The characters of the tenth adventure path, Skull & Shackles.
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Captain Barnabas Harrigan
Race: Human (Garundi)
Class: Fighter/rogue
Alignment: Neutral Evil
The brutal master of the Wormwood, Harrigan is one of the most feared pirates in the Inner Sea Region. Unbeknownst to almost all, he is currently enslaved to Admiral Druvalia Thrune of Cheliax and, under her orders, is preparing to open the Shackles for a Chelish invasion.
- Archenemy: There are other, more powerful adversaries out there, but few the players will hate more than Harrigan. If he somehow survives his last encounter with the party, he returns with a new identity and a new ship to plague them once again.
- Bald of Evil: He shaves his head completely bald.
- Beard of Evil: He keeps a long, black, heavily braided pirate beard.
- Disc-One Final Boss: Harrigan looks like the Big Bad of the Adventure Path. In reality he's a pawn of Druvalia Thrune, the actual Big Bad, who takes center stage after his defeat in Part 5.
- Eyepatch of Power: In classic piratical style.
- It's Personal: Making the PCs pay for deserting is already quite person for him, but after the party humiliates him at the Free Captains' Regatta taking them down becomes a matter of personal pride.
- Manipulative Bastard: He plays his fellow Pirate Lords and Free Captains off against one another, spreading rumours of treachery throughout the council in order to hide his own deceit.
- The Mole: He's Druvalia Thrune's agent in the Shackles, feeding her information and sowing division in preparation for her invasion.
- Revenge: If he survives The Price of Infamy, Harrigan dedicates his life to vengeance on the PCs.
- Scary Black Man: A huge, intimidating Garundi man.
- Starter Villain: Subverted. Harrigan appears to be this, but parts ways with the PCs early on, leaving them with the real Starter Villain, Mister Plugg.
- Turncoat: After being captured by Druvalia, Harrigan turned his allegiance from the Shackles to Cheliax.
Mister Plugg
Race: Human
Class: Fighter
Alighnment: Neutral Evil
The vicious and sadistic first mate of the Wormwood, Plugg is an angry young man who has never overcome the scars of a life as a dockside beggar in the Shackles. He takes an instant dislike to the players, and does everything he can to make their lives miserable.
- Bald of Evil: He keeps his head bald except for a single long ponytail.
- The Bully: He bullies and harasses all of the players to make up for the fact that he does not truly have the captain's trust.
- The Captain: He becomes captain of the Man's Promise partway through the first part of the Adventure Path. If he somehow survives, he can return with his own ship, the Severe.
- The Dragon: Toyed with. Plugg is first mate, and ostensibly the captain's right hand man, but he has only been onboard a year and has failed to truly penetrate Harrigan's inner circle, which contains many pirates more experienced than himself.
- Hate Sink: He and his henchman, Master Scourge, are there to absorb all the hate that the PCs might otherwise direct towards Harrigan, presenting a CR 4 adversary whom they can eventually beat as a substitute for his CR 15 boss.
- Not So Harmless: If Plugg escapes the PCs at the end of The Wormwood Mutiny, he can return as a Pirate Lord in his own right, with a handpicked crew of cutthroats and a new ship.
- Sadist: He enjoys making his crew suffer, as payback for his rough life.
- Smug Snake: He's relentlessly unpleasant and convinced of his superiority.
- Starter Villain: The mutiny against him is at the core of the first part of the Adventure Path.
Admiral Druvalia Thrune
Race: Human (Chelaxian)
Class: Inquisitor of Geryon
Alignment: Lawful Evil
A distant cousin of Queen Abrogail Thrune, Druvalia is an ambitious social climber who joined the Chelaxian Navy in order to make her reputation. Having cut a deal with the archdevil Geryon for support, Druvalia has suborned Captain Barnabas Harrigan to her will, and aims to bring down the Shackles once and for all.
- Ambition Is Evil: Druvalia's goal is to climb the ranks of Cheliax's aristocracy, no matter how many bodies she drops in the process.
- Aristocrats Are Evil: In Cheliax they certainly are, and, as a member of House Thrune, Druvalia is more evil than most.
- The Big Bad: Druvalia may not be the most powerful adversary the PCs will encounter in the campaign, but everything that happens to them, from being press-ganged onward to the final violent confrontation with Bonefist, is a direct result of her manipulation of Harrigan and subsequent assault on the Shackles.
- Bow and Sword in Accord: Crossbow and mace actually, but the result is the same.
- The Chessmaster: Everything that happens to the players transpires according to Druvalia's design.
- Dark Action Girl: Druvalia's a capable fighter, boasting a respectable CR of 13.
- Deal with the Devil: She bargained with Geryon for an army of devils to support her invasion of the Shackles. If Druvalia's plan fails, Geryon will take her soul.
- Despotism Justifies the Means: Putting Cheliax's boot on the Shackles' throat justifies anything to Druvalia, including risking her own soul via a deal with Geryon.
- Enfante Terrible: In the backstory. Druvalia had a penchant for blackmail even as a child, and was eventually shipped off to boarding school after she tried it on her own mother.
- Even Evil Has Loved Ones: She genuinely loves Valeria, who is probably the only person she actually trusts.
- The Family That Slays Together: Druvalia's mother is a rapist who enjoys preying on peasant men. Her cousin Queen Abrogail II is the autocratic tyrant of one of Avistan's most repressive nations. Her great-uncle is a fellow devil-worshipper and the one who helped her make contact with Geryon. Her cousin Barzillai is the main villain of the Hell's Rebels Adventure Path. Suffice it to say, most of the Thrunes are bad news.
