For over two hundred years Midwinter's underworld was controlled by a group of afiliated crime syndicates known as the Shadow Guild. Each of the syndicates was known as a Chapter. There were seven chapters in the city. Each one was based around the area of the city that gave the chapter it's name. Midwinter had a chapter in the Shambles, Harbour, Docklands, Norn Hill, Outlands and Market districts. The Fairfield, Beaconsfield, Walks and Merchant's districts had no associated chapter and were considered fair game for all members.

Each chapter has a Guildmaster in charge. There is also a Grandmaster, who is only known to the six Guildmasters. The six Guildmasters regularly meet to discuss inter-chapter disputes and future operations. Each chapter has a Daymaster and a Nightmaster. These are the Guildmaster's second-in-command, overseeing the day to day operations of the chapter.

Below the Daymaster and Nightmaster are the Taskmasters. Each of the Taskmasters is responsible for overseeing an area of guild activity. Generally, a thief will be given jobs by the Taskmasters as part of their duties. If a thief wishes to perform non-sanctioned work, he must first discuss it with the appropriate Taskmaster. The guild requires members to work at least one week of every month directly for the guild. Taskmasters get 10% of the income operations under their control.

Like any guild, the Shadow Guild exists to benefit its members. It provides training, protection, resolves disputes and acts as a source of information and jobs. The guild also acts to regulate crime in their respective areas, for example, preventing or punishing freelance thieves who steal from establishments under their "protection."

Overall, however, the purpose of the Shadow Guild is there to enrich the pockets of the guildmasters who control it, with lesser rewards going to the lesser officers. The guild is run for profit, and many times their wrath can be turned aside by a suitable tribute or service.

The guild takes a dim view of freelancers. Their random actions can stir up trouble with the authorities, bringing trouble on guild operatives. Freelancers may rob those protected by the guild, thus causing the guild to lose face and revenue. Occasionally freelancers will pick the same targets as the guild, interfering with guild business.

The guild's main activities are burglary, counterfeiting, forgery, mugging, pick-pocketing, blackmail, brothels, gambling, moneylending, protection racketeering and smuggling. Each chapter will have a taskmaster in charge of one or more of these activities.