Anon Asks:

Would it be possible for say a powerful merchant prince or pirate king to sweep away most of the pirates in the stepstones and establish a lsting kingdom there? The closest we see is Daemon Targaryen but he just got bored and gave it up, he had his dragon and the velaryon fleet but he also had to deal with the triarchy.
Also why are the free cities static, like no new city rises up and replaces an existing one, its just the nine and no new ones appear? Its mentioned that the flatlands are bare of villages because of the dothraki, but there are other non-free cities like the ghiscari or Elyria and such, why don’t we see any of them rising into greater prominence?

1. Probably not. If it took the Triarchy to sweep the Stepstones clean of pirates in the first place, you’re unlikely to see a single merchant prince or pirate king manage on their own. There is one caveat: Racallio Ryndoon did build a pirate kingdom in the Stepstones, but we don’t know whether he held the whole of them, and in any case the Oakenfist put paid to him rather quickly. 

2. I mean, there are other significant cities in Essos: 

“We speak of Nine Free Cities, though across the width of Essos one may find many other Valyrian towns, settlements, and outposts, some larger and more populous than Gulltown, White Harbor, or even Lannisport. The distinction that sets the Nine apart is not their size but their origins. At their height before the Doom, other cities, such as Mantarys, Volon Therys, Oros, Tyria, Draconys, Elyria, Mhysa Faer, Rhyos, and Aquos Dhaen were grand and glorious and rich, yet for all their pride and power, none ever ruled itself.”

And you can add on the Ghiscari cities and Qarth and so on and so forth. The Nine Free Cities are a historically and culturally derived term that specifically counts the self-governing cities that existed before the Doom. 

To use a real world analogy: the Ivy League in the U.S consists of a particular subset of particularly old elite colleges and universities that have been sportsballing one another for a long time now. Stanford or MIT are still elite universities even though they’re not Ivies.