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Anne Bonny, Dread Corsair of the Tides

Anne Bonny
My Images (midjourney.com)
  • Alias: Anne Bonny
  • Gender: Female
  • Race: Human
  • Occupation: Pirate
  • Religion: Not specified
  • Allies: Fellow pirates and crew members
  • Enemies: Naval authorities and rival pirates
  • Abode/Base of Operations: Nassau and various pirate strongholds and ships
  • Nationality: Irish
  • Languages: English
  • Alignment: Chaotic Neutral
  • Affiliation(s): Pirate crews and the pirate lifestyle, Brethren of the Coast
  • Significant Others: Calico Jack Rackham (fellow pirate and possibly lover), Significant others –  Mary Read

Anne Bonny, a woman of undeniable charisma and unrivaled audacity, sails the tumultuous seas with a fiery spirit that matches the blaze of her notorious red hair. Unfazed by societal expectations, Anne scoffs at the norms that confine women, preferring the freedom of the open ocean. Her heart pulses with the rhythm of the waves, and her every step on the ship’s deck resonates with the thunderous beat of her adventurous soul.

Fear is a foreign concept to Anne; instead, she embraces the thrill of uncertainty. The rolling waves, the clash of swords, and the creaking timbers beneath her feet only heighten her senses. Her swift maneuvers and keen eyes have made her an unparalleled force in the world of piracy. Anne Bonny navigates through treacherous waters with a devil-may-care attitude, challenging both the elements and the authorities that seek to restrain her.

Driven by a deep-seated desire for autonomy, Anne’s rebellious spirit is the compass that guides her. She spurns the constraints of a conventional life, reveling in the chaos of the pirate’s existence. Loyalty is earned, not given freely, and Anne aligns herself with those who share her vision of freedom on the open seas. Her cunning mind and sharp blade are formidable tools, carving a path towards the fulfillment of her ambitions.

What Anne seeks transcends mere riches or infamy; she yearns for a legacy that echoes across the waves, a tale of a woman who defied norms and left an indelible mark on the pages of history. With every plundered ship, every daring escape, and every clash of swords, Anne Bonny forges her destiny as a pirate queen, unshackled and unyielding in her pursuit of a life unrestrained.


  • Anne Bonny 5e
  • Anne Bonny 5e
Anne Bonny

Medium humanoid (human), neutral

Armor Class 15 (leather armor) Hit Points 112 (15d8 + 45) Speed 30 ft.

STRDEXCONINTWISCHA
12 (+1)18 (+4)16 (+3)14 (+2)12 (+1)18 (+4)

Skills Acrobatics +7, Athletics +4, Intimidation +7, Perception +4 Senses Passive Perception 14 Languages Common, Thieves’ Cant Challenge 6 (2,300 XP)

Actions

  • Multiattack. Anne Bonny makes two cutlass attacks.
  • Cutlass. Melee Weapon Attack: +6 to hit, reach 5 ft., one target. Hit: 8 (1d8 + 4) slashing damage.
  • Pistol Shot. Ranged Weapon Attack: +7 to hit, range 30/90 ft., one target. Hit: 10 (1d10 + 4) piercing damage.

Reactions

  • Parry. Anne Bonny adds 2 to her AC against one melee attack that would hit her. To do so, Anne must see the attacker and be wielding a melee weapon.

Legendary Actions Anne Bonny can take 3 legendary actions, choosing from the options below. Only one legendary action option can be used at a time and only at the end of another creature’s turn. Anne regains spent legendary actions at the start of her turn.

  • Move. Anne Bonny moves up to her speed without provoking opportunity attacks.
  • Cutlass Attack. Anne makes one cutlass attack.
  • Intimidating Presence (Costs 2 Actions). Anne issues a menacing challenge. Each creature of Anne’s choice within 30 feet of her that can see and hear her must succeed on a DC 15 Wisdom saving throw or be frightened until the end of Anne’s next turn.

Equipment Anne Bonny carries a cutlass, a brace of pistols, leather armor, and a pirate’s tricorn hat. She also possesses a treasure map hinting at the location of a legendary pirate hoard.

Roleplaying Notes Anne Bonny, known for her fiery spirit, is a masterful swordsman and skilled pistol marksman. With a fierce loyalty to her crew, she navigates the high seas in search of fortune and adventure. Her intimidating presence strikes fear into the hearts of those who dare cross her path. Anne’s legendary actions represent her agility and combat prowess, making her a formidable adversary on land or sea.

