A further order forcing the conscription of all able-bodied men into Union militias convinced many young men in Missouri to join the guerrillas instead. The guerrillas responded with a policy of no quarter, and black flags began to appear in the rebel ranks. Halleck issued an order in March 1862 that declared the Confederate guerrillas to be outlaws subject to summary execution. Lane became known as the “Grim Chieftain.”

There they burned down the entire town of Osceola and executed nine male civilians. Senator Jim Lane, for example, led his Jayhawkers into Missouri in September 1861. The activities of the Jayhawkers were even more counter-productive – Union General Henry Halleck complained that their outrages had done as much for the enemy in Missouri as could be done by 20,000 Confederate troops. While it is possible that at least half the Missouri population were against secession, repressive measures by out-of-state Union forces turned many into reluctant supporters of the Southern cause. It was the first public sign of the combination of vicious anger and callous regard for life that would characterize his short career as a guerrilla leader.

Baxter shot himself in the head to escape death in the flames, and the boy escaped through a window but soon died from his terrible injuries.

Both Baxter and his 16-year-old brother-in-law were wounded by the Andersons, who then locked them in the cellar of their house and set it on fire. In May 1862, Bill and Jim took revenge on a man named Baxter who had killed their father in a dispute.

Soon Bill was mounting small raids into Missouri, though his devotion to the Confederate cause was questionable – he told a friend he was trying to recruit that he didn’t care anything about the South, but there was good money in bushwacking. When the war started, the 21-year-old Bill appeared to be running a business in stolen horses with his younger brother Jim. The Jayhawkers typically had access to Union arms and supplies while the guerrillas depended on foraging and the support of pro-secession families.īill Anderson arrived in Kansas as a child in 1857 along with his Southern parents, two brothers, and three sisters. By the time the war started, Missouri’s pro-rebel guerrillas were known as “Bushwackers,” while their pro-Federal counterparts in Kansas were known as “Jayhawkers” or “Redlegs” from their preference for red pants as a type of uniform. Fueling this conflict was a dispute over whether Kansas should be a slave-holding state or not. A low-level conflict had already been raging in the Missouri-Kansas borderlands in the years preceding the outbreak of the Civil War.

Bloody Bill Anderson by Thomas Goodrich