Content of the article: "reconsider thieves’ guilds"
People typically underuse thieves' guilds. Obviously, your standard thieves' guild is just a group of people who steal and collaborate in stealing. But they can be so much more. All a thieves' guild really has to be is a criminal organization.
So the easy way to make a thieves' guild more interesting is to add just one law which is morally wrong in some way. There are plenty of examples from history.
When the Underground Railroad helped enslaved people escape the South in America, it was against the law. Technically, these human beings were considered property under the law, which made the Underground Railroad not just, in effect, organized crime, but also a literally a group of thieves. In many countries, the Holocaust was legal, too, so people who helped Jews escape it were forming criminal conspiracies in the process. Before medicinal marijuana laws, the only way for a cancer patient to get relief from their pain was, again, through organized crime.
You can use these ideas in a D&D game. All you have to do is make a law that is evil. A vampire king outlaws healing magic because he doesn't want clerics around who can turn undead. So, while you're travelling through this monster's kingdom, you can still get healing potions, but you have to be careful where you buy them and who you buy them from. Thieves' cant becomes way more useful than average in a place like that.
But there can also be problems if you make a thieves' guild which is just unequivocally in the right. First, you're kind of railroading your players into a "fight the unjust government" storyline. That can be a ton of fun, but only if they're into it, and there's all the standard tradeoffs around railroading. (Some people love it, some people hate it, and most people want some railroading, but not too much.)
The second problem with a thieves' guild fighting some injustice is that, if you have a lawful good player, there's nothing for them to do except roleplay their head exploding. If the laws are evil, being lawful good is difficult. Alignment isn't as big a part of D&D as it used to be, and this is a good thing, but you want everybody in the party to have some stuff to do.
So you can have a thieves' guild which is unequivocally good, by having them conspire to break a law that is bad, and you can have the very standard thieves' guild which is unequivocally evil, because they conspire to break laws that are good, like "don't steal" or "don't murder people."
But you can also have thieves' guilds which are both good and bad.
And so, again, look at real-world examples for a second. Many bandit gangs in medieval Europe started out as a group of soldiers cut off from their main army who needed a way to survive. The Triads in Hong Kong have a similar history. All you have to do to make a morally ambiguous group of bandits is have them fight in a just war, but then turn to stealing out of desperation, and have some of them decide they like it.
So a good king gives your PCs a mission: "retrieve for me my son the prince, who was separated from the main army during our last war." So the PCs go and find the prince. They find that the prince and his soldiers have become bandits. The prince sees it as a necessary evil. He doesn't want to be a bandit, but the local government would hunt him either way, because of who he is, and he has an obligation to feed his soldiers. But the prince also has a second-in-command who likes being a bandit, so that guy tries to kill the PCs, or tries to convince the prince that the PCs don't really work for the king. He says they're spies, or something.
And spies are another great way to use a thieves' guild. You're going into Country A. It's at war with Country B, the country you're in. You need to get into Country A to delve into a dungeon and retrieve a magic sword, but nobody from Country B is allowed to cross the border under any circumstances. Good thing the Inquisitive Rogue is hooked into the thieves' guild which operates in Country A as a network of spies for Country B, because you're going to need somebody to sell you some stolen passports.
etc etc etc
The standard thieves' guild that just steals from people, has a headquarters in the sewers, and wears hoods at all times can be fun, but there are a million other ways to do it. (Plus, you're not actually going to be that good at sneaking if you spend a lot of time in the sewers, because the smell makes you conspicuous.)
- A civil war that’s retroactively a bit too on the nose.
- [Spoiler warning!] I need to talk about how much I love the thieves guild for a hot minute
- What would be fairy tale-esque requirements to become the bandit king?
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