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The crew of Hunters expedition, and his privateer, the Cassandra.
Charles Hunter:The main protagonist of the book, Charles Hunter is regarded as one of the best privateers in Jamaica. In spite of his personality and attitude, he has a classical education, and is inheritantly badass.
- Awesome McCool Name: Admit it, you'd wish you were called Hunter.
- An Ax To Grind: How he decides to kill the kraken.
- Anti-Hero: Bordering on Villain Protagonist. His only really good attributes is that he has a sense of honor, is loyal to his men, and that his adversaries—Cazalla, and then later the likes of a Cannibal Clan and Hacklett—are ultimately even worse.
- Bad Ass Beard
- Brilliant, but Lazy: Actually educated at Harvard, but fails to see the use of knowing classical mathematics, in practical use.
- The Captain
- The Casanova: His habits as a womanizer are well-known.
- Genius Bruiser: His education.
- Handsome Lech: See The Casanova.
- The Hero
- You Killed My Father: Played with. Cazalla killed his brother, but for the most part, Hunter took this expedition because he's Mostly In It For The Money.
Enders:The "sea artist", regarded as the best sailor in the Caribbean, he is hired by Hunter as the steerer to his ship, the Cassandra. Is also a Doctor in Port Royal, and his skills repeatedly saves the crew.
- Deadly Doctor: The only one in Port Royal who isn't one.
- Dropped a Bridge on Him: A year after the book, he is killed in a storm.
- The Lancer: Though he could go as The Smart Guy.
- The Red Baron: The sea wizard, and the sea artist.
Lazue:A corruption of the name Les Yeux, Lazue is a woman, having lived most of her life disguised as a man, and despite the fact that most know her secret, keeps going on with her life as a man. Her breasts can be very distractive to her enemies.
- Action Girl
- Belligerent Sexual Tension: With Enders.
- The Chick
- My Sibling Will Live Through Me: Started her male life, because she had to be disguised as her dead brother, lest her mothers philandery would be exposed.
- Show Some Leg: The distraction of the spaniards, mentioned below.
- Sweet Polly Oliver
- We Need a Distraction: She brutally distracts and murders several Spaniards at Matanceros, be exposing her breasts, then slicing their throats.
- Wholesome Crossdresser
Don Diego de RamanoAlso known as Black Eye, or the Jew, Don Diego is an old, Spanish gunpowder expert, living in Port Royal. His skills in gunpowder, makes him useful for Hunters expedition.
- Bad Ass Spaniard
- Cool Old Guy
- Fingore: Lost all his fingers in the backstory.
- Handicapped Bad Ass: His right hand has lost all its fingers.
- The Red Baron: Black Eye, and The Jew
- The Smart Guy: A straighter example than Enders, due to his skills with gunpowder.
- You Killed My Father: Cazalla tortured and killed his son.
BassaAlso known as The Moor, Bassa is a former slave, from Nubia, whose wife was killed by a slave owner whom he killed. He is the brute force of the crew.
- The Big Guy
- A Load of Bull: He got killed by a bull in the epilogue, during the Henry Morgan attack on Panama in 1671.
- Made a Slave: Was in the backstory.
- Scary Black Man: A heroic example.
- Tongue Trauma: Inflicted on him in the backstory, by the slave owner that killed his wife.
- The Voiceless
Andre SansonA large French, former priest, whom Hunter is suspicious of, but still lets join the crew due to his skills as an assassin. Betrays Hunter in the ending, and turns into the final villain of the book.
- The Archer: Uses a crossbow.
- Bad Ass Preacher: He is a priest, though not saintly at all.
- Bad Ass Beard
- The Big Guy: Competes with The Moor.
- Exit, Pursued by a Bear: Getting eaten by sharks.
- French Jerk
- Hoist by His Own Petard: Ends up getting killed by Hunter, using his own crossbow. Rather, the crossbow doesn't kill him, but wounds him, and sends him to the death by the sharks.
- Just Desserts: the sharks, again.
- Sinister Minister: Though he is not a practicing priest anymore.
- Sixth Ranger: Could count as this, since he does not serve any specific purpose to the Five-Man Band.
- Threatening Shark: Sharks are the only creatures on the planet he fears. Gives some karma, in that this is exactly what ends up killing him.
- Weapon of Choice: Always uses a crossbow.
- Why Did It Have to Be Snakes?: He fears nothing but sharks.
Sir James AlmontThe British governor of Jamaica, hiring Hunter to attack Matanceros.
- Cool Old Guy
- Dirty Old Man: Has, at age 55 mind you, a relationship with the 15 year old Anne Sharpe.
- Insistent Terminology: Similar to Hunter, he takes disgust in the word pirate, while finding no problem with privateer.
- Kill It with Fire: Dies a few years after the novel, form the Great London Fire, along with his niece.
- Reasonable Authority Figure
- Surrounded by Idiots: His usual assistants, namely Hacklett and Commander Scott.
Robert Hacklett:The bureaucratic assistant of Almont, he is very loyal to the British crown, and takes it upon him to extort piracy and privateering form Port Royal, and turn it into a more respectable British town. However, despite these somewhat noble intentions, after Hunter's departure, he takes control of the town, imprisons Almont, and starts hanging privateers, stealing their treasures, and finally loses it when letting his wife get raped.
- Big Bad: Of the ending.
- Groin Attack: Dies by getting shot in the groin.
- Hanging Judge: When running the pirate trials.
- Karmic Death: Getting shot in the groin by his wife.
