Roll20 Marketplace Product

Thieves’ Guild expands the familiar back-alley criminal trope into a full, encounter-ready hierarchy designed for 5e play. Rather than treating thieves as a single low-level nuisance, this supplement presents a complete ladder of street operatives, professional criminals, disciplined enforcers, and unseen masterminds—from lookouts and runners to burglars, lieutenants, and elusive guildmasters—each built to fill a specific role at the table.

Whether you need disposable eyes to flood an alley, agile cutpurses to harass and scatter a crowd, brutal muggers to apply pressure, skilled infiltrators to bypass locks and wards, or a calculating crime boss directing the encounter from the shadows, Thieves’ Guild provides mechanically distinct stat blocks at every tier of play. The ladder is designed to scale naturally, allowing urban encounters to grow from petty crime and street violence into coordinated operations, territorial wars, and campaign-defining confrontations.

Each guild role is designed with clear encounter purpose, strong internal synergy, and GM-friendly abilities that emphasize coordination, control, and leverage over raw damage. Use them as pickpocket rings, organized crime syndicates, shadowy city guilds, or sprawling underworld networks—the structure is provided, the city they control is yours.

Thieves' Guild Ladder

Guild Lookout (CR 0): Unarmed sentries and street eyes who warn the guild of danger. They flee at the first sign of trouble and value survival over loyalty.
Guild Runner (CR 0): Messengers, decoys, and bait used to draw attention, deliver information, or lead pursuers into traps. Fast, disposable, and hard to catch.
Guild Cutpurse (CR 1/8): Pickpockets and petty thieves who work crowds, markets, and festivals. They rely on distraction and escape rather than confrontation.
Guild Forger (CR 1/8): Document falsifiers who create fake permits, writs, seals, and ledgers. Dangerous not for combat skill, but for the chaos their work causes.
Guild Mugger (CR 1/4): Alley predators who ambush isolated targets for quick profit. Brutal but undisciplined, they strike hard and retreat faster.
Guild Grave Robber (CR 1/4): Tomb looters and crypt crawlers who strip corpses and forgotten sites. Superstitious, filthy, and often carrying unsettling relics.
Guild Tough (CR 1/2): Enforcers and bodyguards who protect guild interests through intimidation and violence. Loyal while paid, ruthless when cornered.
Guild Smuggler (CR 1/2): Specialists in moving illicit goods through docks, borders, and city gates. Skilled at concealment, bribery, and escape.
Guild Burglar (CR 1): Professional infiltrators who bypass locks, traps, and alarms. Prefer stealth and planning to open conflict.
Guild Highwayman (CR 1): Roadside robbers who ambush travelers with threats and negotiation before violence. Confident, theatrical, and always prepared to disengage.
Guild Scout (CR 2): Reconnaissance experts who track targets, map routes, and set ambushes. Rarely fight alone and withdraw once their task is complete.
Guild Witchknife (CR 2): Criminal specialists trained to steal from spellcasters and temples. Use stolen charms, wards, and countermeasures rather than true spellcasting.
Guild Assassin (CR 3): Precision killers hired for specific targets. They strike decisively and disappear, avoiding prolonged fights whenever possible.
Guild Fence (CR 4): Influential brokers who control stolen goods, information, and contacts. More dangerous socially than physically, with reach across the city.
Guild Lieutenant (CR 5): Trusted crew leaders who command cells and coordinate operations. Pragmatic tacticians who know when to fight and when to retreat.
Guildmaster (CR 6): The unseen hand behind the guild’s operations. Rarely encountered directly, relying on preparation, leverage, and layered escape plans to survive.

Compatible Products

These thieves fit naturally into any of our Fantasy Maps.

You might also like...

License: Roll20 End User License Agreement
(Personal Use Only, Do Not Distribute)