William T . Anderson William T . Anderson ( 1840 – October 26 , 1864 ) , better known as Bloody Bill , was one of the deadliest and most brutal pro - Confederate guerrilla leaders in the American Civil War . Anderson led a band that targeted Union loyalists and Federal soldiers in Missouri and Kansas . Raised by a family of Southerners in Kansas , Anderson began supporting himself by stealing and selling horses in 1862 . After his father was killed by a Union - loyalist judge , Anderson fled Kansas for Missouri . There , he robbed travelers and killed several Union soldier s . In early 1863 , Anderson joined Quantrill ' s Raiders , a pro - Confederate group of guerrillas that operated in Missouri . He became skilled at guerrilla warfare , earning the trust of the group ' s leaders , William Quantrill and George M . Todd . Anderson ' s acts as a guerrilla led the Union to imprison his sisters ; after one of them died in custody , Anderson devoted himself to revenge . He took a leading role in the Lawrence Massacre , and later participated in the Battle of Fort Blair . In late 1863 , while Quantrill ' s Raiders spent the winter in Texas , animosity developed between Anderson and Quantrill . Anderson , perhaps falsely , implicated Quantrill in a murder , leading to the latter ' s arrest by Confederate authorities . Anderson subsequently returned to Missouri as the leader of a group of raiders and became the most feared guerrilla in the state , killing and robbing dozens of Union soldiers and civilian sympathizers throughout central Missouri . Although Union supporters viewed him as incorrigibly evil , Confederate sympathizers in Missouri saw his actions as justified , possibly owing to their mistreatment by Union forces . In September 1864 , he led a raid on Centralia , Missouri . Unexpectedly , they were able to capture a passenger train , the first time Confederate guerrillas had done so . In what became known as the Centralia Massacre , possibly the war ' s deadliest and most brutal guerrilla action , his men killed 24 Union soldiers on the train and set an ambush later that day that killed more than 100 Union militiamen . A month later , Anderson was killed in battle . Historians have made disparate appraisals of Anderson : some see him as a sadistic , psychopathic killer , but for others , his actions can not be separated from the general lawlessness of the time . Early life . William T . Anderson was born in 1840 in Hopkins County , Kentucky , to William C . and Martha Anderson . His siblings were Jim , Ellis , Mary Ellen , Josephine and Janie . His schoolmates recalled him as a well - behaved , reserved child . During his childhood , Anderson ' s family moved to Huntsville , Missouri where his father found employment on a farm and the family became well respected . In 1857 , the family relocated to Kansas , traveling southwest on the Santa Fe Trail and settling east of Council Grove , Kansas . The Anderson family supported slavery , although they did not own slaves ; however , their move to Kansas was likely for economic rather than political reasons . At that time , there was significant debate about slavery in Kansas , and many residents of the northern United States had moved there to ensure that it would not become a slave state . Animosity soon developed between these immigrants and Confederate sympathizers , but there was little unrest in the Council Grove area . After settling near Council Grove , the family became friends with A . I . Baker , a local judge who was a Confederate sympathizer . By 1860 , William T . Anderson was a joint owner of a property that was worth $ 500 and his family had a net worth of around $ 1 , 000 . On June 28 , 1860 , Martha Anderson died after being struck by lightning . In the late 1850s , Ellis Anderson fled to Iowa after killing an Indian . Around the same time , William T . Anderson fatally shot a member of the Kaw tribe outside of Council Grove ; he related that the man had tried to rob him . He joined the freight shipping operation that his father worked for and was given a position known as " second boss " for a wagon trip to New Mexico . The trip was not successful : he returned to Missouri without the shipment , and stated that his horses had disappeared with the cargo . After he returned to Council Grove , he began horse trading , taking horses from towns in Kansas , transporting them to Missouri , and returning with more horses . Horse trading and outlawry . After the Civil War began in 1861 , the demand for horses increased , and Anderson transitioned from trading horses to stealing horses , reselling them as far away as New Mexico . He worked with his brother Jim , their friend Lee Griffith , and several accomplices strung along the Santa Fe Trail . In late 1861 , Anderson traveled south with brother Jim and Judge Baker , in an apparent attempt to join the Confederate Army . Anderson had stated to a neighbor that he sought to fight for financial reasons , rather than loyalty to the Confederacy . However , the group was attacked by the Union ' s 6th Regiment Kansas Volunteer Cavalry in Vernon County , Missouri ; the cavalry likely assumed they were Confederate guerrillas . The Anderson brothers escaped , but Baker was captured and spent four months in prison before returning to Kansas , professing loyalty to the Union . One way that he