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The Bloodiest Man In American History

July 2024
11min read

On the flaming Kansas-Missouri border the name of Quantrill struck terror in men’s hearts. He was a cruel and ruthless guerrilla who burned, robbed, and killed without mercy; but legend made of him a hero dashing and bold

We like to think of the Civil War as the last romantic war—as a sort of gallant duel between gentlemen. There was a certain aura of “swords and roses” in the East, but west of the Mississippi, that neglected area of Civil War history, quite a different atmosphere prevailed. Here the fighting was grim, relentless, and utterly savage—a “battle to the knife, and the knife to the hilt.”

Nowhere was this more true than in the bloody war-within-a-war that raged along the Kansas-Missouri border. There the people did not even wait for the bombardment of Fort Sumter. As early as 1855, armies of proslavery “border ruffians” from Missouri and antislavery Kansas “jayhawkers” clashed in the fierce struggle which determined that Kansas would enter the Union as a free rather than as a slave state.

This prelude to the Civil War engendered a mutual hatred and bitterness which, in 1861, flared into vicious reprisals and counterreprisals. As one Kansan later remarked, “The Devil came to the border, liked it, and decided to stay awhile.” Led by Tim Lane, Charles Jennison, and Dan Anthony, Kansan raiders swirled through western Missouri, looting, burning, and killing. Missouri “bushwhackers” in turn made quick, devastating guerrilla forays into Kansas. Soon a border strip forty miles wide was a no man’s land of desolate farmhouses, brush-grown fields, and prowling gangs of marauders.

One man rapidly came to dominate this border war: William Clarke Quantrill, chief of the Missouri bush-whackers. For dashing boldness and murderous ferocity his raids into Kansas had no parallel. In March, 1862, his men sacked the little village of Aubrey: at Olathe in October they captured 125 Kansas militiamen and shot down helpless civilians “like so many hogs; and a month later they reduced the entire town of Shawnee to ashes. Hundreds of terrified Kansans moved to the interior or fled the state entirely.

This “fiend,” as the Kansans called him, was a tall, slender young man with wavy hair and a mild, almost effeminate face. Only his cold blue eyes, half concealed by thick, drooping lids, bespoke the ruthless killer. Born July 31, 1837, at Canal Dover, Ohio, he had spent most of his adult life in Kansas. As a boy, he is said to have delighted in nailing snakes to trees, torturing dogs and cats, and stabbing cows and horses. He received a good education for his day—his father was a schoolteacher—and for a time Followed his father’s profession in Illinois, Indiana, and Ohio. In the spring of 1857, accompanied by two other men from Canal Dover, Quantrill migrated to Kansas, where he engaged in farming and also, apparently, got into trouble with his neighbors for stealing. In 1858 he joined an army expedition to Utah as a teamster, spent some time in the Pike’s Peak gold fields, and then returned to Kansas, eventually settling in Lawrence.

There, for reasons unknown, he went by the name of Charley Hart (an alias he had occasionally used out west) or, sometimes, William Clarke. The townspeople found him somehow strange and suspicious and were inclined to shun him. Once, when out riding with a girl, he pointed to a tree and said that it would be a good place to hang a man. Ultimately he became a member of a gang of Kansas border bandits engaged in stealing Negroes and horses from Missouri; he was arrested once but jumped bail and thereafter managed to evade arrest.

Quantrill’s first real notoriety came in December, 1860. He persuaded three Kansas “practical abolitionists” to accompany him on a raid into Missouri for the purpose of liberating the slaves of Morgan Walker, a well-to-do Jackson County farmer. But prior to the raid he secretly forewarned Walker, with the result that the three abolitionists walked into a deadly trap. Quantrill remained in Jackson County the rest of the winter, regaining the sympathy and trust of the Missourians by telling them he had engineered the ambush to revenge the murder of an elder brother by Kansas jayhawkers. It was a lie, but to this day many Missourians firmly believe it.

Following the outbreak of full-scale hostilities along the bolder, Quantrill joined one of the Missouri bushwhacker bands, then formed his own outfit. His spectacular forays gained him recognition as head of all the guerrillas, and in the summer of 1862 the Confederate Army granted him a captain’s commission. Union authorities, however, regarded the bushwhackers as outlaws and treated them accordingly. In retaliation, the latter vowed to show no quarter to Federal prisoners.

