The violence they wrought left scars on the borderlands of Kansas and Missouri.
By Matthew A. McIntosh
Public Historian
Brewminate
Introduction
The American Civil War is often remembered for its massive battles, industrial warfare, and sweeping political ramifications. Yet, some of the most brutal and chaotic fighting occurred far from the main battlefields in a more intimate and localized form: guerrilla warfare. Nowhere was this more evident than in the borderlands of Kansas and Missouri, where two rival factions—Bushwhackers and Jayhawkers—fought a vicious and deeply personal civil war within the larger national conflict. These groups embodied the region’s deep ideological divisions over slavery, state loyalty, and federal power. Their tactics, rooted in ambush, sabotage, and retaliatory violence, left an indelible mark on American history and foreshadowed the complexities of irregular warfare in the modern age.
Origins in the Bleeding Kansas Crisis
The roots of the Bushwhackers and Jayhawkers can be traced to the passage of the Kansas-Nebraska Act of 1854, which allowed settlers in these new territories to determine the legality of slavery through popular sovereignty. This nullified the Missouri Compromise, which had previously prohibited slavery in much of the Louisiana Purchase north of the 36°30′ line. As Kansas became a battleground over the expansion of slavery, both pro-slavery and anti-slavery advocates flooded into the region, hoping to sway the vote and establish dominance. The resulting conflict gave rise to two loosely organized but fiercely combative groups: Bushwhackers, largely Missourians supporting slavery, and Jayhawkers, typically Free-Staters and abolitionists from Kansas. These groups did not emerge from centralized authorities but rather from local tensions, reflecting deep political and cultural divisions that predated the national war by nearly a decade.1
Missouri and Kansas had already harbored mutual suspicions long before the 1850s. Missouri, a slave state admitted to the Union in 1821, bordered the newly opened Kansas Territory and feared the rise of abolitionist sentiment next door. Many Missourians considered Kansas an extension of their cultural and political landscape and saw the influx of Northerners—many of them evangelical reformers from New England—as a direct threat to their way of life. In response, Missourians formed informal militias and voting blocs known as “Border Ruffians,” who crossed into Kansas to vote illegally in territorial elections and intimidate Free-State settlers. These early aggressors would evolve into what later became known as Bushwhackers, guerrilla fighters who engaged in sabotage and assassination during the Civil War.2
The opposing force—the Jayhawkers—emerged from the Free-State movement. Drawing inspiration from anti-slavery ideology, Jayhawkers saw their efforts as a righteous crusade against the “Slave Power.” Many of them were part of the New England Emigrant Aid Society, which encouraged abolitionist families to settle in Kansas and help establish it as a free state. These settlers often arrived armed and prepared for conflict. Jayhawker activity extended beyond defense, however; they launched raids into Missouri, attacking pro-slavery towns and farms, often looting and burning property. While their actions were driven by ideological fervor, they also bore the hallmarks of vigilante justice and opportunistic plundering.3
The violence escalated rapidly into what became known as “Bleeding Kansas”—a term coined by New York Tribune editor Horace Greeley—which saw a series of deadly confrontations, including the Sack of Lawrence in 1856 and John Brown’s Pottawatomie Massacre that same year. These events polarized the population and solidified the identities of the two groups. Bushwhackers saw themselves as defenders of Southern honor and Missourian sovereignty, while Jayhawkers positioned themselves as enforcers of moral justice and anti-slavery progress. In reality, both groups committed atrocities and operated largely outside the rule of law, setting a precedent for the irregular warfare that would dominate the Missouri-Kansas border throughout the Civil War.4
By the late 1850s, the ideological conflict had become deeply personal. Families were divided, communities shattered, and any pretense of political negotiation dissolved into cycles of vengeance. The federal government’s inability to enforce order only deepened the crisis. When the Civil War officially began in 1861, Kansas entered the Union as a free state, while Missouri remained bitterly divided. The Bushwhackers and Jayhawkers, by then seasoned in guerrilla tactics and hardened by years of violence, transitioned seamlessly into the larger conflict, bringing with them a regional war that was as much about neighbor against neighbor as it was about Union versus Confederacy.5
The Bushwhackers: Confederate Guerrillas and Irregulars
