Non-boring Thieves Guilds

So there's this old Japanese computer system called the FM Towns, which was named after Nobel prize winning physicist Charles Hard Townes even though the spelling is different.  The other day I discovered that several early Ultima games were ported over to it, with some interesting new graphics.  Here's my favorite one:

That's what you see in the FM Towns port of Ultima I when you're about to encounter a Thief in a dungeon.  I love his skull T-shirt.  His pants and boots look like they're from a pro wrestler, which fits the dude's beefy physique pretty well.  And what the crap is he carrying?  Is that a baton, or maybe a length of pipe?

Remember that because of the limitations of the software, every thief in this game looks just like the guy above.  Someone is issuing skull t-shirts to these dudes.  At first I thought maybe that when you sign up to join the Thieves Guild they hand you a free t-shirt with the guild logo on it.  But then it struck me.  Just last week I re-watched a certain cinematic classic:

So here's the concept.  Thieves aren't a secret brotherhood family sneaky burglars in black cloaks.  Nor is the Thieves Guild some sort of the fantasy mafia.  Rather, it's a loosely connected confederation of petty criminal gangs, each with their own colorful outfits and traditions. Each of these component gangs was founded by some name level thief and the 2d6 random punks that showed up when he built his hideout.  Some high-Charisma Cyrus figure with a lot of heavy muscle keeps the Guild together as best as he can, but petty breeches of the Truce are common.  

This scheme works particularly well for the Encounter Critical version of Sosaria that I've been working up, as the Criminal class in EC encompasses a lot more varieties of illegal activity besides sneak thievery.  I also like how this idea flips the normal expectations about the Thief in D&D play: Instead of the cowardly figure in the dark cloak, a thief is now a flamboyant, colorful character who struts around like he owns the place.

To really make this version of the Thief work the DM needs to be prepared to make some rival gangs for thief PCs to squabble with.  Statting up the rest of the PCs gang also sounds like a good idea.

Now can you dig it?