- Obstructive Bureaucrat: Starts as this.
- The Purge: Conducts this after taking over Port Royal, exterminating all privateers and his political enemies. Eventually including Hunter.
- Smug Snake
- Tyrant Takes the Helm: After imprisoning Almont.
- Villainous Breakdown: After realizing Emily is pregnant.
Anne Sharpe:A young girl, 15 or so, that is accused of petty crime in England, having stolen bread, and send to Almont in Jamaica. He starts a relationship with her, and she helps free Hunter, and distracts Sanson in the climax, allowing Hunter to kill him.
- Femme Fatale: Bordering on Fille Fatale.
- The Immodest Orgasm: Used as a signal to Hunter, while she has sex with Sanson in the climax.
- Show Some Leg: All. The. Time.
- The Vamp: Heroic variety.
- We Need a Distraction: She distracts both prison guards and Sanson in the climax.
Emily HacklettThe promiscuous wife of Robert Hacklett, subjected to the misfortune of an impotent husband. S He becomes pregnant during and infraction with Hunter early on, and bears his only son.
- The Dog Bites Back: Shoots Hacklett in the groin, after he has allowed Commander Scott to rape her.
- Really Gets Around
- Your Cheating Heart
Lady Sarah AlmontThe niece of James Almont, taken prisoner by Cazalla at Matanceros, and subsequently rescued by Hunter.
- Brainless Beauty
- Distressed Damsel: Repeatedly. Was captured by Cazalla as a trophy of his conquest, gets kidnapped by the Caribs, and the kraken ambushes her cabin. Hunter saves her every single time.
- Dumb Blonde: Does not know what a hurricane is, and does not understand the way Hunter governs the ship.
- Grande Dame
- The Heart
- Kill It with Fire: Along with her uncle, killed in the Great London Fire.
- The Load: Never really does anything useful to the expedition, and constantly getting herself in danger, both at the hands of the Caribs, and at the tentacles of the kraken.
- Stay in the Kitchen: In response to her Dumb Blonde, and The Load actions, Hunter tells her to stay in her cabin constantly. That is, until the kraken attacks her cabin...
- Took A Level In Bad Ass: It does give her some credit, that she helps her uncle kill the guards to his mansion in the climax.
Commander ScottThe sleazy commander of Port Royals military garrison, and The Dragon to Hacklett, after his takeover.
- The Dragon: To Hacklett.
- Professional Butt-Kisser: Is constantly trying to please Almont, and changes this to Hacklett.
- Smug Snake
- Sociopathic Soldier: Although he seems, just like a Professional Butt-Kisser, when he rapes Emily, he shows to be more than that.
WhisperAn old privateer, and the only survivor of the previous Edmunds expedition towards Matanceros, he has a minor role, to give Hunter the essentials of the island.
- Every Body Calls Him Barkeep: His real name is never revealed.
- Shell-Shocked Veteran: Is scared to death of Cazalla and Matanceros, understandably.
- Slashed Throat: Cazalla slashed his throat, though he survived, which is the reason he whispers.
- Sole Survivor: Of the Edmunds expedition.
RichardsThe butler to Sir James Almont.
CazallaThe Ax-Crazy commander of Matanceros, widely feared by the privateers, for his cruelty and intelligence. He is the main antagonist of most of the story.
- Bad Ass Spaniard
- Bad Ass Beard
- Beard of Evil
- Big Bad: Until his early death.
- But for Me, It Was Tuesday: Does not remember the killing of The Jews son, and Hunters brother.
- Cold-Blooded Torture: Is a wide practitioner of it.
- The Dreaded: Is widely feared by the privateers.
- Drugs Are Bad: He is a coca addict.
- For the Evulz: His primary motivation.
- General Ripper
- Impromptu Tracheotomy: How he is gloriously killed.
- Loves the Sound of Screaming: Said to take pleasure in the agony of his victims.
- Slashed Throat: He likes killing people, including a crewmember this way. He dies in a glorious variation of this.
- The Stoner: Chews coca leaves.
- Villainous Breakdown: After Hunters crew successfully invades Matanceros, he kinda loses it.
BosquetsA renegade French soldier, and the gunnery master at Matanceros, Cazallas second-in-command.
- The Dragon: To Cazalla
- Dragon Ascendant: Takes charge of the warship after Cazallas death.
- The Ghost: He is seen, but always through telescopes, and the protagonists never really meets him.
- Lean and Mean: Described as tall and somewhat thin.
- The Quiet One: Is never heard speaking.
- Satellite Character: To some extent to Cazalla.
The KrakenA vast creature that attacks El Trinidad, the Spanish treasure galleon, under Hunters command, as his final obstacle before Port Royal. Is probably a giant squid.
- Attack of the Monster Appendage: In the beginning of the attack, the only thing the crew sees, are tentacles flinging soldiers into the sea, Hunter only sees the main body of the beast later.
- Animals Not to Scale: Is way larger than real giant squid and colossal squid as well, but being a colossal squid would make it Misplaced Wildlife.
- Combat Tentacles: Obviously.
- Early-Bird Cameo: Although, given the size differences, it is probably not the same individual spotted by Hunter earlier, the crew does see a Giant Squid, that is passive to their presence, even before encountering Bosquets' warship.
- Everything's Squishier with Cephalopods: The arrival of a kraken serves as the only deviation from realism in the book. But it is awesome.
- Eye Scream: Hunter defeats it by plunging an ax into the creature's eye.
- Giant Squid
- Kraken and Leviathan
- Sea Monster