William Quantrill spent most of his early life as a schoolteacher and gambler. Shortly after war broke out, Quantrill assembled a ragtag band of guerrillas and began harassing and killing Union forces and sympathizers along the Missouri-Kansas border. His exploits earned him the rank of captain from the Confederate Army, but he was also labeled an outlaw by the Union, which viewed his unconventional tactics as illegal and even murderous.

Quantrill’s most famous attack came in 1863 when he led 450 guerrillas on a raid on the Union stronghold of Lawrence, Kansas. Union forces responded by burning four nearby Missouri counties and driving the citizens off their land. 

In the confusion that followed, Quantrill’s raiders disbanded and formed smaller guerrilla units in Texas and Oklahoma. His forces now weakened, Quantrill continued to operate outside of the Confederate Army, which had withdrawn support following his attack on Lawrence. 

In 1864 Quantrill briefly assembled a band of soldiers with the intention of riding east and assassinating President Abraham Lincoln, but he abandoned the idea after recognizing the strength of Union defenses. Undeterred, Quantrill continued his bloody raids against Union troops well into 1865, when he was killed in Kentucky after suffering a gunshot wound to the chest.