Lawrence Massacre The Lawrence Massacre , also known as Quantrill ' s Raid , was a rebel guerrilla attack during the American Civil War by Quantrill ' s Raiders , led by William Quantrill , on the pro - Union town of Lawrence , Kansas . The attack on August 21 , 1863 , targeted Lawrence due to the town ' s long support of abolition and its reputation as a center for Jayhawkers and Redlegs , which were free - state militia and vigilante groups known for attacking and destroying farms and plantations in Missouri ' s pro - slavery western counties . Background . By 1863 , Kansas had long been the center of strife and warfare over the admission of slave versus free states . In the summer of 1856 , the first sacking of Lawrence sparked a guerrilla war in Kansas that lasted for months . John Brown might be the best known participant , but numerous groups fought for each side in Bleeding Kansas . By the beginning of the American Civil War , Lawrence , Kansas , was already a target for pro - slavery ire , having been seen as the anti - slavery stronghold in the state and more importantly , a staging area for Union and Jayhawker incursions into Missouri . Initially the town and surrounding area were extremely vigilant and reacted strongly to any rumors that enemy forces might be advancing on the town . However by the summer of 1863 , as none of the threats had materialized , citizen fears had declined and defense preparations were relaxed . Motivations . Quantrill himself said his motivation for the attack was , " To plunder , and destroy the town in retaliation for Osceola . " That was a reference to the Union ' s attack on Osceola , Missouri in September 1861 , led by Senator James H . Lane . Osceola was plundered and nine men were given a drumhead court - martial trial and executed . Several other Missouri towns and large swaths of the Missouri countryside had been similarly plundered and burned by Unionist forces from Kansas . Castel ( 1999 ) concludes that revenge was the primary motive , followed by a desire to plunder . The retaliatory nature of the attack on Lawrence was confirmed by the survivors . " The universal testimony of all the ladies and others who talked with the butchers of the 21st ult . Is that these demons claimed there were here to revenge the wrongs done their families by our men under Lane , Jennison , Anthony and Co . " Lawrence was also a headquarters for a band of redlegs that had initiated a particularly vicious jayhawking campaign in late March 1863 . The purported objective of this group was to eliminate civilian support for the Confederate guerillas , but their tactics ( executions , arson , and plundering ) were employed rather indiscriminately . As one observer ( apparently a member of the Fifth Kansas Cavalry ) noted , “ " I believe the Red Legs will kill any man in this country for a good horse ; and they have glorified themselves considerably over finishing some unarmed sympathizers " . ” In describing the activities of the redlegs , Union General Blunt stated , “ " A reign of terror was inaugurated , and no man ’ s property was safe , nor was his life worth much if he opposed them in their schemes of plunder and robbery " . ” It is difficult to quantify the number of civilians killed by the redlegs , but a letter written from the Lexington area early in the redlegs campaign ( April 1863 ) stated the redlegs had , “ " killed at least fifty men , who were unarmed and heretofore lived in peace and quiet " " Collapse of the Women ' s Prison in Kansas City . In a bid to put down the Missouri guerrilla raiders operating in Kansas , General Thomas Ewing , Jr . issued in April 1863 " General Order No . 10 , " which ordered the arrest of anyone giving aid or comfort to Confederate guerrillas . This meant chiefly women or girls who were relatives of the guerrillas . Ewing confined those arrested in a series of makeshift prisons in Kansas City . The women were sequentially housed in two buildings which were considered either too small or too unsanitary , before being moved to an empty property at 1425 Grand . This structure was part of the estate of the deceased Robert S . Thomas , George Caleb Bingham ' s father - in - law . In 1861 Bingham and his family were living in the structure , but in early 1862 after being appointed treasurer of the state of Missouri , he and his family relocated to Jefferson City . Bingham had added a third story to the existing structure to use as a studio . At least ten women or girls , all under the age of 20 , were incarcerated in the building when it collapsed August 13 , 1863 , killing four : Charity McCorkle Kerr , Susan Crawford Vandever , Armenia Crawford Selvey , and Josephine Anderson — the 15 - year - old sister of William T . " Bloody Bill " Anderson . Anderson ' s 13 - year old sister , who was shackled to a ball - and - chain inside the jail , suffered multiple injuries including two broken legs . Rumors circulated ( later promulgated by Bingham who held a personal grudge against Ewing and who would seek financial compensation for the loss of the building ) that the structure was undermined by the guards to cause its collapse . However , a 1995 study of the events and affidavits surrounding the collapse concludes this is " the least plausible of the theories . " Instead , testimony indicated that alterations to the first floor of the adjoining Cockrell structure for use as a barracks caused the common wall to buckle . The weight of the third story on the former Bingham residence contributed to the resultant collapse . Even before the collapse of the jail , the arrest and planned deportation of the girls had enraged Quantrill ' s guerillas ; George Todd left a note for General Ewing threatening to burn Kansas City unless the girls were freed . While Quantrill ' s raid on Lawrence was planned prior to the collapse of the jail , the deaths of the guerrillas ' female relatives undoubtedly added to their thirst for revenge and blood lust during the raid . Attack . The attack was the product of careful planning . Quantrill had been able to gain the confidence of many of the leaders of independent Bushwhacker groups , and chose the day and time of the attack well in advance . The different groups of Missouri riders approached Lawrence from the east in several independent columns , and converged with well - timed precision in the final miles before Lawrence during the pre - dawn hours of the chosen day . Many of the men had been riding for over 24 hours to make the rendezvous and had lashed themselves to their saddles to keep riding if they fell asleep . Almost all were armed with multiple six - shot revolvers . Between three and four hundred riders arrived at the summit of Mount Oread , then descended on Lawrence in a fury . Over four hours , the raiders pillaged and set fire to the town and killed most of its male population . Quantrill ' s men burned to the ground a quarter of the buildings in Lawrence , including all but two businesses . They looted most of the banks and stores and killed between 185 and 200 men and boys . According to an 1897 account , among the dead were 18 of 23 unmustered army recruits . By 9 a . m . , the raiders were on their way out of town , evading the few units that came in pursuit , and splitting up so as to avoid Union pursuit of a unified column . The raid was less a battle than a mass execution . Two weeks prior to the raid , a Lawrence newspaper boasted , " " Lawrence has ready for any emergency over five hundred fighting men . . . every one of who would like to see [ Quantrill ' s raiders ] " " . However , a squad of soldiers temporarily stationed in Lawrence had returned to Fort Leavenworth , and due to the surprise , swiftness , and fury of the initial assault , the local militia was unable to assemble and mount a defense . Most of the victims of the raid were unarmed when gunned down . With revenge a principal motive , Quantrill ’ s raiders entered Lawrence with lists of men to be killed and buildings to be burned . Senator James H . Lane was at the top of the list . Lane was a military leader and chief political proponent of the jayhawking raids that had cut a swath of death , plundering , and arson through western Missouri ( including the destruction of Osceola ) in the early months of the Civil War . Lane escaped death by racing through a cornfield in his nightshirt . John Speer had been put into the newspaper business by Lane , was one of Lane ’ s chief political backers , and was also on the list . Speer likewise escaped execution , but two of his sons were killed in the raid . ( One of Speer ' s sons was have been the same John L . Speer that appeared on a list of redlegs previously issued by the Union military . ) Speer ’ s youngest son , fifteen - year - old Billy , may have been included on the death lists , but he was released by Quantrill ’ s men after giving them a false name . The Speer boy later shot one of the raiders during their exit from Lawrence , causing one of the few casualties among Quantrill ’ s command while in Lawrence . Charles Robinson , first governor of Kansas and a prominent abolitionist , may also have been on the list , though he