William T. “Bloody Bill” Anderson was a notorious Confederate guerrilla leader with whom Jesse James associated for a brief period during the Civil War. Anderson’s nickname was “Bloody Bill” because he murdered and butchered Union soldiers and sympathizers during the Civil War. He is considered one of the vilest figures on either side of the war.

Little is known about Anderson’s early life. Even the state of his birth is uncertain. While Anderson claimed Missouri as his native state, it is more likely that he was born in Kentucky around 1838. His father, a hatter with Southern sympathies, moved his family to Kansas where they were met with hostility because they refused to fight against the South. After Anderson’s father was killed in a confrontation over a horse in 1862, Anderson sought revenge and killed a local judge and his brother-in-law. Then two of his sisters were imprisoned by order of Union commander General Thomas Ewing because they were suspected of being guerrilla supporters. One sister died and the other was crippled when the Kansas City building they were imprisoned in collapsed. This event further fueled Anderson’s hostility towards all Union soldiers.

Anderson then conducted one brutal raid after another. He joined forces with fellow bushwhacker William Clarke Quantrill and tortured and terrorized people in Kansas, Missouri, and Texas. Bushwhackers were bands of soldiers that did not belong to an organized military force. Anderson was the most feared and vicious bushwhacker in Missouri, especially after he ordered and conducted the massacre of Union soldiers at Centralia, Missouri, on September 27, 1864. Jesse James participated in the event.

On October 26, 1864, Anderson was killed by the Missouri State Militia who had found his camp near Albany, Missouri, in Ray County. His body was placed in a wagon and transported to Richmond, Missouri. After his photograph was taken, Anderson was decapitated by militia officers. He continues to be regarded as one of the most brutal Civil War guerillas.