sought to prove his loyalty to the Union was by severing his ties with Anderson ' s sister Mary , his former lover . Upon his return to Kansas , Anderson continued horse trafficking , but ranchers in the area soon became aware of his operations . In May 1862 , Baker issued an arrest warrant for Griffith , whom Anderson helped hide . Some local citizens suspected that the Anderson family was assisting Griffith and traveled to their house to confront William C . Anderson . After hearing their accusations against his sons , he was incensed — he found Baker ' s involvement particularly infuriating . The next day , he traveled to the Council Grove courthouse with a gun , intending to force Baker to withdraw the warrant . As he entered the building , he was restrained by a constable and fatally shot by Baker . William Anderson buried his father , and was subsequently arrested for assisting Griffith . However , he was quickly released owing to a problem with the warrant , and fled to Agnes City , fearing that he would be lynched . There he met Baker , who temporarily placated him by providing a lawyer . Anderson remained in Agnes City until he learned that Baker would not be charged , as the judge ' s claim of self - defense had been accepted by legal authorities . Anderson was outraged and went to Missouri with his siblings . William and Jim Anderson then traveled southwest of Kansas City , robbing travelers to support themselves . On July 2 , 1862 , William and Jim Anderson returned to Council Grove and sent an accomplice to Baker ' s house claiming to be a traveler seeking supplies . Baker and his brother - in - law brought the man to a store , where they were ambushed by the Anderson brothers . After a brief gunfight , Baker and his brother - in - law fled into the store ' s basement . The Andersons barricaded the door to the basement and lit the store on fire , killing Baker and his brother - in - law . They also burnt Baker ' s home and stole two of his horses before returning to Missouri on the Santa Fe Trail . William and Jim Anderson soon formed a gang with a man named Bill Reed ; in February 1863 , the " Lexington Weekly Union " recorded that Reed was the leader of the gang . In his 2003 history of Civil War Missouri , Bruce Nichols stated that Reed led the gang until mid - July of that year . William Quantrill , a Confederate guerrilla leader , later claimed to have encountered them in July and rebuked them for robbing Confederate sympathizers ; in their biography of Anderson , Albert Castel and Tom Goodrich speculate that this rebuke may have resulted in a deep resentment of Quantrill by Anderson . Anderson and his gang subsequently traveled east of Jackson County , Missouri , avoiding territory where Quantrill operated and continuing to support themselves by robbery . They also attacked Union soldiers , killing seven by early 1863 . Quantrill ' s Raiders . 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 . Quantrill was at the time the most prominent guerrilla in the Kansas – Missouri area . In early 1863 , William and Jim Anderson traveled to Jackson County , Missouri , to join him . William Anderson was initially given a chilly reception from other raiders , who perceived him to be brash and overconfident . In May 1863 , Anderson joined members of Quantrill ' s Raiders on a foray near Council Grove , in which they robbed a store west of the town . After the robbery , the group was intercepted by a United States Marshal accompanied by a large posse , about from the Kansas – Missouri border . In the resulting skirmish , several raiders were captured or killed and the rest of the guerrillas , including Anderson , split into small groups to return to Missouri . Castel and Goodrich speculated that this raid may have given Quantrill the idea of a launching an attack deep in Kansas , as it demonstrated that the state ' s border was poorly defended and that guerrillas could travel deep within the state before Union forces were alerted . 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 City , 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 of a band of guerrillas . He commanded 30 – 40 men , one of whom was Archie Clement , an 18 - year - old with a predilection for torture and mutilation who was loyal only to Anderson . 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 Jefferson County , 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 . Castel and Goodrich maintain that killing became more than a means to an end at that point for Anderson : it became an end in itself . Lawrence Massacre . Although Quantrill had considered the idea of a raid on Lawrence , Kansas , before the building collapsed in Kansas City , the deaths convinced the guerrillas to make a bold strike . Quantrill attained near - unanimous consent to travel into Union territory to strike Lawrence . The guerrillas gathered at the Blackwater River in Johnson County , Missouri . Anderson was placed in charge of 40 men , of which he was perhaps the angriest and most motivated — his fellow guerrillas considered him one of the deadliest fighters there . On August 19 , the group , which proved to be the most guerrillas under one commander in the war , began the trip to Lawrence . En route , some guerrillas robbed a Union supporter , but Anderson knew the man and reimbursed him . After reaching Lawrence , the