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Bitter hatred on both sides of the Kansas-Missouri border prompted the Civil War’s most notorious guerrilla attack. (Library of Congress)

August 21, 1863, was an oddly still summer day. The Kansas winds did not blow; there was nothing to dissipate the tower of smoke in the perfectly clear sky, a pall that rose like a dark monument built by the horrors of war. The smoke was fueled not only by the death and destruction of this August day, but also by the years of increasingly abhorrent events on the Kansas-Missouri border. It was visible to dozens of counties on both sides of this bloody border, to the innocent and the guilty alike.

When the dust and smoke of those years cleared, the Lawrence raid would be recalled as the bloodiest day from the opening of Kansas Territory in 1854 to the end of the Civil War in 1865. In four hours, the second largest town in Kansas, with a population of around 3,000, was effectively destroyed. Only a few businesses and a handful of homes survived. The dead were counted at 150 men and boys but may have numbered as many as 200. Some bodies were burned beyond recognition in the town’s conflagration. With a shortage of coffins and the summer heat demanding immediate burial, remains were taken to local Pioneer Cemetery on boards or in buckets. As the task of interment went on deep into the night, lanterns lit the gruesome parade from downtown to the hilltop graveyard. Widows sifted ashes for their husbands’ bones and all wondered quietly or wailed aloud, “Why?”

Every man among the 450 Confederate guerrillas who had put the torch to Lawrence knew why. Each had ridden into Kansas with memories of years of harassment and humiliation, images of their respective homes and farms made smoking ruins, and hands callused from digging graves. Their anger was past appeasement; their sorrow could not be assuaged. All that was left to them was retribution.

Historian Donald L. Gilmore, author of Civil War on the Missouri-Kansas Border, said, “To understand the attack on Lawrence, a historian cannot view it as an isolated event; one must fit the raid into the context of nearly a decade of struggle between leaders in Kansas, Missouri, the South, and the influential Northeast.”

For Missourians, it had seemed a foregone conclusion that they would settle the new Kansas Territory, established by the 1854 Kansas-Nebraska Act, and thereby eventually bring Kansas into the Union as another slave state. Since slaveholding Missouri was bounded by the free states of Illinois on the east and Iowa to the north – havens and welcoming refuges for slaves who managed to escape from bondage – those Missourians whose wealth depended upon slave labor feared the creation of another free state to the west. Therefore, pro-slavery Missourians crossed into Kansas Territory, staked claims and voted, but they often returned to their homes in Missouri. And when New England abolitionists organized bands of settlers to populate Kansas Territory with anti-slavery votes, radical Missourians determined to drive them out.

The struggle between the pro-slavery and antislavery factions turned violent, with each side launching attacks and reprisals. This 1854-61 Border War became known as “Bleeding Kansas” and it produced a legacy of smoldering hatred on both sides of “the line” – the boundary between Kansas and Missouri – that burst into flames when the Civil War erupted in 1861. After suffering through the Bleeding Kansas era, many of Kansas’ abolitionist settlers were convinced that the Missourians’ despised pro-slavery politics more than justified looting, burning and murder in western Missouri when the tables turned in the Kansans’ favor early in the Civil War. Leading the Kansans’ charge across the line into Missouri was Indiana-born James Henry Lane.

The charismatic Lane had proved to be an effective, albeit erratic and controversial, leader during the struggles of the Bleeding Kansas years. The Mexican War veteran and politician would wreak havoc in western Missouri from mid-1861, and his actions eventually would earn him a spot at the top of the “death lists” guerrillas carried in their pockets to Lawrence. Yet as welcome as his leadership was in defending their homes, some Kansans viewed Lane as an opportunist who took advantage of the border strife to enrich himself. One Kansas newspaper article published during the war said of Lane: “To-day he boasts a princely fortune, drives splendid horses, caparisoned with a hundred and twenty-five dollar set of harnesses, lives in the finest residence in the city, owns over twelve hundred acres of heavy timbered land across the river, worth at least twenty-five dollars per acre, is building miles of stone wall, as he says, on his farm … and is really an English lord among the toiling people in Kansas. Such are the rewards of patriotism!”

