Later known as “Bloody Bill” because of his cold-blooded acts against Union soldiers, William T. Anderson entered the War with a well-established outlaw reputation, having already murdered a judge who had killed his father over accusations of horse theft. 

Known for his brash behavior and piercing eyes, Anderson took up with William Quantrill’s raiders in 1863 and soon began leading attacks against Union forces. When one of his sisters was captured by U.S. soldiers and then killed in an "accidental" building collapse, Anderson’s dislike for the Union intensified into pathological hatred. He is known to have personally executed several people during William Quantrill’s raid on Lawrence, Kansas.

In 1864 Anderson’s band—which included famed outlaw Jesse James—attacked a train in Centralia, Missouri, and killed 22 Union soldiers.

When Union troops were sent in pursuit, Anderson’s outfit—dressed in stolen Federal uniforms—ambushed them and killed another 120 men. Desperate to put a stop to Anderson’s bloodshed, the Union Army eventually raised a small militia to hunt him down. In October of 1864, Anderson’s unit was trapped and outnumbered in Missouri, and “Bloody Bill” was killed when he tried to charge the Union troops.