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His ruthless nature earned his moniker— and obscured a flair for strategy.

As armies march across America from 1861 to 1865, other combatants shot soldiers from ambush and terrorized civilians of opposing loyalties in a fierce guerrilla war. Guerrillas tied down thousands of troops that could have been used on the battlefield, destroyed millions of dollars of infrastructure, disrupted communications and transport, and destroyed isolated outposts.

The names of many of these partisans have come down to us—William Quantrill, Champ Ferguson, “Tinker Dave” Beaty, Frank and Jesse James. But none caused more terror than “Bloody Bill”Anderson of Missouri.

William T. Anderson was born sometime in the late 1830s in Kentucky, the son of a hat maker. His family moved to Missouri when he was still an infant, and then to Kansas in 1857, a time when pro-slavery and antislavery factions fought for control.As working class Missourians, the Andersons were scorned by their mostly Northern neighbors. To Northerners all Missourians were “Border Ruffians” who wanted to bring slavery to the territory.

Classmates remembered Anderson as a quiet and reliable boy, but growing up in Bleeding Kansas hardened him. He started stealing horses in Missouri to sell to merchants headed down the Santa Fe Trail. Raids were common on the border, with pro-slavery Missouri “bushwhackers”raiding Kansans—and Free-Soil Kansas “Jayhawkers” looting Missourians. Most bushwhackers felt some allegiance to the South, or at least a hatred for the North—although every Confederate state had Union guerrillas. But a violent minority were simply bandits. Anderson belonged to that third group, which profited from the chaos while having no political affiliation.

It’s not clear why Anderson turned to crime, but poverty, opportunism and the deaths of his mother and one of his brothers may have all contributed. It’s certain that early in the war he had no head for politics. He once said to an acquaintance,“I don’t care any more than you do for the South…but there’s a lot of money in this business.” His attitude began to change when his father was killed in a dispute with a local judge of Northern sympathies. When a jury acquitted the judge of murder, An derson shot him and burned him alive in his own store.

Anderson had finally taken a side. He and his gang fled to Missouri,where they robbed farms and skirmished with Union militia. “There is no act of arson, robery [sic] or murder, from which they shrink,” reported the Lexington Weekly Union.

In the spring of 1863, Anderson merged his group with William Quantrill’s. Anderson became one of the famed partisan leader’s trusted lieutenants, under the direct command of George Todd. He learned much from the more experienced guerrilla, but he didn’t like taking orders and soon led raids of his own. Bushwhacker bands were loosely organized, with a fluid command structure and a constantly changing membership. In the face of the enemy, however, the seemingly rowdy and disorganized outlaws became an efficient fighting unit.

Among Southern guerrillas, Missouri bushwhackers were a breed apart. Sporting shoulder-length hair and elaborately embroidered shirts, they rode the best horses, either gifts from Southern sympathizers or stolen from Unionists. They carried several pistols each and their main tactic was to rush small Union detachments, closing quickly and pouring heavy fire on the soldiers before the troops could reload their rifles.

Many operated out of the Kansas-Missouri border counties. The Union district commander, Brig. Gen. Thomas Ewing, decided to undercut their support by arresting their female relatives.

Women were usually sacrosanct, but Ewing knew the bushwhackers’ womenfolk provided them with supplies and information.Anderson’s sisters, Mary and Josephine, were in the habit of going to Kansas City to buy him ammunition. They were arrested along with other relatives of Quantrill’s band and imprisoned in a rickety building in Kansas City. The structure collapsed on August 13, 1863, and Josephine Anderson and four other women were killed.

Anderson was a changed man after that. The bushwhackers were convinced the Union jailers had deliberately undermined the building, and Anderson’s hatred for the North grew pathological. He was the most bloodthirsty of a bloodthirsty crew, galloping into battle calling Josephine’s name and foaming at the mouth. Every time he made a kill, he tied a knot in a silken cord he carried with him. At his death, the cord reportedly had 53 knots.

Other members of Quantrill’s band lost relatives as well, and the wily chieftain saw an opportunity. He longed to raid Lawrence, Kan., a center of abolitionism and home to the notorious Jayhawker Senator Jim Lane. Forty miles across a heavily guarded border, Lawrence looked too tough to take. But now Quantrill had no trouble convincing his men to attack.

Quantrill gathered about 450 bushwhackers, recruits and Southern farmers, and crossed the state line. They traveled by night, kidnapping local farmers for guides—then killing them when they got too far from home to give adequate directions. Quantrill’s band worked its way through nine guides before the dawn of August 21 found them at Lawrence.

