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Bleeding Kansas
The opening of Kansas Territory to settlement in 1854 threatened the delicate balance between free and slave states, therefore pro and anti slavery zealots struggled to send more settlers to ensure that it would vote to enter the Union on their side. Since Kansas bordered Missouri, a slave state, the pro-slave side initially had the advantage. Residents of Missouri would cross the border to vote in local elections and intimidate free soil (anti-slavery) settlers to leave, which earned them the nickname “Border Ruffians.”

As the number of free soilers increased, some adopted the Border Ruffians’ violent tactics, and attempted to drive out pro-slavery settlers, thus acquiring the nickname Jayhawkers. Charles “Doc” Jennison, a physician from New York, and James Montgomery, a preacher from Ohio, became leading Jayhawkers. Jennison proved to be especially successful in forcing out pro-slavery settlers, so after a period of time he only needed to make a single warning and the targeted family would soon be gone. They also worked with fanatical abolitionist John Brown before he made his disastrous attempt to spark a slave revolt by seizing the federal arsenal at Harper’s Ferry, Virginia in October 1859. However, when a convention decided on August 2, 1858 that the territory would enter the Union as a free state, Bleeding Kansas came to an end. Montgomery and Jennison saw most of their support disappear and the endless series of tit for tat raids finally ceased.
  
The Civil War Begins
Unfortunately, the settlers would not know peace for very long. The Republican Party had campaigned against the expansion of slavery to new states, so long-simmering tensions between northern and southern states exploded when Republican candidate Abraham Lincoln was elected president in 1860. Seven southern states seceded in February 1861 and formed the Confederate States of America. Lincoln vowed to preserve the Union by force if necessary and the civil war started when Confederate soldiers attacked Fort Sumter on April 12.

Kansas Senator Jim Lane was appointed a brigadier general of volunteers by President Lincoln in June 1861 in gratitude for leading a unit of Kansas volunteers to provide protection for him in Washington until federal troops arrived a few weeks later. As a leader of the free soilers during Bleeding Kansas, he naturally used former Jayhawkers as the core of the brigade. Montgomery was given the 3rd Kansas Infantry and was second-in-command of the brigade while Jennison led the 7th Kansas Volunteer Cavalry. With most able-bodied men joining the Confederate army, Jennison and his men saw Missouri as a playground for looting and murder. Kansas had been the battleground for the past few years, so Missouri would be repaid for Border Ruffian raids. The homes of known pro-slavery families were torched and everything of value would be thrown into wagons and taken back to Kansas, including any slaves.

The Fight for Control of Missouri
Although Clairborne Jackson, the governor of Missouri, supported secession, he was unable to persuade a majority of state legislators to join the newly formed Confederacy. Learning that a force of pro-slavery militia were planning to occupy the federal arsenal at St. Louis, its commander, Captain Nathaniel Lyon, raised four regiments of volunteers, largely German immigrants who had settled in eastern Missouri, and captured the militia on May 10. This decisive action won Lyon promotion to brigadier general and command of Union forces in Missouri.

Governor Jackson appointed Sterling Price, a former governor of Missouri and veteran of the Mexican-American War, a major general, and he recruited seven thousand volunteers, which linked up with another Confederate force under Brigadier General Ben McCulloch in July 1861. When the two armies encountered each other on August 10 Lyon was outnumbered almost two to one, but many of Price’s troops were unarmed. The battle was bloody but indecisive until Lyon’s death panicked the Union soldiers into retreating. A couple of weeks later, McCulloch led his troops to Arkansas, claiming to be following orders, but primarily motivated by a lack of respect for both the Missouri recruits and their general. Price then advanced towards the border hoping to destroy the Kansas Brigade, but Lane knew he was heavily outnumbered and avoided a fight. When the main Union army in Missouri surrendered at Lexington on September 20 after a three day siege, it appeared that the Confederates had won control of the state.

