Twilight of an Age
Shadow Port owns up to its name pretty well. It’s a city of smugglers, pirates, and general scoundrels. A variety of thieves’ guilds set up bases here, and while the competition is pretty fierce here it’s still technically an Imperial city so Imperial laws still hold.
Which is to say, it’s corrupt as all hell. As long as the blood stays off the streets during guild squabbles and your average traveler can walk through the city in the daytime with only a small chance of being pickpocketed, the Imperial guards are happy to look the other way.
Unsurprisingly, rumor has it that the Prince of Shadows makes his home here, though that’s never been confirmed. If true, that’s quite probably another very good reason that the Empire doesn’t try to enforce stricter order here. the last thing that they need is to tip the Prince over into outright antagonism.