How big is a Thieves' guild?

The way I usually organize my thieves' guilds is, there's a core of about 30 to 50. These are analogous to made men. Planners, enforcers, skilled burglars. Outside that core, you have about 50 to 100 people "who know people" in the guild, do jobs for them, don't know very much, and while they may get help in the dungeon if they land there, they aren't the ones the guild's gonna bust out of jail or anything. Outside of that you have a hundred or so informants and colluders who take bribes and feed the guild info.

The structure of a typical guild – that doesn't have some mystical/religious component gluing it together – doesn't support much more than that. Now, in large crime-ridden metropolises, what'll happen is the Thieves' Guild (or Assassin's Guild) will sit at the top of a pyramid of less powerful more specialized organizations, gangs, or possibly clans. Then you might get to a thousand or so. But they're not going to be directly reporting to the Guildmaster.

In a town of 10k I'd have about 20 core members, 15 hands-on skilled rogues, 5 older people with connections, all with at least a few levels. The low-level muscle comes from town roughs outside the organization.

Admittedly I have been watching a lot of The Wire lately.

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