The titular head of the Riddleport government is the self appointed Overlord of Riddleport, a position traditionally held for life. Riddleport’s 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 rule over Riddleport for three decades by entrenching himself in a wholly new manner. Rather than rely on the loyalty of pirate crews and fellow captains, Overlord Cromarcky opened the coffers of his deceased predecessor and hired mercenaries and enforcers from land-bound groups with no connection to piracy. Calling this new breed of enforcers the Riddleport Gendarmes (“gentlemen-at-arms”), 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 that flies 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 protection of visiting ships ensures that there are always enough ships 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 of Riddleport’s 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, only a longtime Riddleport native would ever 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 crime bosses 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 speciality 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 the ranks of the city’s crimelords.
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 crimelord 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 include the following characters: