William Quantrill William Clarke Quantrill ( July 31 , 1837 – June 6 , 1865 ) was a Confederate guerrilla leader during the American Civil War . After leading a Confederate bushwhacker unit along the Missouri - Kansas border in the early 1860s , which included the infamous raid and sacking of Lawrence , Kansas in 1863 , Quantrill eventually ended up in Kentucky where he was mortally wounded in a Union ambush in May 1865 , aged 27 . Early life . Quantrill was the oldest of twelve children , four of whom died in infancy . He was born at Canal Dover ( now just Dover ) , Ohio , on July 31 , 1837 . His father was Thomas Henry Quantrill , formerly of Hagerstown , Maryland . His mother , Caroline Cornelia Clark , was a native of Chambersburg , Pennsylvania . They were married on October 11 , 1836 , and moved to Canal Dover the following December . Quantrill was well educated and followed in his father ’ s footsteps , becoming a school teacher at the age of sixteen . In 1854 , his abusive father died of tuberculosis , leaving the family with a huge financial debt . Quantrill ' s mother had to turn her home into a boarding house in order to survive . He helped support the family working as a school teacher , but left home a year later and headed to Mendota , Illinois . Here , Quantrill took up a job in the lumberyards , unloading timber from rail cars . One night while working the late shift , he shot a man to death . Authorities briefly arrested Quantrill , who claimed self - defense . Since there were no eye - witnesses and the victim was a stranger who knew no one in town , William was set free . But police strongly urged him to leave Mendota . Quantrill continued his career as a teacher , moving to Fort Wayne , Indiana in February 1856 . And although the district was impressed with Quantrill ' s teaching abilities , the wages remained meager . Bill journeyed back home to Canal Dover that fall , with no more money in his pockets than when he had left . Quantrill spent the winter in his family ' s dumpy shack in the impoverished town , growing restless . It was around this time that many of Ohioans began to migrate to Kansas Territory in search of cheap land and opportunity . This included Henry Torrey and Harmon Beeson , two local men hoping to build a large farm for their families out west . Although they didn ' t trust the 19 - year old William , Bill ' s mother ' s pleadings persuaded them to let her son accompany them to Kansas in an effort to get him to turn his life around . The party of three departed in late February 1857 . Torrey and Beeson agreed to pay for Quantrill ' s land in exchange for a couple months worth of work . They settled at Marais des Cygnes , but things did not go as well as planned . After about two months , Quantrill began to slack off when it came to working the land and he spent most days wandering aimlessly about the wilderness with a rifle . A dispute arose over the claim , and he went to court with Torrey and Beeson . The court awarded the men what was owed to them , but Quantrill only paid half of what the court had mandated . His relationship with Beeson was never the same , but he remained friends with Torrey . Shortly afterwards , Quantrill accompanied a large group of hometown friends in their quest of starting a settlement on Tuscarora Lake . But soon neighbors began to notice Bill stealing goods out of other people ' s cabins , so they banished him from the community in January 1858 . He signed on as a teamster with the US Army expedition heading to Salt Lake City , Utah in the spring . Little is known of Quantrill ' s journey out west , except that he excelled at the game of poker . He racked up piles of winnings by playing the game against his fellow comrades at Fort Bridger , but flushed it all on one hand the next day , leaving him dead broke . Quantrill then joined a group of Missouri ruffians and became somewhat of a drifter . The group helped protect Missouri farmers from the Jayhawker s for pay and slept wherever they could find lodging . Quantrill traveled back to Utah and then to Colorado but returned in less than a year to Lawrence , Kansas , in 1859 . It was at this time that his political views started to take shape , and his attitude towards the slavery issue began to form . Before 1860 , Quantrill ’ s political view appeared to be in support of the anti - slavery side . He wrote to his good friend W . W . Scott in January 1858 that the Lecompton Constitution was a “ swindle ” and that James H . Lane , a Northern sympathizer , was “ as good a man as we have here . ” He also called the Democrats “ the worst men we have for they are all rascals , for no one can be a democrat here without being one . ” One year later , in 1859 , he was back in Lawrence , Kansas where he taught school until it closed in 1860 . He then took up with brigands and turned to cattle rustling and anything else that could earn him a dollar . He also learned the profitability of capturing runaway slaves and devised treacherous plans to use free black men as bait for runaway slaves , whom he captured and returned to their masters in exchange for reward money . His new lifestyle may have been the reason for his change of political views . In February 1860 , Quantrill wrote a letter to his mother expressing his views on the anti - slavery supporters . He told her that the pro - slavery movement was right and that he now detested Jim Lane . He said that the hanging of John Brown had been too good for him and that , “ the devil has got unlimited sway over this territory , and will hold it until we have a better set of man and society generally . " Guerrilla leader . In 1861 , Quantrill went to Texas with a slaveholder named Marcus Gill . There he met Joel B . Mayes and joined the Cherokee Nations . Joel B . Mayes was a Confederate sympathizer and a war chief of the Cherokee Nations in Texas . Mayes was half Scotch - Irish , half Cherokee Indian and had moved from Georgia to the old Indian Territory in 1838 . Mayes enlisted and served as a private in Company A of the 1st Cherokee Regiment in the Confederate army . It was Mayes who taught Quantrill guerrilla warfare tactics . He would learn the ambush fighting tactics used by the Native Americans as well as sneak attacks and camouflage . Quantrill , in the company of Mayes and the Cherokee Nations , joined with General Sterling Price and fought at the Battle of Wilson ’ s Creek and Lexington in August and September 1861 . Quantrill deserted General Price ’ s army and went to Blue Springs , Missouri to form his own ‘ Army ’ of loyal men who had great belief in