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
- 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)
- Explain the various advantages and disadvantages of coin clipping, sweating, shaving, punching, and plugging
- How many copper and silver pieces are required for the change-raising scam?
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
So have some random charts.
1-Department of Acquisitions
2-I'm sorry that was the only idea I had
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.
- 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!
- Cute Girls- The bane of male tourists, who are easily led into scams such as this
- 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
- 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.
- 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!
- 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.