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Stede Bonnet, ‘The Gentleman Pirate’

“The Pirate Escapist: The Extraordinary Story of Stede Bonnet, Who Set Sail to Escape His Troublesome Marriage!”

Stede Bonnet, 'The Gentleman Pirate'
  • Alias: The Gentleman Pirate
  • Gender: Male
  • Race: Human
  • Occupation: Pirate Captain
  • Religion: Not specified
  • Allies: Benjamin Hornigold, Edward Teach (Blackbeard), pirate crews
  • Enemies: Naval authorities, rival pirates, forces of law and order
  • Abode/Base of Operations: Pirate ships and hideouts in the Atlantic Ocean, along the East Coast of the British Colonies, and the Caribbean Sea
  • Nationality: Barbadian (English)
  • Languages: English
  • Alignment: Chaotic Neutral
  • Affiliation(s): Pirate Brotherhood, informal alliances with other pirates
  • Significant Others: Mary Allamby (wife), Edward Bonnet (son), Allamby Bonnet (son), Stede Bonnet Jr. (son), Mary Bonnet (daughter)

    Stede Bonnet, a wealthy plantation owner from Barbados, finds himself trapped in a troubled marriage and burdened by the responsibilities of his life. Longing for freedom and a taste of adventure, he becomes increasingly disillusioned with his mundane existence. The allure of the sea and the stories of daring pirates become an irresistible temptation, offering an escape from his troubles and a chance to start anew.

    Driven by a yearning to break free from the shackles of his mundane life, Bonnet makes a radical decision. He abandons his comfortable plantation and sets sail, seeking a new identity as a pirate. Despite his lack of seafaring experience, he immerses himself in the pirate world, aligning himself with notorious figures such as Benjamin Hornigold and Edward ‘Blackbeard’ Teach.

    As Bonnet embraces the life of a pirate, he discovers a hidden side of himself. The thrill of the open sea, the camaraderie among fellow outlaws, and the spoils of plunder become his new reality. He strives to prove his worth and establish a reputation among the pirate fraternity, eager to shed his former life and carve out a new existence as a feared and respected pirate captain.

    Along his journey, Bonnet faces numerous challenges and dangers. He engages in fierce battles on the high seas, captures valuable prizes, and navigates the treacherous waters of pirate politics. Despite his initial lack of experience, he learns to adapt, displaying resourcefulness and determination in the face of adversity.

    However, Bonnet’s life as a pirate is not without its consequences. The authorities are relentless in their pursuit of him, branding him a criminal and a threat to the established order. Eventually, Bonnet’s luck runs out, and he is captured at Sullivan’s Island. His journey of rebellion and self-discovery comes to a tragic end as he faces trial and is ultimately hanged in Charleston.

    Stede Bonnet’s story is one of personal transformation, driven by a yearning for freedom and adventure. It is a tale of a man who, in his pursuit of a life beyond the confines of societal norms, finds himself entangled in a world of piracy, danger, and ultimately, his own downfall.

    Stede Bonnet, The Gentleman Pirate

    Print engraving of Stede Bonnet in Charles Johnson's A General History of the Pyrates Date circa 1725, Stede Bonnet
    Print engraving of Stede Bonnet in Charles Johnson’s A General History of the Pyrates Date circa 1725

    Stede Bonnet, The Gentleman Pirate

    Medium humanoid (human), neutral evil

    Armor Class 15 (studded leather) Hit Points 135 (18d8 + 54) Speed 30 ft.

    12 (+1)16 (+3)16 (+3)12 (+1)10 (+0)14 (+2)

    Saving Throws Dex +7, Con +7 Skills Athletics +4, Deception +6, Perception +3, Stealth +7 Senses passive Perception 13 Languages Common, Thieves’ Cant Challenge 7 (2,900 XP)


    Multiattack. Stede Bonnet makes two melee attacks: one with his rapier and one with his main-gauche.

    • Rapier. Melee Weapon Attack: +7 to hit, reach 5 ft., one target. Hit: 8 (1d8 + 4) piercing damage.
    • Main-gauche. Melee Weapon Attack: +7 to hit, reach 5 ft., one target. Hit: 6 (1d6 + 4) piercing damage.
    • Pistol Shot. Ranged Weapon Attack: +7 to hit, range 40/120 ft., one target. Hit: 10 (2d6 + 3) piercing damage.

    Reactions: Parry. Stede Bonnet adds 3 to his AC against one melee attack that would hit him. To do so, Bonnet must see the attacker and have a rapier or main-gauche in hand.

    Legendary Actions: Stede Bonnet can take 2 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. Stede Bonnet regains spent legendary actions at the start of his turn.

    Riposte. Stede Bonnet makes one rapier attack against a creature that missed him with a melee attack.

    Dirty Trick (Costs 2 Actions). Stede Bonnet attempts a dirty trick to distract or hinder a creature within 5 feet of him. The target must succeed on a DC 15 Wisdom saving throw or be disadvantaged on its next attack roll or ability check.


    • Rapier
    • Main-gauche (Off-hand dagger)
    • Pirate-style clothing
    • Tricorn hat
    • Boots
    • Belt with pouches for ammunition and supplies
    • Belt with various tools and gadgets
    • Bonnet’s Wedding Band (magic item).

    Bonnet’s Wedding Band provides the wearer with a +1 circumstance bonus to saving throws against magic used by females, and a +2 circumstance bonus to opposed skill checks made against women.

    Magic Item

    Bonnet’s Wedding Band

    Ring, legendary (requires attunement)

    This simple gold band, known as Bonnet’s Wedding Band, holds a powerful enchantment that resonates with Stede Bonnet’s desire for freedom from his troubled marriage.


