Setting up a Thieves Guild

A while ago, I started experimenting with faction systems in my game—cult hierarchies, inner circles, secret handshakes, that sort of thing. One of my players had a character who was rising through the ranks of a shady cult, and I had set up rules for access levels and promotion rites. It was going great… until he went insane, betrayed the party, and got executed. I barely had time to test anything.

Luckily, another player stepped in with a brilliant pivot. He’s playing a big orc warrior, and after getting sick of paying tolls to the endless stream of bandits in my dungeon, he thought: what if I join them instead? He had already discovered their surface headquarters and decided joining would be cheaper than constant extortion. Thus, a new opportunity opened up: the orc’s slow initiation into the local thieves’ guild.

What We Know So Far

At that point, the guild wasn’t very fleshed out. All I knew was that they controlled the first underground level of the dungeon. They run the toll roads, manage the entrances, and are instantly recognizable: bald heads, tattooed skulls.

That was more than enough to start giving them some real character.

The system is simple—more tattoos (and more complex designs) mean higher rank. Members earn their ink through feats, missions, and proving their value. They're loose and chaotic, but not disorganized. They charge tolls, but aren’t overly aggressive unless provoked. Their vibe reminded me of that Adventure Time episode with the City of Thieves—everyone’s robbing everyone, but it still sort of works.

In the Adventure Time episode, the City of Thieves is a chaotic but functional place where everyone is constantly stealing from each other. It’s legal to rob, and the citizens are all thieves, but despite the backstabbing, the city runs on an unspoken, bizarre understanding—everyone steals, everyone survives. It’s not all-out war, just the reality of life. That kind of balance between utter lawlessness and strange survival was exactly what I was going for with this guild. I pictured their leader as a massive, imposing man—part Kingpin, part street legend—who rewards cleverness and nerve over blind loyalty. He doesn’t care if you lie, cheat, or backstab… as long as you know when not to.




The Guild's Commandments

  • Better a snake than a fool.

  • What’s stolen fair is fairly mine.

  • Guild first, friends behind, self last.

  • Speak the signal, seal the pact—no betrayal until it’s broken.

  • If the guild eats, you eat. If the guild bleeds, you bleed.

These commandments aren’t just painted on walls—they’re tattooed into skin, whispered in initiation rites, and recited before high-stakes jobs.

Number four refers to a special signal or phrase used by members to invoke a temporary pact—during this time, betrayal is strictly forbidden.

The Pact Phrase:

“Tonight, our blood is one.”

The Ritual to Seal the Pact:

  • Members cut their hands (or a finger) with a small blade or knife.

  • They shake hands, mixing their blood together, symbolically binding their fates.

  • While they do this, they say the phrase: “Tonight, our blood is one.”

  • The pact is sealed. No member can betray the others until the task is completed or dawn breaks.

This could be a common ritual for every important job, or reserved for high-stakes missions. The gesture, though simple, adds a physical, permanent connection to the bond. The blood might even leave behind a scar or mark that stays with the members as a reminder of the pact. 


The Initiation:

To prove their worth and commitment, the new recruit's first task is to pay the membership fee and deliver a sealed envelope to a guild watchpost on the first sublevel. The catch? The envelope must never be opened, and the recruit is warned to follow the instructions exactly. Inside the envelope, there’s a note telling them they must hand over a substantial sum of money to the guards at the post.

What happens if...

  • They open the envelope or find a way to avoid paying? The guild rewards cunning and cleverness. Instead of a simple transaction, the recruit will be marked with a more elaborate tattoo (possibly a rune or a more intricate design) to recognize their resourcefulness. This may even bring them respect among their peers, though it’s also likely to raise some eyebrows among those who value loyalty.

  • They follow the instructions to the letter and pay the guards? Well, they'll receive what they were told: a small, simple line tattooed on their scalp, marking them as someone who obeys rules without question. They’ll become the subject of mockery within the guild, seen as someone who lacks the wit to think outside the box. But they’ll still have passed their first test.

Once this task is completed, the recruit’s head will be shaved clean, and they will receive their first tattoo as a permanent reminder of their initiation. They’ll now have free access to the guild’s tolls on the first level. The guild’s commandments will be read to them, ensuring they understand the rules of the organization, and they will learn the secret pact phrase that bonds the guild members together:


Stealing from fellow guild members is not explicitly punished within the organization, but doing so can result in healthy rivals or mortal enemies, depending on the severity of the theft. The guild is known for its intimidating and bully nature, so if someone robs you within the guild, they will publicly humiliate you. While there's no direct punishment, the damage to your reputation can be harmful, creating internal tensions and conflicts.

Additionally, guild members can recruit others for major heists or high-stakes jobs.

For now, I don't want to define the initiation steps or rituals too rigidly, but here are some ideas for missions they could be assigned, along with the rewards for completing them:

Tasks and Rewards:

Task: Steal a specific item from a well-guarded merchant in the city.
Reward: A rune tattoo that grants the ability to sense valuable items or gold within a certain range.

Task: Smuggle a rare, illegal item past the city's checkpoints without getting caught.
Reward: Increased access to restricted guild areas and an increase in reputation with other thieves.

Task: Find and dispose of a rival thief who's been stealing from guild-controlled areas.
Reward: A special dagger engraved with the guild's symbol, which never dulls and can be used to perform clean kills.

Task: Sabotage a competitor's business by planting incriminating evidence.
Reward: A tattoo marking you as a trusted operative, giving you access to higher-ranking guild members and more dangerous jobs.

Each mission or task should be completed with a rune or a tattoo on the head as a "scout badge" type of mark, symbolizing progression and success within the guild.

Comments

Post a Comment

Popular posts from this blog

The Dungeon's Heart: City Building Tips

Image
One of the challenges in dungeon-delving RPG campaigns is figuring out what to do with all the gold. Players often amass large sums of money without knowing how to spend it. The usual recommendations are upgrading equipment or managing a stronghold , but these are often vague suggestions without clear mechanics to support them. One aspect I appreciate about His Majesty the Worm , the game I'm currently running, is its structured approach to the economy. When adventurers return to the surface, the City Phase begins, requiring them to pay taxes on their expedition's earnings, choose their level of comfort for lodging, and perform a City Action . These special actions allow gold to be spent in interesting ways with clear mechanics: commissioning a rare artifact (with a cost based on the number of words in its description), going on a spree to gain experience, hiring training services, building a tavern, and more. These actions are standard, but the rulebook encourages adding dist...
Read more

Building a Modular Megadungeon: Design, Challenges, and First Impressions

Image
 The dungeon in my campaign is created by a Dream Worm , so I thought it would be a great opportunity to experiment with a modular dungeon . The idea is that every time the players leave, the dungeon reconfigures itself based on their dreams and fears. Additionally, random events can trigger shifts in the module layout during exploration. Designing the Modules To simplify the process, I decided to make square modules . I then had to determine how many rooms each module should have and how many modules would make up each floor. Module and Room Count I settled on 12 modules per floor to ensure a good variety of layouts without making the combinations too predictable. Each module contains between 8 and 15 rooms . Initially, I considered 30 rooms per module , but that would result in 300 rooms per floor , making exploration too slow. I want my players to move through multiple levels, so I reduced the number. For reference, adventures like The Hole in the Oak and Against the Cult of...
Read more