Thieves' Guild of Greyhawk

To the average citizen of Greyhawk, thieves are everywhere and involved in everything. There is little that escapes their notice, and rumors abound that they report all they see to their masters. If something goes missing, the Thieves' Guild is the first to be blamed—from stolen coins to the cheese in the larder. Even mothers warn their children that if they misbehave, the thieves will come in the night and steal them away.

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The Greyhawk Thieves' Guild has become legendary across the Flanaess. In tales told around campfires and taverns, they are the pinnacle of stealth, cunning, and unmatched skill. The city's notorious reputation as a den of thieves has spread far and wide. Travelers are often warned by innkeepers hundreds of miles away of the guild’s ruthless efficiency and their almost supernatural ability to separate people from their wealth.

The Guild’s Modern Reality

In truth, the Thieves' Guild is but a shadow of its former self. While still skilled and influential, it has diminished from the massive clandestine force it once was. As Greyhawk’s economic strength grew, more time and effort were spent thwarting the guild’s schemes. Additionally, the brutal war between former Guildmaster Arentol and Theobald’s Beggars' Union culled many low-level thieves and apprentices, depleting the guild’s talent pool.

Yet, the guild remains a force to be reckoned with. The Guildmaster openly sits on the Directing Oligarchy, the Lord Mayor is secretly the Assistant Guildmaster, and two senior members of the Merchants' and Traders' Union are deeply tied to the guild.

The Guild’s Operations

Contrary to popular belief, actual thievery is not as rampant as many assume. The guild prefers to rob outsiders—merchants and adventurers—while avoiding conflict with the city’s powerful guilds.

• Merchants' and Traders' Union members are subject to strict quotas dictating how much can be stolen per month.
• The Greyhawk Guild of Wizardry is considered off-limits (for good reason!).
• Non-union traders and adventurers, however, are fair game.

Though thieving remains part of their craft, the guild supplements its income through extortion—demanding protection money from small businesses and middle-class households.

Guild Structure

The guild is organized by quarter, with each controlled by a Master Thief who reports to the Guild Directorship. The exception is the Thieves' Quarter, where a large number of apprentices train before being assigned elsewhere.

Each quarter has its own specialization, reflecting its unique character and leadership:

The High Quarter – Elite Operatives

Though small in number, the High Quarter thieves are exceptionally skilled. Most operate outside Greyhawk, engaging in high-stakes theft, espionage, and artifact recovery across the Flanaess.

• Membership: No more than 20, all level 8+ thieves, literate, and multilingual.
• Missions: Wealth extraction, artifact recovery, and espionage for the Directing Oligarchy.
• Rumors: The legendary thief known as “Shadow”—who famously stole the Jacinth of Inestimable Beauty from Niole Dra—is said to be among them.

Guildmaster: Org Nenshen

• Age: 43, Height: 5’9”, Weight: 180 lbs.
• Appearance: Blond hair, violet eyes, tan skin, always well-dressed.
• Background: Trained alongside Nerof Gasgol, the current Lord Mayor.
• Personality: Though highly respected, he doubts his worthiness as Guildmaster and constantly pushes himself to prove his skill.

The Garden Quarter – Masters of Blackmail

Unlike the High Quarter, the Garden Quarter’s guild thrives on blackmail, extortion, and the occasional kidnapping. These thieves are highly connected socially, blending seamlessly into the city’s elite circles.

Master Thief: Pavel Alektrion

• Age: 30, Height: 6’0”, Weight: 160 lbs.
• Appearance: Debonair, fashionable, and charming.
• Background: A wealthy merchant’s son turned thief and adventurer.
• Specialties: Manipulating and conning adventurers, using blackmail or trickery to rob them.

The River Quarter – The Guild’s Stronghold

The busiest region for guild activity, the River Quarter is home to burglary, smuggling, and violent crime. Here, thievery is brutal and direct.

Master Thief: Tomas Ratek

• Age: 45, Height: 5’11”, Weight: 210 lbs.
• Appearance: Bald, overweight, covered in scars.
• Personality: A ruthless brute who relies on brute force rather than finesse.
• Goal: Aspires to overthrow Org Nenshen and become Guildmaster.

The Foreign Quarter – Chaos and Opportunism

The Foreign Quarter is a hotbed of thievery, often devolving into a free-for-all as gangs of thieves work the crowded markets and streets.

Master Thief: Simpkin Furzear (“The Weasel”)

• Age: 72, Height: 3’2”, Weight: 72 lbs.
• Appearance: Greasy black hair, rasping speech, appalling fashion sense.
• Role: Oversees gambling and petty crime at The Pit.
• Personality: A cruel and dangerous bully who enjoys making taller folk squirm.

The Slum Quarter – Agents of Chaos

Traditionally the domain of the Beggars’ Union, the thieves maintain a small but vital presence. Here, they act as agents provocateur, inciting riots and unrest to distract authorities when needed.

Master Thief: Larrat Helfdene

• Age: 38, Height: 5’11”, Weight: 190 lbs.
• Appearance: Silver-haired, clean-shaven, dark-eyed.
• Background: Lost a hand on a mission, now operates as a “sleeper agent” inside the Beggars' Union.
• Role: Manipulates the beggars, though they secretly feed him misinformation in return.

The City Outskirts – Intimidation and Smuggling

Guild activities reach outside the city walls into the quarter known as The Outskirts, this growing community is ripe to be taken advantage of by a brutal strongman. Close ties to the Rhennee and their smuggling operations.

Master Thief: Sorn Blackfist

• Age: 32, Height: 6’1”, Weight: 260 lbs.
• Appearance: Burly with close clipped brown hair and dark eyes that lack empathy.
• Personality: Known to be cruel and takes pleasure from torture of those that cross him using fighting dogs.
• Goal: Wants to move up to control of one the city quarters within the walls but his psychotic nature makes him untrustworthy to the other guildmasters.

Conclusion

The Thieves' Guild of Greyhawk, though reduced in size, remains a powerful and insidious force. Its members lurk in every shadow, manipulating commerce, politics, and crime. Whether operating in plain sight or from the darkened alleys, the guild’s influence is felt throughout the city and beyond. Adventurers beware—for in Greyhawk, the thieves are always watching.