Bloody Bill Anderson was a prominent Confederate guerrilla chieftain in the conflict that engulfed Missouri during the war. Along with the likes of Quantrill, the Youngers, Frank James, Anderson’s brand of warfare involved ambush, rape, espionage, arson, infighting, scalping, beheading, torture, theft, ethnic vendetta, and even outright massacre. The guerrilla war in Missouri was a distinct conflict, separate from the rest of the war and highly personalized but in trying to understand Anderson, readers should beware not to instinctively assume his environment as a moral justification for his behavior. Starting a career as a horse thief before the outbreak of the war, by 1862 Anderson had formed a band of guerrillas and began terrorizing civilians along the Kansas-Missouri border. In 1863 Anderson and his bushwhackers joined William Quantrill’s band. He was with Quantrill when Quantrill’s force attacked Lawrence Kansas killing between 150 and 200 men and boys in the Lawrence Massacre. In the spring of 1864 Anderson and his most loyal followers left Quantrill’s band and set up his own guerrilla company. Throughout the summer of 1864 Anderson’s band ambushed, raided and scalped its way across central Missouri. They killed soldiers and civilians, burnt railway property, stole money and military supplies. The pinnacle of Bill Anderson’s career as a guerrilla commander unfolded the next day in Centralia, Missouri. On the morning of September 27, 1864, Anderson and a sizable group of bushwhackers (perhaps 60-70) helped themselves to local liquor, looted the town, and robbed stagecoach passengers of their money and jewelry. Soon after, they overtook a passenger train destined for the rail depot in Centralia. Aboard the train, which belonged to the North Missouri Railroad, Anderson and company discovered a group of approximately 20 to 30 Union soldiers. The outnumbered federals were disarmed and removed from the train. Anderson then had nearly all of them executed on the spot. Civilian passengers were subsequently relieved of their valuables and allowed to exit the train which was then set ablaze. Later that afternoon, Anderson and a much larger assemblage of guerrillas (estimates vary between 300 and 700) caught Major A. V. E. Johnston and his 39th Missouri Infantry (Mounted) in a lethal trap. After the morning’s slaughter, it did not take much for a small detachment of guerrillas to lure Johnston and his mounted infantry into an open field on the outskirts of Centralia. The field was surrounded by dense foliage on three sides; deep canals (deep enough to conceal men and horses) hid the great mass of Anderson’s command. As Johnston and his men rode to the middle of the field, Anderson’s force revealed its true size. Wielding revolvers on horseback, the guerrillas charged Johnston’s men from three directions. The Union position was quickly swarmed, overrun, and the second massacre of the day at Centralia ensued. Multiple reports indicate that Anderson’s guerrillas took scalps and mutilated the bodies of several slain Union soldiers. Major Johnston and approximately 150 of his men died in the battle. On October 26, 1864 in a mounted skirmish with Union infantry near Albany, Ray County, Missouri Anderson was shot twice in the head and died. Anderson’s body was triumphantly paraded by Union soldiers through the streets of nearby Richmond, Missouri. Still clad in his ornate guerrilla shirt and made to clutch a revolver, Anderson’s corpse was propped into position for a now famous posthumous photograph. 150 years after his death, Anderson has remained a controversial figure in both academic history and social memory. Critics of Anderson’s guerrilla career frequently depict him as having been a glorified cutthroat, delusional, paranoid, and even as a full-fledged sociopath. Others point to the dehumanizing effects of guerrilla warfare as an explanation for Anderson’s wartime exploits; they posit that he was not the only guerrilla gradually transformed by his Civil War experience and should therefore not be viewed as exceptional or uniquely deranged.
William T. "Bloody Bill" Anderson
Photograph Courtesy of: The State Historical Society of Missouri Photograph Collection
“Name’s Anderson. Bloody Bill’s what they call me.” For myriad Americans this laconic introduction, plucked from the opening moments of The Outlaw Josey Wales (1976), has constituted the first and only encounter with the figure Civil War historians and western enthusiasts know well as William “Bloody Bill” Anderson. Unlike the more familiar of his Confederate contemporaries - Virginians and Lost Cause mainstays like Robert E. Lee and Thomas “Stonewall” Jackson - Anderson earned his “Bloody Bill” moniker on a different sort of battlefield. As a prominent guerrilla chieftain, he was both a major part and product of the notorious guerrilla conflict that engulfed Missouri during the Civil War.