The Bushwhackers were a loosely organized group of pro-Confederate guerrilla fighters who operated primarily in Missouri during the American Civil War. Unlike formal Confederate military units, Bushwhackers conducted irregular warfare that involved ambushes, raids, and sabotage. Their origins lay in the already violent border conflicts of the 1850s but escalated sharply after Missouri remained in the Union while harboring many Southern sympathizers. These guerrillas saw themselves as defenders of Southern rights and Missouri’s sovereignty, resisting Union control through any means necessary. The nature of their warfare—often brutal and personal—distinguished them from conventional soldiers and blurred the lines between military combat and outlaw behavior.6
William Clarke Quantrill emerged as one of the most infamous leaders of the Bushwhackers. Quantrill’s Raiders were notorious for their daring raids and ruthless tactics, including the burning of towns and the execution of Union sympathizers. Their most notorious act, the Lawrence Massacre of 1863, involved the killing of approximately 150 men and boys in Lawrence, Kansas, a Free-State stronghold. This attack was both a reprisal for Union actions in Missouri and a strategic effort to terrorize anti-slavery communities. Quantrill’s methods exemplified the ruthless nature of guerrilla warfare and deepened the hatred between opposing factions in the border region.7
The Bushwhackers were often motivated by a mixture of ideological commitment to the Confederate cause and personal vendettas. The violent atmosphere of the Missouri-Kansas border, combined with a fractured society where neighbors could be bitter enemies, fueled cycles of retribution. These fighters exploited the rough terrain and local knowledge to conduct surprise attacks on Union forces, supply lines, and civilian targets deemed loyal to the North. Their actions often provoked harsh Union responses, including General Order No. 11, which forced the evacuation of entire counties in Missouri to deprive guerrillas of support. This scorched-earth tactic further inflamed tensions and devastated local populations, illustrating the war’s brutal impact on civilians.8
Many Bushwhackers had backgrounds as former Border Ruffians, the pro-slavery irregulars active during Bleeding Kansas, who carried their experience in irregular warfare into the Civil War. Their tactics included ambushes, raids on farms, and assassination of Union officials and sympathizers. Notably, leaders like “Bloody Bill” Anderson gained reputations for savage violence, including mutilation and torture. Such brutality was often personal, reflecting deep-rooted animosities rather than mere military strategy. This made the Missouri-Kansas border one of the bloodiest and most chaotic theaters of the Civil War, where lawlessness and violence became entrenched aspects of daily life.9
Despite their notoriety and brutal methods, Bushwhackers enjoyed considerable support among many Missouri residents who opposed the Union government’s policies. Their irregular warfare disrupted Union control and tied down large numbers of troops who might otherwise have been deployed to larger battles. However, their actions also alienated moderates and Unionists, creating a fractured society torn by fear and suspicion. After the war, many former Bushwhackers, including Jesse James and the Younger brothers, turned to outlawry, further blurring the line between guerrilla fighters and criminals. Their legacy remains controversial, viewed by some as folk heroes resisting Northern aggression and by others as violent bandits.10
The Jayhawkers: Unionist Militias and Raiders
The Jayhawkers were irregular Unionist militias and raiders who operated mainly in Kansas and along the Missouri border during the Civil War era. Emerging from the Free-State movement in Bleeding Kansas, the Jayhawkers were motivated by a strong abolitionist ideology and a commitment to preserving the Union. Unlike formal military units, Jayhawkers engaged in guerrilla tactics such as raids, ambushes, and scorched-earth campaigns aimed at disrupting Confederate sympathizers and pro-slavery forces. Their activities were both defensive and offensive, as they sought to protect their communities from pro-slavery Bushwhackers and to undermine Confederate resources in border states. The Jayhawkers became a symbol of militant Northern resistance in a region marked by bitter sectional conflict.11
The origins of the Jayhawkers can be traced to the influx of abolitionist settlers encouraged by organizations such as the New England Emigrant Aid Company, which sought to ensure Kansas would enter the Union as a free state. These settlers brought with them not only anti-slavery convictions but also a willingness to defend their homes through force if necessary. Early skirmishes and raids during the Bleeding Kansas period galvanized the Jayhawkers’ identity as a vigilante force. With the outbreak of the Civil War, these militias formalized and expanded their operations, coordinating with Union military efforts while maintaining a level of autonomy typical of irregular warfare.12
