The titular head of Riddleport’s government is the self-appointed Overlord of Riddleport, a position traditionally held for life. The current overlord is a former pirate captain named Gaston Cromarcky. Since the city’s founding, Riddleport has been ruled by a series of pirate lords, buccaneers, and other unsavory sailors in a bloody cycle of betrayal and violent coups. Overlord Cromarcky has maintained his position for 3 decades by entrenching himself in a wholly new manner. Rather than relying on the loyalty of pirate crews and fellow captains, the Overlord opened the coffers of his deceased predecessors and hired mercenaries and enforcers from land-bound groups with no connection to piracy. Calling this new breed of enforcer the Riddleport Gendarmes, he created a military force loyal to his coin.
Under Cromarcky’s rule, life in Riddleport has become more stable than ever before. Open street-warfare between rival gangs is a rarity now, and the gendarmes have made it safe enough for brave or desperate merchants from Magnimar to bring in trade. By Overlord Cromarcky’s decree, any ship flying the flag of Riddleport at full mast is under his protection and is not to be raided by any pirate who wishes to call Riddleport home. That Cromarcky charges scandalously high prices for this flag of protection for visiting ships ensures there are always enough unprotected vessels plying the Lost Coast or the southern waters for Riddleport’s traditional pirates to prey upon as well. The stability and semi-regular influx of imported goods has begun to spoil the citizens of Riddleport, but these days may be numbered. Rumors abound that Cromarcky’s coffers might finally be running low (despite his protection racket), and the rise in power of Cromarcky’s most vocal public enemy, Elias Tammerhawk, has many citizens expecting a shift in leadership soon, an eventuality that many Riddleport traditionalists would greet with relief.
Despite the unheard-of political stability that Riddleport currently enjoys, no one would think of the city as truly civilized. The overlord rules with a light touch and with the consent of several powerful individuals who likewise shape the direction of Riddleport’s future. These individuals are the various crimebosses who hold sway in the city. Pirates may have founded the city, but many more bandits and scoundrels soon saw the value of having a place to call home, the wilds of Varisia hardly being a safe place to camp. The crimelords each have their own particular specialty and focus, and they play the role that noble families take in most other cities: they are the movers and shakers, the leaders whom the average citizen idolizes and fears. When an overlord dies, the new overlord invariably rises from these ranks.
Traditionally, eight crimelords rule Riddleport under the Overlord. Like the overlord, these crimelords form affiliations with various pirate captains to further secure their positions, though such alliances are unreliable and subject to the vagaries of the pirate lifestyle. Each crimeboss maintains his own small army of contacts, snitches, foot soldiers, fences, loan sharks, specialists, and favored lieutenants (called “capps” in local parlance). The current eight crimelords are:
• Avery Slyeg – ties to the overlord the extent of which are yet to be determined. He handles most of the major smuggling operations into and out of the port and has a wide network of fences and black-marketeers to move stolen goods and contraband. He operates out of the River Runner Inn.
• Varnal “Split Face” Knocmar – a beggar master who runs a number of small-time cons, street gangs, and pickpockets as well as some information brokering. He has several hideouts among the seediest alleys and slums of the Wharf and Rotgut Districts. He is particularly sensitive about his cleft palate and goes to great lengths to disguise it.
• Boss Croat – an immensely fat half-orc who runs several street gangs and controls most of the trade in illicit substances on the streets. He is well-known for employing only half-orcs enforcers and has a reputation as a primary contact for hiring of professional assassinations. His fortified compound sits at the end of Silk Street in northern Riddleport.
• Clegg Zincher – Runs Zincher’s Arena, numerous other fighting venues, and all of the gambling associated with such bouts. He also runs most of the organized labor in town and wields great power in his ability to call for strikes or ruin competition through industrial sabatoge.
• Elias Tammerhawk – Speaker of the Order of Cyphers and the most unlikely crimelord in town, is as much as scholar as he is a scoundrel. He’s maintained his position of power in Riddleport through cutthroat manipulation and disposing of rivals, and over time has become the most powerful of the eight, and the most likely next overlord should Cromarcky fall.
• Shorafa Pamodae – the high priestess of the temple of Calistria, the House of the Silken Veil, and a tiefling. Shorafa is madam to all the temple’s prostitutes and patron of the “hospitality industry” throughout the city, she is also the city’s major information broker due to the persuasive skills of her employees and their extensive clientele.
• Ziphras – leads the smallest street gang but his methods and nature make him uniquely formidable. As a wererat, he and his boys are always on the lookout to recruit willing members into his gang of lycanthropes. His people patrol the Rogue District in rat form, seeking potential opportunities and marks.