- Fate Worse than Death: If Druvalia is killed, Geryon claims her soul, a fate far worse than simply dying.
- Four-Star Badass: An admiral in the Chelish Navy, an inquisitor of Geryon who can more than hold her own in combat, and commander of the invasion herself from her flagship Abrogail's Fury.
- Glory Hound: All Druvalia's crimes are committed with the intent of bolstering her own reputation.
- Improbable Age: As an admiral in her early thirties, Druvalia knows she's looked at as little more than a product of nepotism. One of her major objectives is to change people's views.
- Insane Admiral: A Chelish admiral who sold her soul to Geryon for higher social status and a shot at crushing the Shackles.
- Knight Templar: Piracy undoubtedly needs to be stamped out, but the lengths Druvalia goes to are insane.
- The Man Behind the Man: She's the one holding Harrigan's leash.
- Manipulative Bastard: Druvalia has been blackmailing people since she was a child and is an expert in using their desires against them.
- Nepotism: How she got her job. She's kept it through talent and her deal with Geryon.
- Psycho Lesbian: Averted. Druvalia's relationship with Valeria is one of her few redeeming qualities — while the relationship isn't really equal or fair, Druvalia still feels genuine affection for the other girl.
- Royals Who Actually Do Something: Druvalia's a leading figure in the Chelish Navy, making her a far cry from your average, idle aristocrat.
Paralictor Valeria Asperixus
Race: Human (Chelaxian)
Class: Fighter (polearm master)/Hellknight
Alignment: Lawful Evil
A simple peasant girl who became a servant in Druvalia Thrune's household, Valeria is the Admiral's confidante and lover, and would be her only friend if it weren't for the class divide between them. When Druvalia entered the Naval Academy, Valeria was apprenticed to the Hellknight Order of the Scourge, so as to better serve her mistress and rose to the rank of paralictor.
- Bodyguarding a Badass: Thanks to her pact with Geryon, Druvalia is actually a more dangerous combatant than Valeria.
- Dark Action Girl: A female Hellknight.
- The Dragon: She acts as Druvalia's bodyguard and right hand.
- Dumb Muscle: A very rare female example. Valeria's tough, but about as dumb as a box of rocks. She has an Intelligence score of 8 and is repeatedly described as simple-minded.
- Even Evil Has Loved Ones: She's madly in love with Druvalia.
- Knight Templar: As per the usual for a Hellknight, she firmly believes that enforcing order and obedience justifies ridiculous levels of force and oppression.
- Psycho Lesbian: Averted. Valeria's love for, and loyalty to, Druvalia, is her main redeeming quality.
- Spikes of Villainy: Her armour is covered with them.
- Undying Loyalty: Valeria is unquestioningly, slavishly loyal the Thrunes as a group and Druvalia in particular — insofar as she's concerned, the House of Thrune is an exalted nobility that can do no wrong and serving it utterly is the highest calling a commoner like her can aspire to.
Kerdak Bonefist, the Hurricane King
Race: Human
Class: Fighter/Inner Sea Pirate
Alignment: Neutral Evil
The reigning Hurricane King, Kerdak Bonefist has grown increasingly paranoid and distrustful as he edges towards the 40th year of his rule. Dismissive of the threat from Druvalia Thrune, the Hurricane King would rather let his kingdom go down in flames than trust the players.
- Asskicking Leads to Leadership: A pirate can only be Hurricane King for as long as he can hold Port Peril and the Hurricane Crown. Bonefist has held it longer than any before him, and is the strongest opponent the players will fight in the Adventure Path.
- Bad Boss: He would sooner see his confederacy collapse than trust any of his subordinates.
- The Captain: Of the Filthy Lucre.
- Final Boss: Bonefist has little to do with the plot, but once the revolution against him begins, he will be the final adversary whom the protagonists face.
- The Gunslinger: One of the only characters in the Adventure Path to carry a firearm, though he's not of the actual Gunslinger class.
- King of Thieves: As Hurricane King, Bonefist is the ruler of the pirates and Free Captains of the Shackles, and the leading political and criminal power in the islands.
- Orcus on His Throne: An even more extreme case than usual. Bonefist has essentially nothing to do with the plot, and remains in his headquarters until the players try to overthrow him at the end.
- The Paranoiac: Bonefist no longer trusts anyone, believing that most of his subordinates are simply after his crown.
- Red Right Hand: One of his hands was reduced to a skeleton via a curse.
- Seadog Beard: He sports and impressive and archetypal black beard.
- Unholy Matrimony: With his lamia girlfriend, whom he genuinely loves.
First Mate Tsadok Goldtooth
Race: Half-orc
Class: Barbarian (Scarred Rager)
Alignment: Chaotic Evil
The brutal first mate of the Filthy Lucre, Tsadok is a former gladiator rescued from slavery by Kerdak Bonefist, who made the grateful half-orc his right-hand man. As Bonefist has withdrawn from the business of actually ruling the Shackles, Tsadok has become increasingly erratic and violent as he attempts to maintain order in the islands through sheer terror.
- Appropriated Appellation: The nickname "Goldtooth" was slapped on him because of how yellow his tusks had become. Tsadok now sports actual gold inlays for his teeth in order to make the name his own.
- The Berserker: Like most Barbarians, this is a part of Tsadok's class function.
- Cool Sword: His +1 furious falchion.
- The Dragon: To Kerdak Bonefist.
- Good Scars, Evil Scars: Tsadok is covered with brand marks and scars from his days in the fighting pits.
- The Gunslinger: He's a Barbarian rather than a member of the Gunslinger class, but still comes armed with a doubleshot pepperbox.
- Undying Loyalty: To Kerdak, who saved him from slavery.