guerrillas immediately killed a number of Union Army recruits and one of Anderson ' s men took their flag . The Provost Marshal of Kansas , a Union captain who commanded military police , surrendered to the guerrillas and Anderson took his uniform . ( Guerrillas often wore uniforms stolen from Union soldiers . ) They proceeded to pillage and burn many buildings , killing almost every man they found , but taking care not to shoot women . Anderson 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 guerrillas 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 . After a dead raider was scalped by a Union - allied Lenape Indian during the pursuit , one guerrilla leader pledged to adopt the practice of scalping . Texas . On August 25 , 1863 , General Ewing retaliated against the Confederate guerrillas by issuing General Order No . 11 , an evacuation order that evicted almost 20 , 000 people from four Missouri counties and burned many of their homes . The order was intended to rob the guerrillas of their support network in Missouri . On October 2 , a group of 450 guerrillas under Quantrill ' s leadership met at Blackwater River in Jackson County and left for Texas . They departed earlier in the year than they had planned , owing to increased Union pressure . En route , they entered Baxter Springs , Kansas , the site of Fort Blair . They attacked the fort on October 6 , but the 90 Union troops there quickly took refuge inside , suffering minimal losses . Shortly after the initial assault , a larger group of Union troops approached Fort Blair , unaware that the fort had been attacked and that the men they saw outside the fort dressed in Union uniforms were actually disguised guerrillas . The guerrillas charged the Union forces , killing about 100 . 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 . On October 12 , Quantrill and his men met General Samuel Cooper at the Canadian River and proceeded to Mineral Springs , Texas , to rest for the winter . Anderson married Bush Smith , a woman from Sherman , Texas , who worked in a saloon . Anderson ignored Qantrill ' s request to wait until after the war and then separated his men from Quantrill ' s band . The tension between the two groups markedly increased — some feared that open warfare would result — but by the wedding , relations had improved . The couple lived in a house he built in Sherman and had one child , who died as an infant . In March , at the behest of General Price , Quantrill reassembled his men , sending most of them into active duty with the Confederate Army . He retained 84 men and reunited with Anderson . Quantrill appointed him a first lieutenant , under only he and Todd . A short time later , one of Anderson ' s men was accused of stealing from one of Quantrill ' s men . Quantrill expelled him and warned him not to come back , and the man was fatally shot by some of Quantrill ' s men when he attempted to return . It is likely that this incident angered Anderson , and he took 20 men to visit the town of Sherman . They told General Cooper that Quantrill was responsible for the death of a Confederate officer ; the general then had Quantrill arrested . Sutherland described Anderson ' s betrayal of Quantrill as a " Judas " turn . Quantrill was taken into custody , but soon escaped . Anderson was told to recapture him and gave chase , but he was unable to locate his former commander and stopped at a creek . There , his men briefly engaged a group of guerrillas loyal to Quantrill , but no one was injured in the confrontation . Upon returning to the Confederate leadership , Anderson was commissioned as a captain by General Price . Return to Missouri . Anderson and his men rested in Texas for several months before returning to Missouri . Although he learned that Union General Egbert B . Brown had devoted significant attention to the border area , Anderson led raids in Cooper and Johnson County , Missouri , robbing local residents . On June 12 , Anderson and 50 of his men engaged 15 members of the Missouri State Militia , killing and robbing 12 . After the attack , one of Anderson ' s guerrillas scalped a dead militiaman . The next day , in Southeast Jackson County , Anderson ' s group ambushed a wagon train carrying members of the Union 1st Northeast Missouri Cavalry , killing nine . The attacks prompted the " Kansas City Daily Journal of Commerce " to declare that rebels had taken over the area . Anderson and his men dressed as Union soldiers , wearing uniforms taken from those they killed . In response , Union militias developed hand signals to verify that approaching men in Union uniforms were not guerrillas . The guerrillas , however , quickly learned the signals , and local citizens became wary of Union troops , fearing that they were disguised guerrillas . On July 6 , a Confederate sympathizer brought Anderson newspapers containing articles about him . Anderson was upset by the critical tone of the coverage and sent letters to the publications . In the letters , Anderson took an arrogant and threatening , yet playful , tone , boasting of his attacks . He protested the execution of guerrillas and their sympathizers , and threatened to attack Lexington , Missouri . He concluded the letters by describing himself as the commander of " Kansas First Guerrillas " and requesting that local newspapers publish his replies . The