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Eustace The Monk

Eustace The Monk
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  • Alias: Eustace the Monk
  • Gender: Male
  • Race: Human
  • Occupation: Mercenary, pirate, outlaw
  • Religion: Potentially Christian, considering his background as a Benedictine monk
  • Allies: Varies depending on his shifting allegiances, initially associated with King John of England, later supporting the rebel barons and Prince Louis of France. Potential allies could include other pirates, mercenaries, and individuals sympathetic to his cause.
  • Enemies: English forces, particularly those who turned against him, and those who stood in opposition to his chosen side during the civil war. Additionally, rival pirates, rival mercenaries, and individuals seeking to bring him to justice would likely be considered enemies.
  • Abode/Base of Operations: Channel Islands, including Castle Cornet in Guernsey, and various pirate strongholds along the English Channel and the Strait of Dover. He may also have utilized temporary hideouts and bases in coastal areas for raiding and operations.
  • Nationality: French, as he primarily operated in the English Channel and had connections with French forces.
  • Languages: Old French (primary), potentially some knowledge of English and other languages due to his varied interactions and travels.
  • Alignment: Neutral Evil (based on his unpredictable actions, shifting loyalties, and pursuit of personal vengeance)
  • Affiliation(s): Initially aligned with King John of England, later joining the rebel barons and supporting Prince Louis of France. He may have also had loose associations with other pirate crews, mercenaries, and outlaw factions.
  • Significant others: No specific information available about his romantic relationships or family connections.

Eustace the Monk is an enigmatic and formidable figure, known for his unconventional path in life as a mercenary and pirate. Born as Eustace Busket, he hails from the county of Boulogne and possesses a mysterious past. Legends speak of his study of black magic in Toledo, Spain, where he supposedly accomplished extraordinary feats. However, his true motives and the events that led him down this path remain shrouded in mystery.

Despite his dark origins, Eustace’s life takes a surprising turn when he becomes a Benedictine monk at St Samer Abbey near Calais. However, tragedy strikes as his father is brutally murdered, compelling Eustace to abandon his monastic vows and seek vengeance. His quest for justice leads him to become a pirate, both for personal gain and as a mercenary serving the interests of France and England.

Eustace’s allegiance shifts as the winds of fortune change. Initially employed by the King of England, he raids the Normandy coast and establishes bases in the Channel Islands. But when the English king outlaws him, Eustace switches sides and supports the rebel barons during the civil war that engulfs England. He even aids the Prince of France, ferrying him across the treacherous Channel to assist the rebels.

Driven by a desire for revenge, Eustace’s actions are fueled by a complex web of loyalties, personal vendettas, and shifting alliances. He strikes fear into the hearts of his former comrades, wreaking havoc among those who once regarded him as an ally. But the tides of fate turn against him in the fateful Battle of Sandwich, where he faces the wrath of the English fleet.

Eustace, despite his cunning and resilience, meets his downfall in this battle. Outnumbered and surrounded, he is eventually captured and offered his life in exchange for immense sums of wealth. However, his cruel reputation precedes him, and his captors refuse to grant him mercy. In a twist of fate, he is left to choose his execution site—either the ship’s rail or the side of the trebuchet that had been carried as deck-cargo to England.

Eustace’s story is one of a complex and intriguing character driven by a thirst for vengeance, navigating treacherous waters, and constantly adapting to survive in a world defined by shifting loyalties. What truly motivates him and what he ultimately seeks to achieve remain enigmatic, leaving behind a legacy of both fear and fascination.

Eustace The Monk
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Medium humanoid (human), neutral evil

Armor Class 16 (studded leather) Hit Points 120 (16d8 + 48) Speed 30 ft.

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

Saving Throws Dexterity +8, Wisdom +5 Skills Acrobatics +8, Deception +7, Perception +5, Stealth +8 Senses Passive Perception 15 Languages Common, Thieves’ Cant Challenge 10 (5,900 XP)

Evasive Maneuvers. Eustace The Monk can take the Disengage or Hide action as a bonus action on each of his turns.


Multiattack. Eustace The Monk makes two attacks: one with his flintlock pistol and one with his shortsword or dagger.

Flintlock Pistol. Ranged Weapon Attack: +8 to hit, range 30/90 ft., one target. Hit: 12 (2d8 + 4) piercing damage.

Shortsword. Melee Weapon Attack: +6 to hit, reach 5 ft., one target. Hit: 8 (1d6 + 4) piercing damage.

Dagger. Melee or Ranged Weapon Attack: +6 to hit, reach 5 ft. or range 20/60 ft., one target. Hit: 6 (1d4 + 4) piercing damage.


Evasive Parry. When Eustace The Monk is hit by a melee attack, he can use his reaction to add 3 to his AC against that attack, potentially causing it to miss.

Legendary Actions

Eustace the Monk 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. Eustace regains spent legendary actions at the start of his turn.

Reload. Eustace reloads his flintlock pistol.

Disarming Strike. Eustace makes a melee attack with his shortsword. If the attack hits, the target must make a DC 14 Strength saving throw or drop one item of Eustace’s choice that it is holding.

