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Long John Silver

“Long John Silver: The Cunning Pirate with a Mysterious Past – Uncover his hidden treasures and secrets!”

By N. C. Wyeth - Transferred from en.wikisource to Commons by Billinghurst using CommonsHelper., Public Domain,, Long John Silver
By N. C. Wyeth – Transferred from en.wikisource to Commons by Billinghurst using CommonsHelper., Public Domain,
  • Alias: Long John Silver
  • Gender: Male
  • Race: Human
  • Occupation: Pirate Captain, Former Quartermaster
  • Religion: Unknown
  • Allies: His crew on the Hispaniola, fellow pirates, individuals willing to assist him in his pursuits
  • Enemies: Navy officers, rival pirate captains, anyone who poses a threat to his goals
  • Abode/Base of Operations: The Hispaniola (pirate ship), various hidden pirate hideouts and secret coves
  • Nationality: English
  • Languages: English, Pirate Slang
  • Alignment: Neutral Evil
  • Affiliation(s): Independent pirate captain, former crew member of the Walrus
  • Significant Others: None specified

Long John Silver is a charismatic and cunning pirate who roams the seas with an air of mystery and danger. With his tall stature, one leg, and a silver-tipped crutch, he commands respect and fear among his crew. Known for his cunning nature and silver tongue, Long John Silver has an uncanny ability to manipulate others to serve his own interests.

As a former quartermaster aboard the infamous pirate ship, the Walrus, Long John Silver had once been a loyal and trusted member of Captain Flint’s crew. However, driven by his desire for power and wealth, he plotted a mutiny against the captain, leading to Flint’s demise. Now, as the captain of his own ship, the Hispaniola, Silver seeks to amass riches beyond his wildest dreams.

Silver is driven by a deep thirst for treasure and the thrill of the pirate life. He is a master strategist, always seeking the next big score and using his cunning to outwit his enemies. Despite his ruthless and self-serving nature, he possesses a certain charm that draws people to him. He effortlessly adapts to various situations, shifting from a jovial and friendly demeanor to a menacing and calculating one, depending on his objectives.

Beneath his charming façade, Long John Silver hides a complex and conflicted character. He is haunted by his past actions and the bloodshed he caused. While driven by his own ambitions, he also struggles with a sense of loyalty and camaraderie toward his crew. Deep down, he yearns for acceptance and validation, longing to be recognized as a legendary pirate captain.

Silver’s ultimate goal is to amass enough wealth and power to secure his place in history as one of the greatest pirates who ever lived. He seeks legendary treasures, hidden maps, and untold riches that will solidify his legacy. With every adventure and encounter, he navigates the treacherous waters of the pirate world, always on the lookout for opportunities to further his own agenda.

Long John Silver’s story is a tale of ambition, cunning, and the constant pursuit of wealth. He is a complex character driven by his own desires and haunted by his past. Whether as an ally or adversary, crossing paths with Long John Silver is sure to lead to a thrilling and dangerous adventure on the high seas.

Long John Silver

Medium humanoid (human), neutral evil

Armor Class 14 (leather armor) Hit Points 112 (15d8 + 45) Speed 30 ft.

16 (+3)14 (+2)16 (+3)12 (+1)13 (+1)18 (+4)

Saving Throws Dex +5, Con +6, Wis +4, Cha +7 Skills Acrobatics +5, Deception +7, Perception +4, Sleight of Hand +5, Stealth +5 Senses passive Perception 14 Languages Common Challenge 7 (2,900 XP)


Multiattack. Long John Silver makes two cutlass attacks. Cutlass. Melee Weapon Attack: +6 to hit, reach 5 ft., one target. Hit: 8 (1d8 + 4) slashing damage. Flintlock Pistol. Ranged Weapon Attack: +5 to hit, range 40/120 ft., one target. Hit: 10 (2d6 + 3) piercing damage. Thrown Knife. Ranged Weapon Attack: +5 to hit, range 20/60 ft., one target. Hit: 5 (1d4 + 3) piercing damage. Silver’s Parrot. The parrot mimics the voice of Long John Silver, adding advantage on Deception checks made by Silver.

Legendary Actions

Long John Silver 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. Long John Silver regains spent legendary actions at the start of his turn.

Quick Strike. Long John Silver makes one cutlass attack.

Dirty Trick. Long John Silver throws sand in a creature’s eyes. The target must succeed on a DC 15 Constitution saving throw or be blinded until the end of its next turn.