Mythological Figures takes to the high seas once again, this time in pursuit of the pirate that may be Ireland’s fiercest, most notorious buccaneer: the one and only Anne Bonny!

Originally Posted by Mike Myler on the Enworld forums.

On this Thread

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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!

Design Notes: Anne here was a pretty easy build to approach—a solid combatant and a crafty rogue. She’s a reliable pirate and sailor, and she can hold her own in a fight. In the months to come if you’re planning on doing some adventuring on the water and need a ship full of formidable pirates, her build should be simple enough to make crewmembers challenging for higher level PCs but not overly complicated. 

Anne Bonny
The woman pirate Anne Bonney (1697-1720). 18th centrury engraving.

Anne Bonny
Medium humanoid (human), chaotic neutral rogue (thief) 4/fighter (archer) 5
Armor Class 16 (studded leather)
Hit Points 60 (5d8+5d10+10)
Speed 30 ft.

STRDEXCONINTWISCHA
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
Tools artisan’s tools (pick one) +4, navigator’s tools +4, thieves’ tools +4, vehicles (water) +4
Senses passive Perception 15
Languages English, Gaelic, Thieves’ Cant
Challenge 6 (2,300 XP)

Background: Nautical. 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.

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 take 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.

Feat: Mobile. 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.

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.

ACTIONS
Extra Attack. Anne attacks twice.

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.

Currently in the World

Anne Bonny stands proudly on the weathered deck of her ship, the salty breeze tousling her vibrant red locks. Her piercing blue eyes, full of mirth and mischief, survey the vast expanse of the open sea. Clad in a worn leather jacket that bears the scars of countless adventures, she exudes an air of both danger and allure. Anne’s breeches and knee-high boots, well-worn from a life at sea, hint at the untamed spirit that courses through her veins.

The sun dips low on the horizon, casting a warm, golden hue over the deck. Anne’s ensemble is adorned with trinkets and tokens collected from various conquests – a testament to her fearless exploits. A cutlass hangs confidently from her belt, its gleaming edge reflecting the fading sunlight. Anne’s mood is one of exhilaration, her heart racing with the thrill of the open ocean and the promise of untold treasures on the horizon.

Surrounded by the rhythmic sounds of lapping waves and the creaking of the ship, Anne Bonny revels in the camaraderie of her crew. Laughter echoes across the deck as they share tales of past victories and dream of the spoils yet to come. The mood is light, yet an undercurrent of determination pulses through the air, for Anne is a captain who leads with both charisma and unwavering resolve.

As the last rays of sunlight dip below the sea’s edge, Anne’s silhouette is etched against the deepening hues of twilight. Her gaze remains fixed on the vastness before her, a canvas of endless possibilities. In the fading light, Anne Bonny, the fearless pirate queen, prepares for another night of adventure on the high seas.

Historically Anne’s story

Romantically involved with and sailing on the crew of Calico Jack Rackham. Anne Bonny is a female pirate fighting in men’s clothing, an expert with pistol and sword, considered as dangerous as any male pirate. She is fearless in battle and often is a member of a boarding party.

The daughter of an attorney and his Maid. The lawyer left Ireland in disgrace but found fortune in the Carolinas. There, he amassed a fortune and bought a large plantation.

A ne’er-do-well pirate/sailor named James Bonny married Anne in an attempt to steal the plantation but Anne’s father instead disowned her. Bonny then took Anne to the Bahamas where he turned informer to Governor Woodes Rogers, turning in any sailor he didn’t like as a pirate for a handsome reward.

Anne quickly grew to dislike her spineless husband and quickly caught the eye of one Calico Jack Rackham, a pirate of some renown. Governor Rogers had recently passed an amnesty for pirates which left Bonny out of work. The admiration between Anne and Calico was mutual. Calico Jack a handsome man who knew how to spend money as well as steal it. Anne was a well endowed lass with a fiery spirit and a temper that matched that of any man.

Calico offered to buy Anne from Bonny but Bonny instead took the matter up with Governor Rogers, who had Anne flogged and returned to her true husband.

That night Calico and Anne slipped out in the harbor, stole a sloop and began a life of piracy together.

But retribution is close at hand. The governor hearing of Calico’s treachery has sent an armed sloop captained by James Bonny to hunt the Captain and crew.

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