maintained he was spared because Quantrill respected his efforts to keep peace on the border at the start of the war . While many of the victims of the raid had been specifically targeted beforehand , executions were more indiscriminate among segments of the raiders , particularly Todd ’ s band that operated in the western part of Lawrence . The men and boys riding with " Bloody Bill " Anderson also accounted for a disproportionate number of the Lawrence dead . The raid devolved into extreme brutality . The survivors reported that one man was shot while in the arms of his pleading wife , that another was killed with a toddler in his arms , that a group of men who had surrendered under assurances of safety were then gunned down , and that a pair of men were bound and forced into a burning building where they died in horrible agony . The youth of some of the victims is often characterized as a particularly reprehensible aspect of the raid . Bobbie Martin is generally cited as being the youngest victim ; some histories of the raid state he was twelve years old , while others state he was fourteen . Most accounts state he was wearing a Union soldier uniform or clothing made from his father ’ s uniform ; some state he was carrying a musket and cartridges . ( For perspective on the age of participants in the conflict , it has been estimated that about 800 , 000 Union soldiers were seventeen years of age or younger , with about 100 , 000 of those being fifteen or younger . ) Most of Quantrill ’ s guerilla fighters were teenagers . One of the youngest was Riley Crawford , who was thirteen when brought by his mother to Quantrill after her husband was shot and her home burned by Union soldiers . Aftermath . 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 . A day after the attack , the surviving citizens of Lawrence lynched a member of Quantrill ' s Raiders caught in the town . On August 25 , General Ewing authorized General Order No . 11 ( not to be confused with Grant ' s famous General Order of the same name ) evicting thousands of Missourians in four counties from their homes near the Kansas border . Virtually everything in these counties was then systematically burned to the ground . The action was carried out by the infamous Jayhawker , Charles " Doc " Jennison . Jennison ' s raids into Missouri were thorough and indiscriminate , and left five counties in western Missouri wasted , save for the standing brick chimneys of the two - storey period houses , which are still called " Jennison Monuments " in those parts . A Missouri abolitionist and preacher described the role of the Lawrence Massacre in the region ' s descent into the horror of total war on the civilian population of Kansas and Missouri : The city seal of Lawrence commemorates Quantrill ' s attack with its depiction of a Phoenix rising from the ashes of the burnt city . For his part , Quantrill led his men south to Texas for the winter . By the next year , the raiders had disintegrated as a unified force , so were unable to achieve similar successes . William Clarke Quantrill died of wounds received in Kentucky in 1865 , with only a few staunch supporters left . Among these appear to have been Frank James and his younger brother , Jesse James . In popular media . In the USA Network dramedy " Psych " , the fictional " Battle of Piper ' s Cove " reenacted in the 2006 episode " Weekend Warriors " seems to be based on the Lawrence Massacre . The battle is also depicted in the Steven Spielberg - produced 2005 miniseries " Into the West " and in Ang Lee ' s 1999 film " Ride with the Devil " , plus the Audie Murphy western " Kansas Raiders " ( 1950 ) . The 1940 film " Dark Command " , based on a novel of the same name , is a fictionalized account of the events in much more of a classic B - movie western style . The film starred John Wayne , Roy Rogers , Gabby Hayes , and Walter Pidgeon , but bore no resemblance to the events of history . The 2010 Coen Brother ' s film , " True Grit " , includes a scene in which the characters played by Jeff Bridges and Matt Damon argue about Quantrill . Damon ' s Texas Ranger calls him a murderer ; Bridges ' US Marshall , who " rode with " Quantrill , calls him a patriot . Damon ends the argument after Bridges refers to " Captain Quantrill , " ridiculing the title : " Captain of what ? " This conversation appeared first in Charles Portis ' book of the same name published in 1968 . The same exchange existed in the original 1969 film . " Wildwood Boys " ( William Morrow : New York , 2000 ) is a novel about Bloody Bill Anderson by James Carlos Blake .