Jackson O'Reilly is a 17-year-old New Englander who in 1805 sails with his parents on the "Perdido Star" to Cuba, his mother's birthplace, to claim the land she has inherited. But his hopes of a new life descend into violence and revenge. His parents are murdered, their land confiscated and his own life nearly taken, and Jack is forced to rejoin the "Star" as a member of the crew, sailing the world's most treacherous waters under a drink-crazed captain. His soul searched, the boy Jackson O'Reilly becomes the pirate "Black Jack", the relentless scourge of any who stand in his path to retribution.
For Jack remains obsessed with returning to Cuba and finally facing his sworn enemy the Count de Silva, evil incarnate, a murderer's soul breathing beneath his surface charm.