Standing on the crest of a hill, the guerrillas studied their prize. Lawrence looked big, too big, and they hesitated. Quantrill urged them on, reminding them of the crimes against their families. Anderson needed no urging. Soon the guerrillas galloped into town and found it unguarded. They tore through the streets, shooting every man in sight as Quantrill stood high in his stirrups shouting, “Kill! Kill and you will make no mistake!”

Quantrill issued a list of houses he wanted burned and the guerrillas set to work with gusto. At the top of the list was the home of Senator Lane.

The Jayhawker had fled town dressed only in his nightshirt, but he was no coward. Lane gathered men and weapons from outlying farms and prepared a counterattack. Meanwhile the guerrillas showed up at his home and found only his wife. The rough men helped her remove some prized possessions, then torched the house. Quantrill had given strict instructions not to harm any women. Burning their homes down or killing their husbands and sons in front of them, however, was fair game.

Scouts spotted a Union relief column approaching and Quantrill ordered his men to saddle up. Nearly 200 bodies littered the streets, half the buildings were in flames, and Anderson rode beside Quantrill with a satisfied gleam in his eye. “Bloody Bill,” as people started calling him, had done as much killing as anyone, but it would never be enough.

Quantrill’s men hurried east with Union troops and Lane’s vigilantes hot on their trail. One drunken bushwhacker lingered too long in Lawrence and was set upon by enraged citizens. Others died in the running battle across the state line.When the survivors reached the forests of Missouri, they split up and escaped.

The sacking of Lawrence appalled people on both sides, but General Ewing’s response was equally cruel. On August 25, he issued General Order No. 11, commanding all residents of Jackson, Bates and Cass counties—and part of Vernon County—who didn’t live within a mile of a Union post, to prove their loyalty and move to a military base or leave the area. It was the largest removal of U.S. citizens until the roundup of Japanese Americans in World War II.

Order No. 11 provokes anger in Missouri to this day. One Missouri writer estimates it forced up to 100,000 people from their homes, but the 1860 census reveals the total population of the counties numbered 44,772. Three years of enlistment, bloodshed and emigration must have greatly reduced this figure, so the total number of refugees is impossible to calculate with precision. But thousands were left with what few possessions they could carry, adrift in a war zone and hounded by a hostile government. Union soldiers and Jayhawkers torched many of the homes and for decades the area was called the“Burnt District.”Order No. 11 did achieve Ewing’s goal—it made the border counties unappealing to bushwhackers. With no civilian population for support, most guerrillas moved operations to the pro-Southern “Little Dixie” counties along the Missouri River in the center of the state.

After Lawrence, Quantrill led his band to winter quarters in Texas. Inactivity soon wore on them, how ever, and Quantrill’s command fragmented. Some felt sickened over Lawrence. Others chafed at Quantrill trying to stop them from boozing it up in town and robbing people. Todd and Anderson each left with their own followers. Anderson’s group attracted some of the toughest fighters in Missouri, including young Frank and Jesse James.

In the spring of 1864, Anderson returned to Missouri with about 50 men disguised in Union uniforms. They plundered the homes of Unionist civilians, cut telegraph wires and fought patrols. In one skirmish they came upon 15 members of the Missouri State Militia and rode at them, guns blazing. They killed a dozen soldiers without suffering a single casualty. Triumphant, they looted the bodies and scalped one of the dead.

Anderson tarried near the Missouri River town of Rocheport, sniping at steamboats until traffic on one of the Midwest’s main waterways came to a halt. More skirmishes with militia followed, and more scalping.

At the home of the Mitchell family, the gang ordered the women to cook them a meal, a common method of foraging for both sides. As the guerrillas relaxed, a group of local men crept up and opened fire. The volley only succeeded in injuring two of the women and a baby. The guerrillas replied with a murderous fire, making the skittish locals beat a hasty retreat. In his rush to escape, one farmer fell off his horse and a guerrilla set upon him with a Bowie knife, cutting off his head and mutilating the body.

During the fight one of the women ran off. Anderson ordered her to stop, and when she didn’t he shot and wounded her. This was too much for even some of his battle-hardened bushwhackers, who criticized him for hurting a woman. Anderson merely shrugged. “Well it has got to come to that before long anyhow,” he said.

The Union command was frantic, as independent bushwhackers clamored to join Bloody Bill.“Having looked the situation over I determined to join the worst devil in the bunch,”guerrilla Jim Cummins remembered,“so I decided it was Anderson for me.”Patrols searched for the bushwhackers,but usually had only brief skirmishes before the guerrillas galloped away. Many couldn’t find Anderson’s fast-moving group at all. On August 28, Captain Joseph Parks of the 4th Missouri State Militia Cavalry set out with 44 men hoping to catch Anderson. As the soldiers headed toward Rocheport,Anderson’s self-proclaimed capital, Parks stopped to interview some farmers.

“Any of Bill Anderson’s men around here?”he asked.

“Captain,your men are no match for Bill Anderson’s boys; take warning, don’t follow them,” said one man.

“Show me the road, I’ll find them,” the captain blustered.

Shortly after this conversation Parks stumbled upon a pair of bushwhackers, wounded one, scared off both and captured their horses. This buoyed his courage.

But Anderson, always careful to have the area well scouted, knew where Parks was and looked for a suitable place to set up an ambush.

He found one directly in Parks’ line of march—an east-west road called Rawling’s Lane branching off from the road to Rocheport. Rawling’s Lane had a heavy rail fence on each side. Anderson ordered his hundred men to enter the lane by fours, leaving a clear trail for Parks to follow. After riding east a short distance he turned north and cut through the woods and farmers’ fields, countermarching to the beginning of the lane. There he hid his men behind a low hill just north of the entrance.

The trap set, he then sent out bait in the form of a dozen bushwhackers under his right-hand man Archie Clement, a dapper little fellow with a penchant for scalping. They rode west until they found Parks and fired on his column. When the Union troops returned fire the guerrillas swiftly withdrew. Parks, thinking he had the advantage, hurried after. Soon the decoys entered Rawling’s Lane with the Union militia right behind. Anderson waited until the rear of the Union column entered the lane and shouted, “Charge ’em, boys!”

The guerrillas pounded around the hill, blazing away with their pistols. Eight of the Union rear guard died almost instantly and the rest fled. The fenced lane corralled the soldiers, making them easier targets and allowing no space to form up. Six more soldiers fell during the chase down the road. That all weren’t killed is a testament to the speed of the Union retreat, or the difficulty of firing a pistol while galloping on horseback. The guerrillas pursued the soldiers five miles to Sulphur Springs, where the militia holed up in an abandoned cabin. There the bluecoats kept up a spirited defense by firing through chinks in the walls.

Captain Parks wasn’t among them. He had galloped north at the first shot and headed for the nearby garrison town of Fayette. On the way he bumped into 200 Union troops on patrol. Parks did an abrupt about face and led the way back to the fight.

Once again, Anderson knew his enemy’s movements and he ordered his men to retire. He had hurt the Yanks at no cost to himself other than six horses killed, and it was time to leave before the tide turned. He did delay long enough to mutilate the bodies on Rawling’s Lane. Some were scalped, others’ throats were cut. One man was scalped and hanged. These injuries imply some were still alive when Anderson’s men found them, a stark reminder of the no quarter policy followed by both sides in the guerrilla war.

Anderson’s band broke into small groups and hid in Missouri’s thick woods until word came that General Sterling Price was leading a Confederate army out of Arkansas with the intention of taking St. Louis. All Missouri bushwhackers were called upon to redouble their efforts. Anderson linked up with George Todd’s band and a small command under the increasingly irrelevant Quantrill, and attacked Fayette on September 24. The 9th Missouri State Militia Cavalry had fortified the brick courthouse and built a log blockhouse on a hill overlooking town. The guerrillas, wearing Union uniforms, managed to enter town unopposed, but as soon as they opened fire, the soldiers hurried into their fortifications. Three attacks on the blockhouse resulted in nothing but a hillside covered with dead bushwhackers, and Anderson and Todd called for a retreat. Quantrill, disgusted at the proceedings, disappeared with his men.

It was one of Anderson’s few tactical blunders, and one he would never repeat.

Although bloodied, the bushwhackers still had plenty of fight left. With traffic on the Missouri River held up, they decided to stop communications along Missouri’s other important east-west corridor, the North Missouri Railroad. On September 27, they rode into the tiny ungarrisoned town of Centralia. They robbed a stagecoach and the local shops, and stopped a train carrying 23 unarmed Union soldiers on furlough. One was taken prisoner to exchange for a captured guerrilla and the rest were lined up and shot, along with a German civilian who happened to be wearing a blue shirt. Frank James discovered more than $13,000 in the mail car, giving him and his brother Jesse a lesson in how to make easy money.

The Centralia massacre is often held up as an example of Bloody Bill’s savagery, but an engagement later that day shows Anderson’s other side—a brilliant tactician. Hunting Anderson were 158 mounted riflemen from the 39th Missouri Infantry under Major A.V.E. Johnston. The Union force arrived in Centralia shortly after Anderson left. As usual, Bloody Bill knew the soldiers were coming and set a trap. He had a small group of bushwhackers ride around the prairie near Centralia where he knew they would be spotted. Johnston, watching from the roof of a hotel, cried, “There they are now!”

