After his father was killed in a dispute in 1862, Anderson and his brother Jim gunned down the killer and then moved back to western Missouri. Anderson became the head of a band of guerillas, and his activities cast a shadow of suspicion over the rest of his family. The Union commander along the border, General Thomas Ewing, arrested several wives and sisters of another notorious band, led by William Quantrill, that was terrorizing and murdering Union sympathizers. While Anderson commanded his own band, he often collaborated with Quantrill’s larger force. As a result, the group Ewing arrested also included three of Anderson’s sisters, who were imprisoned in a temporary Union jail in Kansas City, Missouri. On August 14, 1863, the structure collapsed, killing one of Anderson’s sisters along with several other women. Quantrill assembled more than 400 men to exact revenge against the abolitionist community of Lawrence, Kansas. On August 21, the band killed at least 150 residents and burned much of the town. Anderson was credited with 14 murders that day.
Anderson went to Texas that winter, married, and returned to Missouri in 1864 with a band of about 50 fighters. He embarked on a summer of violence, leading his group on a campaign that killed hundreds and caused extensive damage. The climax came on September 27, when Anderson’s gang joined with several others to pillage the town of Centralia, Missouri. When more than 100 Union soldiers pursued them, the guerillas ambushed and massacred the entire detachment. Just a month later, on October 26, Anderson’s band was caught in a Union ambush outside of Albany, Missouri, and Anderson was killed. The body of the “blood-drenched savage,” as he became known in the area, was placed on public display. Anderson kept a rope to record his killings, and there were reportedly 54 knots in it at the time of his death.