Bill Anderson and his irregular comrades - bushwhackers such as William Clarke Quantrill, George M. Todd, Clifton Holtzclaw, Dave Poole, Cole Younger, Charles Fletcher Taylor, Archie Clement, William H. Gregg, and Frank James, along with numerous others—operated predominantly on what is typically, though perhaps misleadingly, designated as the home front in Civil War Missouri. Under moonlit skies, down Arcadian roads, and in backcountry fields they hunted Union militiamen, federal soldiers, and alleged Union sympathizers with little regard for more formal standards of wartime conduct. Their brand of guerrilla warfare involved ambush, rape, espionage, arson, infighting, scalping, beheading, torture, theft, ethnic vendetta, and even outright massacre.
Thus, while assessing the relatively short life and blood-soaked career of William T. Anderson, it is essential that his story be read with two fundamental precepts in mind. The first: that guerrilla violence in Missouri was a highly localized and intensely personalized experience. In more ways than not, the guerrilla war equaled a distinct conflict raging within the folds of the Civil War itself -part of the whole, but very much detached from its core. In other words, readers should be aware that Anderson’s wartime environment was radically different than the familiar portraits of long-bearded generals and macro-scale war offered by Ken Burns, Shelby Foote, or popular films like Glory (1989) and Gettysburg (1993). The second: that in the process of trying to understand Anderson, readers should beware not to instinctively assume his environment as a moral justification for his behavior.
On December 1, 1836, William C. Anderson and Martha Jane Thomasson were married in Hopkins County, Kentucky. Three years later in 1839, they welcomed the addition of a son, William T. Anderson, to their household. William - better-known as Bill - was the oldest of five children who would live past childhood. His brothers Ellis and Jim were born in 1841 and 1844, respectively, while sisters Mary Ellen, Josephine, and Martha Jane were born in 1845, 1848, and 1853, respectively. William and Martha Anderson were rumored to have had another child, Charles, while later living in Kansas, who died as an infant.
Early in Bill Anderson’s childhood the family relocated to Missouri. Throughout the late-1830s and early-1840s, William C. Anderson worked as a hatter with his father-in-law, William Thomasson. Their business was not overly successful and financial issues prompted a move to Iowa. By the late-1840s, the Anderson family had returned to Randolph County, Missouri. In 1850, William C. Anderson left his family in Missouri to try his hand as a gold prospector in California. With little to show for his effort, he again returned to Missouri in 1854 and, sometime around 1857, moved his family to Kansas where they lived on a farm valued at approximately $1,000. Sometime around 1859 or 1860, Bill and Ellis Anderson both took up work as hands on a nearby ranch but, following a violent encounter in which he allegedly killed a local Indian over a bottle of whiskey, Ellis Anderson fled to Iowa to avoid prosecution and was later killed there.
Around the time his son Ellis cut out for Iowa, William C. Anderson had taken to selling liquor and other goods in a small store to make ends meet. By 1860, Bill Anderson had worked as an assistant on a wagon train hauling cargo to New Mexico. Apparently the contents of the train - and even the wagons and animals themselves - disappeared; this episode likely marked the beginning of Bill Anderson’s career as a horse thief. On June 28, 1860, Bill Anderson’s mother, Martha, was struck and killed by lightning at the age of 35 or 36 in the yard of the family’s home.
With tension along the Kansas-Missouri border at an all-time high and the nation on the brink of Civil War, Bill Anderson figured that there was substantial money to be made trafficking animals. He and his brother Jim formed a small gang along with Arthur Baker, the judge, justice of the peace, and postmaster in Council Grove, Kansas. In 1861 the group was attacked by a Union patrol and Baker was captured; he was imprisoned at Fort Scott in Kansas. Baker was paroled on March 24, 1862, and with his wife recently dead, kindled a romantic relationship with Mary Ellen Anderson. After an extended courtship, Baker left her for Annis Segur, a young school mistress in Council Grove. This turn of events, coupled with a warrant put out for Bill Anderson by Baker, enraged William C. Anderson. Drunk and totting a shotgun, William Sr. confronted Baker at his home (on or around the day of his wedding to Segur) and was killed by a shotgun blast to the chest. To preempt any potential retaliation from Anderson’s two sons, Baker had Bill Anderson arrested for horse theft. Due to a legal technicality, however, Anderson was released and moved what was left of the family back to Missouri. Before leaving Kansas, Bill and Jim Anderson paid Arthur Baker a final visit. The brothers, along with Lee Griffin and another man, surprised Baker at his home after dark, shot him in the leg, and locked him - along with his new brother-in-law George Segur - in the cellar. The Anderson brothers then set the Baker home on fire. Segur was found alive but died of his burns the following day and Baker was found dead with a bullet in his head; he had committed suicide rather than die slowly in the flames.