Those who knew Quantrill in Lawrence afterward recalled that he did not appear to possess any special ability, and that although “somewhat of a horseman,” he was “only a fair shot.” But Kansans have tended to underrate him. One of his followers described him as being “a good commander and a brave man,” and stated that in combat his men would try to keep him in the rear, not only so he could direct the fighting but also because they “did not want to lose him.” Another guerrilla testified that with one or two exceptions Ouantrill was the “fastest draw,” best shot, and finest horseman of all the bushwhackers.

Quantrill’s band was composed of tough young Missourians with Southern sympathies who resented jayhawker raids, and of border ruffians and outlaws like Quantrill himself. A Confederate general who encountered them in Texas said all of them were killers who “deemed the life of a man less than that of a sheep-killing dog.” Some of the more notorious members included “Bloody Bill” Anderson (who bedecked the bridle of his horse with human scalps); the fearless, sadistic George Todd; and three young men serving their apprenticeship in outlawry under Quantrill: Cole Younger and Frank and Jesse James. (See “The Wild, Wild West,” AMERICAN HERITAGE, August, 1960.)

Quantrill and his men saw duty with Confederate troops at the battles of Independence and Lone Jack, Missouri, in August, 1862, and at the Battle of Prairie Grove, Arkansas, in December of that year. It was after the Independence clash that Quantrill received his Confederate captain’s commission, but he and his men resisted all efforts by the Confederate authorities to have them join the regular forces on a permanent basis. They were more interested in their personal war with the Kansans and with Missouri Unionists than in the Southern cause as such. Confederate generals in the West were quite willing to make use of the bushwhackers’ services, despite the atrocity stories which followed them wherever they went.

The bushwhackers dressed in picturesque guerrilla shirts—loose, gaudily beaded blouses worn over their ordinary clothes and having a low scooped neck and capacious pockets for ammunition. Much of the time, however, they wore captured Federal uniforms. So disguised, they were often able to approach within point-blank range of a Union detachment, then wipe it out. Taken as a whole, they were the most formidable “revolver fighters” the West ever knew.

After each foray across the border the bushwhackers scattered with their loot into the rugged hills of western Missouri. The intensely pro-Southern people of this region regarded them as heroic defenders against the jayhawkers, and so sheltered them and helped them evade the Union pursuit columns.

By the spring of 1863 Quantrill, with several hundred men under his command, was at the peak of his power and confidence. According to one unauthenticated account, he even journeyed to Richmond, Virginia, and had an interview with the Confederate Secretary of War in which he urged that the South wage a “black flag” war and that he be commissioned a colonel of “partisan rangers.” In any case, he adopted the title of colonel and on occasion wore a colonel’s uniform. And he began laying plans for what was to be his most famous and ambitious undertaking: the raid on Lawrence, Kansas.

For years the people of western Missouri had made no secret of their determination someday to wipe out Lawrence. To them the town was the citadel of Kansas abolitionism, the symbol of all that they hated in Kansas. It had been the “Free-State Fortress” during the fifties, and it was now headquarters for the hated Kansas guerrillas known as the Red Legs. With a population of nearly three thousand, it was also one of the largest and wealthiest towns in Kansas. When Ouantrill announced, “Let’s go to Lawrence-we can get more revenge, and more money, there than anywhere else,” his men required no further urging.

On August 19, 1863, three hundred bushwhackers began marching westward from the Blackwater River in Johnson County, Missouri. Along the way 150 more joined them, bringing their total number up to 450—the largest force of its kind assembled under one command during the Civil War. Late in the afternoon of August 20 they crossed into Kansas five miles south of Aubrey. Here they were favored by a tragic failure in the Union border defenses. The commander of the Federal post at Aubrey was notified by a scout that a large body of guerrillas was entering the state. But instead of pursuing Quantrill and sending couriers to alert the towns to the west, he merely forwarded the report to the other Union posts along the line and to headquarters at Kansas City.