Two days later, Lane’s brigade captured Osceola, Missouri but it quickly turned into a drunken riot, and the town of 3,000 burned to ground. From eye-witness testimony, it seems that much of the destruction was due to a lack of discipline caused by liberated liquor, rather than intent. Aside from a few large scale raids like that of Osceola, small groups of Jayhawkers launched many uncoordinated raids throughout Missouri.

While the Jayhawkers were a threat to small towns and isolated farms, they were incapable of driving Price’s army out of Missouri. However, Major General John Fremont, commander of the Union Army’s Department of the West, had arrived in Missouri with 38,000 troops. Faced with an enemy twice the size of his army, Price had no other option but to retreat into Arkansas and disband much of his army, since he did not have enough supplies and weapons.

Fremont, had declared martial law in August 30, 1861, which required every resident to swear loyalty to the United States. Thousands of men suspected of southern sympathies were jailed or forced to pay heavy fines.

The Jayhawkers were aware of the advantages of their irregular status, they could go where they wanted, keep their plunder, and disband whenever they felt like it. Although they claimed to only take from southern sympathizers, they did not inquire too closely about a person’s political sympathies but looted indiscriminately from each town, bringing caravans of loot back to Kansas to be auctioned off. Their greed reached such a level that even the provisional Missouri governor, Hamilton R. Gamble, wrote Lincoln to complain that they were out of control. Naturally, these raids drove more men to join the growing bands of guerrillas. Little, if any, of the loot was turned over to the federal government, although Jennison and his followers became known for selling stolen goods at cheap prices. The looting raised so much outrage in Washington that Montgomery was sent east in January 1863 to take charge of a regiment of black volunteers, while Jennison was relieved of command in January 1862 but Lane’s influence quickly ensured that he was reinstated.

Thousands of slaves made their way to Kansas in search of freedom, either on their own or as part of the returning Jayhawker expeditions. However, most slaves simply made their way across the Missouri-Kansas border, often by taking their former owners’ horses and wagons. Officially, any escaped slaves were to be returned to their owners because Lincoln wanted to encourage slave owners to remain loyal but most Union officers turned a blind eye to the numerous escaped slaves that ended up in their jurisdiction. In the summer of 1862, the formation of black regiments was finally permitted and two regiments were formed in Kansas. A few blacks joined the Bushwhackers, but they were rare exceptions.

By March 1862, Union soldiers had occupied all of Missouri, so most Jayhawkers had stopped raiding, mainly because there was nothing left to steal. Hundreds of old men and boys had been killed, thousands left homeless, and Western Missouri had been turned into a desolate wasteland. They had enjoyed their ten months of raiding and looting, and had little thought that retribution might come back to them.

Bushwhacker Raids
They did not have to wait long. William Clarke Quantrill began leading Bushwhackers (pro-southern Missouri guerrillas) into Kansas in late March, running rings around Union troops, who usually arrived to protect towns after they were smoking rubble. Since Missouri had been brought under Union control, most of the troops were assigned to the front lines, leaving only second-rate units to deal with the guerrillas. Quantrill was only twenty-four years old and most of his followers were several years younger, able to ride all day and hardened by the harsh treatment that had turned them into brutal killers. The fighting had become increasingly vicious when Major General Henry Halleck, commander of Union forces in Missouri, announced on December 22, 1861 that captured guerrillas would be executed instead of exchanged for Union soldiers. When Quantrill heard of this, he began killing prisoners. While the change in policy drove away many recruits, it attracted those who were desperate for revenge.

Fed up with constant guerrilla raids, the Union commander of Missouri, Brigadier General John Schofield, issued General Order No. 19 on July 22, 1862, which forced all male able-bodied Missourians to serve in the militia and help hunt down the Bushwhackers. Unwilling to fight friends and relatives, many either joined the guerrillas or enlisted in the Confederate army. In addition, Union troops pursuing guerrillas often lived off the land, taking food and livestock from the homes of suspected Southern sympathizers, thus guaranteeing their victims a hungry winter and fueling their hatred. Combined with the closure of any newspaper that expressed pro-southern sympathies, these measures drove many people to aid the guerrillas.