Once settled in Missouri, Bill and Jim Anderson formed a group of guerrillas and began terrorizing civilians along the Kansas-Missouri border. Much to the chagrin of other pro-Confederate guerrilla bands, the Andersons apparently neglected to distinguish between Confederate and Union sympathizers. Their lack of attention to this detail drew the ire of William C. Quantrill, then the most prominent guerrilla chieftain in Missouri. According to ex-guerrilla William H. Gregg, Quantrill took away the Anderson’s horses and informed them that further harassment of Confederate sympathizers would result in their immediate executions. This first encounter between William C. Quantrill and Bill Anderson marked the beginning of a grudge that would smolder until one of them was dead.
Later in 1863, Bill Anderson and his small group of bushwhackers begrudgingly joined forces with Quantrill and participated in raids throughout the Kansas-Missouri area. Because guerrillas depended upon local support - the majority of which came from women - for information, food, clothing, and other supplies, several women related to members of Quantrill’s command had been captured and imprisoned in Kansas City, Missouri, by Union army officials. On August 13, 1863, the old building that served as a prison for the women collapsed. All three of the Anderson sisters had been among the inmates. Mary escaped with minor injuries. Martha suffered a pair of broken legs. Josephine, however, did not survive the disaster; she was crushed to death in the rubble.
On August 21, 1863, William C. Quantrill led the assault of his entire command, Anderson included, on Lawrence, Kansas. In what came to be known as the Lawrence Massacre, Quantrill and his men pillaged and burned large swaths of the town in the process of killing between 150 and 200 men and boys. Though Brigadier General Thomas Ewing, Jr., had, for some months, been concocting a plan to strip guerrillas in Missouri of their civilian support network, the atrocities committed at Lawrence finally prompted him to issue his General Order #11. Released on August 25, 1863, the order stipulated that all residents of Jackson, Cass, and Bates counties not living near enough to a specified military outpost had to evacuate their homesteads by September 9, 1863. Those who refused to move and attempt to establish loyalty to the United States by that date could be forcibly removed and subjected to military punishment.
As the summer of 1863 turned to fall, William C. Quantrill and his men decided to take up winter quarters in Texas. On their way, though, they stopped long enough to engage a large force of Union troops at Baxter Springs, Kansas. On October 6, 1863, Brigadier General James Gilpatrick Blunt and a force of nearly 100 mounted federal soldiers were making their way from Fort Scott to Baxter Springs when another group of mounted men in blue emerged from a tree line in front of them. Blunt initially believed the group was a welcoming party; he became more suspicious as the group moved into an attack formation. Blunt ordered his men into a line as between 250 and 300 bushwhackers - clad in stolen Union uniforms - approached and began firing at them. As some of Blunt’s men broke and ran from the attack, Quantrill and most of his command charged and scattered Blunt’s line. A chase ensued and, though Blunt himself escaped on horseback, between 70 and 100 of his men did not. Despite their successful attack, tempers flared among the guerrillas after the fighting was all over. Several men under Anderson’s command had stopped to gather loot from the abandoned Union column rather than aiding in the charge.
While wintering in Sherman, Texas, Bill Anderson married Bush Smith on March 3, 1864. Controversy surrounded the marriage from the beginning. By some accounts, Quantrill had urged Anderson to postpone the wedding until after the war; according to other guerrillas, Smith had earned herself a seedy reputation by working as a prostitute prior to meeting Anderson. Either way, Quantrill’s command was on the verge of collapse. Quantrill accused Anderson and his men of theft which prompted Anderson to accuse Quantrill and his men of murder. Local authorities sent Anderson out to arrest Quantrill but the guerrilla leader could not be located. George M. Todd, Quantrill’s top lieutenant, ultimately seized leadership of the core command from Quantrill. Anderson and his most loyal followers, between 45 and 65 men, simply did not return to Missouri with the rest of the group. While in Texas, Confederate Major General Sterling M. Price made Bill Anderson the Captain of his own guerrilla company.