One of the most notorious Jayhawker leaders was James Henry Lane, a former U.S. senator from Kansas who became a Union general and a leading figure in organizing Kansas militias. Lane’s Jayhawkers were known for their aggressive tactics, including raids into western Missouri to disrupt Confederate sympathizers and supply lines. These raids often involved looting, destruction of property, and the freeing of enslaved people. While their actions were celebrated by Union supporters, they also earned a reputation for excess and brutality, sometimes targeting civilians suspected of aiding the Confederacy. The dual nature of their warfare—rooted in both ideology and opportunism—mirrored the complex dynamics of the border conflict.13
Jayhawker raids contributed significantly to the destabilization of Confederate influence in the border region but also exacerbated cycles of violence and retribution. Their incursions into Missouri provoked fierce responses from Bushwhackers, and the resulting tit-for-tat violence devastated communities and polarized populations. Despite their unofficial status, Jayhawkers played a strategic role by tying down Confederate sympathizers and guerrillas who might otherwise have reinforced larger Confederate armies. However, their reputation for lawlessness and extrajudicial actions complicated postwar reconciliation and challenged traditional notions of military conduct and justice in wartime.14
After the Civil War, many former Jayhawkers continued to influence Kansas and Missouri’s social and political landscape. Some transitioned into formal law enforcement roles or political offices, while others engaged in banditry similar to their Confederate counterparts. The legacy of the Jayhawkers is contested: they are remembered both as defenders of freedom and Union loyalty and as violent vigilantes who contributed to the chaos and suffering of the border war. Their story highlights the blurred lines between soldier and outlaw in irregular warfare and illustrates the enduring impact of the Civil War’s border conflicts on American memory and identity.15
Guerrilla Warfare in the Borderlands
The borderlands between Kansas and Missouri during the Civil War became a violent crucible of guerrilla warfare, where traditional military tactics gave way to irregular and often brutal combat between the pro-Confederate Bushwhackers and the pro-Union Jayhawkers. This region’s complex social, political, and geographical landscape fostered a unique form of warfare characterized by ambushes, raids, and acts of terror directed not only at opposing forces but also at civilians perceived to be supporting the enemy. The conflict in the borderlands was less about conventional battles and more about attrition through constant harassment, undermining the enemy’s ability to maintain control, and enforcing local dominance through fear and intimidation.16
One of the defining features of this guerrilla warfare was its highly personal nature. Many of the combatants—on both sides—were neighbors, relatives, or former acquaintances, making the conflict intensely local and often fueled by longstanding personal grievances in addition to ideological differences. Violence frequently manifested as retaliatory raids and massacres, with each side seeking vengeance for previous attacks. The lines between military action and criminality blurred, as both Bushwhackers and Jayhawkers engaged in looting, arson, and summary executions. The consequences for civilians were devastating, as entire communities could be targeted for collective punishment or suspicion of aiding the enemy.17
The strategies employed by these guerrillas leveraged the rough terrain and the fluid political situation of the border region. Dense forests, river crossings, and a patchwork of farms and towns allowed guerrilla bands to strike quickly and disappear before Union or Confederate forces could respond effectively. The Bushwhackers often conducted nighttime raids into Kansas to destroy Jayhawker sympathizers’ property and disrupt supply lines, while Jayhawkers reciprocated with incursions into Missouri. Both groups used surprise attacks, sabotage, and psychological warfare to maintain pressure on their opponents. This style of fighting necessitated small, mobile units capable of rapid movement and stealth, often relying on intimate knowledge of the local landscape.18
