Jackboy was born into slavery on a Barbados sugar plantation. His constant attempts to escape finally pushed the masters too far. They punished the whole family by splitting them up and selling them off. His father’s last words had been, “It’s okay, son, don’t never give up.”

Several years later, wracked by guilt, but still obsessed with freedom, he slips away from a South Carolina tobacco plantation and outsmarts the Confederacy’s most vicious slave patrol captain who is hot on his trail. He swims across the Savannah River and taunts his pursuers by hurling obscenities at them from the opposite bank.

After days of searching for the safety of Sherman’s Army in Georgia, he stumbles across a Confederate soldier behind enemy lines and gets into a life or death fight. A maverick Union lieutenant named Jack Johnson happens upon him just as he is about to bash in the skull of this rebel sniper the officer has been chasing for days. After taking control of the situation and assuring Jackboy that he is safe, Johnson interrogates the young man and discovers he is remarkably intelligent and resourceful. He takes Jackboy under his wing, enlists him into the army, and teaches him to read, write, and use a gun.

Jackboy is beguiled and confused as he witnesses the soft-spoken young officer transform into a cold-blooded battlefield killer with his small squad of seasoned troops wielding sixteen shot Henry repeating rifles. When Jackboy asks him about it, Johnson says, “My folks had money and sent me to war with a dozen Henrys. They told me to use them wisely and not to come home dead. I only hand them out to a few veteran soldiers I really trust. We’re usually outnumbered, but we’re never out-gunned. I figure the faster we kill them all the safer my men will be.” Jackboy embraces the logic and hopes to be in that rare company one day..