NPCs

Master Thieves, Enforcers, and Spies: The Syndicate Uncovered (Thieves Guild NPCs #3)

This week, we continue our exploration of the infamous criminal organization, "The Syndicate," introducing the next wave of unique Non-Player Characters. From Ylva Mistcloak, the nimble half-elf master thief, to Isadora Ithelar, the resourceful changeling bard and intelligence gatherer, this installment delivers a compelling and multifaceted cast for your campaigns.

Published: June 30th, 2023

Written by: JL

Each week, I assemble a range of prewritten Non-Player Characters (NPCs) that can be flawlessly integrated into your campaign.

This week, we've got the third entry into the notorious underworld organization, "The Syndicate".

These characters are part of a wider, more intricate project I've been deeply involved in—a comprehensive guidebook on crafting and managing criminal organizations for your immersive narratives.

This week, we're going to meet:

Ylva Mistcloak: As the Master Thief of The Syndicate, Ylva, a half-elf rogue, is the epitome of agility and stealth, known for her unparalleled skills in burglary and disguise.

Brutus Ironfist: A formidable half-orc fighter and The Syndicate's hulking enforcer, Brutus is an intimidating presence whose prosthetic iron fist is a symbol of his unwavering strength.

Felix Stone: A fierce dragonborn barbarian, Felix is the Guild Enforcer of The Syndicate, renowned for his loyalty and ruthless efficiency in executing the guild's orders.

Gavin Blackheart: A dwarf fighter, Gavin is the backbone of The Syndicate's operations, overseeing their enforcers with his mastery in hand-to-hand combat and strategic planning.

Isadora Ithelar: A changeling bard, Isadora serves The Syndicate as an Information Broker and an Undercover Agent, mastering the art of disguise and subterfuge to gather critical intelligence.

For each character, there are:

Stat Blocks: Everything you need to manage these characters in combat.

Backgrounds: Vibrant histories that bring these characters to life, enabling a more profound understanding of their motivations and alignments.

Plot Hooks: Potential storylines or incidents that can weave these characters into your campaign, ensuring smooth incorporation.

As always, I hope you find these characters as exciting and compelling as I did when creating them.

Ylva Mistcloak

Name: Ylva Mistcloak

Race: Half-Elf

Class: Rogue

Description:

The Master Thief of The Syndicate. Ylva is a sleek and agile cat burglar who can scale any wall and slip through any window undetected. She is a master of disguise and subterfuge, able to blend in seamlessly with any crowd. She is fiercely independent and has a reputation for being difficult to work with, but her skills are undeniable.

Physical Appearance

Ylva is a sleek and agile half-elf with a lithe build, standing at 5'7". Her long, crimson red hair is often tied back in a ponytail, and her sharp, ice-blue eyes are always scanning her surroundings. She wears dark, form-fitting clothing that allows her to blend into the shadows, and a dark cloak that seems to shimmer like mist when she moves.

Background

Ylva was raised by her human mother in a crowded city, where she learned the art of thievery from a young age. As she honed her skills, she caught the attention of The Syndicate, a powerful criminal organization. They offered her a place among their ranks, and she quickly rose up to become their Master Thief. Ylva is fiercely independent and has a reputation for being difficult to work with, but her skills are undeniable.

Motivations

Short term: Ylva seeks to maintain her position within The Syndicate and continue to build her reputation as the Master Thief.

Long term: She desires to eventually break free from The Syndicate's control and carve out her own criminal empire.

Tactics

Ylva relies on her agility, stealth, and cunning to infiltrate secure locations and steal valuable items. She is a master of disguise and subterfuge, able to blend in seamlessly with any crowd. When necessary, she uses her charisma and negotiation skills to manipulate others into helping her achieve her goals.

Plot Hooks

Ylva is hired to steal a valuable artifact from a local noble, which the party has also been tasked with retrieving.
The party encounters Ylva while she is in disguise, and she attempts to use them as pawns in her latest heist.
The Syndicate tasks Ylva with recruiting the party for a high-stakes mission, forcing her to work alongside them despite her reluctance to cooperate.