SIDEBAR: See those Men! They Have No Flag

Throughout the moonless night Quantrill’s column moved steadily across the Kansas prairie “like a monstrous snake, creeping upon its prey.” Many of the bushwhackers slept as they rode, strapped to their saddles. They made only a few brief halts, to rest the horses or to get a bearing. During one such stop George Todd went to a nearby farmhouse and with a musket stock clubbed to death a Unionist refugee from Missouri, possibly to settle an old personal grudge. The raiders murdered numerous others along the way, including ten different guides they pressed into service. Some carried lists of intended victims with them. Many Kansans saw them as they passed and guessed their identity and destination, but, paralyzed by fear, made no effort to send a warning to Lawrence.

“At the first glimmer of day” on August 21, Lawrence came into sight. Quantrill halted the column on a summit southeast of the town and sent several men ahead to reconnoiter. Some of his followers suggested turning back—surely the inhabitants had been alerted by now and would be waiting for them. “You can do as you please,” replied Quantrill. “I am going into Lawrencel” Then, without waiting for his scouts to return, he gave the order to charge.

The first inkling the sleeping townspeople had of the bushwhackers was the rattle of gunfire, the pounding of hoofs, and the agonized screams of the wounded and dying. Witnesses never forgot the sight—hundreds of bearded, long-haired, wild-looking men, in slouch hats and greasy, sweat-stained shirts, yelling, shooting, and riding with reckless skill.

Upon arriving at the Kansas River, which bordered the town on the north, they turned back and surrounded the four-story Eldridge House, Lawrence’s central building. They approached cautiously, but the occupants, bewildered by the sudden onslaught, possessed neither the will nor the means to defend the place. One guest, Captain A. R. Banks, waved a white sheet from a window and called for Quantrill.

He rode forward, attired in his elaborately ornamented guerrilla shirt, four pistols in his belt, two more in saddle holsters.

“What is your object in coming to Lawrence?” cried Banks.

“Plunder!” replied Quantrill.

“We are defenseless and at your mercy. The house is surrendered, but we demand protection for the inmates.”

Quantrill promised that they would not be harmed if they offered no resistance. He then ordered them to come down to the street, where two bushwhackers relieved them of money and valuables while others pillaged the rooms, then set fire to the hotel.

As the flames shot skyward, Quantrill rose in his stirrups, turned to his men, and shouted: “Kill! Kill! Lawrence must be thoroughly cleansed, and the only way to cleanse it is to kill! Kill!”

With a wild yell the raiders spread out through the town. Some, screaming “Whiskey! Whiskey!” broke into the saloons. Others ransacked the stores and shops. At the Johnson House, bushwhackers lined up all the male residents in an alley and mowed them down with revolvers. Farther up the street they shot and wounded two men, then threw them screaming into the flames of a burning building. And everywhere they plundered and burned private houses, after first slaying every male occupant they discovered. They did not, however, kill or rape any women.

The panic-stricken men of Lawrence endeavored frantically to escape. Many fled to cornfields and woods, or concealed themselves along the riverbank. Others, whose dwellings were surrounded before they could get away, hid in cellars, attics, barns, and gardens, or even disguised themselves as women. Still others sought refuge under the board sidewalks.

Women who talked with the bushwhackers subsequently related that they all asserted they had come to Lawrence to avenge wrongs done to their people in Missouri by jayhawkers and Red Legs. They claimed, too, that they were being more merciful than the Kansans, whom they charged not only with robbery, arson, and murder, but also with molesting women.

Most of the raiders obtained fresh horses to replace their own jaded mounts or to bear additional plunder. What they could not use or carry, they burned. They proceeded systematically from building to building, setting fire to each one; the smoke swirled straight up into the sky and “stood like great black columns along the street.” Soon an overhanging shroud darkened the entire town.

During the early part of the massacre Quantrill sat in a hotel lobby eating a hearty breakfast and conversing with former acquaintances—many of whom hastened to claim a friendship which under other circumstances they would have denied. Later he took a buggy and drove triumphantly about the burning town. When, at nine o’clock, his lookouts atop a nearby hill reported seeing the dust of approaching Union troops, he ordered his men to form into columns of four, and almost as suddenly as they had come, they were gone.