Throughout the summer of 1864, Anderson and his guerrilla band - now back from Texas - ambushed, raided, and scalped its way across central Missouri. On June 11, they ambushed a patrol from the 1st Missouri Cavalry and killed eleven. On June 13, they killed another eight men and shot fifteen mules during an assault against a wagon train escort. All the while, they cut telegraph lines, held up stages, and impeded the flow of mail between Union outposts. During the first three weeks of July, Union forces headed up by Brigadier General Egbert Benson Brown sent out more than 200 separate patrols to track down bushwhackers, engaged them more than twenty-five times, killed more than 100 guerrillas, and lost more than forty men in the process. On July 11, yet again disguised in stolen Union uniforms, Anderson and his men slaughtered nine Union sympathizers in Carroll County. A few days later on July 15, they stole $45,000 from Anderson’s one-time hometown of Huntsville, Missouri. On July 23, the guerrillas hit the North Missouri Railroad at Renick and Allen, both towns in Randolph County, Missouri. They burned the rail depot in Renick while Union militia drove them out of Allen before it could be torched. The next day, July 24, Anderson’s men killed two Illinois cavalrymen and left a note pinned to one of them that read: “You come to hunt bush whackers. Now you are skelpt. Clemyent Skept you. Wm. Anderson.” From Renick, Anderson’s band fought and burned its way through Lakenan and Shelbina.
In August 1864, Confederate General Sterling Price began employing guerrilla units as diversions for his ill-fated invasion of Missouri. On August 5, Anderson’s command robbed several Unionist civilians in Clay County. On August 20, Anderson joined forces with guerrilla chief Clifton Holtzclaw and assaulted a patrol from the 4th Missouri Cavalry. In the wake of the attack, Union losses stood at seven dead, three wounded, and three missing. Of the seven killed, four had been scalped, one of the scalped men had also been hanged, and three of the soldiers’ throats had been cut. In mid-September, guerrillas under the command of Anderson, John Thrailkill, and George M. Todd attacked a wagon train and killed fifteen federal soldiers. Three of the deceased were black; the guerrillas made a point to burn their bodies separately and made off with thousands of rounds of ammunition.
About a week later, Quantrill, Anderson, Thrailkill and Todd brought their commands together to plan a joint maneuver. Over the objection of Quantrill, the rest of the group, led mostly by a stubborn Anderson, determined to take the fortified Union force in Fayette, Missouri. Their initial attack, which involved approaching the town in stolen federal uniforms, was unsuccessful. After several failed charges and multiple guerrillas downed by the town’s well-entrenched Union defenders, the attack was abandoned. Because of his insistence on targeting Fayette, the botched assault likely represents “Bloody Bill” Anderson’s greatest failure as a guerrilla commander. Following the Fayette debacle, Quantrill, Todd, and Thrailkill each parted ways with Anderson. Leading his men away from Fayette, Todd flirted with the idea of seizing Huntsville, Missouri, but a fortified Union position and fresh memories of a similar situation in Fayette persuaded him otherwise. On September 26, 1864, Anderson got word that Todd and Thrailkill were in Boone County and joined them in camp. In hindsight, this seemingly random gathering of so many guerrillas meant the stage was set for unthinkable bloodshed in nearby Centralia.
The pinnacle of Bill Anderson’s career as a guerrilla commander unfolded the next day in Centralia, Missouri. On the morning of September 27, 1864, Anderson and a sizable group of bushwhackers (perhaps 60-70) helped themselves to local liquor, looted the town, and robbed stagecoach passengers of their money and jewelry. Soon after, they overtook a passenger train destined for the rail depot in Centralia. Aboard the train, which belonged to the North Missouri Railroad, Anderson and company discovered a group of approximately 20 to 30 Union soldiers. The outnumbered federals were disarmed and removed from the train. Anderson then had nearly all of them executed on the spot. Civilian passengers were subsequently relieved of their valuables and allowed to exit the train which was then set ablaze.
