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Jenny Diver, Skilled Pickpocket and Thief

“Jenny Diver: The Sly Siren of Shadows – Master of Deception and Mistress of Mayhem!”

Jenny Diver
  • Alias: Jenny Diver
  • Gender: Female
  • Race: Human
  • Occupation: Skilled Pickpocket and Thief
  • Religion: Secular
  • Allies: Fellow Criminals in Macheath’s Gang
  • Enemies: Law Enforcement, Rival Gangs
  • Abode/Base of Operations: Hidden Den in the Underworld of London
  • Nationality: English (Londoner)
  • Languages: English, Thieves’ Cant
  • Alignment: Chaotic Neutral
  • Affiliation(s): Part of Macheath’s Gang
  • Significant Others: Romantically Involved with Macheath

In the bustling streets of London, Jenny Diver emerges as a captivating figure whose presence is as enigmatic as it is alluring. Known for her cunning and resourcefulness, she is a woman of many faces, adept at navigating the shadows and blending into the world of deception. With a mysterious air that veils her true intentions, Jenny weaves a complex web of intrigue in the heart of urban chaos.

Jenny’s life is a tapestry of survival and adaptation. Born into the lower echelons of society, she learned early on that the world could be both cruel and opportunistic. Her experiences have made her resilient, molding her into a character who thrives on her wits and ability to exploit the weaknesses of those around her. Her motives are not driven by grand ideals, but rather a desire for personal gain and a refusal to be confined by societal norms.

Fear is a concept that Jenny Diver knows intimately. The ever-present danger of being caught in her intricate schemes serves as a constant reminder of the stakes she plays for. Her ability to blend in, disappear into the crowd, and charm those around her masks the apprehension that often gnaws at her. This fear, however, fuels her determination to succeed, pushing her to master the art of manipulation and to never let her guard down.

Jenny’s actions are a dance of calculated risks, guided by a pragmatic philosophy that embraces both opportunity and uncertainty. She understands that the world is a place of limited resources and cutthroat competition, and she seeks to secure her own place within it. Her skills in deception, persuasion, and quick thinking serve her well as she navigates the treacherous alleys and secret dealings of the city’s underbelly.

Amid the chaos and intrigue, Jenny Diver yearns for more than just survival. Her ambitions are twofold: to secure her own prosperity and to establish a legacy that will ensure her name lives on beyond her years. While the world may brand her as a rogue, she envisions herself as a master of her own destiny, determined to carve a niche in history on her own terms.

Jenny Diver’s story is one of contradictions and complexity, a tale of a woman who thrives in the shadows, embracing her role as both manipulator and survivor. Her life’s journey unfolds as a series of calculated moves, each one aimed at securing her position in a world where power is reserved for those bold enough to seize it.

Jenny Diver

Medium humanoid (human), neutral

Armor Class 12 (leather armor) Hit Points 55 (10d8 + 10) Speed 30 ft.

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

Skills Deception +6, Sleight of Hand +5, Stealth +5 Senses passive Perception 11 Languages English, Thieves’ Cant Challenge 3 (700 XP)

Evasion. If Jenny Diver is subjected to an effect that allows her to make a Dexterity saving throw to take only half damage, she instead takes no damage on a successful save and half damage on a failed save.

Sneak Attack (1/Turn). Jenny Diver deals an extra 7 (2d6) damage when she hits a target with a weapon attack and has advantage on the attack roll, or when the target is within 5 feet of an ally of Jenny that isn’t incapacitated and Jenny doesn’t have disadvantage on the attack roll.

Pickpocket. Jenny can use her Sleight of Hand skill to attempt to steal a small object from a creature without the creature noticing.

Thieving Abilities. Once per turn, Jenny can use her bonus action to attempt to disarm a creature she hits with a melee weapon attack. The creature must succeed on a DC 14 Strength saving throw or drop one held object of Jenny’s choice that isn’t being worn or carried.


Multiattack. Jenny makes two attacks.

  • Dagger. Melee or Ranged Weapon Attack: +5 to hit, reach 5 ft. or range 20/60 ft., one target. Hit: 5 (1d4 + 3) piercing damage.
  • Hidden Blade. Melee Weapon Attack: +5 to hit, reach 5 ft., one target. Hit: 6 (1d6 + 3) slashing damage. If the target is surprised, this attack deals an extra 7 (2d6) damage.
  • Derringer Shot. Ranged Weapon Attack: +5 to hit, range 20/60 ft., one target. Hit: 6 (1d6 + 3) piercing damage.


Uncanny Dodge. When an attacker Jenny can see hits her with an attack, she can use her reaction to halve the attack’s damage against her.

Equipment Derringer, dagger, hidden blade, leather armor

Currently in the World

Jenny Diver is a striking woman of average height with a mischievous glint in her dark eyes. Her raven-black hair cascades in loose waves around her shoulders, framing a face adorned with a few freckles that hint at her youthful spirit. She moves with a confidence that belies her seemingly delicate appearance, her lithe form possessing a grace that comes from years of navigating the bustling streets of London.

Currently, Jenny is perched on a dimly lit corner of a bustling London tavern, her keen eyes scanning the room with an air of both curiosity and caution. Her attire is a clever blend of street-smart practicality and subtle elegance—a worn but well-maintained blouse and skirt that allow her to move with ease as she skillfully maneuvers through the crowd. A small dagger is discreetly tucked into a concealed pocket, a testament to her readiness for any unexpected challenges.

The tavern’s atmosphere is a mix of laughter, clinking glasses, and lively conversation, creating the perfect backdrop for Jenny’s activities. She maintains an air of nonchalance while keeping a watchful eye on her surroundings, always ready to identify potential targets or thwart any unwanted attention. Her mood seems to shift between amusement and calculation, a testament to her ability to blend seamlessly into her surroundings while constantly evaluating the situation.

As she sips her drink, Jenny’s fingers occasionally drum against the tabletop in rhythm with the lively music playing in the background. Her body language exudes a sense of anticipation, as if she’s awaiting a signal from a fellow gang member or assessing the right moment to execute a skillful theft. In this bustling corner of London’s underworld, Jenny Diver thrives as a master of her craft, both an enigmatic presence and a force to be reckoned with.

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