KENTUCKY (FOX 56) — Hopkins County was the birthplace of a Confederate guerilla whose exploits were so savage he was awarded the nickname “Bloody Bill”.

The exact year William Anderson was born is not abundantly clear, but it’s believed to be sometime between 1837 and 1839.

As a child, his family moved from Hopkins County to Huntsville, Missouri, and in 1857 the family settled in Kansas. The family personally experienced the “Bleeding Kansas” conflict surrounding slavery at the time.

Pre-Civil War illustration depicting a gun fight from “Bleeding Kansas,” a war fought in the 1850’s between abolitionists and slavery advocates for control of the territory of Kansas. (Getty Images)

In 1860, Anderson was a property owner and went into the family business of freight shipping, along with horse trading. The outbreak of the Civil War would change Anderson’s life forever.

In 1861, he and his friend, a pro-slavery judge, I.A. Baker, attempted to join the Confederate Army but were attacked by the 6th Kansas Cavalry in Missouri. After being captured, Baker turned on Anderson and his family, even going so far as to issue an arrest warrant against Anderson’s brother, Griffith.

Anderson and Baker got into an altercation after Anderson tried to get the arrest warrant suspended. The altercation ended with Baker killing Anderson’s father.

On July 2, 1862, Anderson murdered Baker, burned his home, and fled to Missouri.

Becoming ‘Bloody Bill’

Anderson and his brother, Jim, rode with William Quantrill, a Confederate guerilla leader following the death of their father. Anderson was once asked why he joined Quantrill, and he replied, “I have chosen guerrilla warfare to revenge myself for wrongs that I could not honorable revenge otherwise. I lived in Kansas when this war commenced. Because I would not fight the people of Missouri, my native State, the Yankees sought my life but failed to get me. [They] revenged themselves by murdering my father, [and] destroying all my property.”

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Anderson’s three sisters were operating as Confederate spies and were arrested by Union authorities under the command of Gen. Thomas Ewing Jr., who placed them and multiple other women in makeshift jails. The building would collapse, killing one of Anderson’s sisters, crushing and forever crippling another, and seriously injuring the third sister.

Believed to be intentional, the building collapse shifted Anderson’s motivation and routine, wanton killing became the norm for him. Anderson and his associates went on to earn reputations for their brutality, torture, and mutilation. “Bloody Bill” was born.

The rise, split, and fall of ‘Bloody Bill’

Anderson rose to the rank of Capt. under Quantrill’s command. Anderson and his men were said to openly conduct themselves with excessive brutality. However, as retaliations against Anderson’s actions increased, he made for Texas where tensions between Andreson and Quantrill broke out, leading to a split between the two.

William “Bloody Bill” Anderson via the State Historical Society of Missouri

Free from Quantrill’s rule, Anderson and his men were said to have disguised themselves as Union soldiers and staged a series of raids where they ambushed federal troops and murdered and even scalped civilians.

Anderson soon became the most notorious guerilla in Missouri, which attracted bloodthirsty recruits, including Jesse James.

In the “Little Dixie” region of Missouri, Anderson staged a raid. On Sept. 27, 1864, after robbing Congressman James S. Collins, Anderson proceeded to capture a Union passenger train and murder 22 furloughed Union soldiers who had surrendered.

Anderson and his men were pursued by a Union infantry in Missouri. After the “Battle of Centralia“, a minor skirmish that took place during the day, Anderson and his men ambushed the outgunned Union pursuers. Anderson and his men mutilated and tortured the men.


Anderson, who acted out of suspected emotional distress, following the death and scalping of men of his own, told the captives, “You Federals have just killed six of my men, scalped them, and left them on the prairie. I will show you that I can kill men with as much skill and rapidity as anybody. From this time on, I ask no quarter and give none.”

These murders became known as the Centralia Massacre.

Union soldiers heavily pursued Anderson and his men, who looted and tortured Union sympathizers after escaping from Centralia. Eventually, Lt. Col. Samuel P. Cox caught up with Anderson and his men.

On Oct. 27, 1864, a brief battle took place, during which Anderson died after he was shot through the head.

Union soldiers photographed and paraded his body through the streets of Richmond, Missouri, and Cox became a Union hero.

William “Bloody Bill” Anderson dead via Wikimedia

Anderson’s death would later become the motivation for the 1869 Jesse James bank robbery in Gallatin Missouri, in which he mistakenly shot someone he believed was Cox.

Editors note: A special thank you to the efforts of Civil War on the Western Border, Legends of America, and the Columbia Missourian for their contributions to this story.