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John Rann, “Sixteen String Jack”, “The Dandy Highwayman”

“Meet Sixteen String Jack: The Flamboyant Rogue Who Stole Hearts and Fortunes!”

John Rann, "Sixteen String Jack"
Midjourney
  • Alias: “Sixteen String Jack”, “The Dandy Highwayman”
  • Gender: Male
  • Race: Human
  • Occupation: Highwayman
  • Religion: Unknown (Likely not a devout practitioner)
  • Allies: Criminal associates, accomplices, and various romantic interests
  • Enemies: Law enforcement, rival criminals, and those he targeted during his crimes
  • Abode/Base of operations: Varied safe houses, inns, and hidden spots across London and the countryside
  • Nationality: English
  • Languages: English, Thieves Cant
  • Alignment: Chaotic Neutral
  • Affiliation(s): None officJohn Rannially, although he was known to collaborate with fellow criminals on occasion
  • Significant others: Eleanor Roach (one of his romantic interests)

In the heart of England’s bustling streets emerges John Rann, a flamboyant figure whose charm and audacity define his very existence. His life revolves around the pursuit of extravagant pleasures and the thrill of the unexpected. Rann is a character of captivating charisma, yet beneath his showmanship lies an insatiable appetite for the finer things in life, a hunger he satisfies through unconventional means.

This charismatic rogue fears the drudgery of a mundane existence, loathing the prospect of a life without the glittering allure of opulent parties and extravagant garments. It is this fear that propels him into a world of audacious criminality. In his eyes, society’s strictures and conventions are stifling, and he yearns for the freedom to indulge in the extravagant without restraint.

Rann’s actions, though criminal in nature, are driven by a desire to defy societal norms, to challenge the confines of a class-based society that relegates him to the margins. His heists and daring escapades are a form of rebellion against a world that seeks to confine him to a life of destitution.

What John Rann aims to achieve is not merely wealth but the power to transcend the constraints of his birthright. He seeks to become an enigmatic legend, a man whose name is whispered in awe and admiration, even as he eludes the grasp of those who seek to bring him to justice.

John Rann, “Sixteen String Jack”

John Rann, "Sixteen String Jack"
Midjourney

Medium humanoid (human), chaotic neutral


  • Armor Class 13 (leather Coat)
  • Hit Points 60 (8d8 + 24)
  • Speed 30 ft.

STRDEXCONINTWISCHA
10 (+0)16 (+3)16 (+3)14 (+2)12 (+1)18 (+4)

  • Skills Deception +6, Insight +4, Persuasion +6, Sleight of Hand +5
  • Senses passive Perception 11
  • Languages English, Thieves Cant
  • Challenge 5 (1,800 XP)

Cunning Action (1/turn). John Rann can use a bonus action to Dash, Disengage, or Hide.

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

Charmer. John Rann has advantage on Charisma (Persuasion) checks.

Actions


Flintlock Pistol. Ranged Weapon Attack: +5 to hit, range 30/90 ft., one target. Hit: 10 (1d10 + 3) piercing damage.

Sword Cane. Melee Weapon Attack: +5 to hit, reach 5 ft., one target. Hit: 7 (1d6 + 3) piercing damage.

Silver Tongue (Recharge 5-6). John Rann attempts to charm a creature within 30 feet of him. The target must make a DC 15 Wisdom saving throw or be charmed by Rann for 1 minute. A creature can repeat the saving throw at the end of each of its turns, ending the effect on a success.


Equipment. Studded leather armor, flintlock pistol, sword cane, vibrant silk breeches, frock coat, extravagant clothing and accessories.

Reactions


Evasive Maneuvers. When John Rann is hit by an attack, he can use his reaction to attempt a Dexterity saving throw (DC 15). On a success, he takes no damage from the attack.

Legendary Actions.


John Rann 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. He regains spent legendary actions at the start of his turn.

Shoot. John Rann makes one Flintlock Pistol attack.

Silver Tongue (Costs 2 Actions). John Rann uses his Silver Tongue ability.

Currently in the World

John Rann stands before you, a striking figure who defies the conventional norms of his time. He exudes an air of flamboyance and nonchalance that is nothing short of captivating.

Clothing: He is dressed in an ensemble that demands attention. His silk breeches, a vibrant cerulean blue, are a testament to his extravagant taste. Beneath them, he sports polished black leather boots that gleam in the sunlight. A frock coat, adorned with a riot of colors and patterns, drapes over his shoulders, and a riot of flowers bursts from the lapel of his coat. On his legs, eight silver-tipped strings of various hues dangle just below the knee, an ostentatious display that earned him the moniker “Sixteen String Jack.”

Currently Doing: As you observe him, he leans against a lamppost at the bustling corner of a cobbled street in London. His gaze is fixed on a group of well-dressed nobles exiting a nearby theater, and a sly, mischievous grin plays upon his lips. He seems to be contemplating his next daring move, considering which mark to select from the rich tapestry of potential victims.

Surroundings: The street is alive with activity, with carriages clattering by and pedestrians in elaborate attire strolling past. Gas lamps cast a warm, flickering glow, illuminating the ornate facades of nearby buildings. A sense of anticipation hangs in the air, as if the city itself is holding its breath, waiting for Sixteen String Jack to make his move.

Mood: In this moment, Sixteen String Jack appears relaxed, confident, and utterly in his element. The world is his stage, and he revels in the audacious theater of his own creation. There’s a sparkle of amusement in his eyes, as if he’s fully aware of the grand performance that is his life, and he relishes every moment of it.

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