This article was first broadcast in Episode One Hundred Seventy Three on 14 July 2021.
Ryu (panicked): I didn’t take it. The hat’s in the vault. Lennon gave me the money for socks.
Ostron: Do you even wear socks? I thought you had those footwrap shoe-like things for climbing?
Ryu: Let’s change the subject. Did you need something?
Ostron: Yeah, I need some materials to repair one of the artifacts and they’re…not the sort of thing you can pick up in the marketplace, if you know what I mean.
Ryu: Right. You want the Jinjja Haengbokhan Jeulgeoun Sarinjoe Keurreob.
Lennon: Hey! I told you people to stop summoning stuff!
Ryu: I wasn’t. That’s the group name: Jinjja Haengbokhan Jeulgeoun Sarinjoe Keurreob.
Lennon: Group of what? Demons?
Ryu: No! They’re…creatively independent business people.
Lennon: Ah, so the thieves’ guild.
Ryu: They would consider that kind of insulting. Also they aren’t organized like a guild.
Ostron: Does that matter?
Ryu: Oh boy. Here, sit down and let me give you the basics.
So whether organized crime existed in the way we think of it in real medieval history is something that’s debatable and depends on what group and period of history you’re looking at. But regardless, thanks to modern medieval fantasy stories, now when a lot of people think of a functional medieval society, they assume there is some sort of large, organized group of people that are largely focused on illegal operations. Usually the three main things they cover are robbery, smuggling, and assassinations. If there are any illegal materials like drugs, they handle the transportation and distribution.
However, it’s not always clear how the “organization” part of the organized crime groups function. Even in most cases where the group is in an official module (like Bregan D’earthe or the Zhentarim), there will only be a summary of who is in charge of the group, what they focus on, and occasionally how someone becomes a member, but beyond that there’s not much detail. Now, you may not need detail in most cases unless the organized crime group is a major focus of the campaign, but if you do want it to be there, how would that look?
The first thing you need to determine is whether this is to be a group more like a modern organized crime ring, or if it’s following the guild model. Many of the groups grab the guild title, such as the Xanathar Guild or the more generic Thieves’ Guild, but that may or may not have anything to do with how they’re set up. Given how many groups do use the “guild” title (possibly because people think it sounds more medieval), and the fact that it’s a little less known, we’ll start with that.
Guilds in general have three official layers of membership, with an optional fourth layer depending. In order, you have apprentices, journeymen, and masters. The optional level is grand masters, who are usually nominated from within the guild to form a leadership or directorial body.
In this model, apprentices don’t have any specific requirements other than an interest in joining. They will be apprenticed to a specific master, who will teach them all of the basics of the craft, whatever it might be. To reach journeyman rank, the apprentices have to demonstrate a level of knowledge about the craft and then produce a piece of work as a sort of test. If their work is acceptable, they are promoted to journeyman.
Journeymen in the literal sense refers to their ability to travel. Rather than being attached to a single master, they are free to travel and learn from multiple different masters. In the original model journeymen were also capable of earning their own money, rather than relying on a master for their livelihood. They could not set up their own shop, however. To gain that privilege, they had to produce a literal “masterpiece,” or a piece of work that demonstrated everything they’d learned. If the masterpiece was accepted by other masters, they were promoted to the same rank. That allowed them to operate independently and take on apprentices of their own.
As mentioned, some guilds have grand masters. Those ranks matter less in terms of skill and more in terms of politics as the grand masters generally become the people who determine overall guild policy and settle disputes. In more egalitarian guilds the grand masters would be still chosen based on ability, but it’s not guaranteed.
For a guild focused on illegal activities, such as assassination, the journeymen and master pieces would probably be tasks, rather than literal items. So moving from apprentice to journeyman might require someone complete an assassination without any assistance, and going from journeyman to master may mean something higher profile, like assassinating a noble or carrying out an assassination during daylight.
An illegal group operating as a guild would have members with only loose association with each other, and the masters would set up a lot of their own rules. So if you have a city, for example, and different districts or territories are each controlled by a master, the only concerns between them would be making sure that any activity their guild controls is always done by members of the guild, and that the overall rules of promotion and membership are consistent. Other masters wouldn’t dictate how their peers run things in their territory and they wouldn’t directly compete with each other, but one member’s business may be very different in details from another.
If that doesn’t sound like what you’re looking for, a crime group based on a more modern model is going to look a lot more like a business or a military organization. This one is more familiar to many people because almost all modern shows or movies that involve organized crime follow this model. For these groups, there is usually one clear leader. How they got there and how their successor is chosen varies a lot; it could be an election, it could be passed down like a noble title, or there could be some sort of a competition, up to and including fighting to the death.
