Salutations, nerds! Today we’re going to talk about a fantasy staple: the thieves guild. A group of stylish rogues with a secret code language who are much of the time the best organized and most numerous group of people in the city. You see those street urchins playing over there? They’re informing for the Guild Master. The guy at the bazaar who sells terrible bread you never actually see anybody buying? I mean, you had to know he was a fence.
I’ve got a soft spot for a good heist story and I’ve always kind of wanted to run a fifth edition Dungeons & Dragons game where the entire party are rogues and center it around the inner dealings of the thieves guild. So often my home town party ends up going off on tangent of stealing things anyway, after all, so why not cut out the middle man? Which got me wondering…why do people end up doing crimes so often in 5E D&D anyway?
What makes 5E D&D rogues so glamorous
Are you more afraid of the guy in the leather loincloth running barefoot across the cobblestones screaming while holding an axe, or the graceful one you didn’t see until she was right behind you with the point of her stiletto against the soft flesh of your throat?
There’s something about supple black leather that just makes anybody look like a lethal bad ass, but it runs deeper than this. When we sit down at the gaming table we’re all looking for experiences we can’t get in real life. None of us have actually slain a dragon.
I suppose it’s possible for us to go out, plan a heist and steal a bunch of things. It’s dangerous, and most of us wouldn’t do it because of the risks involved (and maybe a few because stealing things is bad) but that’s not at all the case at the 5E D&D gaming table. And even players who draw the line at murdering an innocent person at the gaming table are usually down for a rogue heist story.
Part of this probably goes back to tales of Robin Hood, stealing from the rich and giving to the poor. To this day he remains a cultural icon because the rich can spare it and should be giving to the poor anyway. In committing crimes Robin Hood is actually doing a service for people who need it while not actually harming the rich people he’s stealing from so much as tweaking their noses.
Stealing is like one of those small crimes that doesn’t feel like it has a victim when you’re stealing super valuable things. Those nobles are well enough off to have an opulent painting like this in the first place so why not take it, right? It’s a good outlet for your players to do something bad without feeling too bad as a result.
Power of the criminal underground
The Master of the Thieves Guild is almost always portrayed as being a powerful person. I mean, when you have every set of sticky fingers in the city working for you, you’re going to have an amount of influence. Some of those people are going to be stealing coin and gems and jewelry, sure, but some of them are going to be stealing information and being in a position for all of that to cross your desk puts you in a bit of a unique position as far as influencing what goes on in the city.
And it’s not like most of the nobles who are often portrayed as just engaging in hedonism and having affairs, oh no. The Thieves Guild Master actually has to work for every scrap of power they have. It isn’t as simple as moving the pieces around. They can’t simply send their operative into the ball to stop this business arrangement, they have to find a way to secure their invitation and get them in before they can have that access, or their agent will have to sneak in. Which, admittedly, rogues are good at.
The point is their power comes from being unseen and the fact they shouldn’t be doing any of what they are, and yet there they go, doing it anyway. Thieves guilds break the rules or flat out ignore them. And there’s something really cool and powerful about that.
What the thieves guild can do for rogues
Of course the thieves guild could provide interesting antagonists for player characters and are often used this way. They know everything. They can stop PCs from getting into places. They can steal things (and nothing makes your players angrier than stealing their stuff).
These guys have their fingers in everything, and crossing them is generally considered a bad idea. Of course anything that can add tension to a scene is a good thing to have in your back pocket as a Dungeon Master, so having PCs walk out of a tavern and right into an ambush is a fun time.
However, once they’ve gotten in with the thieves guild they have a convenient place to fence their stolen goods and characters proficient with lockpicks ready to help spring them out of jail if things go south. Not to mention, as allies, members of the thieves guild make for excellent quest givers.
There’s a whole plethora of things you can do that involve stealing things, changing numbers in ledgers, casing joints or roughing somebody up for protection money…crimes! They’re relatively easy to come up with, relatively easy to run, and you cannot possibly exhaust them because there’s always going to be somebody who wants something that does not belong to them.
In conclusion, rogues are awesome. Heists are awesome. The thieves guild is probably awesome and if it’s not, you should go make it awesome. Have you got some interesting rogue stories? Especially heists that went sideways, those are my favorites. Please let me know in the comments below. And of course, stay nerdy!