River Rats
River Rats are the smugglers that ferry illicit goods through rivers and canals of the great city state. Their operations used to be under the purview of the Thieves Guild but separated itself from it in an act of bloody rebellion that ended in sinking bunch of guild owned ships and ritual drowning many of guild representatives and their allies. It is said that the close knit group of inland pirates curried favor with the Fisherman and were granted good fortune during their uprising.
The schism prompted the establishment of the Triumvirate and the Shadow Council and paved the way for a much less bloody and more regulated way for quarreling crime syndicates to resolve their differences. This directly enabled Dog Fen halflings to break away as the Barkers.
River Rats members are almost exclusively sailors and seamen who ferry elicit goods across Fynwell's rivers and canals. They proudly display their drowned rat tattoos. They also use rat skulls as jewelry (necklaces, earrings, etc..)
The leader of the River Rats has always been, and will always be Jay Sweetwater. When a new leader takes on the mantle of leadership of the organization, and don the Flotsam Crown they abandon their old life and assume not only the name, but also the image and personality of the famous leader of the rebellion. In a ritual coronation they are said to commune with the spirit of every leader before them, and adopt the unique mannerisms, speech patterns and style of the legendary leader, but also imbue them with their own quirks and sensibilities, which will be copied and expanded by the next leader. And thus the legend of Jay Sweetwater lives on forever. Jay can be, and has likely been anyone: a man, a woman, a dwarf, a half orc, a halfling, etc..
River Rats are loud, rambunctious and irreverent, but also deeply loyal and respectful of their own code of honor. Snitches and traitors are hung from the rafters on land, because drowning is too honorable death for them.
While they have no love for Thieves Guild they respect their mutual agreement under which the Guild gets to control the sea ports, but Rats control all inland routes and freshwater ports.