letters were given to Union generals and were not published for 20 years . In early July , Anderson ' s group robbed and killed several Union sympathizers in Carroll and Randolph counties . On July 15 , Anderson and his men entered Huntsville , Missouri , and occupied the town ' s business district . Anderson killed one hotel guest whom he suspected was a U . S . Marshall , but spoke amicably with an acquaintance he found there . Anderson ' s men robbed the town ' s depository , gaining about $ 40 , 000 in the robbery , although Anderson returned some money to the friend he had met at the hotel . Growing infamy . In June 1864 , Todd usurped Quantrill ' s leadership of their group , and forced him to leave the area . Todd rested his men in July to allow them to prepare for a Confederate invasion of Missouri . As Quantrill and Todd became less active , Anderson emerged as the best known , and most feared , Confederate guerrilla in Missouri . By August , the " St . Joseph Herald " , a Missouri newspaper , was describing him as " the Devil " . As Anderson ' s profile increased , he was able to recruit more guerillas . Anderson was selective , turning away all but the fiercest applicants as he sought fighters similar to himself . His fearsome reputation gave a fillip to his recruiting efforts . Jesse James enlisted , joining his brother Frank ; they later became famous outlaws . 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 . Many militia members had been conscripted and lacked the guerillas ' boldness and resolve . In 1863 , most Union troops left Missouri and only four regiments remained there . These regiments were composed of troops from out of state , who sometimes mistreated local residents — further motivating the guerrillas and their supporters . The Union militias sometimes rode slower horses and may have been intimidated by Anderson ' s reputation . On July 23 , 1864 , Anderson led 65 men to Renick , Missouri , robbing stores and tearing down telegraph wires on the way . They had hoped to attack a train , but its conductor learned of their presence and turned back before reaching the town . The guerrillas then attacked Allen , Missouri . At least 40 members of the 17th Illinois Cavalry and the Missouri State Militia were in town but took shelter in a fort . The guerrillas were only able to shoot their horses before reinforcements arrived , killing three of Anderson ' s men . In late July , the Union military sent a force of 100 well - equipped soldiers , and 650 other men , after Anderson . On July 30 , Anderson and his men kidnapped the elderly father of the local Union militia ' s commanding officer . They tortured him until he was near death and sent word to the man ' s son in an unsuccessful attempt to lure him into an ambush , before releasing the father with instructions to spread word of his mistreatment . On August 1 , while searching for militia members , Anderson and some of his men stopped at a house full of women and requested food . While they rested at the house , a group of local men attacked . The guerrillas quickly forced the attackers to flee , and Anderson shot and injured one woman as she fled the house . This action angered his men , who saw themselves as the protectors of women , but Anderson dismissed their concerns , stating that such things were inevitable . They chased the men who had attacked them , killing one and mutilating his body . By August 1864 , they were regularly scalping the men that they killed . In early August , Anderson and his men traveled to Clay County . Around that time , he received further media coverage : the " St . Joseph Morning Herald " deemed him a " heartless scoundrel " , publishing an account of his torture of a captured Union soldier . On August 10 , while traveling through Clay County , Anderson and his men engaged 25 militia members , killing five of them and forcing the rest to flee . After hearing of the engagement , General Fisk commanded a colonel to lead a party with the sole aim of killing Anderson . Missouri River and Fayette . On August 13 , Anderson and his men traveled through Ray County , Missouri , to the Missouri River , where they engaged Union militia . Although they forced the Union forces to flee , Anderson and Jesse James were injured in the encounter and the guerrillas retired to Boone County , to rest . On August 27 , Union soldiers killed at least three of Anderson ' s men in an engagement near Rocheport . The next day , the 4th Missouri Volunteer Cavalry pursued them , but Anderson launched an ambush that killed seven Union soldiers . Anderson ' s men mutilated the bodies , earning the guerrillas the description of " incarnate fiends " from the " Columbia Missouri Statesman " . On August 30 , Anderson and his men attacked a steamboat on the Missouri River , killing the captain and gaining control of the boat . They used it to attack other boats , bringing river traffic to a virtual halt . In mid - September , while traveling through Howard County , Union soldiers ambushed two of Anderson ' s parties , killing five men in one day . They found the guerrillas ' horses decorated with the scalps of Union soldiers . A short time later , another six of Anderson ' s men were ambushed and killed by Union troops ; after learning of these events , Anderson was outraged and left the area to seek revenge . Anderson