With the leader there is usually a group known as the “inner circle”. This is often made up of all the people who are the next rank down, plus one person who is a direct advisor to the leader. The number of people depends on how many different things are going on in the organization and how it’s organized. Sometimes there are three people: one person in charge of all the so-called military operations, one in charge of administrative stuff, and one in charge of training and initiation of new members, plus the advisor. In other cases, you have an inner circle made up of the heads of all the group’s activities, so you have a group of the head thief, head assassin, head smuggler, etc.
As far as that advisor goes, usually this is a person who functions as the surrogate leader if the person in charge isn’t there or is busy, and isn’t directly tied to any specific area of operation. They can’t contradict the leader, but they can make decisions the leader would normally be responsible for. If the leader is smart or wants to keep their job for any length of time, the advisor is someone very trusted.
After the inner circle, the rank structures are mostly like the military; you hold a certain rank depending on how many people you manage, how much territory you’re responsible for, or both. Everyone reports to the person the next rank up, and they’re the one usually responsible for promoting or punishing you. There’s a lot more direct accountability in this setup as compared to the guild model, so it’s very likely operations will be more consistent across the entire groups, with only very minor details differing from leader to leader.
The division of responsibilities varies from group to group like the setup of the inner circle. Using real world examples, usually the various Mafias divide things up based on leadership; a boss at some level will be given control of all operations in one area and will be responsible for the security and muscle of that area as well. So with that model, a single person will be the go-to for any drugs, assassinations, smuggling, or anything else, but just in that area. There may also be limits on how much so-called “business” they’re allowed to handle; if you want to smuggle one magic artifact in off a boat, you talk to a lower level boss. If you’re smuggling in a crate of magic swords that may need to be kicked up the chain.
Other organized crime groups, particularly those with Eastern traditions like Triads or the Yakuza, separate out the so-called security operations from everything else, and the various non-combat business operations are dealt with as a whole. There may still be individual bosses in charge of specific operations, but they will have wider areas of responsibility, and will be overseeing more overlapping operations as you climb the rank ladder.
So addressing the elephant in the room: you may have noticed we left one major area off the list of things some organized crime groups engage in. Partly that’s an organizational concern, but it’s also because you should probably think carefully about whether prostitution should be a thing in your campaign. Definitely bring it up well before it appears in-game to make sure everyone is okay with it.
With that in mind, if we’re talking about individual prostitution it’s usually folded into the other business of a crime group along with the drugs and the smuggling etc. However if there’s an actual brothel sometimes it can sit outside the group’s hierarchy. Historically this is partly because organized crime tends to very much be a boys club and they’re either against or afraid to let women into the hierarchy. In those cases the brothel may pay some sort of tribute to the local group, but are otherwise left alone. In other cases the brothel is a part of the organization and the person in charge of it (usually called a Madam and traditionally a former prostitute who has either voluntarily or practically aged out of service) is part of the leadership at whatever level makes sense. Particularly in the case of the eastern model of organization, you could end up with a boss in charge of all prostitution.
As we said before, need for this kind of information is situational. If you just need a non-specific “crime group” operating in an area so a couple of characters can make a few risky skill checks in a dark alley to secure an imported Displacer Beast, you probably don’t need to worry about the hierarchy. On the other hand, if the city guard is looking at a dead nobleman with a dagger sticking out of his back, it might be worth figuring out a more detailed leadership structure for the characters to infiltrate and investigate.
Lennon: What did you need anyway?
Ostron: It’s a specific type of psionic crystal that’s shaped like a mobius strip. It’s for ROSTRO.
Ryu: What are you doing to that machine now?
Ostron: Well, I had in my notes that I needed to install a…what did I call it…yeah a “horizontal rippling telekinetic surface projector with variable speed control.” Though I’m not actually sure what for.
Ryu (skeptically): Uh huh, why don’t you give me a minute to look into this…
Ryu (shouting): KAYDEE!
(angry stomping off)
Ostron: I didn’t think it was that big a deal.
Lennon: Well you know how she feels about ROSTRO. Hey have you considered sending that…whatever she called it group a message in the scrying pool?
Ostron: I didn’t think RaeRae would be on board with that idea.
Lennon: Can’t hurt to ask, right?
Ostron: This is RaeRae we’re talking about.
Lennon: Well…I bet if we clear all the messages out she’ll be in a better mood. Gotta be worth a try, right?