Ylva Mistcloak

Medium Half-Elf

Armor Class

Hit Points

65 (10d8 + 20)

Speed

30 ft.

STR

10 (0)

DEX

18 (4)

CON

14 (2)

INT

14 (2)

WIS

14 (2)

CHA

16 (3)

Skills

Acrobatics +7, Deception +6, Insight +5, Perception +5, Stealth +7

Senses

darkvision 60 ft., passive Perception 15

Languages

Common, Elvish, Thieves' Cant

Challenge

Sneaky:

Ylva has advantage on Dexterity (Stealth) checks.

Damaging Weapon:

Ylva's short sword attacks deal an extra 6 (2d6) piercing damage.

Delights in Suffering:

When attacking a target whose current hit points are below half their hit point maximum, Ylva has advantage on attack rolls and deals an extra 6 (2d6) damage when she hits.

Actions

Multiattack:

Ylva makes two short sword attacks.

Short Sword:

Melee Weapon Attack: +7 to hit, reach 5 ft., one target. Hit: 7 (1d6 + 4) piercing damage plus 6 (2d6) extra piercing damage if the target's current hit points are below half their hit point maximum.

Reactions

Parry and Riposte (1/round):

Ylva adds +3 to her Armor Class against one melee attack that would hit her. If the attack misses, Ylva can immediately make a short sword attack against the creature making the parried attack.

Brutus Ironfist

Name: Brutus Ironfist

Race: Half-Orc

Class: Fighter

Description:

A hulking enforcer with a short temper and an iron grip. Brutus is the muscle behind the Syndicate, and he's not afraid to use force to get what he wants.

Physical Appearance:

Brutus is a hulking, heavily-muscled half-orc standing at 6'8" tall. His skin is a dull grayish-green, and his head is shaved clean, leaving only a few scars visible. His left eye is milky white, and his right eye is a piercing yellow. He has a prosthetic iron fist that replaces his left hand, which he uses to intimidate his enemies.

Background:

Brutus was once a fearsome gladiator, but after losing his hand in a brutal fight, he was cast aside by his former masters. He eventually found his way to the Syndicate where he quickly became their enforcer. The Syndicate understood his prowess and value, hiring a local blacksmith to construct a prosthetic hand for Brutus. Brutus is now the muscle behind the Syndicate, using his strength and iron fist to ensure their will is carried out.

Motivations:

Short term: Maintain his position within the Syndicate and protect its interests.

Long term: Gain enough power and influence within the organization to one day take control.

Tactics:

Brutus relies heavily on his physical prowess and intimidating presence to achieve his goals. He is not afraid to use force or violence when necessary, often making examples of those who dare to defy the Syndicate. He is also skilled in the art of interrogation, using his iron fist to inflict pain and fear into those who withhold information.

Plot Hooks:

The party is hired by a rival organization to infiltrate the Syndicate and gather information. They must deal with Brutus, who is suspicious of their intentions and will stop at nothing to protect the Syndicate.
A member of the party has a personal vendetta against Brutus, perhaps stemming from a past encounter or a shared history. The party must confront him and bring him to justice.
The party discovers that Brutus is involved in a plot to overthrow the current leader of the Syndicate. They must decide whether to help him, hinder his plans, or use the situation to their advantage.

Brutus Ironfist

Medium Half-Orc

Armor Class

15 (chain mail)

Hit Points

95 (10d10 + 30)

Speed

30 ft.

STR

20 (5)

DEX

12 (1)

CON

16 (3)

INT

8 (-1)

WIS

10 (0)

CHA

8 (-1)

Skills

Athletics +7, Intimidation +1

Senses

darkvision 60 ft., passive Perception 10

Languages

Common, Orc

Challenge

5 (1,800 XP)

Damaging Weapon:

Brutus's melee weapon attacks deal an extra 5 (1d6) bludgeoning damage.

Delights in Suffering:

When attacking a target whose current hit points are below half their hit point maximum, Brutus has advantage on attack rolls and deals an extra 5 (1d6) damage when he hits.

