‘Bloody Bill’ Anderson and his Missouri Bushwhackers

This entry is part 11 of 12 in the series The Partisan Rangers

Bloody Bill AndersonNo account of the Civil War in Missouri would be complete without an account of the life of ‘Bloody Bill’ Anderson. He actions as a guerrilla and bushwhacker in Kansas and Missouri are legendary.

William T. Anderson was born in Kentucky in 1840 and moved with his family to Missouri as a child. As a teenager he moved with his family across the border to Kansas. It was during this time that the conflict known as ‘Bleeding Kansas’ was taking place and the Andersons were on the pro-slavery side. Anderson became a horse trader in 1860 but soon turned to horse stealing, reselling them as far away as New Mexico.

In late 1861, Anderson traveled south with brother Jim and Judge A.I. Baker, in an apparent attempt to join the Confederate Army. But they soon ran into Union cavalry in Vernon County, Missouri. They fled back to Kansas but one of their number was captured and imprisoned for four months under the suspicion that the group members were Confederate guerrillas.

Anderson’s father was killed by Judge A.I. Baker in a legal dispute in May 1862. Anderson vowed revenge and eventually killed Baker by locking him in the basement of his store and burning the building down. He then fled to Missouri with his brother Jim robbing travelers along the way.

In Missouri, the Andersons soon joined Quantrill’s Raiders early in 1863 having supported themselves by robbing people and stealing horses throughout the latter part of 1862.

Missouri had a large Union presence throughout the Civil War, but also many civilians whose sympathies lay with the Confederacy. From July 1861 until the end of the war, the state suffered up to 25,000 deaths from guerrilla warfare, more than any other state. Confederate General Sterling Price failed to gain control of Missouri in his 1861 offensive and retreated into Arkansas, leaving only the guerrillas to challenge Union dominance.

The most active guerrilla band was led by William Quantrill who operated in the Jackson County area. Anderson participated in a raid near Council Grove, Kansas with Quantrill’s Raiders. After robbing a store 15 miles from the town they were pursued by the United States Marshal and a large posse. They split into smaller groups and made their way back into Missouri and safety.

This early raid might have given Quantrill and his lieutenants the idea of raids deeper into Kansas. The border was poorly defended and the raiders could travel deep into the state before Union defenders were alerted to their presence.

In early summer 1863, Anderson was made a lieutenant, serving in a unit led by George M. Todd. In June and July, Anderson took part in several raids that killed Union soldiers, in Westport, Kansas and Lafayette County, Missouri. The first reference to Anderson in Official Records of the American Civil War concerns his activities at this time, describing him as the captain who commanded 30–40 men guerrillas. 

By late July, Anderson led groups of guerrillas on raids, and was often pursued by Union volunteer cavalry. Anderson was under Quantrill’s command, but independently organized some attacks.

Quantrill’s Raiders had a support network in Missouri, that provided them with numerous hiding places. Anderson’s sisters aided the guerrillas by gathering information inside Union territory. In August 1863, however, Union General Thomas Ewing, Jr., attempted to thwart the guerrillas by arresting their female relatives, and Anderson’s sisters were confined in a three-story building on Grand Avenue in Kansas City with a number of other girls. While they were confined, the building collapsed, killing one of Anderson’s sisters. 

In the aftermath, rumors that the building had been intentionally sabotaged by Union soldiers spread quickly. Anderson was convinced that it had been a deliberate act. Biographer Larry Wood wrote that Anderson’s motivation shifted after the death of his sister, arguing that killing then became his focus—and an enjoyable act. 

The collapse of the Grand Avenue Jail became the impetus for Quantrill’s raid on the town of Lawrence, Kansas. On August 21, 1863 Quantrill’s Raiders attacked the town and began a slaughter that would become known as the Lawrence Massacre.

The raiders immediately killed a number of Union Army recruits. They proceeded to pillage and burn many buildings, killing almost every man they found, but taking care not to shoot women. Anderson was reported to have personally killed 14 people. Although some men begged him to spare them, he persisted, but he relented when a woman pleaded with him not to torch her house. 

The group under Anderson’s command, notably including Archie Clement and Frank James, killed more than any of the other group. They left town at 9 a.m., after a company of Union soldiers approached the town. The raiding party was pursued by Union forces, but eventually managed to break contact with the soldiers and scatter into the Missouri woods. 