met Todd and Quantrill on September 24 , 1864 ; although they had clashed in the past , they agreed to work together . Anderson suggested that they attack Fayette , Missouri , targeting the 9th Missouri cavalry , which was based at the town . Quantrill disliked the idea because the town was fortified , but Anderson and Todd prevailed . Clad in Union uniforms , the guerrillas generated little suspicion as they approached the town , even though it had received warning of nearby guerrillas . However , a guerrilla fired his weapon before they reached the town , and the cavalry quickly withdrew into their fort while civilians hid . Anderson and Todd launched an unsuccessful attack against the fort , leading charge after futile charge without injury . The defeat resulted in the deaths of five guerrillas but only two Union soldiers , further maddening Anderson . On September 26 , Anderson and his men reached Monroe County , Missouri , and traveled towards Paris , but learned of other nearby guerrillas and rendezvoused with them near Audrain County . Anderson and his men camped with at least 300 men , including Todd . Although a large group of guerrillas was assembled , their leaders felt that there were no promising targets to attack , because all of the large towns nearby were heavily guarded . Raid on Centralia . On the morning of September 26 , Anderson left his camp with about 75 men to scout for Union forces . They soon arrived at the small town of Centralia and proceeded to loot it , robbing people and searching the town for valuables . They found a large supply of whiskey and all began drinking . Anderson retreated into the lobby of the town hotel to drink and rest . A stagecoach soon arrived , and Anderson ' s men robbed the passengers , including Congressman James S . Rollins and a plainclothes sheriff . The two were prominent Unionists , and hid their identities from the guerrillas . As the guerrillas robbed the stagecoach passengers , a train arrived . The guerrillas blocked the railroad , forcing the train to stop . Anderson ' s men quickly took control of the train , which included 23 off - duty Union soldiers as passengers . This was the first capture of a Union passenger train in the war . Anderson ordered his men not to harass the women on the train , but the guerrillas robbed all of the men , finding over $ 9 , 000 and taking the soldiers ' uniforms . Anderson forced the captured Union soldiers to form a line and announced that he would keep one for a prisoner exchange , but would execute the rest . He addressed the prisoners , castigating them for the treatment of guerrillas by Union troops . After selecting a sergeant for a potential prisoner swap , Anderson ' s men shot the rest . Anderson gave the civilian hostages permission to leave but warned them not to put out fires or move bodies . Although he was alerted of the congressman ' s presence in the town , he opted not to search for him . 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 . Battle with Union soldiers . Anderson arrived at the guerrilla camp and described the day ' s events , the brutality of which unsettled Todd . By mid - afternoon , the 39th Missouri Volunteer Infantry had arrived in Centralia . From the town , they saw a group of about 120 guerrillas and pursued them . The guerrillas heard that the cavalry was approaching , and Anderson sent a party to set an ambush . They drew the Union troops to the top of a hill ; a group of guerrillas led by Anderson had been stationed at the bottom and other guerrillas hid nearby . Anderson then led a charge up the hill . Although five guerrillas were killed by the first volley of Union fire , the Union soldiers were quickly overwhelmed by the well - armed guerrillas , and those who fled were pursued . One Union officer reached Centralia and gave word of the ambush , allowing a few Union soldiers who had remained there to escape . However , most were hunted down and killed ; Anderson ' s men mutilated the bodies of the dead soldiers and tortured some survivors . At Centralia , 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 . The attack led to a near halt in rail traffic in the area and a dramatic increase in Union rail security . Anderson achieved the same notoriety that Quantrill had previously enjoyed , and he began to refer to himself as " Colonel Anderson " , partly in an effort to supplant Quantrill . Sutherland saw the massacre as the last battle in the worst phase of the war in Missouri , and Castel and Goodrich described the slaughter as the Civil War ' s " epitome of savagery " . However , Frank James , who participated in the attack , later defended the guerrillas ' actions , arguing that the federal troops were marching under a black flag , indicating that they intended to show no mercy . Aftermath of Centralia . Anderson left the Centralia area on September 27 , pursued for the first time by Union forces equipped with artillery . Anderson evaded the pursuit , leading his men into ravines that the Union troops would not enter for fear of ambush . In the aftermath of the attacks , Union soldiers committed several revenge killings of Confederate - sympathizing civilians . They burned Rocheport to the ground on October 2 ; the town was under close scrutiny by Union forces , owing to the number of Confederate sympathizers there , but General Fisk