Although Quantrill had led 150 guerrillas to spend the winter of 1862-63 in Arkansas, a large number remained in Missouri. Dividing themselves into small groups, they built lean-tos or dug caves in hills to hide from Union patrols. Meanwhile, most of Quantrill’s men served with Jo Shelby’s Missouri Brigade during a winter campaign in Arkansas.

Raid on Lawrence
In an attempt to eliminate the network of supporters that enabled the guerrillas to keep operating, seventeen young Missouri women were arrested as Confederate spies. When the building housing them in Kansas City, Kansas collapsed on August 14, 1863, killing five and seriously injuring the rest, the guerrillas believed that it had been deliberate. Several of the women were relatives of Bushwhacker leaders, therefore it was decided to raid Lawrence, Kansas even though it was deep in enemy territory. Lawrence was the target instead of Kansas City because it had been the headquarters of abolitionist supporters during Bleeding Kansas. Quantrill and Bloody Bill Anderson led 450 guerrillas and Confederate recruits into Lawrence shortly after dawn on August 21. When they rode out four hours later, 185 men and boys were lying dead on the ground and the town had been torched. The massacre caused horror and revulsion throughout the North, but many in the South were aware of Jayhawker atrocities in Missouri and praised Quantrill.

Any sympathy that Southerners had for the victims disappeared in the wake of the retaliatory burning and looting carried out in Missouri by Kansas troops. On August 25, Brigadier Thomas Ewing, Jr, commander of the Missouri-Kansas border region, issued General Order No. 11, which banished all Confederate sympathizers, basically everyone, from an area 85 miles long and 50 miles wide. The few people who could prove their loyalty to the Union were permitted to stay. Every building was burned to the ground, and 20,000 families were forced to leave their homes. Since most of the men were away fighting, the huge task of moving each family’s possessions was usually left to women, children and old men. No assistance was provided and those who traveled south found that the Confederacy lacked the resources to provide for them. Jayhawkers and Kansas Union soldiers viewed this order as license to loot and any men who protested were killed. The number of deaths caused by the expulsion is believed to be in the hundreds.

The Fall of the Confederacy
Despite the increased number of Union troops, the guerrillas continued to rampage through Kansas and Missouri when they returned in the spring of 1864, so everyone lived in terror of the next raid. Although people worried about Quantrill, he had retired after he had lost control of his band to George Todd, but other guerrilla leaders were operating. Furthermore, the terrain was the guerrillas’ greatest ally and they succeeded in isolating the individual towns from each other.

The failure of the regular Union troops to control the situation meant that greater leeway was given to Jayhawker units. By the summer, the guerrilla war had become so savage that both sides regularly committed atrocities, and some raiders began making necklaces from body parts. Bill Anderson soon became the most notorious of the guerrilla leaders. For example, he executed and scalped twenty-four unarmed soldiers that he found on a train that he captured in Centralia on September 27.

Quantrill only started raiding again after General Price asked the guerrillas to distract Union troops in preparation for his invasion of Missouri in the fall. Unfortunately, Anderson and Todd forced Quantrill to agree to an attack on well-defended Fayette on September 24 and they were badly mauled.

Price's army entered Missouri in September but he failed to capture any major cities. The campaign was quickly cut short when his army was defeated by a much larger Union force at Westport on October 23. His retreat into Arkansas ended the last attempt of the Confederacy to gain control of Missouri and ensured that most of Kansas was safe from Bushwhacker raids. Although many confederates surrendered during the winter of 1864-65, several guerrilla bands were still operating in the spring of 1865 but the Union commander’s decision to accept the surrender of guerrillas lured a number of raiders to give up.

Refusing to believe that General Robert E. Lee had actually surrendered at Appomattox on April 9, roughly a hundred bushwhackers arrived in Missouri under Dave Pool and Archie Clements in early May. A couple of weeks later, Pool had seen the writing on the wall and led 48 men in to lay down their weapons. By June 10, most of the remaining guerrillas had either come in or had fled to Texas. Although Union soldiers accepted their surrender, more than a few bushwhackers later found themselves accused of crimes and strung up by vigilantes.