Refuse to Surrender:

When Brutus's current hit points are below half his hit point maximum, he deals an extra 5 (1d6) damage with each of his attacks.

Reposition (1/Day):

Each ally within 60 feet of Brutus who can see and hear him can immediately move their speed without provoking opportunity attacks.

Actions

Multiattack:

Brutus makes two melee attacks.

Iron Fist:

Melee Weapon Attack: +7 to hit, reach 5 ft., one target. Hit: 15 (2d10 + 4) bludgeoning damage.

Greataxe:

Melee Weapon Attack: +7 to hit, reach 5 ft., one target. Hit: 11 (1d12 + 5) slashing damage.

Reactions

Parry and Riposte (Recharge 6):

Brutus adds +3 to his Armor Class against one melee attack that would hit him. If the attack misses, Brutus can immediately make a weapon attack against the creature making the parried attack.

Felix Stone

Name: Felix Stone

Race: Dragonborn

Class: Barbarian

Description:

The Guild Enforcer of The Syndicate. Felix is a towering brute who serves as Marius Blackwood's right-hand man. He is a skilled fighter and is not afraid to get his hands dirty when necessary. Felix is fiercely loyal to Marius and will stop at nothing to protect the guild's interests.

Physical Appearance

Felix is a very large dragonborn, standing 6'7" tall and weighing around 280 pounds. His muscular physique is covered in scars from his many battles. He has a shaved head, a thick beard, and piercing blue eyes. He wears heavy armor adorned with The Syndicate's emblem, and carries a massive battleaxe on his back.

Background

Felix Stone grew up in a rough neighborhood, learning to fight from a young age. He eventually found his way into The Syndicate, where he quickly gained a reputation for his ruthless efficiency and unwavering loyalty. Over time, he rose through the ranks and became the Guild Enforcer, serving as Marius's right-hand man.

Motivations

Short term: Ensuring the safety and security of The Syndicate's operations.

Long term: Join the Blackwood family through marriage (Marius' daughter), despite the opposition within the Syndicate.

Tactics

Felix uses his size and strength to intimidate and overpower his enemies. He is unafraid to take risks and will not hesitate to use violence to achieve his goals. He is also highly organized and responsible, making sure that all tasks are completed efficiently and effectively.

Plot Hooks

Felix is sent to collect a debt from a local merchant who has fallen behind on their payments to The Syndicate.
A rival criminal organization is encroaching on The Syndicate's territory, and Felix is tasked with eliminating their leadership.
Felix is sent to track down a former member of The Syndicate who has betrayed the organization and stolen valuable information.

Felix Stone

Medium Human

Armor Class

Hit Points

127 (17d8 + 51)

Speed

30 ft.

STR

20 (5)

DEX

14 (2)

CON

16 (3)

INT

10 (0)

WIS

12 (1)

CHA

10 (0)

Skills

Athletics +9, Intimidation +3

Senses

passive Perception 11

Languages

any one language (usually Common)

Challenge

7 (2,900 XP)

Damaging Weapon:

Felix's greataxe attacks deal an extra 14 (2d8 + 5) slashing damage.

Defender:

When an ally adjacent to Felix is targeted by an attack or spell, Felix can make himself the intended target of the attack.

Delights in Suffering:

When attacking a target whose current hit points are below half their hit point maximum, Felix has advantage on attack rolls and deals an extra 7 (2d6) slashing damage when he hits.

Actions

Multiattack:

Felix makes two greataxe attacks.

Greataxe:

Melee Weapon Attack: +9 to hit, reach 5 ft., one target. Hit: 22 (3d12 + 5) slashing damage.

Reposition (1/Day):

Each ally within 60 feet of Felix who can see and hear him can immediately move their speed without provoking opportunity attacks.

Legendary Actions

Greataxe Attack:

Felix makes one greataxe attack.

Mark the Target:

When Felix hits a target with a melee weapon attack, allies of Felix who can see the target have advantage on attack rolls against the target until the start of Felix's next turn.