A local warned him that while only 80 guerrillas had attacked Centralia, they totaled about 400, the majority being camped at a nearby farm.“They largely outnumber you,” the man said, “and they are much better armed and mounted, having four good revolvers each and splendid horses.”

“They may have the advantage of me in numbers but I will have the advantage of them in arms,” Johnston replied.“My guns are of long range and I can fight them successfully from a distance.”

What the major forgot was that his men carried single-shot Enfields, and the guerrillas were happy to take a volley if it meant they could close with the enemy and bring their revolvers into play. Leaving a detachment in Centralia to restore order, Johnston took about 120 men and followed the guerrillas.

Johnston chased the decoys over a low rise and saw a large field enclosed on three sides by woods. Anderson and about 75 men stood by their horses near the back of the field.What Johnston could not see was that the woods to either side teemed with guerrillas waiting for Anderson’s signal to reveal themselves.

Johnston ordered every fourth man to take the horses and withdraw about a hundred yards. The rest formed a line.

Anderson studied the soldiers for a moment and said, “Boys, when we charge, break through the line and keep straight on for the horses. Keep straight on for the horses!” He looked again at the Union soldiers and laughed. “Not a damned revolver in the crowd!”

Anderson’s plan was simple—rush through the Union line, killing as many as he could before hitting the horse holders while his flanks came out of the woods and cleaned up any survivors.

The guerrillas swung into the saddle and rode up the low rise toward Johnston’s command. The panicky bluecoats, most of whom had only been in service two weeks, fired a volley that went high. Three bushwhackers fell from the saddle, one splashing his brains on Frank James’ boot. A few more were injured, one mortally, but these paltry losses didn’t even slow Bloody Bill’s men down. They descended howling on Johnston’s line, firing as fast as they could. Some soldiers desperately tried to reload, others used their bayonets, still others surrendered. Men died whether their hands were around a gun or raised in the air. Anderson’s men smashed through the line and went after the horse holders as a second wave of guerrillas washed over the remnants. Frank James claimed his brother Jesse traded shots with Johnston and killed him.

Everyone in Johnston’s front line died and most of the horse holders were hunted down, their plow horses and mules no match for the guerrillas’ blooded steeds. Some of Anderson’s men pounded back to Centralia and massacred the rest of the Union column. Of the 158 men under Johnston’s command, fewer than 30 survived. The bodies of the rest were mutilated, some decapitated, and one man’s penis was cut off and shoved into his mouth.

The guerrillas scattered to avoid the usual sweep of patrols that followed any of their big victories. Shortly afterward they met with General Price’s army, which had abandoned its plans to take St. Louis and now marched through Missouri gathering recruits. Price was disgusted at the scalps dangling from Anderson’s bridle but decided he could be useful, and ordered him to destroy the North Missouri Railroad to impede the gathering Union forces.

Instead,Anderson looted the town of Danville, cavalierly leaving the local girls’ school untouched. A few days later in Glasgow, he tortured a wealthy Unionist named Benjamin Lewis, made his neighbors buy his freedom for $5,000 and raped his 12-year-old maid.

As Bloody Bill’s morals disappeared, so did his time. On October 27, while Price retreated south after a disastrous defeat at Westport, Lt. Col. Samuel P. Cox and 150 men of the 33rd and 51st Enrolled Missouri Militia were hunting Anderson. Cox learned the location of Anderson’s camp and sent a detachment to engage him. As the fighting heated up, the soldiers retreated down a narrow lane enclosed by thick woods where Cox had formed his troops. Cox was luring Anderson into a classic bushwhacker trap.

Whether Anderson thought these Yankees would break as easily as Johnston’s command is unknown, but he charged the soldiers without hesitation. A volley unhorsed several guerrillas. Anderson and two others kept going and rode right through the Union line. As he turned for another pass, Anderson was hit by two bullets in the head and toppled out of the saddle, dead.

Bloody he was, to a point that cannot be justified by the bitterness of the times or his personal loss. Others had lost just as much but did not scalp or rape. His reputation for madness also appears accurate, although it was of a focused and clear-headed nature. The engagements at Rawling’s Lane and Centralia reveal a keen tactical mind and a sharp eye for terrain. He disrupted rail and boat traffic at a critical time when Missouri was struggling to resist Price’s invasion, and inflicted great loss of life and property on Union troops and their supporters. While history remembers him as “Bloody Bill,” he should also be remembered as a resourceful and brilliant fighter for the Confederacy.


Sean McLachlan is the author of American Civil War Guerrilla Tactics (Osprey, 2009) and is working on a book about Confederate cavalry raider J.O. Shelby. He is on the Web at

Originally published in the November 2010 issue of America’s Civil War. To subscribe, click here.