Elusive Dash. Eustace moves up to his movement speed without provoking opportunity attacks.


Eustace the Monk is equipped with studded leather armor, a flintlock pistol, a shortsword, and several daggers. He also carries a hidden stash of stolen gold and a navigational chart leading to his secret pirate cove.

Magic Item

Eustace possesses a legendary magic item known as the “Shadowstep Boots.” These boots allow him to cast the Misty Step spell once per long rest without requiring a spell slot.

Plot Hooks

Eustace's death at the 1217 Battle of Sandwich (13th century illustration by Matthew Paris) Eustace The Monk
Eustace’s death at the 1217 Battle of Sandwich (13th century illustration by Matthew Paris)
  • The Pirate’s Ransom: Eustace the Monk, possesses vital information about a legendary pirate treasure hidden in a remote island. He offers to guide the players to the location in exchange for their assistance in dealing with a rival pirate crew seeking the same fortune.
  • The Vengeance Seeker: Eustace the Monk,seeks revenge against a corrupt noble who wronged him in the past. He enlists the players’ help to infiltrate the noble’s heavily guarded mansion, uncovering evidence of their misdeeds and bringing them to justice.
  • The Mysterious Map: Eustace possesses a cryptic map leading to a powerful artifact, but he lacks the knowledge to decipher it. The players must aid him in deciphering the map’s riddles and overcoming dangerous obstacles to reach the artifact before a sinister cult does.
  • The Pirate King’s Heir: Rumors spread that Eustace is the long-lost heir to a powerful pirate king, and various factions seek to either claim him as their leader or eliminate him to secure their own dominance. The players become entangled in a web of political intrigue and must decide Eustace’s fate.
  • The Ghost Ship: Eustace the Monk, recounts tales of a ghostly ship haunting the seas, crewed by vengeful spirits. He hires the players to join his crew in a perilous expedition to confront the supernatural threat and put the restless spirits to rest.
  • The Smuggler’s Run: Eustace recruits the players for a daring smuggling operation, evading the authorities and rival smugglers while transporting valuable contraband across dangerous territories. They must outsmart customs officers, navigate treacherous routes, and deal with double-crossing informants.
  • The Code of Honor: Eustace the Monk, follows a strict personal code of conduct, valuing loyalty and honor among thieves. He seeks to establish a crew of like-minded individuals and tests the players’ mettle, challenging them to prove their worth and loyalty before accepting them into his inner circle.
  • The Naval Blockade: Eustace is cornered by a powerful naval blockade that seeks to bring him to justice. He needs the players’ assistance in devising an audacious plan to break through the blockade and escape capture, all while outsmarting the enemy’s skilled naval officers.
  • The Lost Love: Eustace pines for a lost love, a noblewoman who rejected him due to his life of piracy. He tasks the players with finding her and delivering a heartfelt message, hoping for a chance at reconciliation or closure.
  • The Pirate Council: Eustace is a key member of an underground pirate council, working to maintain a delicate balance of power among various pirate factions. The players must navigate the treacherous world of pirate politics, making alliances and outmaneuvering rivals to preserve the council’s influence.

These roleplaying hooks provide various opportunities for players to engage with Eustace the Monk, exploring his past, motivations, and the thrilling adventures he embarks upon.

Currently in the World

Eustace the Monk stands tall, his weathered face bearing the marks of a life lived on the edge. His dark, unkempt hair falls loosely around his shoulders, framing a pair of piercing, calculating eyes. A rough beard adds to his rugged appearance, hinting at the untamed spirit within him. He wears a tattered, brown leather jerkin adorned with numerous straps and pockets, providing easy access to his tools of the trade.

Currently, Eustace The Monk finds himself in the dimly lit tavern, his usual haunt in the coastal town. The air is thick with the scent of salt, ale, and whispered conversations. Surrounded by a motley crew of fellow rogues and misfits, he leans against the bar, nursing a tankard of ale. His mood is a mix of cautious vigilance and smoldering determination, as he contemplates his next move.

As he scans the room, his keen eyes take note of every face, every subtle gesture, and the whispers that reach his ears. He remains ever watchful, keeping his guard up, aware that danger lurks in the shadows. Despite the tense atmosphere, there is an air of silent confidence around him, born from years of surviving treacherous encounters and outsmarting his adversaries.

Eustace The Monk’s surroundings reflect his chosen lifestyle. The tavern is adorned with weathered wooden beams, its walls adorned with faded maps and symbols of the sea. The flickering candlelight casts dancing shadows across the room, revealing glimpses of worn pirate flags and trinkets from distant lands. The sound of raucous laughter and clinking tankards intermingles with hushed conversations, creating a backdrop that conceals secrets and whispered deals.

In this moment, Eustace is poised on the precipice of another daring adventure, his mind filled with plans and schemes. The sea beckons, and he knows that amidst the crashing waves and treacherous shores, there are riches to be plundered and scores to be settled. As he takes another sip of ale, his eyes glimmer with a fierce determination, for he is Eustace the Monk, a man driven by his own code, forever seeking his own brand of justice in the tumultuous world he inhabits.

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