    • While wearing Bonnet’s Wedding Band, you gain a +1 circumstance bonus to saving throws against magic used by female creatures.
    • You also gain a +2 circumstance bonus to opposed skill checks made against women.

    Attunement To attune to Bonnet’s Wedding Band, you must wear the ring for 24 hours and focus on your desire for freedom and independence.

    Characteristics Bonnet’s Wedding Band represents Stede Bonnet’s longing for liberation from his troubled marriage. It serves as a reminder of the sacrifices he made and the path he chose to find his own freedom. The ring symbolizes his determination to break free from the constraints imposed upon him and live life on his own terms.

      Plot Hooks

      • Desperate Allure: The players encounter a wealthy landowner named Stede Bonnet who, dissatisfied with his mundane life, seeks adventurers willing to help him make a daring and unexpected decision. Bonnet offers them a significant reward if they assist him in acquiring a ship and setting sail as pirates. The players must weigh the allure of riches and adventure against the moral implications of joining Bonnet’s life of crime. Their choice will shape their own destiny and test their commitment to their principles.
      • Blackbeard’s Pact: The players find themselves caught between the enigmatic pirate captain Stede Bonnet and the notorious Blackbeard. Bonnet seeks the players’ aid in negotiating a meeting with Blackbeard to discuss a potentially lucrative collaboration. As intermediaries, the players must navigate the treacherous waters of pirate politics, convince Blackbeard of Bonnet’s worth, and broker a pact between the two formidable pirates. The outcome of their diplomatic efforts will determine the balance of power in the pirate world and shape the fate of Bonnet’s future.
      • River of Conflict: The players are thrust into the midst of the Battle of Cape Fear River, where they witness the intense clash between Stede Bonnet’s ship and the forces led by Colonel William Rhett. As the battle unfolds, they must make a difficult choice: assist Bonnet in his fight against overwhelming odds or align themselves with Rhett to bring an end to Bonnet’s reign of piracy. Their decision will have far-reaching consequences, as they become pivotal players in the outcome of this historic conflict.
      • The Pardon’s Dilemma: The players are approached by a high-ranking official who offers them a unique opportunity. They are tasked with convincing the elusive Stede Bonnet to accept a full pardon and abandon his life of piracy once and for all. However, Bonnet is determined to resist and continue his unlawful activities. The players must navigate the treacherous world of pirate hideouts, engage in intense negotiations with Bonnet’s crew, and uncover the deep-rooted motivations behind Bonnet’s defiance. The success or failure of their mission will shape the future of piracy in the region.
      • Escape from the Gallows: The players encounter a desperate Stede Bonnet on the run after his escape from custody. Bonnet pleads for their assistance in evading capture and reclaiming his ship to resume his life as a pirate. As they navigate a web of deceit, pursue leads, and outwit pursuing authorities, the players must decide whether to aid Bonnet in his escape or turn him over to justice. Their choice will determine their own reputation and test their allegiance to the pirate code.
      • Trial of the Damned: The players are thrust into the heart of a high-stakes trial as key witnesses in the case against Stede Bonnet. They must navigate a web of legal proceedings, gather evidence, and confront Bonnet’s charismatic defense attorney who seeks to manipulate the trial’s outcome. As the trial unfolds, the players must decide whether to align with the prosecution, the defense, or even Bonnet himself. The outcome of the trial will not only determine Bonnet’s fate but also shape the perception of justice in the world of piracy.

      Currently in the World

      The Flag of Stede Bonnet is known as "The Pirates Scale." It represents the balance between life and battle. 
      The Flag of Stede Bonnet is known as “The Pirates Scale.” It represents the balance between life and battle.

      Stede Bonnet, a refined gentleman pirate, stands tall and dignified, despite the disheveled state of his appearance. His once pristine powdered wig now bears signs of the sea, with saltwater-streaked curls and a slightly askew positioning. His well-groomed salt and pepper beard, though slightly windswept, retains an air of sophistication. His piercing blue eyes, sharp and perceptive, gaze out from beneath furrowed brows, revealing a mix of determination and weariness earned through his life’s adventures.

      His attire, once lavish and extravagant, now shows signs of wear and tear. The once richly embroidered coat carries faded patterns and patches, a testament to the harsh conditions of life at sea. The shimmering gold thread has dulled, yet glimpses of its former opulence can still be seen. His ruffled cuffs and lace jabot, though slightly tattered, retain a touch of elegance amidst the disarray. Worn leather boots bear the scuffs and scratches of countless treks across the ship’s deck, while his walking cane, once finely crafted, now displays signs of weathering.

      Currently, Stede Bonnet finds himself aboard his weather-beaten ship, the Revenge, sailing across the open seas. The deck beneath his worn boots shows signs of frequent use, with faded wood and patches to reinforce weak spots. Standing at the helm, his calloused hands grip the wheel with steady determination, their roughness contrasting with the refined air he exudes. The salty breeze tousles his disheveled attire, reminding him of the relentless forces of nature that he navigates.

      Surrounded by the vast expanse of the ocean, the horizon stretches endlessly, offering both treacherous challenges and boundless possibilities. The sun’s rays cast a harsh light upon the weathered ship, highlighting the scars and marks that tell tales of past battles and encounters. The rhythmic creaking of the timbers and the relentless crash of the waves against the hull create a symphony of sound, a constant reminder of the rugged life he leads.

      In this moment, Bonnet’s mood is one of resilience and a longing for the comforts of civilization. While his refined demeanor remains intact, there is an underlying fatigue and yearning for respite from the hardships of the pirate’s life. The allure of adventure and the pursuit of wealth still beckon, but the toll of his experiences weighs heavily on his shoulders. Behind his weathered visage lies a complex blend of determination, weariness, and a glimmer of hope for a better tomorrow.

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