Lane had met Abraham Lincoln in 1859 when the future president visited Leavenworth, Kan. Lincoln made public addresses in a handful of Kansas towns, testing speeches he would use in the East once his presidential bid in the 1860 campaign began in earnest. Lane campaigned for Lincoln, thus beginning a relationship that would serve Lane well until Lincoln’s assassination in 1865. After Kansas entered the Union as a free state on January 29, 1861, Lane was elected one of its first U.S. senators. In Washington, D.C., during the first days of the Lincoln presidency and the opening of the Civil War, Lane had formed the “Frontier Guard” composed mainly of Kansans, most seeking political appointments but nonetheless welcome in providing Lincoln security in the face of virulent threats hurled at the new president. Lane’s unit bivouacked in the White House East Room until other arrangements could be made to protect him. Lane’s dedication earned Lincoln’s everlasting gratitude, which translated to Lane having a distinct advantage in securing political appointments for his supporters in the new state of Kansas.

As nearby states seceded to join the Confederacy in 1861, Missouri stayed in the Union but remained divided – a slave-holding state loyal to the United States with deeply ingrained Southern culture and ties. More than 100,000 Missourians answered Lincoln’s call for Union troops, while 40,000 others joined Confederate ranks. Some areas were clearly in one column or the other, like pro-Union St. Louis, but most Missouri neighborhoods and many families had men serving in both armies. With the entire nation ripped apart, the previous years of conflict on the Kansas-Missouri border had left an open wound, and there to pour salt into it was Jim Lane.

Lane became radicalized by his obsession to “punish” western Missouri. In the summer and fall of 1861, Kansas volunteers in Union Army service (still called by their “Jayhawkers” nickname from the Border War) raided and/or burned the western Missouri towns of Harrisonville, Platte City, Osceola, Pleasant Hill, Butler and Papinville. Especially egregious was the Kansans’ raid on Osceola.

Osceola was a thriving trading post at the head of navigation on the Osage River. Union forces suspected it also housed a Confederate arsenal. A raiding column of Kansas volunteers headed by James Montgomery picked off targeted towns along their route and arrived at Osceola in the wee hours of September 22, 1861. There was in fact a cartridge factory in the town, to some extent legitimizing Osceola’s designation as a military target; nevertheless, the town was looted and burned on a scale hitherto unheard of on the border. While there was discussion of destroying the factory but leaving the town intact, Lane’s directive to the raiders before they departed Kansas to “pitch into” and “clear out” the offensive bordering Missouri counties doomed Osceola. Even though Lane was not present at Osceola, he was the motivating force behind the town’s destruction.

Montgomery ordered barrels of liquor found in the town destroyed, but some accounts claimed his men partook liberally of the alcohol first. The soldiers helped themselves to whatever they came across and destroyed what they could not carry – salt, sugar, molasses, bacon, even clothing. The burning and looting of Osceola was bad enough, but the story became greatly exaggerated, further outraging Missourians, and those exaggerations have been perpetuated by many historians. For example, the fact that some raiders filled their canteens with the whiskey before it could be destroyed morphed into the claim that hundreds were so drunk they had to be carried back to Kansas in wagons.

Other widely reported accounts claimed that Lane personally acquired loot from the raiders that included a piano and a quantity of silk dresses, as well as a substantial amount of cash from the Osceola bank. Whether true or not, the claim was widely accepted as fact, inflaming the hatred many Missourians, and some Kansans, already possessed for the “Grim Chieftain,” as Lane had come to be called. No matter who actually carried out the depredations, Lane was always perceived as the guiding hand behind the destruction of western Missouri.

As Kansan raiders “punished” Missourians, Union General John C. Fremont, commander of the Department of the West, which included Missouri, issued General Order No. 1 on August 20, 1861, establishing martial law throughout the state. The order read: “All property, real or personal, of those in opposition to the U.S. government … will be confiscated and slaves freed … [and those affected will be] subject to courts martial and death.” Lincoln, unwilling to antagonize other slave states still loyal to the Union, reversed the part about freeing slaves but allowed them to be “confiscated” as contraband of war.