Parry and Riposte:

Felix adds +3 to his AC against one melee attack that would hit him. If the attack misses, Felix can immediately make a greataxe attack against the creature making the parried attack.

Gavin Blackheart

Name: Gavin Blackheart

Race: Dwarf

Class: Fighter

Description:

A cold and calculating dwarf, Gavin is the muscle behind The Syndicate's operations. He oversees the guild's enforcers and ensures that everyone follows the code of conduct. Gavin is a master of hand-to-hand combat and weaponcraft, able to take down even the toughest of opponents with ease.

Physical Appearance

Gavin is a stocky and muscular dwarf with a height of 4'6". His skin is rough and tanned, a result of years spent training outdoors. He has piercing, ice-blue eyes that seem to cut through anyone who meets his gaze. His black hair is kept short and neat, with a well-groomed beard that reaches down to his chest. Gavin wears a suit of dark, well-maintained plate armor, adorned with the emblem of The Syndicate.

Background

Gavin Blackheart was born into a family of skilled blacksmiths and weapon-makers. However, his true calling was in the art of combat. As a young dwarf, he left his family's forge to join a mercenary company and quickly rose through the ranks due to his exceptional skill and unyielding discipline. Eventually, Gavin was recruited by The Syndicate where he now serves as their chief enforcer and oversees the guild's operations.

Motivations

Short term: Maintain order within The Syndicate and enforce the code of conduct.

Long term: Leverage the Syndicate's power and influence to crush his family's rival clan.

Tactics

Gavin uses his exceptional combat skills and strategic thinking to maintain order within The Syndicate. He is not afraid to use force when necessary, but also understands the importance of loyalty and trust among his subordinates. He is an expert at identifying potential threats and neutralizing them before they can cause harm to the organization.

Plot Hooks

The players are hired by a rival organization to infiltrate The Syndicate and gather information on their operations. They must find a way to gain Gavin's trust without arousing suspicion.
Gavin is seeking skilled fighters to join The Syndicate's ranks. He holds a secretive tournament to test the abilities of potential recruits. The players may choose to participate, either to join The Syndicate or to undermine it from within.
The players stumble upon a plot by a rogue faction within The Syndicate to overthrow Gavin and seize control of the organization. They must decide whether to aid Gavin in quelling the rebellion or use the chaos to their advantage.

Gavin Blackheart

Medium Humanoid (Dwarf)

Armor Class

Hit Points

112 (15d8 + 45)

Speed

25 ft.

STR

18 (4)

DEX

14 (2)

CON

16 (3)

INT

12 (1)

WIS

14 (2)

CHA

10 (0)

Skills

Athletics +7, Intimidation +3

Senses

darkvision 60 ft., passive Perception 12

Languages

Common, Dwarvish

Challenge

6 (2,300 XP)

Damaging Aura:

Any creature who moves within 10 feet of Gavin or who starts their turn there takes 6 (1d6+3) slashing damage.

Damaging Weapon:

Gavin's melee weapon attacks deal an extra 6 (1d6+3) slashing damage.

Delights in Suffering:

When attacking a target whose current hit points are below half their hit point maximum, Gavin has advantage on attack rolls and deals an extra 6 (1d6+3) slashing damage when he hits.

Frenzy:

At the start of his turn, Gavin can gain advantage on all melee weapon attack rolls made during this turn, but attack rolls against him have advantage until the start of his next turn.

Reposition:

Each ally within 60 feet of Gavin who can see and hear him can immediately move their speed without provoking opportunity attacks. (1/Day)

Actions

Multiattack:

Gavin makes two melee attacks.

Greataxe:

Melee Weapon Attack: +7 to hit, reach 5 ft., one target. Hit: 14 (1d12+4) slashing damage.

Heavy Crossbow:

Ranged Weapon Attack: +5 to hit, range 100/400 ft., one target. Hit: 10 (1d10+2) piercing damage.

