So I took a quick look at Wikipedia, which has an article that cites an early use of the idea by that father of novels, Cervantes. A few strokes of the keyboard revealed that the relevant story, Rinconete & Cordillo, can be found via the Gutenberg Project, in the collection called The Exemplary Novels of Cervantes. Yes, the internet is awesome.
I've hardly looked at the story, but Wikipedia describes it as involving crime in Seville, with a thieves' guild that one advances in just like a craft guild.
The other fun fact was that the key modern fantasy use of the idea was in the Fafrhd and the Grey Mouser stories by Fritz Leiber. That was an aha moment, I'd been trying to think of why the image of a guild seemed so dominant to me....Fafhrd and the Mouser's struggles against the Thieves' Guild were it.
My first thought was Leiber as well. The Cervantes reference is interesting. I always thought of the Thieves' Guild as being a bit anachronistic, a way of blending modern organized crime with medieval style institutions such as Guilds. I'd look more to early Italian criminal families and organizations for historical inspiration. Or you could just call your uncle. :-)
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