The Shadowcloaks were a rather large organization, but largely comprised minor and unremarkable thieves and spies. To join the society, a prospective member had to complete a perilous mission ordered by the Night Hood themself. One could only leave the guild in death, and the Shadowcloaks ensured this was the case to protect their secrets.
The actions and nature of the Shadowcloaks were mysterious but wide-ranging. Many Calauntans believed they worked closely with the ruling Merchant Dukes of Calaunt, either working for them directly or in alliance, else the dukes would have crushed them early in their reign.
They had a monopoly on all fencing, piracy, and smuggling in the city. Outside pirates and smugglers who wished to conduct their trade in Calaunt had to seek permission from the Shadowcloaks and pay a tithe of one-third the value of their goods. Those who did could trade freely in the city. Those who didn't were killed. For this reason, pirates of the Inner Sea were reluctant to stop at or raid Calaunt. Some few who did and made arrangements with Shadowcloaks were sometimes recruited as a makeshift navy for the city, usually against rival pirates.
When dealing with transgressors like renegades of the organization or unauthorized smugglers and pirates, the Shadowcloaks maintained a mockery of a legal system, holding full trials detailing their alleged crimes and seeking so-called justice. These trials had a prosecutor, but of course no council for defense. Punishments came from a Court Executioner. However, they could just dispense with these formalities and resolve the matter with a discreet murder.
The Shadowcloaks could well hire mercenaries to carry out tasks that they could not otherwise do.
When they joined the guild, every member was granted a shadowcloak, for which the guild was named, a hooded, voluminous cloak or cape of dull gray cloth. This magical cloak granted a variety of powers useful to their trade, but its hidden curse ensured their loyalty to the guild. Every member had to protect their cloak, and if they lost it to an enemy, they had to reclaim it within three days or be killed.
Andreas Vanderslyke and Honus once visited Calaunt and were ambushed by black-bladed dagger-throwing Shadowcloaks, who pursued them through the streets. They were finally trapped in a room, and there Shartana conducted a trial for the renegade thief Honus and Andreas too.
Circa 1367 DR, the Shadowcloaks were rumored to be raising their prices for taking stolen goods into Calaunt, which risked conflict with pirates.
Around this time, a mysterious group appeared in Calaunt and tried to set up a thieves' guild to rival the Shadowcloaks. They stole weapons, tools, and magical items; intimidated independent thieves by demanding they "join or die"; and brutally murdered those who resisted or got too close, leaving mangled bodies seemingly blinded by poison. For a few months, a one-sided gangland war was waged on the streets of Calaunt after dark. The Shadowcloaks themselves tried to keep their people out of it and to watch and wait. Eventually, someone—a merchant, a threatened thief, or a captain of the Calauntan guard—would hire adventurers to investigate.
- ↑ Although the "Rogues of the Vast" section of Wizards and Rogues of the Realms correctly names the organization "Shadowcloaks", the accompanying Andreas Vanderslyke journal calls them "Greycloaks" instead. This is assumed to be in error, likely confusing them with the Greyclaws of Tantras.
- ↑ 1.0 1.1 1.2 1.3 1.4 Jeff Grubb and Ed Greenwood (1990). Forgotten Realms Adventures. (TSR, Inc), p. 80. ISBN 0-8803-8828-5.
- ↑ 2.0 2.1 2.2 2.3 2.4 Ed Greenwood, Julia Martin, Jeff Grubb (1993). Forgotten Realms Campaign Setting 2nd edition (revised), A Grand Tour of the Realms. (TSR, Inc), p. 72. ISBN 1-5607-6617-4.
- ↑ 3.0 3.1 3.2 3.3 Ed Greenwood (November 1998). The City of Ravens Bluff. (TSR, Inc), p. 149. ISBN 0-7869-1195-6.
- ↑ 4.0 4.1 4.2 4.3 4.4 4.5 William W. Connors (November 1995). Wizards and Rogues of the Realms. Edited by Anne Gray McCready. (TSR, Inc), p. 101–104. ISBN 0-7869-0190-X.
- ↑ 5.0 5.1 Curtis Scott (March 1992). Pirates of the Fallen Stars. (TSR, Inc), p. 40–41. ISBN 978-1560763208.
- ↑ Tim Beach (1992). Gold & Glory. (TSR, Inc), p. 60. ISBN 1-56076-334-5.
- ↑ Nicky Rea & Sam Witt (January 1995). Book of Lairs. (TSR, Inc.), pp. 61–63. ISBN 978-1560769248.