Anne Bonny

Medium humanoid (human), chaotic neutral rogue (thief) 5/fighter (sharpshooter) 5

Armor Class 16 (studded leather)
Hit Points 60 (5d8+5d10+10)
Speed 40 ft.

STR	DEX	CON	INT	WIS	CHA
12 (+1)	18 (+4)	12 (+1)	13 (+1)	12 (+1)	14 (+2)

Saving Throws Dex +8, Int +5
Skills Athletics +5, Deception +9, Insight +5, Perception +5, Persuasion +9, Stealth +8; artisan’s tools (pick one) +5, navigator’s tools +5, thieves’ tools +8, vehicles (water) +8
Senses passive Perception 15
Languages English, Gaelic, Thieves’ Cant
Challenge 6 (2,300 XP)

Special Traits

• Action Surge (1/short Rest). On her turn, Anne can take an additional action on top of her regular action and a possible bonus action.
• Cunning Action (1/turn). Anne can use a bonus action to take the Dash, Disengage, Hide, Use Object action, to make a Dexterity (Sleight of Hand) check, or to use thieves’ tools to disarm a trap or open a lock.
• Excellent Aim (3/short Rest). Anne can spend a bonus action to aim a wielded ranged weapon at a target within its range. Until the end of her turn, ranged attacks that Anne makes against the target deal an extra 4 damage. fight. In the months to come if you’re planning on doing some
• Second-Story Work. Climbing does not cost Anne extra movement. When she makes a running jump, the distance she covers increases by 4 feet.
• Second Wind (1/short Rest). On her turn, Anne can use a bonus action to regain 1d10+5 hit points.
• Sneak Attack (1/turn). Anne deals an extra 10 (3d6) damage when she hits a target with a weapon attack and has advantage on the attack roll, or when the target is within 5 feet of an ally of Anne’s that isn’t incapacitated and Anne doesn’t have disadvantage on the attack roll.
• Mobility. Anne can Dash through difficult terrain without requiring additional movement. Whenever she makes an attack against a creature, she doesn’t provoke opportunity attacks from that creature until the end of her turn.

Actions

• Multiattack. Anne attacks twice when she takes the Attack action.
• Cutlass. Melee Weapon Attack: +8 to hit, reach 5 ft., one target. Hit: 7 (1d6+4) slashing damage.
• Pistol (4). Ranged Weapon Attack: +8 to hit, range 30/90 ft., one target. Hit: 9 (1d10+4) piercing damage.

Reactions

• Uncanny Dodge. When an attacker Anne can see hits her with an attack, Anne can use her reaction to halve the attack’s damage against her.

About

Born as the illegitimate child of William McCormac and one of his servant girls (Mary Brennan) sometime around 1700, Anne mostly grew up in London while disguised as a boy. Eventually her father’s charade failed, he lost his allowance from his wife, and then they moved (along with Mary) to the Province of Carolina. of note from this time: Anne’s mother passed away when she was 12, the next year she used a knife to stab another girl, she met and married James Bonny, and her father disowned her because he disapproved of her husband. Sometime before 1718 the pair moved to Nassau, the Republic of Pirates, where James became an informant for the royally appointed governor.

Anne was not a fan of her husband’s snitching and soon fell in with John Rackham a.k.a. Calico Jack, becoming both his lover and (disguised as a man) a member of his crew.

Together they had a child (for the pregnancy and birth she stayed in Cuba) and went about pirating for a couple of years aboard a ship they stole called William—until Jonathan Barnet captured Calico Jack’s (at the time very drunk) crew. Everyone else got the rope but Anne and Mary Read “pleaded their bellies”, using pregnancy to get a stay of execution until their babies were out.

Nobody is certain what happened to Anne Bonny after that. Signs point to her not dying in prison, however where she ended up is a mystery. Did she head back to the colonies to remarry and raise a family? Take up a new identity for some piracy on the high seas? Spend decades incarcerated and perishing in Jamaica as an old woman? We might never know!

Anne is able to acquire passage on a sailing ship for her and her allies free of charge. She has no control over the ship’s route, departure, or return, and although no coin is required she and her companions do have to help crew the vessel.