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Bartholomew Roberts ‘Black Bart’, The Dread Pirate

Bartholomew Roberts 'Black Bart'
  • Alias: Black Bart
  • Gender: Male
  • Race: Human
  • Occupation: Pirate Captain
  • Religion: Unspecified
  • Allies: Fellow pirates who served under him, such as Howell Davis and others.
  • Enemies: The naval forces of various nations, including the Royal Navy and Portuguese authorities.
  • Abode/Base of Operations: Various pirate ships, including the Royal Rover, Fortune, Royal Fortune, and others. His piracy operations spanned the coast of the Americas and West Africa.
  • Nationality: Welsh (born in Wales)
  • Languages: English, Pirate Cant
  • Alignment: Chaotic Neutral
  • Affiliation(s): Pirate crews he led during his career.
  • Significant Others: No notable romantic relationships or family mentioned in historical records.

Bartholomew Roberts, known as Black Bart, stands as a legendary figure in the annals of piracy. His name alone is enough to strike fear into the hearts of sailors and merchants alike. Despite his fearsome reputation, he is not a one-dimensional character but rather a complex individual driven by a unique set of motivations and desires.

At his core, Black Bart is a man who fears the mundane and despises the constraints of a conventional life. The allure of a predictable existence with its “thin commons, low wages, and hard labour” holds no appeal for him. Instead, he seeks the thrill of adventure, the taste of freedom, and the promise of riches beyond imagination that only a life of piracy can offer.

What drives Black Bart most is his insatiable desire for power and wealth. He recognizes that in the world of piracy, there is “plenty and satiety, pleasure and ease, liberty and power.” It’s a life where he can dictate his own destiny, amass a fleet of ships, and plunder over 470 prize vessels during his notorious career.

In pursuit of his goals, Black Bart is unrelenting and cunning. His audacious raids and strategic brilliance have earned him the title of the most successful pirate of the Golden Age of Piracy. With every conquest, he inches closer to his ultimate objective: to achieve unparalleled wealth and secure a place in history as a pirate of legendary status.

Bartholomew Roberts with his ship and captured merchant ships in the background. A copper engraving[1] from A History of the Pyrates by Captain Charles Johnson c. 1724
Bartholomew Roberts with his ship and captured merchant ships in the background. A copper engraving[1] from A History of the Pyrates by Captain Charles Johnson c. 1724

Medium humanoid (human), neutral evil

Armor Class 16 (studded leather) Hit Points 144 (17d8 + 68) Speed 30 ft.

14 (+2)18 (+4)18 (+4)14 (+2)14 (+2)20 (+5)

Skills Acrobatics +7, Deception +9, Insight +6, Perception +6, Persuasion +9 Senses passive Perception 16 Languages Common Challenge 12 (8,400 XP)


Multiattack. Black Bart makes three melee attacks: two with his cutlass and one with his pistol.

  • Cutlass. Melee Weapon Attack: +7 to hit, reach 5 ft., one target. Hit: 10 (1d8 + 4) slashing damage.
  • Pistol. Ranged Weapon Attack: +7 to hit, range 30/90 ft., one target. Hit: 9 (1d10 + 4) piercing damage. If the target is within 5 feet of Black Bart, he has disadvantage on the attack roll.

Legendary Actions

Black Bart 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. Black Bart regains spent legendary actions at the start of his turn.

Attack. Black Bart makes one cutlass or pistol attack.

Intimidate (Costs 2 Actions). Black Bart uses his commanding presence to force one creature within 30 feet of him to make a DC 17 Wisdom saving throw. On a failed save, the creature becomes frightened for 1 minute.

Pirate’s Parry (Costs 3 Actions). Black Bart can expend 3 legendary actions to attempt to parry an incoming attack. He adds +4 to his AC for that attack.


Evasion. When Black Bart is subjected to an effect that allows him to make a Dexterity saving throw to take only half damage, he instead takes no damage on a success and half damage on a failure.


  • Cutlass. A finely crafted cutlass adorned with intricate designs.
  • Pistol. A flintlock pistol with a silver-inlaid barrel.
  • Studded Leather Armor. Black Bart’s custom-made, black studded leather armor.
  • Pirate Hat. A feathered tricorn hat that adds an air of intimidation.
  • Pirate’s Compass. A magical compass that always points towards the nearest ship or significant treasure horde.
  • Diamond Cross. A magnificent diamond-studded cross (+5 Charisma-related skill checks, attempts to turn undead, and Sway efforts).