The Union and Confederate governments struggled to control or contain the violence, as guerrilla warfare in the borderlands defied traditional military hierarchies and legal frameworks. Union General Thomas Ewing’s issuance of General Order No. 11 in 1863, which forced the depopulation of several Missouri counties along the border, was a drastic response aimed at depriving guerrillas of local support. While the order devastated civilian populations, it failed to completely eliminate guerrilla activity and arguably intensified local resentment toward the Union. On the Confederate side, leadership often had limited control over guerrilla bands, which sometimes acted autonomously or pursued their own agendas, complicating broader Confederate military strategy.19
The legacy of guerrilla warfare in the Missouri-Kansas borderlands is one of profound social disruption and enduring animosity. The violence left scars that persisted long after the war’s end, as former combatants and communities grappled with the memories of betrayal and brutality. The blurred boundaries between soldier and outlaw in these conflicts complicated efforts at postwar reconciliation and law enforcement. Many former guerrillas, including notable figures such as Jesse James, transitioned into criminality, perpetuating the cycle of violence. The border warfare between Bushwhackers and Jayhawkers stands as a stark example of how civil conflict can devolve into internecine violence that leaves deep, lasting wounds on the social fabric.20
Postwar Legacies and the Rise of Outlaw Culture
The violent guerrilla warfare waged by the Bushwhackers and Jayhawkers during the Civil War left deep and enduring scars on the border region of Missouri and Kansas. When the war ended in 1865, the societal fabric of these states was frayed and destabilized. Many former combatants, especially Bushwhackers who had fought under Confederate banners, found reintegration into peaceful society difficult, if not impossible. The lawlessness and brutal tactics of wartime had normalized violence as a means to resolve conflict. This atmosphere of instability helped pave the way for the rise of outlaw culture in the postwar years, as many ex-guerrillas and militia members turned to banditry and criminal enterprise rather than abandoning their wartime habits.21
Perhaps the most famous example of this transition from guerrilla fighter to outlaw was Jesse James, a former Bushwhacker who became an iconic figure of the American West. James and his gang engaged in a series of bank and train robberies that captured national attention. Their exploits were widely romanticized in newspapers and popular culture, casting them as folk heroes resisting Reconstruction-era authority and Northern economic domination. However, beneath this mythology was a reality of violent crime, including murder and intimidation. Jesse James’s career illustrates how the blurred lines between wartime guerrilla violence and peacetime outlawry complicated efforts to restore law and order in the borderlands.22
The Jayhawkers, too, experienced a complicated postwar legacy. Many former Unionist militia members moved into positions of political power or law enforcement in Kansas, leveraging their wartime reputations. However, the Jayhawker label was sometimes used pejoratively by Missourians and former Confederates to describe what they saw as Northern carpetbaggers or corrupt officials enforcing Reconstruction policies. While some Jayhawkers sought to rebuild communities and uphold the law, others exploited the chaotic postwar environment for personal gain, engaging in acts of vigilantism or extralegal retribution against former enemies. This tension highlighted the persistent divisions in the border region long after the cessation of formal hostilities.23
The lingering bitterness and fractured loyalties in Missouri and Kansas created fertile ground for ongoing violence and social unrest throughout the Reconstruction era and beyond. Local vigilante justice often supplanted formal legal systems, as communities struggled with distrust toward both former guerrillas and newly installed authorities. The cycle of violence that began with the Bushwhackers and Jayhawkers evolved into broader patterns of outlawry, banditry, and feuding that typified the “Wild West.” This phenomenon was not unique to the borderlands but was especially pronounced there due to the intensity of the Civil War guerrilla conflict and the political complexities of Reconstruction in a divided society.24
The postwar experiences of the Bushwhackers and Jayhawkers reveal how civil conflict can leave a lasting imprint on regional identity and culture. The outlaw legends that emerged from their ranks continue to shape American popular imagination, embodying themes of rebellion, resistance, and frontier justice. Yet these stories also mask the harsh realities of violence, trauma, and societal disruption that accompanied the transition from war to peace. The borderlands’ legacy serves as a powerful reminder of the ways in which wartime irregular violence can morph into enduring social challenges and cultural myths that resonate long after the guns fall silent.25
