Although Quantrill was not really military, and therefore had no rank, he became one of the most feared participants of the War of Northern Aggression, and am admired leader of the Confederate Cause in the western states.
Quantrill was well-educated and followed in his father’s footsteps, becoming a schoolteacher at the age of sixteen.
Before 1860, Quantrill’s political view appeared to support the anti-slavery side.
In 1859,he then took up with brigands and turned to cattle rustling and anything else that could earn him a dollar as teachers wages were very meager, indeed.
He also learned the profitability of capturing runaway slaves and devised plans to use free black men as bait for runaway slaves, whom he subsequently 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 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.”
In 1861, Quantrill went to Texas with a slaveholder named Marcus Gill. There he met Joel B. Mayes and joined the Cherokee Nations. Mayes was a half Scots-Irish, half Cherokee Indian Confederate sympathizer and a war chief of the Cherokee Nations in Texas. He 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 Confederate 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, John Jarrett, John Brown, Cole Younger, as well as William T. “Bloody Bill” Anderson and the James brothers would join Quantrill’s army.
The most significant event in Quantrill’s guerrilla career took place on August 21, 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 known in Missouri for his staunch anti-slavery views and also a leader of the Jayhawkers (outlaws masquerading as Union soldiers).
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 dead 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.
Some 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 guerrilla fighters. 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 around 150 men and boys that were able to carry a rifle. When Quantrill’s men rode out at 9 a.m., most of Lawrence’s buildings were burning, including all but two businesses.
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 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. On May 18, 1864 Quantrill’s forces lynched Texas Sheriff James L. Read in Collin County, Texas.
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, Quantrill joined them briefly in the fall of 1864 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. Confederate General Robert E. Lee surrendered to Ulysses Grant on April 9, and General Johnston surrendered most of the rest of the Confederate Army to General Sherman on April 26. On May 10, Quantrill and his band were caught in a Union ambush at Wakefield Farm. Unable to escape on account of a skittish horse, he was shot in the back and paralyzed from the chest down. 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.