Lair Actions

Black Bart does not have a lair of his own, but his presence can influence the actions of nearby pirates and sea creatures. While aboard his ship or in a coastal environment, he can take one of the following lair actions:

  • Summon Crew. Black Bart calls forth 1d4 loyal pirate allies to join the battle. These allies are under his command and act on his initiative.
  • Sea Shanty. Black Bart begins singing a haunting sea shanty, causing creatures within 60 feet to make a DC 17 Wisdom saving throw. On a failed save, they are charmed and must use their turn to move towards Black Bart.
  • Cursed Waters. Black Bart utters a curse, causing the surrounding waters to churn and become treacherous. This lair action creates difficult terrain in a 30-foot radius centered on Black Bart.
  • Pirate’s Parley. Black Bart invites a single enemy to parley, suspending combat for one minute. If the enemy accepts, they have a chance to negotiate a deal, but Black Bart is always one step ahead.
The Diamond Cross

Magic Item: The Diamond Cross

Item Type: Relic

Rarity: Legendary

Description: The Diamond Cross is a magnificent and historically significant relic, originally intended as a gift to the Pope but now in the possession of the infamous pirate, Bartholomew Roberts. Crafted by a skilled jeweler in New Spain, this cross is a breathtaking work of art. It is made of pure gold adorned with an array of exquisite diamonds, each one meticulously placed to form intricate patterns. The cross itself is a symbol of opulence and power, a testament to the wealth of the New World.


  • Charismatic Aura: When worn, the Diamond Cross bestows upon its wearer an undeniable aura of charisma and authority. This aura grants a +5 enhancement bonus to all Charisma-related skill checks, making the wearer exceptionally persuasive and charming in social interactions.
  • Divine Influence: The cross carries with it a hint of divine favor. It provides a +5 enhancement bonus to attempts to turn undead, making it a potent tool for those who battle creatures of the dark.
  • Sway Mastery: Those who wear the Diamond Cross find themselves exceptionally skilled at swaying others to their cause. It grants a +5 enhancement bonus to all Sway efforts, allowing the wearer to manipulate opinions, negotiate favorable deals, and inspire unwavering loyalty.

History: Originally intended as a gift to the Pope, this priceless artifact was intercepted by pirates before it could reach its destination. Bartholomew Roberts, the fearsome pirate known as Black Bart, claimed it as his own. For him, the Diamond Cross became a symbol of his influence and command, a tangible representation of his prowess as a pirate captain.

Over the years, the Diamond Cross has passed through the hands of various adventurers and treasure seekers, each recognizing its immense power and historical significance. Its allure is undeniable, but its history is fraught with bloodshed and piracy.

Note: The Diamond Cross is a legendary relic of immense value and power. Its abilities can greatly influence the course of events in any campaign and should be used judiciously by the Game Master.

Currently in the World

He's designed a flag for himself, portraying a giant figure of himself standing, sword in hand, astride two skulls labelled A.B.H. ("a Barbadian's head") and A.M.H. ("a Martinican's head").
He’s designed a flag for himself, portraying a giant figure of himself standing, sword in hand, astride two skulls labelled A.B.H. (“a Barbadian’s head”) and A.M.H. (“a Martinican’s head”).

Black Bart stands tall and imposing, his weathered face bearing the scars of countless battles beneath a tangle of dark, salt-stiffened hair. His piercing eyes, as deep and foreboding as the unforgiving sea, hold a fierce determination. A black tricorn hat with a macabre red feather rests atop his head, casting a shadow over a face etched with rugged experience.

He wears a crimson waistcoat, a vivid contrast to the sea-salted black coat draped over his shoulders. His scarlet breeches and tall leather boots complete the attire of a man who commands both respect and fear. Around his neck hangs a gold chain, rumored to be stolen from the treasure of the King of Portugal, and a diamond cross glints in the sunlight.

Currently, Black Bart stands at the helm of his ship, the Royal Fortune, one hand firmly gripping the wheel, while the other clutches a gleaming cutlass. The ship creaks and groans under the strain of the open sea, its black sails billowing against the azure sky. The crew scurries about the deck, a motley collection of hardened pirates, their faces a mix of reverence and apprehension.

The mood aboard is tense but determined, as Black Bart and his crew sail in search of their next prize. His eyes burn with a fierce resolve, for he knows that every voyage could be his last in this treacherous world of piracy. Yet, the promise of riches and the thrill of the hunt keep his spirit alive, driving him forward into the unknown.

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