Quantrill experienced a turbulent childhood, became a schoolteacher, and joined a group of bandits who roamed the Missouri and Kansas countryside to apprehend escaped slaves.

Frank Dalton, a cousin of the James brothers, recalls what Federal troops did to Zerelda, "Jennison's Jayhawkers, visiting the home of the James brothers and taking the women, Aunt Zerelda, the mother of Frank and Jesse, their sister, and my mother and sisters, and after stripping them to the waist they tied them to trees and taking a blacksnake whip that they found in the stable they whipped them until they got tired and then rode away, leaving the women and girls to be cut down and carried into the house by our negro slaves, who washed and bandaged their bleeding backs and bodies and put them to bed.

"[1] Other men, such as the Berry brothers, Dick, James and Issac, from Callaway County, rode with Quantrill because of atrocities committed against their civilian families by Union troops from the nearby town of Danville.

His father was Thomas Henry Quantrill, formerly of Hagerstown, Maryland, and his mother, Caroline Cornelia Clark, was a native of Chambersburg, Pennsylvania.

This included Henry Torrey and Harmon Beeson, two local men hoping to build a large farm for their families out west.

[citation needed] Soon, Quantrill accompanied a large group of hometown friends in their quest to settle near Tuscarora Lake.

[citation needed] Soon thereafter, Quantrill signed on as a teamster with the US Army expedition heading to Salt Lake City, Utah in early 1858.

Quantrill racked up piles of winnings by playing the game against his comrades at Fort Bridger but lost it all on one hand, leaving him broke.

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.

By Christmas 1861, ten men followed Quantrill full-time in his pro-Confederate guerrilla organization:[5][page needed] William Haller, George Todd, Joseph Gilcrist, Perry Hoy, John Little, James Little, Joseph Baughan, William H. Gregg, James A. Hendricks, and John W. Koger.

After what became known as the First Battle of Independence, the Confederate government decided to secure the loyalty of Quantrill by issuing him a "formal army commission" to the rank of captain.

[12] In the early hours of September 7, 1862, William Quantrill and a force of 140 men seized control of Olathe, Kansas, capturing 125 US Army soldiers.

[13] On October 5, 1862, Quantrill attacked and destroyed Shawneetown, Kansas; William T. Anderson soon revisited and torched the rebuilding settlement.

During the weeks immediately preceding the raid, US Army General Thomas Ewing, Jr., ordered the detention of any civilians giving aid to Quantrill's Raiders.

Some historians have suggested that Quantrill planned to raid Lawrence before the building's collapse, in retaliation for earlier Jayhawker attacks[16][page needed] as well as the burning of Osceola, Missouri.

Early in the morning of August 21, Quantrill descended from Mount Oread and attacked Lawrence with a combined force of 450 guerrilla fighters.

Lane, a prime target of the raid, managed to escape through a cornfield in his nightshirt, but the guerrillas, on Quantrill's orders, killed around 150 men and boys who could carry a rifle.

The edict ordered the depopulation of three and a half Missouri counties along the Kansas border except for a few designated towns, which forced tens of thousands of civilians to abandon their homes.

Union troops marched through behind them and burned buildings, torched planted fields, and shot down livestock to deprive the guerrillas of food, fodder, and support.

One was led by his lieutenant, "Bloody Bill" Anderson, and Quantrill joined it briefly in the fall of 1864 during a fight north of the Missouri River.

The unit that successfully ambushed Quantrill and his followers was led by Edwin W. Terrell, a guerrilla hunter charged with finding and eliminating high-profile targets by General John M. Palmer, the commander of the District of Kentucky.

In the early 1990s, the Missouri division of the Sons of Confederate Veterans convinced the Kansas State Historical Society to negotiate with authorities in Dover, which led to three arm bones, two leg bones, and some hair, all of which were allegedly Quantrill's, being re-buried in 1992 at the Old Confederate Veteran's Home Cemetery in Higginsville, Missouri.

Sharp claimed that he had survived the ambush in Kentucky but received a bayonet and bullet wound, making his way to South America, where he lived some years in Chile.

He then moved to Oregon, acting as a cowpuncher and drover, before he reached British Columbia in the 1890s, where he worked in logging, trapping, and finally as a mine caretaker at Coal Harbour at Quatsino.

[26] The family of Major Cornelius Boyle believed that Quantrill had actually served as a bodyguard for the Provost Marshal General when he visited Mexico after the war, while Jubal Early was also in the country as they sought out an alternate resolution.

James M. McPherson, one of the most prominent experts on the American Civil War, calls Quantrill and Anderson "pathological killers" who "murdered and burned out Missouri Unionists".

[28] The historian Matthew Christopher Hulbert argues that Quantrill "ruled the bushwhacker pantheon" established by the ex-Confederate officer and propagandist John Newman Edwards in the 1870s to provide Missouri with its own "irregular Lost Cause".