Later that afternoon, Anderson and a much larger assemblage of guerrillas (estimates vary between 300 and 700) caught Major A. V. E. Johnston and his 39th Missouri Infantry (Mounted) in a lethal trap. After the morning’s slaughter, it did not take much for a small detachment of guerrillas to lure Johnston and his mounted infantry into an open field on the outskirts of Centralia. The field was surrounded by dense foliage on three sides; deep canals (deep enough to conceal men and horses) hid the great mass of Anderson’s command. As Johnston and his men rode to the middle of the field, Anderson’s force revealed its true size. Wielding revolvers on horseback, the guerrillas charged Johnston’s men from three directions. For reasons unknown, the 39th Missouri had dismounted to form a defensive line. The Union position was quickly swarmed, overrun, and the second massacre of the day at Centralia ensued. Multiple reports indicate that Anderson’s guerrillas took scalps and mutilated the bodies of several slain Union soldiers. Major Johnston and approximately 150 of his men died in the battle. Today, placards mark both the spot of the train massacre and the ambush in which Johnston’s command was obliterated.
In the aftermath of the Centralia massacres, First Lieutenant Thomas B. Wright of Company B, 5th Missouri State Cavalry, filed a report on September 30, 1864, from Waynesville, Missouri, in which he claimed to have attacked a large squad of guerrillas and killed one whom local citizens thought was Bill Anderson. Unfortunately for Wright, his declaration was premature - “Bloody Bill” was still loose somewhere in Central Missouri. On October 14, 1864, Anderson and his men were in Glasgow, Missouri, soon after General Joseph Orville Shelby captured the town in Howard County. While in Glasgow, Anderson visited the home of Benjamin Lewis. Lewis was reportedly the wealthiest Unionist in the town and had freed his slaves sometime during the war. Anderson and his associates savagely beat Lewis and robbed him of $5,000. According to historians Larry Wood, Albert Castel, and Thomas Goodrich, Anderson became infuriated at the thought of Lewis having freed his slaves and raped a black twelve-year-old house servant in retaliation. Lewis died the following day from injuries inflicted by Anderson.
Almost two weeks later, Anderson and his guerrilla band engaged Lieutenant Colonel Samuel P. Cox and his 33rd Infantry (Enrolled Missouri Militia) in a mounted skirmish near Albany, in Ray County, Missouri. Anderson had no idea at the time, but Cox and a specially-trained group of Union soldiers had been assigned the task of hunting down and eliminating the guerrilla chief. According to Cox’s rendition of the encounter, Anderson was in command of nearly 300 guerrillas. Union scouts made contact with guerrilla pickets on the morning of October 26, 1864, and a fight ensued through the town of Albany. A portion of Cox’s cavalry dismounted and took cover in the town while infantrymen relentlessly pursued the bushwhackers into nearby woods. Following a failed charge against the fortified Union position, Anderson and one other guerrilla - whom Cox believed was Captain John Rains, son of Confederate general James S. Rains - charged headlong into the Union line. Miraculously, the reckless duo actually managed to break through the line; seconds later, though, Anderson fell dead with two minié balls lodged in his head. Rains safely made it back to the rest of the guerrilla band which then scattered as Union cavalry thundered down on it.
Cox noted that Anderson’s private correspondence and orders from General Sterling Price were used to identify him beyond doubt. Reports also indicated that Anderson had been carrying a cord of silk marked by several knots - each knot, it was presumed, represented a dead Unionist. Anderson’s horse as well as his watch and six revolvers were distributed as trophies to several officers. Meanwhile, $300 in gold and $150 in treasury notes lifted from Anderson’s pockets was to be donated to the wounded men and widowed wives of Cox’s command. Anderson’s body was triumphantly paraded by Union soldiers through the streets of nearby Richmond, Missouri. Still clad in his ornate guerrilla shirt and made to clutch a revolver, Anderson’s corpse was propped into position for a now famous posthumous photograph. Some historical accounts note that Union soldiers cut off one of Anderson’s fingers in order to retrieve a ring before burying him. In any event, the soldiers buried Anderson in a field on the outskirts of Richmond. In 1908, ex-bushwhacker Cole Younger, by then released from prison in Minnesota, had Anderson’s body reburied in Richmond’s Pioneer Cemetery (where it remains today).