In all, Quantrill’s men killed 182 men and boys, many in front of their families. They burned some 185 buildings in Lawrence. The Lawrence Massacre was one of the bloodiest events in the whole history of Kansas. The Plymouth Congregational Church in Lawrence survived the attack, but a number of its members were killed and records destroyed.

General Thomas Ewing reacted to the massacre by issuing General Order No. 11. It called for the forced evacuation that evicted almost 20,000 people from four Missouri counties and burned many of their homes. The four Missouri counties became a devastated “no man’s land,” with only charred chimneys and burnt stubble showing where homes and thriving communities had once stood, earning the sobriquet “The Burnt District.”

After the Lawrence Massacre, Quantrill’s Raiders decided to move further south into Texas but before they left the area they attacked Fort Blair, Kansas. Many of the raiders were wearing Union uniforms that they had pillaged from warehouses in Lawrence.

Fort Blair was garrisoned by 90 Union soldiers who were able to hold off the raiders. But during the attack a larger group of Union soldiers approached the fort. Thinking that the raiders were their fellow Unionists, they were ambushed by Quantrill’s men, losing 100 of their number.

 Anderson and his men were in the rear of the charge, but gathered a large amount of plunder from the dead soldiers, irritating some guerrillas from the front line of the charge. Not satisfied with the number killed, Anderson and Todd wished to attack the fort again, but Quantrill considered another attack too risky. He angered Anderson by ordering his forces to withdraw.

While in Texas, Anderson married a woman who worked in a saloon in Sherman, Texas. Anderson separated his men from Quantrill’s larger group but eventually the tension between the two men eased. Most of Quantrill’s men eventually joined the regular Confederate Army but he retained 84 men and reunited with Anderson.

After one of Anderson’s men was shot to death by Quantrill for stealing, Anderson reported him to General Samuel Cooper who had Quantrill arrested. Quantrill soon escaped and was pursued by Anderson who was unable to recapture him. Anderson was commissioned a captain and after several months returned to Missouri.

Anderson led his band on numerous raids both in Missouri and into Kansas. As his raids increased so too did his group of guerrillas. It was during this time that Jesse James joined his brother Frank as a member of Anderson’s command. General Clinton B. Fisk ordered his men to find and kill Anderson, but they were thwarted by Anderson’s support network and his forces’ superior training and arms.

Throughout most of 1864 and into 1865, Anderson and his raiders conducted a reign of terror against Union targets in Missouri. The Union authorities sent a force of 100 well-trained soldiers and 650 militia after the guerrillas. The two sides had a number of engagements. By August 1864 Anderson’s men were regularly scalping the men that they killed.

On September 27, 1864, Anderson led his 75-man band into Centralia, Kansas where they looted the town, a stagecoach and a train. They slaughtered captured Union soldiers, executing them in cold blood. The guerrillas set the passenger train on fire and derailed an approaching freight train. Anderson’s band then rode back to their camp, taking a large amount of looted goods.

They were pursued by the 39th Missouri Volunteer Infantry but after a pitched battle routed them. Anderson’s men killed 125 soldiers in the battle and 22 from the train in one of the most decisive guerrilla victories of the Civil War. It was Anderson’s greatest victory, surpassing Lawrence and Baxter Springs in brutality and the number of casualties.

In a response to the Centralia raid, Union troops began a relentless pursuit of Anderson’s raiders. Eventually they evaded their pursuers and William T. Anderson in deatharrived in Boonville, Missouri where he met with Confederate General Sterling Price who ordered him to travel to the Missouri railroad and disrupt rail traffic. Anderson ignored Price’s orders and continued to loot and pillage Union strongholds.

The Union Army assigned Lieutenant Colonel Samuel P. Cox to kill Anderson, providing him with a group of experienced soldiers. Soon after
Anderson left Glasgow, a local woman saw him and told Cox of his presence. 

On October 26, 1864, he pursued Anderson’s group with 150 men and engaged them in battle. Anderson and his men charged the Union forces, killing five or six of them, but turned back under heavy fire. Only Anderson and one other man continued to charge after the others retreated. Anderson was hit by a bullet behind an ear, likely killing him instantly. Four other guerrillas were killed in the attack. The victory made a hero of Cox and led to his promotion.

Union soldiers identified Anderson by a letter found in his pocket and paraded his body through the streets of Richmond, Missouri. The corpse was photographed and displayed at a local courthouse for public viewing, along with Anderson’s possessions. Union soldiers claimed that Anderson was found with a string that had 53 knots, symbolizing each person he had killed.

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