A short time later, Lincoln authorized Major General Henry W. Halleck, who had replaced Fremont, to suspend habeas corpus, allowing imprisonment of individuals on suspicion without formal charges. Then, just before Christmas in 1861, Union policy toward Missouri civilians took a deadly turn. Halleck issued General Order No. 32, which on the surface seemed to target specific saboteurs but in reality let Union authorities cast a very wide net. It specified that those caught in the act of sabotaging a railroad would be summarily shot. Additionally, “Any pretended Union man having information of intended attempts to destroy such roads and lines or of the guilty parties who does not communicate such intention to the proper authorities and give aid and assistance in arresting and punishing them will be regarded as particeps criminis [an accomplice] and treated accordingly.” The final provision of the order said that the Missouri towns or counties in which such activities occurred had to pay for repairs unless the people of those towns or counties could prove they could not have prevented the destruction because they were outnumbered.

Then, on March 13, 1862, Halleck raised the “Black Flag” of no quarter. He issued General Order No. 2, which read: “Evidence has been received at these Headquarters that [Confederate] Major General Sterling Price has issued commissions or licenses to certain bandits in this State authorizing them to raise ‘Guerrilla forces,’ for the purpose of plunder and marauding. General Price ought to know that such a course is contrary to the rules of civilized warfare, and that every man that enlists in such an organization forfeits his life, and becomes an outlaw. All persons are hereby warned that, if they join any guerrilla band, they will not, if captured, be treated as ordinary prisoners of war, but will be hung as robbers and murderers. Their lives shall atone for the barbarity of their General.”

All these events were occurring in a state that was loyal to the Union. Halleck’s orders were open to interpretation depending on the good nature and principles of those executing them. While the intent was to curtail outrages on the border, the draconian methods of forcing loyalty to the Union pushed many Missourians to the other side.

The Youngers of Jackson and Cass counties in western Missouri were such a family. Cole, the oldest surviving son, recalled the strife. “Political hatreds are always bitter,” he wrote, “but none were ever more bitter than those which existed along the border line of Missouri and Kansas during my boyhood Jackson county in the former state from 1856 to ’60. These hatreds were soon to make trouble for me of which I had never dreamed.”

The “trouble” for the Youngers included the July 1862 murder of Cole’s father, Henry, who, although a Unionist and at the time a United States government employee, was waylaid and shot to death after he reported a raid by Kansans on his livery stable. Cole recalled that “his body was left where it fell.” He also chronicled the constant abuse of his mother, who was forced by Union troops to set fire to her own home. “Leaving her burning walls behind her,” Cole wrote, “she and the four youngest children … began their eight mile trudge through the snow to Harrisonville,” the nearest town.

With his father murdered and his mother made homeless, Cole Younger became one of the 450 Confederate guerrillas who rode into Lawrence at dawn on August 21, 1863. Yet had the family been treated fairly, it is conceivable that the Youngers might have been kept, if not enthusiastically committed to the Union, at least from joining the Confederate cause.

The experiences of the Younger family sadly were not isolated. In fact, the Unionists in western Missouri were particularly vulnerable and many fled to towns like Harrisonville, generally occupied by federal troops, for protection. Historian Tom Rafiner wrote that Union families “were literally caught between three fires. They were easy targets for bushwhackers [Confederate guerrillas and sympathizers]. They were suspected by Federal troops, and thus, could easily become targets. Kansas troops made no distinction, all Missouri families, regardless of allegiance, attracted Kansan wrath.” Rafiner called the Kansans “opportunists” who took advantage of the situation to exact revenge and “lash out against anything Missouri.” Once they came into a community, they burned Missourians’ homes without stopping to ask about loyalties. The Kansas-Missouri border became infamous for the escalating violence of irregular warfare.