Following Anderson’s demise his guerrilla band was briefly led by Archie Clement. Standing approximately five feet tall and weighing less than 140 pounds, “Little Arch” Clement was known for scalping and mutilating the bodies of his enemies. Many of Anderson’s men rejoined William C. Quantrill (who was killed in Kentucky in 1865) or simply returned to their homes as the Confederacy gradually disintegrated. For his part, Clement never surrendered; he was killed in a gunfight with pro-Union forces and law enforcement in 1866.
Bill Anderson’s brother, Jim, managed to survive the war. In 1866, the governor of Missouri, Thomas C. Fletcher, dabbled with the idea of having Jim Anderson assassinated for the good of the state. Anderson relocated to Texas before the military could capture or execute him. Shortly thereafter, he helped bushwhacker-turned-bandit Jesse James murder former-guerrilla Ike Flannery to steal his inheritance. In retaliation, George H. Shepard (who also rode under Quantrill and happened to be Flannery’s uncle) caught up with Jim Anderson in 1867 and killed him; Shepard slit Anderson’s throat in front of the state capital building in Austin, Texas.
Despite his wartime celebrity, representations of Anderson in popular culture have been relatively few and far between. Anderson’s cameo in The Outlaw Josey Wales (1976), starring Clint Eastwood, Sondra Locke, and John Vernon is unquestionable his most noteworthy appearance. It is commonly thought by fans of the film that Asa Earl Carter (alias Forrest Carter) - novelist, white supremacist, and former George Wallace speechwriter - modeled the fictional character of Josey Wales on Bill Anderson. In the pro-Confederate versions of their sagas, Anderson and Wales both take to the warpath in response to atrocities committed by pro-Union forces against their families. Upon closer inspection, however, it is much more probable that Carter actually based Wales on another true-life bushwhacker named William; that is, William “Wild Bill” Wilson of Phelps County, Missouri.
150 years after his death, Anderson has remained a controversial figure in both academic history and social memory. Critics of Anderson’s guerrilla career frequently depict him as having been a glorified cutthroat, delusional, paranoid, and even as a full-fledged sociopath. Others point to the dehumanizing effects of guerrilla warfare as an explanation for Anderson’s wartime exploits; they posit that he was not the only guerrilla gradually transformed by his Civil War experience and should therefore not be viewed as exceptional or uniquely deranged. More sympathetic observers of Anderson generally point to the Kansas City prison collapse in 1863 as the beginning of a terrible blood-feud with the Union Army and as a legitimate explanation for his subsequent behavior.
In his 1877 narrative of the guerrilla war in Missouri, Noted Guerrillas, Or, The Warfare of the Border, famed newspaperman John Newman Edwards proclaimed that Anderson had “gathered about him a band of centaurs” and “rode at a gallop into terrible notoriety.” Concerning Anderson’s infamy, it looks as though Edwards was quite correct. Even so, it seems safe to assume that the jury, especially in Missouri’s “Little Dixie” region, will remain split over Anderson’s legacy - as it has been since 1864.
Born: 1839, Hopkins County, Kentucky
Died: October 26, 1864, Ray County, Missouri
Buried: Pioneer Cemetery (Richmond, Missouri)
Father: William C. Anderson
Mother: Martha J. Thomasson
Milestones: Lieutenant of Missouri Guerrillas (Under Todd) | Captain of Missouri Guerrillas
Bert E. Castel & Thomas Goodrich, Bloody Bill Anderson: The Short, Savage Life of a Civil War Guerrilla. Mechanicsburg, PA: Stackpole Books, 1998.
Joseph M. Beilein, Jr., The Guerrilla Shirt: A Labor of Love and the Style of Rebellion in Civil War Missouri, Civil War History 58, No. 2 (June 2012).
Donald R. Hale, They Called Him Bloody Bill. Clinton, MO: The Printery, 1975.
Matthew C. Hulbert, "Constructing Guerrilla Memory: John Newman Edwards and Missouri's Irregular Lost Cause," The Journal of the Civil War Era 2, No. 1 (March 2012).
Larry Wood, The Civil War Story of Bloody Bill Anderson. Austin, TX: Eakin Press, 2003.
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