When all the people forced out by Order No. 11 returned, they learned that anyone who had followed the Confederacy had lost their political rights, which drove a few to turn outlaw.

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Related Movies:

Dark Command (1940)
Directed by Raoul Walsh, starring Claire Trevor and John Wayne
Bob Seton, a Texas cowboy, beats out local schoolteacher Will Cantrell (William Quantrill) for the job of marshall of Lawrence shortly before the Civil War starts. The bitter Cantrell forms a band of lawless guerrillas that rampage through Kansas until Seton learns that they plan to attack Lawrence. (please click here to read the review)

Kansas Raiders (1950)
Directed by Ray Enright, starring Audie Murphy and Brian Donlevy
Jesse James joins Quantrill's band to seek revenge for his parents' deaths but eventually becomes disillusioned by the constant killing of civilians.

The Outlaw Josey Wales (1976)
Directed by Clint Eastwood, starring Clint Eastwood and Chief Dan George
When Missouri farmer Josey Wales’ family is killed by Redlegs, Union guerrillas based in Kansas, he joins a band of Missouri guerrillas that continues to fight even after the war ends. When the band finally surrenders, they are massacred by Union soldiers, he is the only witness and becomes hunted.

Ride With The Devil (1999)
Directed by Ang Lee, starring Tobey Maguire and Skeet Ulrich
A young Missouri man joins the Bushwhackers, irregular guerrillas loyal to the South, but as he sees his friends die, he gradually tires of the killing and savagery. (please click here to read the review)

Further Reading:

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

A large portion of the book is composed of personal accounts which enable the reader to have a firsthand experience of the war. The book also provides a large number of pictures so that the reader can match the name of an eye-witness to a face. However, since it is a slim volume of 164 pages, there is a lack of detailed background needed to make it easier to understand the events.

Quantrill’s War: The Life and Times of William Clarke Quantrill 1837-1865-Duane Schultz, New York: St. Martin’s Press, 1996.

Schultz has produced a well-written, detailed book about Quantrill that shows how he became a savage raider and explains how the chaotic times enabled him to transform himself from a petty outlaw to the leader of a large band of bushwhackers. Almost a third of the book is devoted to the reasons behind the raid on Lawrence, the raid itself and the pursuit of the guerrillas afterwards, which is fitting since the raid is what made Quantrill famous or rather infamous. Schultz succeeds in walking the delicate line between being too gruesome and presenting the horror of the raid through the eyes of the witnesses. Relating the huge number of firsthand experiences makes you understand how thorough the raiders were in their determination to kill any male old enough to carry a gun. While the focus of the book is naturally Quantrill, the author also presents the exploits of the other leading members of Quantrill’s guerrillas, especially Bloody Bill Anderson, George Todd and Cole Younger, showing both the difficulty of leading so many violently inclined men and how Quantrill gradually lost his position as leader of the group.

The Devil Knows How to Ride: The True Story of William Clarke Quantrill and his Confederate Raiders-Edward E. Leslie, New York: Da Capo Press, 1998.

Leslie’s description of his first sight of Quantrill’s head is morbidly hilarious. He provides a solid summary of Bleeding Kansas, the vicious war in Kansas that predated the Civil War to show the environment that shaped Quantrill and his followers. Leslie has clearly performed an impressive amount of research but it suffers from a slight lack of organization. The information is presented but not tied together as well as it could be. The background of Quantrill’s family members is explored in some detail, partially because the adventures of a group of rogues make for an interesting story and possibly to explain their influence on Quantrill’s later actions. Leslie does a good job at showing how difficult it is to find reliable information about Quantrill’s earlier years because the people who knew him at the time were either harsh critics or staunch supporters.

The two books cover largely the same ground. Leslie gives a good overview of the civil war within Missouri as pro and anti-union supporters struggled for control of the state. He spends more time on the other guerrilla leaders, Price’s failed invasion and the increasing savagery that developed after Quantrill lost control, including gang-rapes. The concluding chapter deals with the efforts of Quantrill’s mother to find her son’s body and the final journey of his skull, where it was used for a time as part of a fraternity initiation.

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