Riddleport

77% human, 7% dwarf, 5% aiuvarin, 4% dromaar, 3% cambion, 2% halfling, 1% gnome, 1% other

Most people see Riddleport as an anarchic abode of pirates and brigands, but the city has actually become quite a bit more stable in recent years. This is in large part due to the work and leadership of the titular head of Riddleport, the Overlord Gaston Cromarcky. Cromarcky has held the title of Overlord for over three decades, having inherited it in the usual way: by murdering the pirate captain who held it before him. At the beginning of his reign, he used what funds were left over from the previous Overlord to hire land-based mercenaries to maintain law within the city. These men were beholden only to him, and allowed Cromarcky to consolidate quite a bit of power in his office. In the past, Overlords had drawn their muscle from various pirate crews who owed numerous allegiances to their captains and rival criminal gangs.     Cromarcky rules over the city with a light touch and with the consent and help of several powerful figures. When the time comes to choose a new Overlord, he will be drawn from this group. They include Avery Slyeg, who directs most of the major smuggling operations within the city, Varnal "Split Face" Knocmar, a master beggar and pickpocket, Boss Croat, an obese dromaar who controls the trade in illicit substances, Clegg Zincher who runs Zincher's Arena, Elias Tammerhawk, Speaker of the Order of Cyphers, Shorafa Pamodae, the high priestess of the temple of Calistria, and Ziphras, a wererat and gang leader.     Each crimelord has his own small army of contacts, snitches, soldiers, fences, loan sharks, and specialists. They also form affiliations with pirate captains.

The town of Riddleport was founded in the 45th century AR as a hideout for pirates attacking Chelish shipping in and out of Korvosa. Since that time it has grown to become a true settlement in its own right.   The first official pirate overlord was Captain Cabriem Maskyr, who took control of the settlement in 4558 AR.