This site is games | books | films

Henry Strangways, Strangwish, the Gentleman Pirate

“The Daring Gentleman Pirate: Uncover the Thrilling Life of Henry Strangways!”

Henry Strangways, the Gentleman Pirate
  • Alias: Strangwish
  • Gender: Male
  • Race: Human
  • Occupation: Pirate
  • Religion: Not specified
  • Allies: Cornish Killigrews, influential friends who secure his pardons
  • Enemies: Spanish ships and merchants
  • Abode/Base of operations: Portland Castle (used as a secret den)
  • Nationality: English
  • Languages: English, possibly others
  • Alignment: Chaotic Neutral
  • Affiliation(s): Independent pirate, associated with fellow pirates and buccaneers
  • Significant others: Not specified

Henry Strangways, also known as Strangwish, is a fascinating figure from history who embarks on a daring career as a pirate. Born into a renowned family in Dorset, he becomes a prominent “Gentleman Pirate.” Setting sail he targets Spanish and other ships for plunder and adventure. Throughout his approximately eight-year piratical career, Strangways faces numerous imprisonments but manages to secure pardons from influential acquaintances.

As a young man, Strangways roams the Irish Sea, joining forces with the renowned Cornish Killigrews, who are successful pirates in their own right. Together, they use Portland Castle as a secret hideout to store their ill-gotten treasures. Strangways’ audacity and accomplishments earn him a fearsome reputation, and his name spreads among sailors and seafarers.

While expressing a desire to “steal an island” from Philip II of Spain, Strangways primarily focuses on attacking Spanish ships. Historical records reveal official complaints made against him, detailing the plundering of ships belonging to Spanish merchants. His actions strike fear into the hearts of his enemies and earn him both respect and notoriety among his fellow pirates.

Throughout his piratical exploits, Strangways relies on his wit, cunning, and strategic thinking to outmaneuver his adversaries. He navigates treacherous waters, avoiding capture and escaping from imprisonment time and time again. His ability to secure pardons from influential friends suggests a network of support that allows him to continue his piratical activities.

Strangways is a complex character driven by a thirst for adventure, the allure of riches, and the desire for freedom. He seeks to defy authority, challenge the established order, and carve out a name for himself in the annals of piracy. His audacious nature and willingness to take risks make him both a respected captain among his crew and a feared adversary on the high seas.

Henry Strangways, with his flamboyant personality, quick thinking, and charismatic presence, leaves an indelible mark on the history of piracy. His exploits inspire tales and legends that continue to capture the imaginations of adventurers and storytellers alike, immortalizing him as a symbol of the daring and romanticized era of piracy.

Henry Strangways
By Gerlach Flicke

Medium humanoid (human), neutral alignment

Armor Class 15 (leather armor) Hit Points 93 (14d8 + 28) Speed 30 ft.

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

Skills Acrobatics +5, Deception +6, Perception +2, Stealth +5 Senses passive Perception 12 Languages Common, French Challenge 5 (1,800 XP)


  • Cutlass. Melee Weapon Attack: +5 to hit, reach 5 ft., one target. Hit: 7 (1d8 + 3) slashing damage.
  • Pistol Shot. Ranged Weapon Attack: +5 to hit, range 30/90 ft., one target. Hit: 10 (2d6 + 3) piercing damage.
  • Cunning Action. On each of his turns, Henry can use a bonus action to take the Dash, Disengage, or Hide action.
  • Evasive Maneuvers. Henry gains advantage on Dexterity saving throws against effects that would cause him to become restrained or incapacitated.
  • Nimble Escape. Henry can take the Disengage or Hide action as a bonus action on each of his turns.
  • Pirate’s Cunning. Henry has advantage on saving throws against being charmed or frightened.

Equipment: Leather armor, cutlass, flintlock pistol, dagger, pirate hat, tricorn hat, leather boots, grappling hook, spyglass.

Notable Abilities:

  • Quick Draw. Henry can draw or stow a weapon as part of the same action used to attack with the weapon.
  • Cunning Tactics. Henry gains advantage on ability checks and saving throws made to escape from being bound or restrained.
  • Silver Tongue. Henry has proficiency in the Deception skill and gains a +5 bonus to Charisma (Deception) checks when attempting to deceive others.
  • Sea Legs. Henry has advantage on Dexterity (Acrobatics) checks made to maintain balance and agility on a ship’s deck or in rough seas.
  • Keen Eye. Henry has advantage on Wisdom (Perception) checks made to spot hidden or obscured objects or creatures.

Legendary Actions

Henry Strangways 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. Henry regains spent legendary actions at the start of his turn.

  • Daring Feint. Henry makes a melee weapon attack with his cutlass.
  • Pistol Shot (Costs 2 Actions). Henry makes a ranged weapon attack with his flintlock pistol.
  • Evasive Dodge (Costs 3 Actions). Henry takes the Dodge action, avoiding incoming attacks with swift maneuvers.

Legendary Resistance

Henry Strangways can choose to succeed on a saving throw that would otherwise cause him to fail.

Lair Actions

On initiative count 20 (losing initiative ties), Henry Strangways can take a lair action to cause one of the following effects:

  • Call of the Sea. Henry unleashes a thunderous shout, summoning the spirit of the sea. Each creature within 60 feet of Henry must succeed on a DC 15 Wisdom saving throw or be frightened for 1 minute.
  • Pirate’s Agility. Henry’s agility is unmatched as he maneuvers through the battlefield. He gains a +2 bonus to AC until the start of his next turn.
  • Hidden Treasure. Henry reveals a hidden stash of treasure nearby, distracting his foes. Each creature within 30 feet of Henry must make a DC 15 Intelligence saving throw or be charmed for 1 minute.

Currently in the World

Henry Strangways is a tall and sturdy man with a rugged appearance. He has weathered features, including a prominent scar on his cheek, earned from battles and skirmishes on the high seas. His deep-set eyes carry a fierce determination, reflecting his unwavering spirit and adventurous nature. Strangways sports a thick, unkempt beard and his long hair is often tied back with a simple leather thong.

Currently, Henry Strangways stands on the deck of his ship, the winds whipping through his hair as he gazes out at the vast expanse of the ocean. The salty air fills his nostrils, and the creaking of the ship beneath his feet reminds him of his life as a pirate. Surrounding him are his loyal crewmates, their faces marked with the hardships of a life at sea.

In this moment, Strangways is focused and determined, his mind occupied with thoughts of potential targets and hidden treasures. His mood is a mix of anticipation and readiness, always seeking the next opportunity for adventure and plunder.

Scroll to Top