Are You Bad Enough to Join the Thieves' Guild?

Thieves guilds are a trope that has been beaten to death and beyond but between reading all the kooky schemes of The Arabian Nights and revisiting the sinister Thieves' House of Fritz Lieber's Fafhrd and the Grey Mouser series, a love for the idea has been rekindled in my withered breast.

There are two tests to join the Thieves' guild- the written/oral exam and the practical. If you fail them both, you get murdered to keep their secrets and to keep useless chaff out of their ranks. If you fail one you can join as an apprentice. Pass both and you can actually hop right in as a freepick.

The written/oral exam is very advanced and has fiendish questions like

1. Of what use is a tortoise during home robberies (affixing candles to the shell and sending it to scout dark places and provide hands-free light)
2. Explain the various advantages and disadvantages of coin clipping, sweating, shaving, punching, and plugging 
3. How many copper and silver pieces are required for the change-raising scam?

Assuming you're a thief, you have a level+INT modifier in 10 chance of passing. If you are not a thief, it's out of 20. Note it is a foolish MMORPGism to believe that only thieves can join the thieves guild. Wizards are great at stealing stuff, especially in ways no one expects. Fighters are great at mugging people- subtlety is only a requirement if the guards can actually stop you. Clerics are naturally perfectly suited for con jobs and swindling people out of their money, assuming they aren't too pious.

In any case, the written test is mostly designed to overawe people with the stupendous knowledge of tricks the guild has acquired over the ages of its operation. The practical test is a much more straightforward test, and is in fact an actual crime. The hapless would-be-thief is tasked to steal a purse of a 'disguised agent' or retrieve a valuable item from a 'Guild Simulation Training Center' or whatever. If they pull it off, the thieves guild takes the entirety of the score and congratulates the initiate on passing the test. If they don't, the guild probably leaves them to the tender mercies of the town guard. Either way, the initiate has now officially done a crime, and so is doubly reliant on the guild for a safehouse and protection.

Apprentices get room and board and give all their take to their freepick master that assigned/asked to be in charge of them. They will have ample time to practice picking locks, tying knots, climbing ropes, appraising items, sweeping floors, and other valuable tasks. Once they complete their apprentice training, the total cost of these services is revealed, and they realize they're 20,000 coins in debt and all they have to show for it is a socially unacceptable degree in creative literature thieving. And so they labor to pay off their 'guild dues,' finally earning money for themselves as a freepick. And they hope to pay off this debt faster by getting lots of apprentices and taking all of the money the apprentices steal. And so the circle of life continues, with the master(s) of the guild doing relatively little thieving and mostly just rolling in the fat stacks of cash brought in by their underlings.

So have some random charts.
Guild Names
1-Department of Acquisitions
2-I'm sorry that was the only idea I had

Guild Hideout
1- A secretish cave outside of civilization. Convenient for highway robberies of merchants as they leave or enter the city.
2-A guildhouse like a squat shadow of the local lord's fort. Or maybe just the local lord's fort.
3-A decentralized series of caches and hideouts. Freepicks and their apprentices rarely meet in person
4-Local inn. Isn't really a 'front' it's just that the thieves basically live there for convenience.
5-The walls of the city are hollow, and though they are patrolled by guards, the thieves still slip thru
6-Tent and wagon city of hobos and ne'erdowells. Basically a bandit camp that oozes through city districts and wilderness alike.

Guild Specialty

1. Trained animals. Monkeys that pick locks! Birds that pinch jewelry! Tortoises that aren't trained but they don't need to be to be candleholders!
2. Cute Girls- The bane of male tourists, who are easily led into scams such as this
3. Charm Scam- The guild employed an alleged wizard to throw around alleged curses, and now aggressively pushes 'protective charms' that do nothing but inform said wizard not to curse you
4. Counterfeiting- The guild makes fake coins, fake art, fake documents, fake everything. Caveat emptor, and know that all mines and treasure maps are indubitably salted.
5. Jailbreakers- The right bribes and tricks can get people in and out of jail very fast with a  compromised judicial system. The thieves ARE the law!
6. Spy Network- In addition to trading in secrets and blackmail and badger games, they have the information to seize upon any opportunity for profit they hear of before the players have a fair chance to give it a go unopposed.

 Anyway, I think thieves guilds are viewed as boring and cliche because the baseline thief is too often treated as a cliche, a lithe rogue in dark leathers and light weaponry utilizing skills found in the thief tables and nothing else. If you expand that mental image to an entire group of people, naturally it's not gonna be particularly compelling. But if you take 'Thief' to simply mean 'a person willing to do morally bankrupt things to obtain cash' well, you got the whole world of options And this applies to 'thief' class characters as well, not just DM pet projects! My approach was to look up con jobs on wikipedia and I barely even scratched the surface of inspiration there. I didn't even touch magic nonsense that they could get up to. Imagine thieves who con the restless spirits of the dead into thinking the living have stolen their gravegoods, and that the ghosts should steal it back. And then the thieves steal the stolen goods from the dead, rinse and repeat. I should have written this entire post on those guys. Dang.