maintained that the fire was accidental . Anderson watched the fire from nearby bluffs . Anderson visited Confederate sympathizers as he traveled , some of whom viewed him as a hero for fighting the Union , whom they deeply hated . Many of Anderson ' s men also despised the Union , and he was adept at tapping into this emotion . The Union soldier held captured at Centralia was impressed with the control that Anderson exercised over his men . Although many of them wished to execute this Union hostage , Anderson refused to allow it . On October 6 , Anderson and his men traveled to meet General Price in Boonville , Missouri . Price was disgusted that Anderson used scalps to decorate his horse , and would not speak with him until he removed them . He was , however , impressed by the effectiveness of Anderson ' s attacks . Anderson presented him with a gift of fine Union pistols , likely captured at Centralia . Price instructed Anderson to travel to the Missouri railroad and disrupt rail traffic , making Anderson a " de facto " Confederate captain . Anderson traveled east with 80 men to New Florence , Missouri . The group then traveled west , disregarding the mission assigned by General Price in favor of looting . Anderson reached a Confederate Army camp ; although he hoped to kill some injured Union prisoners there , he was prevented from doing so by camp doctors . After Confederate forces under General Joseph O . Shelby conquered Glasgow , Anderson traveled to the city to loot . He visited the house of a well - known Union sympathizer , the wealthiest resident of the town , brutally beat him , and raped his 12 - or 13 - year - old black servant . Anderson indicated that he was particularly angry that the man had freed his slaves and trampled him with a specially trained horse . Local residents gathered $ 5 , 000 , which they gave to Anderson ; he then released the man , who died of his injuries in 1866 . Anderson killed several other Union loyalists and some of his men returned to the wealthy resident ' s house to rape more of his female servants . He left the area with 150 men . Death . Union military leaders assigned Lieutenant Colonel Samuel P . Cox to kill Anderson , providing him 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 , the son of a Confederate general , 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 . Union soldiers buried Anderson ' s body in a field near Richmond in a fairly well - built coffin . Some of them cut off one of his fingers to steal a ring . Flowers were placed at his grave , to the chagrin of Union soldiers . In 1908 , Cole Younger , a former guerrilla who served under Quantrill , reburied Anderson ' s body , and in 1967 , a memorial stone was placed at the grave . Archie Clement led the guerrillas after Anderson ' s death , but the group splintered by mid - November . Most Confederate guerrillas lost heart around that time , owing to a cold winter and the failure of General Price ' s 1864 Missouri campaign , which ensured that the state would remain under Union control . As the Confederacy collapsed , most of Anderson ' s men joined Quantrill ' s forces or traveled to Texas . Jim Anderson moved to Sherman , Texas , with his two sisters . In 1868 , he married his brother ' s widow . Legacy . After the war , information about Anderson initially spread through memoirs of Civil War combatants and works by amateur historians . He was later discussed in biographies of Quantrill , which typically cast him as an inveterate murderer . Three biographies of Anderson were written after 1975 . Asa Earl Carter ' s novel " The Rebel Outlaw : Josey Wales " features Anderson as a main character . In 1976 , the book was adapted into a film , " The Outlaw Josey Wales " , which portrays a man who joins Anderson ' s gang after his wife is killed by Union - backed raiders . James Carlos Blake ' s novel " Wildwood Boys " is a fictional biography of Anderson . He also appears as a character in several films about Jesse James . Historians have been mixed in their appraisal of Anderson . Wood describes him as the " bloodiest man in America ' s deadliest war " and characterizes him as the clearest example of the war ' s " dehumanizing influence " . Castel and Goodrich view Anderson as one of the war ' s most savage and bitter combatants , but they also argue that the war made savages of many others . According to journalist T . J . Stiles , Anderson was not necessarily a " sadistic fiend " , but illustrated how young men became part of a " culture of atrocity " during the war . He maintains that Anderson ' s acts were seen as particularly shocking in part because his cruelty was directed towards white Americans of equivalent social standing , rather than targets deemed acceptable by American society , such as Native Americans or foreigners . In a study of 19th - century warfare , historian James Reid posits that Anderson suffered from delusional paranoia , which exacerbated his aggressive , sadistic personality . He sees Anderson as obsessed with , and greatly enjoying , the ability to inflict fear and suffering in his victims , and suggests he suffered from the most severe type of sadistic personality disorder . Reid draws a parallel between the bashi - bazouk s and Anderson ' s group , arguing that they behaved similarly . Bibliography . Books Journals Newspapers Websites