by early 1862, but Lane’s raid threatened to undermine the army’s ability to maintain order in the state. That the raid was carried out by Union volunteers only deepened Missourians’ hostility toward the federal presence in their midst, which many came to regard as a menacing occupation.

The “Bushwhackers”

Bushwhacker Cole Younger with his siblings, Robert, Henrietta, and James. Image courtesy of the Library of Congress.

Pro-Confederate guerrillas, derided by enemies as “bushwhackers,” exemplified this hostility. Usually in their late teens and twenties, many guerrillas, like Cole Younger, were the elder sons of Southern families. Some of these households owned slaves. By 1862, an increasing number of enslaved persons in Missouri seized upon the chaos sown by war to escape to freedom in Kansas.

Most fugitives fled of their own daring and volition, but Union troops and jayhawking raiders often facilitated this exodus. In Younger’s family, only one slave, a woman named Suse, remained with Bursheba. For slaveholding households, guerrilla resistance amounted to a defense of the property, wealth, and status that owning slaves represented in Missouri society.

Frank James was one of many guerrillas who had previously fought as a Confederate regular. James saw action at the Battle of Wilson’s Creek in southwest Missouri, near Springfield, but soon thereafter contracted measles and was captured by Union troops. Paroled in exchange for a promise not to take up arms against the Union, he swore an oath of loyalty to the United States and returned home to Clay County. Months later, though, the 20-year-old rejoined the war, now as an irregular fighter.

Bushwhackers preyed upon Union households in Missouri and Kansas alike, and like jayhawkers across the state line, they employed terror as both a means and an end.

Guerrilla violence threatened Union control in many ways. In addition to attacking federal troops, irregular partisans sabotaged bridges, railroads, and telegraph lines. Mounted on horseback and wielding pistols, guerrillas typically struck quickly, and their familiarity with the surrounding landscape enabled them to dissolve into the woods with seeming impunity. Bushwhackers preyed upon Union households in Missouri and Kansas alike, and like jayhawkers across the state line, they employed terror as both a means and an end.

Missouri farmer John Dryden suffered repeatedly for his outspoken Unionist sympathies and antislavery beliefs. Guerrillas attempted to drive Dryden from his home in early 1863. The Vernon County resident held firm, though he spent many nights taking refuge in a nearby field. On May 27, however, five bushwhackers attacked once more and set fire to the family farm. John’s wife, Louisa, extinguished the flames, but soon thereafter the Drydens fled with their infant daughter to Kansas, where they remained for the war’s duration.

Confederate leaders were ambivalent about guerrilla fighters in Missouri and elsewhere. Irregular partisans, on one hand, were useful, serving to tie down vastly larger numbers of Union forces. On the other hand, the bushwhackers’ tactics of arson, robbery, and murder seemed to transgress the bounds of honorable combat. Quantrill and other guerrillas nonetheless sought and sometimes received formal Confederate commissions as partisan rangers.

Suggested Reading: 

Benedict, Bryce. Jayhawkers: The Civil War Brigade of James Henry Lane. Norman: University of Oklahoma Press, 2009.

Fellman, Michael. Inside War: The Guerrilla Conflict in Missouri During the Civil War. Oxford New York: Oxford University Press, 1989.

Goodrich, Thomas. Black Flag: Guerrilla Warfare on the Western Border, 1861-1865. Bloomington: Indiana University Press, 1995.

Neely, Jeremy. The Border Between Them: Violence and Reconciliation on the Kansas-Missouri Line. Columbia London: University of Missouri Press, 2007.

Sutherland, Daniel E. A Savage Conflict: The Decisive Roles of Guerrillas in the American Civil War. Chapel Hill: University of North Carolina Press, 2009.

Cite this page: 
Neely, Jeremy. "“A Most Cruel and Unjust War:” The Guerrilla Struggle along the Missouri-Kansas Border" Civil War on the Western Border: The Missouri-Kansas Conflict, 1854-1865. The Kansas City Public Library. Accessed Jun, 20, 2019 at http://www.civilwaronthewesternborder.org/essay/%E2%80%9C-most-cruel-and-unjust-war%E2%80%9D-guerrilla-struggle-along-missouri-kansas-border


Thanks for the general

Thanks for the general overview. I recognize several of the references, particularly Fellman's great work, Inside War. I wish more Missourians, and even Kansans, (ha!) would study the history and understand the social upheaval in Missouri in the 1850's due to the Compromise of 1850, the promise and hope of expansion westward, the political scramble after the collapse of the Whig Party, and just the impact this had over a period of years on the everyday citizen. You touched on just one example of this progression in explaining the Younger story a bit. At any rate, nice essay and keep up the good work!

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