He wasn’t to change much as he grew older. Purportedly, this bad seed would shoot pigs through the ears to hear them squeal, nail snakes to trees, and tie cats’ tails together for the pure joy of watching them claw each other to death. Leader of the most savage fighting band in the Bleeding Kansas/Missouri Border War, William Quantrill, will long be known as the most ruthless bushwhacker during these turbulent times.īorn on July 31, 1837, to Thomas Henry and Caroline Cornelia (Clarke) Quantrill, the boy displayed his cruel tendencies even as a child. He attracted to his gang some of the most psychopathic killers in American history. Without any ties to the South or to slavery, he chose the Confederacy apparently because, in Missouri, this allowed him to attack all symbols of authority.