They left behind almost total devastation. Lawrence’s business center was destroyed; one hundred houses had been burned to the ground and another hundred damaged by fire. The dead lay scattered everywhere, “some so charred that they could not be recognized and could scarcely be taken up.” Bones were visible among the embers, and the “sickening odor of burning flesh was oppressive.” In all, 150 men of Lawrence (and one of Quantrill’s raiders) lost their lives; another thirty were wounded.

Quantrill evaded the feeble Union pursuit without difficulty. By the next morning he was well back into Missouri, where his men, as usual, scattered into the hills. About a dozen of the raiders were caught and killed, but Quantrill and most of the others escaped.

The Lawrence massacre was the bloody climax of the Kansas-Missouri border conflict. It was also the most atrocious single event of the Civil War. For stark, melodramatic horror, nothing else quite matched it. It has given Quantrill a reputation as the bloodiest man in American history, and placed him in the company of Simon Girty and John Wilkes Booth as one of the great national villains.

But he was not through. In October, he and his men headed south to spend the winter in Texas. On the way, near Baxter Springs, Kansas, they came upon Major General James G. Blunt, commander of Union forces in the Indian Territory, accompanied by his personal escort. Quantrill’s men were wearing Federal uniforms, and Blunt’s soldiers thought they were troops from the garrison at Baxter Springs. Suddenly, at point-blank range, the bushwhackers opened fire. The survivors fled in terror, closely pursued by the exultant guerrillas, who mercilessly killed every man they overtook, including an artist from Frank Leslie’s Illustrated Newspaper and the hapless members of Blunt’s headquarters band. Blunt himself escaped only because he had a fleet horse. In all, nearly a hundred Union soldiers were slain. Afterward Quantrill, ordinarily a light drinker, got roaring drunk and swaggered about the field bragging of his victory.

The bushwhackers continued on to Texas. In the Indian Territory they captured (according to Quantrill’s own report to Confederate General Sterling Price) “150 Federal Indians and Negroes,” but brought “none of them through.” All told, counting numerous minor raids and skirmishes, Quantrill’s raiders probably killed close to a thousand men during 1863.

The Baxter Springs massacre was Quantrill’s last major success. In Texas dissension broke out among the guerrillas; many left Quantrill to form a separate band under Anderson, and Todd took over actual leadership of the remainder. Quantrill retained only a nominal over-all command. The reason for his sudden eclipse is not clear, but apparently Todd, a man of superlative courage and dash, had become more popular with the rank and file, especially the younger, wilder ones.

During most of 1864 Quantrill hid out in northern Missouri with his mistress, Kate Clarke, who is said to have accompanied him on some of his raids dressed in men’s clothes. (After the war she used money given her by Quantrill to establish a brothel in St. Louis.) That autumn Todd and Anderson, along with many other bushwhackers, were killed while participating in an unsuccessful Confederate invasion of Missouri and Kansas. This debacle, along with the general collapse of the Confederacy, broke the hold of the bushwhackers on Missouri. Early in 1865 Quantrill led a small band out of the state into central Kentucky.

They passed the winter and spring there, committing petty depredations and skirmishing with Kentucky Unionist militia. Apparently Quantrill had no real plans, except to continue his freebooting career. On May 10, 1865, the inevitable end came. A party of “Federal guerrillas” surprised his band in a barn near Louisville and severely wounded Quantrill as he attempted to flee. He was taken to Louisville, where, on June 6, he died in a military prison.

“The monster is dead,” rejoiced the Kansas press. But in the legends of the Missouri border he lived on. There, the stories of his dashing exploits and hair-breadth escapes were told and retold, becoming more elaborate with each telling. To have been one of his men soon became a mark of honor and distinction; as late as 1929 those of his followers who survived the war, and escaped the fate of Jesse James, held annual reunions at Independence. There are many men still alive in Missouri who recall the thrill they experienced as children when some bearded veteran was pointed out to them and they were told in a hushed voice: “He was one of Quantrill’s raiders.” And such is the perversity of fame’s allure that well into the present century elderly impostors occasionally appeared to lay claim to the dubious honor of having been William Clarke Quantrill himself.

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