A recent article at DnD Speaks provides a guide to crafting a thieves' guild. Skim-reading it left me inspired to follow along here.
Because I cannot leave well enough alone, I'll be dipping into the Complete Thief's Handbook (chapter 4), both Thief's Challenge adventures, Den of Thieves, Ghosts of Saltmarsh, several d100 lists from DnD Colour (fences, the watch, maybe the city stuff), and Dragon issues: 54, 66 (thieves cant), 115 (several great articles for thieves and guilds), 160 (sample guild), 240 (sample guild), and 301 (sample guild). I would love to use Thieves' Guild from Different Worlds Publications, but I don't own it; even my voyages on the high seas have proven fruitless in my search.
As my homebrew city of Skara Brae is in a constant state of development and flux (and has been for at least a decade of sporadic additions), this is a fine excuse to add some of the shadier organizations to the city.
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Anyhow, back to the DnD Speaks guide.
1. Choose a name. A helpful d10 table is provided, and the dice declare the Shifting Hands and the Casket Crew. Yes, I rolled up two, and from the names alone, the Shifting Hands sound like straight up thieves, while the Casket Crew is unafraid of killing folks to take their stuff. In the end, Skara Brae will feature several small thieves guilds and gangs.
2. Entrance to the guild. Another d10 table (item 2 gives of Skyrim vibes). The Shifting Hands hide out below an abandoned warehouse, while the Casket Crew lair in the catacombs below a burned-out temple (burnt out due to the Casket Crew?). So now I am thinking the Shifting Hands are smugglers and the Casket Crew might have undead or cult-like habits.
3. Guild Services. No d10 table, just a list of 10 services that might be provided by guild members. Reading through them, I don't know that each guild would have them all (except the last one -rumors). To be honest, I don't know that any single guild WOULD have them all. That said, several guilds might 'know a guy' in the city who is the go-to for forgeries, poisons, and such.
4. Guild Quests. A d20 table of possible requests a Guild might demand of its members, specifically the PC and the PC's friends. Most of the 20 look as if they could be accomplished through a mix of stealth and talk, with only the threat of violence instead of actual combat. That said 'destroying wererats in the sewers' promises lots of combat.
5. Further development. The article closes with 5 short questions that would impact the guild(s) and in turn inform players and DM about the city they are in, notably Skara Brae. Stuff that adventures involving the Guild would require knowledge of, if only because the players are likely to ask the DM these questions, anyhow!
That done, I look to the other books, partially for ideas, partially to answer the questions in item 5.
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There is at least one mid-level wizard in town that can cast crime-useful spells (chiefly Invisibility, Knock, and Dispel Magic, among others) and is working with the Shifting Hands. I imagine this is due more to blackmail (a dangerous game, blackmailing wizards) than any genuine business partnership or wizardly agenda.
The Casket Crew, on the other hand, rely chiefly on some demon-worshipping cleric(s) of brutal murder (and maybe a warlock dedicated to the same demon) for their magical might.
Both sides end up needing a fence to move acquired wealth. The Shifting Hands know a discrete Gnome who will gladly reduce precious metals and jewelry to base parts and recast them as trade bars. They also have a (deliberately) unquestioning shopkeeper that gladly sells whatever they bring him. The Casket Crew, however, cannot be bothered with such niceties, so turn their ill-gotten gains over to an unscrupulous, well-guarded, moneychanger and loanshark who provides them less than value, but the Crew don't care, as long as they can buy lotus and drink.
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Leaders dictate the nature and makeup of their organizations, and thieves guilds are little different. I am thinking I need to determine these folks and basic motivations before going further. I suspect that these leaders are the Task Masters that the DnD Speaks guide refers to. From there, I need rough numbers of 'other' guild members. Looking at the Thief's Handbook (p71), I'm thinking the Shifting Hands have 30-40 members (moving smuggled cargo takes lots of hands and fronts), while the Casket Crew is smaller, 15-20 members, using their violent methods to quickly gain and hold power.
The Shifting Hands are led by a determined woman from a disgraced merchant family, ruined by other merchant families in Skara Brae. While she is out for revenge against those merchants, she does have some scruples, so sticks to smuggling goods, not people. She also has a keen sense of irony and uses her family's former warehouse as the entrance to the guild's headquarters.
The Casket Crew is a group of bullies led by a larger, tougher bully (CE) who enjoys the spectacle and power of the demon he has dragged the Crew into worshipping. He and the Crew were approached by a Warlock and Cleric working in tandem for the same demon. Now the local populace and guard are terrified of them all, especially after a temple to a Good deity burned down and its clerics disappeared.
My game world is humanocentric, so the vast majority of both guilds - like Skara Brae, itself - is human. That said, both count a few demihumans among their numbers and contacts. As the Shifting Hands rely on illusion and enchantment to keep smuggling, a Gnome (somehow related or known to their fence) and a half-elf (the blackmail victim) provide magical assistance.
The Casket Crew has a few half-orcs AND a half-ogre, because both are noted for their 'brute force and ignorance' approach to life. Being on the Casket Crew only amplifies their bestial sides. This makes the half-ogre a key member of the Crew. Not a leader, but too dumb to realize that the other members only pretend he leads to manipulate him. Another key member of the Casket Crew is the younger brother of the leader. This scoundrel is smarter, wiser, more charismatic, and all-around more competent than his big brother, but is just as terrible (NE). It is this person that is the go-between with the Crew and moneylender that launders their filthy lucre.
If the Casket Crew is in danger of being destroyed, he will try to escape, to eventually show up again as a professional assassin who would be positively thrilled to take a contract out on one or more PCs.
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Having written these out, the Shifting Hands might become allies or enemies as needed, while the Casket Crew can be put to the sword with no regrets. Both organizations would provide a few sessions' worth of gaming.
The Casket Crew survivor can then become a recurring thorn in the PCs' sides, either as a rival adventurer or a direct threat. He might even find a spot in whichever thieves guild the PC rogue(s) belongs too, because what fool would perform freelance thievery in a place like Skara Brae?
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It seems that Skara Brae is home several competing merchant families, as well as Thieves' Guilds. Frankly, I am getting a Renaissance Italy vibe from it all.
Which is a good thing.
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