Memory, Myth, and Modern Interpretation
The violent and chaotic guerrilla warfare waged by the Bushwhackers and Jayhawkers during the mid-19th century left a profound imprint not only on the physical borderlands but also on the collective memory and cultural mythology of Missouri, Kansas, and the broader United States. In the decades following the Civil War, stories of these irregular fighters became heavily mythologized, often reflecting the divided perspectives of their respective communities. To Southern sympathizers, Bushwhackers were frequently portrayed as valiant defenders of their homeland and the “Lost Cause,” while Unionists lauded Jayhawkers as brave champions of freedom and the Union cause. These competing narratives solidified deeply entrenched regional identities and shaped local folklore for generations.26
The mythic status of figures like William Clarke Quantrill and Jesse James for the Bushwhackers, and James H. Lane for the Jayhawkers, played a significant role in this process. These individuals became larger-than-life icons, their lives and actions romanticized in dime novels, newspapers, and later films. Quantrill, often cast as a fierce Confederate partisan leader, was simultaneously vilified and admired, his legacy complicated by the brutal Lawrence Massacre of 1863. Similarly, Jesse James evolved into a symbol of rebellion against Reconstruction and Northern domination, a “Robin Hood” figure in popular imagination despite his criminal activities. On the other hand, Jayhawker leaders like Lane were memorialized for their abolitionist zeal and dedication to the Union, though their reputations were not without controversy, as some critics highlighted their violent excesses and opportunism.27
Modern historians have sought to move beyond these simplistic myths by contextualizing the Bushwhackers and Jayhawkers within the broader complexities of guerrilla warfare, social conflict, and political upheaval during the Civil War and Reconstruction eras. Scholarship increasingly emphasizes the violent nature of irregular warfare and its impact on civilian populations, highlighting the moral ambiguity and cyclical violence that characterized border conflicts. Researchers point to how economic hardship, ideological fervor, and personal vendettas all fueled the brutality on both sides, complicating any straightforward heroic or villainous interpretation. This nuanced approach challenges earlier romanticized or demonized views and encourages a deeper understanding of the border war’s human cost and legacy.28
In recent decades, public memory of the Bushwhackers and Jayhawkers has also been influenced by shifting social and political attitudes, including debates about race, regional identity, and historical justice. Memorials, reenactments, and museums in Missouri and Kansas reflect ongoing efforts to reckon with this turbulent history, often presenting it as a cautionary tale about the dangers of sectionalism and extremism. However, controversies persist, especially regarding how these groups are commemorated. For example, some descendants and local organizations celebrate Bushwhacker heritage as part of Southern pride, while others see such commemorations as glorifications of violence and treason. Similarly, Jayhawker memory can be both a source of regional pride and a reminder of the harsh wartime measures and reprisals inflicted on civilians.29
The memory and myth of the Bushwhackers and Jayhawkers reveal much about how societies remember conflict and construct identity. These groups embody the enduring tensions between history and legend, fact and folklore, violence and valor. As scholars continue to reinterpret the border wars through modern lenses, they underscore the importance of confronting uncomfortable truths while preserving the rich, though often painful, heritage of this pivotal era. The ongoing dialogue about Bushwhacker and Jayhawker legacies demonstrates how history is never static but continually reshaped by the needs and values of each generation.30
Conclusion
The story of the Bushwhackers and Jayhawkers offers a chilling reminder that civil wars are not only fought on battlefields but also within communities, homes, and hearts. Their conflict was not simply a side note to the Civil War—it was a full-scale war within a war, rooted in ideology, vengeance, and survival. The violence they wrought left scars on the borderlands of Kansas and Missouri that would take generations to heal. In many ways, their legacy lives on—in regional memory, American outlaw mythology, and the continuing struggle to reconcile liberty with justice and order with freedom.
Appendix
Endnotes
- Nicole Etcheson, Bleeding Kansas: Contested Liberty in the Civil War Era (Lawrence: University Press of Kansas, 2004), 3–12.
- Thomas Goodrich, War to the Knife: Bleeding Kansas, 1854–1861 (Mechanicsburg, PA: Stackpole Books, 1998), 23–41.
