Henry Berry Lowry
Over a complicated series of accusations and incidents regarding thefts and conscription, the Home Guard shot Henry Berry Lowry's father and brother while he watched from hiding. Henry Berry and a group of supporters promptly stole a large quantity of rifles (purchased for the local militia) from the Lumberton courthouse and began an eight-year war to avenge the deaths. Henry Berry Lowry's tri-racial band also, Robin-Hood-like, robbed plantations, often showing up at dinnertime and dining with their hosts before carrying off the plunder in a mule and wagon. They stole two safes (one from the Sheriff's office and one from a large company), leaving them empty on the main street in Lumberton.
Henry Berry Lowry escaped from jail twice.
He and his band were outlawed in 1868--meaning anyone could kill them for the reward. The reward for Henry Berry Lowry climbed to $12,000, the largest offered in the 19th century except for Jesse James and Jefferson Davis.