Fleeing from his brutal treatment as an indentured servant on a North Carolina tobacco plantation, fifteen year old orphan Jem Vaughn finds an unexpected rescue by the crew of the pirate ship Ranger. Smuggled aboard, Jem learns a new trade outside the law from the roguish pirate Calico Jack Rackham. Finding courage in the face of danger, Jem fully embraces the adventures of the "sweet trade." Compared with the more straightforward business on board the Ranger, however, Jem finds that life on shore can be a tangled web of relationships. Love and family can be found in unexpected places. Finally, Jem must decide whether to continue sailing with his friend and mentor in their dangerously seductive way of life, or to save himself and Jack, if he can, from the growing threat of capture.