him and the Confederates cause . By Christmas of 1861 , he had ten men who would follow him full - time into his pro - Confederate guerrilla organization . These men were : William Haller , George Todd , Joseph Gilcrist , Perry Hoy , John Little , James Little , Joseph Baughan , William H . Gregg , James A . Hendricks , and John W . Koger . Later in 1862 , the Younger brothers as well as William T . " Bloody Bill " Anderson and the James brothers would join Quantrill ’ s army . Lawrence Massacre . The most significant event in Quantrill ' s guerrilla career took place on August 23 , 1863 . Lawrence had been seen for years as the stronghold of the anti - slavery forces in Kansas and as a base of operation for incursions into Missouri by Jayhawkers and pro - Union forces . It was also the home of James H . Lane , a senator infamous in Missouri for his staunch anti - slavery views and also a leader of the Jayhawkers . Moreover , during the weeks immediately preceding the raid , Union General Thomas Ewing , Jr . , had ordered the detention of any civilians giving aid to Quantrill ' s Raiders . Several female relatives of the guerrillas had been imprisoned in a makeshift jail in Kansas City , Missouri . On August 14 , the building collapsed , killing four young women and seriously injuring others . Among the casualties was Josephine Anderson , sister of one of Quantrill ' s key guerrilla allies , " Bloody Bill " Anderson . Another of Anderson ' s sisters , Mary , was permanently crippled in the collapse . Quantrill ' s men believed the collapse was deliberate , and the event fanned them into a fury . Historians have suggested that Quantrill had actually planned to raid Lawrence in advance of the building ' s collapse , in retaliation for earlier Jayhawker attacks as well as the burning of Osceola , Missouri . Early on the morning of August 21 , Quantrill descended from Mount Oread and attacked Lawrence at the head of a combined force of as many as 450 guerrillas . Senator Lane , a prime target of the raid , managed to escape through a cornfield in his nightshirt , but the guerrillas , on Quantrill ' s orders , killed 183 men and boys " old enough to carry a rifle " , Quantrill , known to be armed with several French pinfire revolvers , his favorite weapon of choice , carried out several personally , dragging many from their homes to execute them before their families . The ages of those killed ranged from as young as 14 all the way up to 90 . When Quantrill ' s men rode out at 9 a . m . , most of Lawrence ' s buildings were burning , including all but two businesses . His raiders looted indiscriminately and robbed the town ' s bank . On August 25 , in retaliation for the raid , General Ewing authorized General Order No . 11 ( not to be confused with General Ulysses S . Grant ' s General Order of the same name ) . The edict ordered the depopulation of three - and - a - half Missouri counties along the Kansas border ( with the exception of a few designated towns ) , forcing tens of thousands of civilians to abandon their homes . Union troops marched through behind them , burning buildings , torching planted fields and shooting down livestock to deprive the guerrillas of food , fodder , and support . The area was so thoroughly devastated that it became known thereafter as the " Burnt District " . Quantrill and his men rode south to Texas , where they passed the winter with the Confederate forces . Last years . While in Texas , Quantrill and his 400 men quarreled . His once - large band broke up into several smaller guerrilla companies . One was led by his lieutenant , " Bloody Bill " Anderson , whose men came to be known for tying the scalps of slain unionists to the saddles and bridles of their horses . Quantrill joined them briefly in the fall of 1863 during fighting north of the Missouri River . In the spring of 1865 , now leading only a few dozen men , Quantrill staged a series of raids in western Kentucky . He rode into a Union ambush on May 10 near Taylorsville , Kentucky , armed with several French pinfire s which bore his name , and received a gunshot wound to the chest . He was brought by wagon to Louisville , Kentucky and taken to the military prison hospital , located on the north side of Broadway at 10th Street . He died from his wounds on June 6 , 1865 , at the age of 27 . Claim of post - 1865 survival . In August , 1907 , news articles appeared in Canada and the United States claiming that J . E . Duffy , a member of a Michigan cavalry troop that dealt with Quantrill ' s raiders during the Civil War , had met Quantrill at Quatsino Sound , on northern Vancouver Island while investigating timber rights in the area . Duffy claimed to recognize the man , living under the name of John Sharp , as Quantrill . Duffy said that Sharp admitted he was Quantrill and discussed in detail raids in Kansas and elsewhere . Sharp claimed that he had survived the ambush in Kentucky , though receiving a bayonet and bullet wound , making his way to South America where he lived some years in Chile . He returned to the United States , working as a cattleman in Fort Worth , Texas . He then moved to Oregon , acting as a cowpuncher and drover , before reaching British Columbia in the 1890s , where he worked in logging , trapping and finally as a mine caretaker at Coal Harbour at Quatsino . Within some weeks after the news stories were published , two men came to British Columbia , travelling to Quatsino from Victoria , leaving Quatsino on a return voyage of a coastal steamer the next day . On that day , Sharp was found severely beaten , dying several hours later without giving information about his attackers . The police were unable to solve the murder . Marriage . During the war , Quantrill met thirteen - year - old Sarah Katherine King at her parents ' farm in Blue Springs , Missouri . They married and she lived in camp with Quantrill and his men . At the time of his death , she was seventeen . Reputation and legacy . Quantrill ' s actions remain controversial to this day . Some historians view him as an opportunistic , bloodthirsty outlaw ; James M . McPherson , one of America ' s most prominent experts on the Civil War today , calls him and Anderson " pathological killers " who " murdered and burned out Missouri Unionists . " Some of Quantrill ' s celebrity later rubbed off on other ex - Raiders – Jesse and Frank James , and Cole and Jim Younger – who went on after the war to apply Quantrill ' s hit - and - run tactics to bank and train robbery . The William Clarke Quantrill Society continues to research and celebrate his life and deeds .