Ride with the Devil 1999

The American Civil War is about to break out and best friends Jake Roedel and Jack Bull Chiles find themselves thrust into battle when Union marauders destroy Jack's family plantation. They join the Bushwackers, a skilled unit of guerilla-style fighters, and fight side-by-side until some of the members begin to distrust Jake and his Union sympathizing father. Jake becomes isolated from the gang and strikes up a friendship with Holt, a former black slave, as his seperation from Jack takes one final, deadly turn.