The Cloak

The Thieves guild of Ashkrim is called The Cloak. Their headquarters are in a tailor shop in Brindol on Hiddleberry Road called Heddle and Weft.
The guild is run by three Kingpins called Rooks. The Rooks oversee all guild activity on Ashkrim, both in Brindol, where the guild is headquartered, and in the various chapters in larger settlements on the island. Though many thieves of the guild have never met the Rooks personally they are still under their sway. For example the Rooks set The Vig, the tithe portion of all profits to be paid to the guild, for all guild members. Members in favor tend to have a lower Vig, while those who are unproven or haven't produced the way the Rooks like, pay a higher share.
Some thieves are independent opperators while others work in a group setting. Gang wars between groups, or even vendettas between individuals, are often stiffled by The Cloak because such conflicts are bad for business. Trouble with the City Watch in Brindol, or any of the forces of the Duke or his banner men, is similarly avoided wherever possible. Proper bribes are paid to the right people keep business moving. These are typically paid by The Cloak, and are funded by the Vig paid by its members.
Work is broken up either geographically, with with group and individuals given different parts of the city to work, or by special assignment doled out by The Cloak's Task Master, Thomas Apsley, who is the owner and proprietor of the Heddle and Weft.
Chapters outside of Brindol operate independently of the Rooks' direct oversight. A chapter has a leader, called a Head, and that leader ensures that business is done properly and a percentage of all profits are paid back to the Cloak's leadership in Brindol. Underperforming chapters often lose their Head and find themselves under new leadership who is eager to increase profits.
The Cloak offers benefits to its members. In addition to paying bribes to the necessary people, keeping the peace, and offering assignments, the guild provides fencing for illicit goods, appraisal for valuable items, facilitates smuggling services for things coming in or out, act as information brokers, and has experts in the areas of forgery, disguise, locksmithing, traps, and even poisons.

"In the intricate dance of cloak and dagger, our strength lies in the finesse of the cloak, but beneath our resolve is sharper than the dagger's edge."