- Jonathan Earle and Diane Mutti Burke, eds., Bleeding Kansas, Bleeding Missouri: The Long Civil War on the Border (Lawrence: University Press of Kansas, 2013), 56–62.
- Michael Fellman, Inside War: The Guerrilla Conflict in Missouri During the American Civil War (Oxford: Oxford University Press, 1989), 17–19.
- Albert Castel, William Clarke Quantrill: His Life and Times (Norman: University of Oklahoma Press, 1999), 6–8.
- Fellman, Inside War, 25-40.
- Castel, William Clarke Quantrill, 95-120.
- Stephen Z. Starr, The Union Cavalry in the Civil War: The War in the West, 1861–1865 (Louisiana State University Press, 2007), 150–155.
- Christopher Phillips, Bloody Kansas: A History of the Kansas-Missouri Border War (New York: Da Capo Press, 1995), 178–195.
- T.J. Stiles, Jesse James: Last Rebel of the Civil War (New York: Vintage Books, 2003), 210–230.
- Etcheson, Bleeding Kansas, 105-120.
- Earle and Burke, eds., Bleeding Kansas, Bleeding Missouri, 73–85.
- Albert Castel, General James H. Lane and the Civil War in Kansas (Norman: University of Oklahoma Press, 1990), 48–67.
- Fellman, Inside War, 83-95.
- Stephen B. Oates, Confederate Cavalry West of the River (Baton Rouge: Louisiana State University Press, 1994), 112–125.
- Fellman, Inside War, 55-70.
- Phillips, Bloody Kansas, 110-125.
- Castel, William Clarke Quantrill, 145-160.
- Starr, The Union Cavalry in the Civil War, 200-215.
- Stiles, Jesse James, 260-275.
- Fellman, Inside War, 230-245.
- Stiles, Jesse James, 280-310.
- Etcheson, Bleeding Kansas, 215-230.
- Phillips, Bloody Kansas, 220-240.
- Castel, William Clarke Quantrill, 200-220.
- Etcheson, Bleeding Kansas, 260-275.
- Castel, William Clarke Quantrill, 180-195; Stiles, Jesse James, 320-340; Earle and Burke, eds., Bleeding Kansas, Bleeding Missouri, 150-165.
- Fellman, Inside War, 245-260; Phillips, Bloody Kansas, 250-270.
- Etcheson, Bleeding Kansas, 280–295; Castel, Quantrill, 200–215; Phillips, Bloody Kansas, 280–295.
- Earle and Burke, eds., Bleeding Kansas, Bleeding Missouri, 170-185; Fellman, Inside War, 270–285.
Bibliography
- Castel, Albert. General James H. Lane and the Civil War in Kansas. Norman: University of Oklahoma Press, 1990.
- Castel, Albert. William Clarke Quantrill: His Life and Times. Norman: University of Oklahoma Press, 1999.
- Earle, Jonathan, and Diane Mutti Burke, eds. Bleeding Kansas, Bleeding Missouri: The Long Civil War on the Border. Lawrence: University Press of Kansas, 2013.
- Etcheson, Nicole. Bleeding Kansas: Contested Liberty in the Civil War Era. Lawrence: University Press of Kansas, 2004.
- Fellman, Michael. Inside War: The Guerrilla Conflict in Missouri During the American Civil War. Oxford: Oxford University Press, 1989.
- Goodrich, Thomas. War to the Knife: Bleeding Kansas, 1854–1861. Mechanicsburg, PA: Stackpole Books, 1998.
- Oates, Stephen B. Confederate Cavalry West of the River. Baton Rouge: Louisiana State University Press, 1994.
- Phillips, Christopher. Bloody Kansas: A History of the Kansas-Missouri Border War. New York: Da Capo Press, 1995.
- Starr, Stephen Z. The Union Cavalry in the Civil War: The War in the West, 1861–1865. Baton Rouge: Louisiana State University Press, 2007.
- Stiles, T.J. Jesse James: Last Rebel of the Civil War. New York: Vintage Books, 2003.
Originally published by Brewminate, 06.10.2025, under the terms of a Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International license.