Most "bushwhackers" wore felt hats, pinned up on one side by a crescent or star shaped pin, perhaps a feather or squirrel tail attached. The shirt was generally a hunting shirt of the period with a very large breast pocket that could carry two or three loaded cylinders for his pistol. Trouser legs tucked into knee-high boots with Mexican spurs and about his middle, two holstered .36 caliber Navy Colts and two more inserted in the waistband of his trousers.

The American Civil War, one of the most violent wars ever contested, started in reality in 1850, when the Compromise of 1850 deposed the Missouri Compromise of 1820 and made "popular vote", the way by which the decision would be made to designate a state "free" or "slave". Kansas became the test, Northerners and Southerners both pouring into the territory, voting to make that new state what either side preferred.

Soon, bands of armed men rode through Kansas and Missouri, some from the anti-slavery north, the "Red Legs" and "Jayhawkers". Other bands, representing the pro-slavery point of view rode in from Missouri. These "border ruffians", who soon became known as "bushwhackers", like the "red legs", killed and burned out people with an opposite point of view.