Missouri answered the attacks with William Clarke Quantrill, and Kansas reeled. (See You Command, January 2013 ACG.) Quantrill was an unlikely candidate for a guerrilla leader. He was an educated yet unremarkable young man from Ohio. He arrived in Kansas Territory in 1857, lured by the promise of wealth and adventure in the American West. Like his contemporaries, he found wealth to be elusive and adventure transplanted by hard work. He hired on as a bullwhacker with an army expedition bound for Utah, and it is likely that the relationships he made with many Missourians on this trip may have swayed his sympathies. The fairhaired boy taught school, gambled, and made friends and enemies. He wrote loving, if complaining, letters to his mother. He quoted poetry. Biographer Albert Castel reported, “Quantrill never told the truth about his life, his apologists have never attempted seriously to discover it, and his detractors have been incapable of presenting it.” Thus, forming an accurate picture of Quantrill’s personality and motivations is difficult. Unlike Cole Younger and many other Confederate guerrillas, Quantrill appears to have held no personal grudge to explain his ferocity in exacting revenge against Kansas. Perhaps the war simply presented him an opportunity to be somebody.

Quantrill started small. On March 7, 1862, he raided Aubry, Kan., a community barely across the state line, in retaliation for the January 1862 Union attacks on Columbus and Dayton, Mo. The minor raid, however, had the desired effect of spreading fear and uncertainty. With additional attacks, Quantrill’s reputation grew and so did his guerrilla ranks. Labeled as outlaws and with no way to remain neutral, more and more men joined Quantrill or the other bands of guerrillas throughout western Missouri. As the war progressed, these bands became more proficient with their tactics and their confidence increased.

Historian Gilmore compared the guerrillas’ tactics to those of the Indians. He explained: “Whenever possible, the guerrillas approached the Federals stealthily and attacked them violently, at a full gallop, screaming their eerie, rebel cries, falling on the bluecoats before they had an opportunity to form and fire. Armed with four to eight .36- caliber Colt Navy revolvers, aimed instinctively and loaded with light [powder load] rounds for accuracy, they fired rapidly, at close range, in an explosion of devastating fire that often panicked Federal troops. Once the Union soldiers broke formation, the guerrillas fell on them individually or in small groups, like wolves upon prey, and destroyed them. Mobility, stealth, and overwhelming, close-range firepower were the keys to [the guerrillas’] tactical successes.”

Integral to the guerrillas’ effectiveness was their ability to “disappear” into the general population between raids. Increasingly pressured to stop the assaults on Kansas, Union officials arrested female relatives of some of the most notorious guerrillas. These women and girls, suspected of spying and passing along information to the guerrillas, were held in a dilapidated row house in Kansas City while awaiting transportation to St. Louis for trial. The very fact that women were arrested was bad enough; when their prison collapsed, killing five of them and crippling others, Missourians were enraged. Among the crushed bodies pulled from the rubble was 15-year-old Josephine Anderson, sister to one of the fiercest of all Confederate guerrillas, “Bloody Bill.” Another of Bill Anderson’s sisters, 18 years old, was crippled, and the youngest Anderson sister detained, a girl of 13, only escaped serious harm because her sisters protected her.

The guerrillas’ long-discussed attack on Lawrence took on new energy. If Union authorities were willing to make war on civilians, Quantrill would give them a war on civilians. He called upon the other guerrilla leaders. All agreed. George Todd expressed the vehemence of their feelings when he replied, “Lawrence, if I knew not a man [of us] would get back alive.” Bloody Bill Anderson, grieving for his sisters, said succinctly, “Lawrence or hell.”

“Give the Kansas people a taste of what the Missourian has suffered at the hands of the Kansas Jayhawkers. … Kill, kill, kill and you will make no mistake,” Quantrill commanded. Women, blacks and children would not be harmed, but white males old enough to carry guns were to be fair game.

The townspeople of Lawrence had become complacent. They had begun to believe they were too far west of the Kansas-Missouri boundary line for the guerrillas’ tactics of a quick strike to be effective. It would be suicide, they thought, for the guerrillas to target Lawrence, given that they typically fought in bands of no more than 70-80 men. No one in Lawrence conceived that 450 guerrillas would risk their lives to bring the war to their doorstep. The townspeople, however, were all proved tragically wrong. Scouts reported back to Quantrill that Lawrence was poorly defended by a handful of raw Union recruits and that the wide streets and space between houses were ideal for a mounted attack.