Reactions

Parry and Riposte:

Gavin adds +3 to his Armor Class against one melee attack that would hit him. If the attack misses, Gavin can immediately make a greataxe attack against the creature making the parried attack. (Recharge 6)

Isadora Ithelar

Name: Isadora Ithelar

Race: Changeling

Class: Bard

Description:

An Information Broker/Undercover Agent of The Syndicate, Isadora Black is a master of disguise and subterfuge. She's a chameleon, able to blend in with any crowd and extract information from even the most guarded individuals. She's known for her quick wit and her fondness for gambling.

Physical Appearance

Isadora has an androgynous and adaptable appearance, with high cheekbones, a slender build, and almond-shaped eyes that seem to change color depending on her surroundings. Her hair is a deep shade of black, which she often changes in style and length to suit her current disguise. She dresses in a variety of clothing, always tailored to blend in with the crowd and never drawing attention to herself.

Background

Isadora grew up in a diverse and bustling city, the child of a human father and an elven mother. Her natural curiosity and adaptability led her to become an information broker for The Syndicate, a secret organization that profits from the exchange of information. As she honed her skills in disguise and subterfuge, she became an undercover agent for the organization, infiltrating various factions and gathering valuable intelligence.

Motivations

Short term: Hide the fact that she is accruing significant debts with a local bookie.

Long term: Rise through the ranks of the organization and become a key decision-maker, using her influence to shape the world according to her vision.

Tactics

Isadora relies on her quick wit, charm, and exceptional skills in disguise to infiltrate various groups and gather information. She uses her gambling prowess to win favors and gain trust among her targets, while her assertiveness and adaptability allow her to navigate complex social situations with ease.

Plot Hooks

The players are hired by a mysterious patron to investigate a series of thefts in a noble's mansion. Isadora is the mastermind behind the thefts, using her disguises to infiltrate the household and gather information for The Syndicate.
The players encounter Isadora in a high-stakes gambling den, where she is using her charm and skill to extract information from a well-guarded individual. If the players can gain her trust, she may become a valuable ally or a dangerous enemy.
The players are tasked with uncovering the identity of a spy within their own organization. As they follow the trail of clues, they discover that Isadora has been posing as one of their own, gathering information for The Syndicate. They must decide whether to confront her, try to turn her to their side, or use her as a double agent.

Isadora Ithelar

Medium Half-Elf

Armor Class

Hit Points

85 (9d8 + 45)

Speed

30 ft.

STR

10 (0)

DEX

18 (4)

CON

14 (2)

INT

14 (2)

WIS

12 (1)

CHA

16 (3)

Skills

Acrobatics +7, Deception +6, Insight +4, Investigation +4, Perception +4, Persuasion +6, Sleight of Hand +7, Stealth +7

Senses

Darkvision 60 ft., passive Perception 14

Languages

Common, Elvish, Thieves' Cant

Challenge

4 (1,100 XP)

Cunning Action (1/Turn):

Isadora can use a bonus action to take the Dash, Disengage, or Hide action.

Sneak Attack (1/Turn):

Isadora deals an extra 10 (3d6) damage when she hits a target with a weapon attack and has advantage on the attack roll, or when the target is within 5 ft. of an ally of Isadora that isn't incapacitated and Isadora doesn't have disadvantage on the attack roll.

Damaging Weapon (Trait):

Isadora's shortswords deal an extra 4 (1d8) damage on a hit.

Sneaky (Trait):

Isadora has advantage on Dexterity (Stealth) checks.

Vanish (Bonus Action):

Isadora can use the Disengage action, then can hide if she has cover.

Actions

Multiattack:

Isadora makes two attacks with her shortswords.

Shortsword:

Melee Weapon Attack: +7 to hit, reach 5 ft., one target. Hit: 9 (1d6 + 4) piercing damage.

Hand Crossbow:

Ranged Weapon Attack: +7 to hit, range 30/120 ft., one target. Hit: 7 (1d6 + 4) piercing damage.

Disguise Kit:

Isadora can spend 1 hour to disguise herself as another person.

Thieves' Tools:

Isadora can use her thieves' tools to pick locks and disarm traps.

Artwork Credits: All artwork in this article was generated by me (JL) using MidJourney V5

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