A ruthless band of guerillas attacks the town of Lawrence, Kansas, killing every man and boy in sight. The town was an abolitionist, pro-Union stronghold, and the guerillas, led by William Quantrill and William "Bloody Bill" Anderson, were said to have carried out the brutal attack on behalf of the Confederacy. Included in their group was Jesse James' brother Frank and Cole Younger, who would later also play a large role in the James gang.
Bloody Bill Anderson got his name for his love of shooting unarmed and defenseless people. Reportedly, he carried multiple handguns, in addition to a saber and a hatchet. His horse was also outfitted with several rifles and backup pistols. Although he claimed to have political motives for his terrorism, Anderson more likely used the Civil War as an opportunity to kill without repercussion.
Jesse James, only 17 at the time, teamed up with Bloody Bill after he split from Quantrill's band of killers. On September 27, 1864, their small splinter group terrorized and destroyed most of the town of Centralia, Missouri, and killed 22 Union solders. Later that day, they ambushed and killed 150 more Union men. A month later, Anderson paid for his crimes: He was caught by a full contingent of Union army troops in Missouri and killed in the ensuing battle. Jesse James was never brought to justice by the North for his war crimes and went on to become the 19th century's most infamous criminal.