Great map. I could think of pirates that hold a civilized city like this one. Imagine the pirates plundering a civilized city - like Henry Morgan plundered Panama or Maracaibo like he did. When the citizens didn´t show up with enough gold (they hid it outside town) the pirates begin to collect ransom for captured citizens. This could go for months where pirates would stay in the city causing havoc. In the caribbean this kind of occupation would be limited to a few months, as the spanish army would have time to prepare for a counter attack and eventually recapture the city. But in a fantasy world the city could lack allies and the pirates simply would establish their own reign in the conquered city for decades to come.