The Shadows

The Shadows are the oldest of the four main criminal syndicates that operate out of Highwater . This group lives by the old creed of 'steal from the rich and give to the poor'. They idolize Robin Hood types, and think of themselves as following the 'true' Highwater norms and values. 'Honor amongst thieves' is one of their core tenets.
The very first Shadow(s) were said to be some/one of the original founders of Highwater, when it was still a criminal hidehout. They were against the idea of letting the Old Empire into their borders and paying tribute, and thus were exiled from the city. They refused to leave however, forming the Shadows and constantly being a thorn in the new 'nobles' sides.
They specialize in breaking and entering, often doing so without leaving a trace. An old saying in Highwater is that The Shadows do not even leave a shadow. Back in the day they were a powerful organization. No chest or vault was out of their reach. Their power was in large part due to the support from the common people, who would help shelter the thieves. In return The Shadows were very generous with their stolen gold among the people.
Unfortunately they are a dying breed in current-day Highwater. Their 'mission' having failed. Other gangs, most notably The Red Knives have changed the game, as well as what it means to be a thief. By most they are believed to be a mere story or legend.
Still, some members of the old guard still remain. It is said that some of their old safehouses are still in use, although most seem to have been abandoned. Their current leader is known as 'The Grandmaster', also known in public as 'Old Man Walder'. It goes without saying that his position within The Shadows is not exactly public knowledge.

The Grandmaster

The current leader of 'The Shadows'. He has been part of The Shadows for a very long time. By now he is an old man and admits he knows he is part of a dying breed. Yet he refuses to stop doing what he believes in: stealing from the rich and giving to the poor. In his daily life The Grandmaster is known as 'Old Man Walder', a rich old man living in the Noble's Quarter of Highwater.
Walder actually tried to retire from The Shadows a couple of years ago. In his years of stealing he saved up enough money to afford a nice place in the Noble's Quarter. Of course his place is marked with secret icons of The Shadows, so that the thieves knew to skip his house. However Walder was unable to give up on the life, and soon returned back to action. After this he was the last to be given to be given the title of Grandmaster of The Shadows. Walder believes that he will be the last to hold this title, and cherishes it greatly.
Walder's home has been restructured to serves as a secret passageway into the Noble Quarter for members of The Shadows. This passageway also contains one of the last hidden safehouses of the organization. Due to his position in the Noble Quarter and the wealth he has build up, he is able to exert quite some influence in Highwater politics as well. Mainly trying to aid The Shadows this way.
Due to his old age, not many expect him to be as nimble and quick as he is. Usually wears a hood when 'on the job', although he does not make that much of an effort to conceal his identity. Those who meet The Grandmaster are usually higher ranking members of The Shadows anyways.

Relations to other Highwater factions

The remaining Shadows hate the The Red Knives. They believe there is no honor in such violence, and that these brutes are only in it for themselves. It is also a shameful secret that their leader, Garrett, was a part of the Shadows in his youth...
They have a neutral attitude to the other criminal organizations like The Buccaneers and Whiskers Incorporated. Their businesses are not based on the virtues of stealth and stealing, but at least they generally do not engage in violence as a first resort.
They have a high degree of respect for the Fishing Guild, which mainly consists of working class individuals.
They have a begrudging respect to the merchant guilds of Highwater. While they engage in mostly honest work, they are "rich in the making". Some of these rich at least form good targets.
The Nobles of the city are of course seen as favorite targets. Walder has joked in the past that they have a 'professional relationship' with the nobles. In turn these nobles hate the Shadows.

Type

Guild, Thieves