On the afternoon of August 20, 1863, the raiders trotted in columns of four across the Kansas border south of Aubry. Union soldiers stationed nearby did not dare attack, fearing such an act would have been suicide considering Quantrill’s superior numbers. The soldiers sent the alarm north and south, but nothing to the west – Lawrence received no warning.

At dawn the next day, the sleeping town that covered a square mile on the south side of the Kansas River lay at the guerrillas’ feet as the raiders looked down on it from Mount Oread, the hill at Lawrence’s southern outskirts. The surprise seemed so complete that some guerrillas feared a Union ambush, but Quantrill rallied his men, shouting, “You can do as you please. I am going into Lawrence!”

The mounted guerrillas quickly rode down the inexperienced, mostly unarmed Union soldiers camped on the town’s south end, killing nearly all 22 of them within moments. As the guerrillas rode farther into town, they split into three thundering columns on the main streets, reached the river and cut the ferry line link to the north bank. A handful of Union troops were stationed on the other side, impotent to do anything but watch. As the raiders overran the town, some were sent to cordon the perimeter while others were sent back to Mount Oread as lookouts to warn of any approaching Union forces.

Inside Lawrence, groups of guerrillas went house to house with their “death lists,” searching out the most notorious among Missouri’s enemies. The man at the top of the list, Jim Lane, alerted by the commotion, leapt from a window in his nightshirt and hid in a cornfield. Another escapee was Minister Hugh Fisher, whose wife wrapped him in a rug and dragged him to safety as their home burned. Others were not so fortunate. Ralph Dix was shot in his wife’s arms, and Ed Fitch was killed in his parlor in front of his wife and small children. Mayor Collamore and a servant drowned hiding in a well.

The guerrillas, already groggy from sleeplessness and adrenalin, gorged on ice cream and oysters, bacon and eggs, and topped it off with whiskey. Yet even amid the chaos some managed civility and even compassion, helping women carry furniture from their burning homes or saving family photographs. More than one Missourian found in Lawrence items stolen from his own family.

By 9 a.m., the work was finished and Quantrill led his command south. Homesteads were burned along the trail and more Kansans were killed as the guerrillas crossed the Wakarusa River and turned southeast toward Missouri. Jim Lane had emerged from hiding and put together a ragtag collection of farmers to keep the raiders in sight until Union reinforcements could reach them. Lane’s weak force was handily repelled near Brooklyn, a hamlet destroyed in the fighting and never rebuilt. More than 1,000 Union troops now were in pursuit, and a second encounter took place outside Paola. However, the guerrillas held off the assault long enough to get back to Missouri. Once across the border, they broke up into small bands or individuals and disappeared into the countryside. Quantrill had lost only a handful of men, one of whom was too drunk to leave Lawrence.

Jim Lane, quick to make political hay of the devastation, declared he would rid the country of Quantrill if he had to fire on Union troops to do it. However, the people of Missouri were the ones who paid the highest price. On August 25, Brigadier General Thomas Ewing, foster brother and brother-in-law of General William T. Sherman, signed General Order No. 11. It read in part: “All persons living in Jackson, Cass and Bates Counties, Missouri, and … part of Vernon … are hereby ordered to remove from their present places of residence within fifteen days from the date hereof.”

When Union troops and Jayhawkers ruthlessly enforced this order, putting mostly women, children and the elderly off their farms with nowhere to go, one witness counted more than 130 columns of smoke from the Missourians’ burning homes. Like the pall over Lawrence on August 21, it was visible for miles in the still summer sky. While Lawrence rebuilt, blackened chimneys stood witness to the devastation of western Missouri – the “Burnt District.” The border of Kansas and Missouri lay in ruins, and two more bloody years would pass before the war was over.


 Deb Bisel is a writer/tour guide who lives in Topeka, Kan., and the co-host of the weekly television show “Around Kansas.” She is the author of “The Civil War in Kansas: Ten Years of Turmoil” (The History Press, 2012) and co-author of “The Day Dixie Died: Southern Occupation, 1865-66” (Stackpole, 2001).

Originally published in the May 2014 issue of Armchair General.