Intimidating Presence. Long John Silver uses his commanding presence to intimidate nearby creatures. Each creature of his choice within 30 feet must make a DC 15 Wisdom saving throw or become frightened for 1 minute. The creature can repeat the saving throw at the end of each of its turns, ending the effect on a success.

Equipment Leather armor, cutlass, flintlock pistol, throwing knives, silver’s parrot (prop)

Special Abilities Pirate’s Cunning: Long John Silver has advantage on saving throws against being charmed or frightened.

Magic Items None

Plot Hooks

  • The Mysterious Map: Long John Silver possesses a cryptic map that supposedly leads to a legendary treasure hidden deep within a treacherous island. The players are approached by Silver, his one-legged figure exuding an air of intrigue and adventure, to join his crew and embark on a perilous journey to uncover the riches. As they decipher the clues on the aged map, they unravel the dark secrets guarding the treasure, facing deadly traps, rival pirates, and supernatural guardians standing in their way.
  • Double-Crossed: Silver’s reputation for betrayal precedes him, leaving the players skeptical of his motives. Yet, circumstances force them into a reluctant alliance. As they venture deeper into their alliance, the players become entangled in a web of deceit, discovering Silver’s hidden agendas and manipulative schemes. They must outwit the master of deception himself, staying one step ahead of Silver’s cunning plans to protect their own interests and ensure their survival in a world where trust is a rare currency.
  • Betrayal and Redemption: The players delve into Silver’s enigmatic past, unearthing a complex tapestry of regrets, secrets, and opportunities for redemption. They uncover the truth behind his darkest deeds and confront the moral dilemma of whether to help him find redemption or expose his misdeeds to the authorities. Along their journey, they encounter individuals whose lives were affected by Silver’s actions, and they must decide whether to offer forgiveness, seek justice, or forge their own path amidst the blurred lines of right and wrong.
  • The Silver Tongue: Silver’s charismatic and persuasive nature is legendary, his honeyed words capable of swaying even the most resolute hearts. The players find themselves drawn into his manipulative schemes, caught between the thrill of adventure and the realization that they are mere pawns in his grand plan. They must navigate a delicate dance of trust and deception, questioning Silver’s every motive and carefully weighing their own desires against the dangers that lie ahead.
  • The Parrot’s Secrets: Silver’s loyal companion, a talkative parrot named Captain Flint, holds valuable information or a secret key to unlocking a hidden treasure. The players must earn the bird’s trust, engaging in a series of tasks and quests that test their resourcefulness and cunning. They may need to decode cryptic messages, solve riddles, or protect the parrot from those who seek to silence its squawks of wisdom. Through their interactions with the parrot, they uncover valuable insights into Silver’s true nature and the hidden depths of their shared adventure.
  • Silver’s Redemption: Haunted by his past misdeeds, Silver seeks redemption for the sins that weigh heavily on his conscience. He approaches the players for help in finding a way to right his wrongs and restore his tarnished honor. The players must decide whether to trust him and embark on a dangerous quest for redemption alongside him or exploit his vulnerabilities for their own gain. Along the way, they confront their own notions of forgiveness, second chances, and the possibility of redemption in a world of piracy and treachery.

Currently in the World

Long John Silver is a tall and imposing figure, with a sturdy build that hints at his past as a sailor. He has a weathered face adorned with a thick, salt-and-pepper beard that reaches his chest. His one-legged stance, supported by a wooden crutch, is a testament to the battles he has fought and the dangers he has encountered.

Currently, Long John Silver finds himself on the deck of his ship, the Hispaniola, standing at the helm with a gleam of cunning in his eyes. The sea breeze tousles his long, unruly hair as he peers into the horizon, scanning for potential targets or hidden treasures. His surroundings are a mix of the salty air, the creaking sounds of the ship, and the ever-present scent of adventure.

Despite the dangers that surround him, Long John Silver wears a charismatic smile, his face alive with a combination of excitement and calculated mischief. His mood is one of confidence, as he knows that he holds the power to navigate the treacherous seas and manipulate those around him to achieve his goals. He is a master of disguise, effortlessly blending into any crowd or situation, concealing his true intentions until the perfect moment to strike.

With a silver tongue and a captivating presence, Long John Silver exudes an air of authority and charm, effortlessly drawing others to his cause. Whether he’s negotiating with fellow pirates, deceiving unsuspecting foes, or inspiring his loyal crew, he is a charismatic and enigmatic figure who thrives in the lawless world of piracy.

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