Tyrosh

Before it was a Free City, Tyrosh was a colony of the Valyrian Freehold, an outpost of the dragonlords set against the eastern coast. When the Doom fell on Valyria and gutted the heart of the empire, the island was left without a master, and its people put together a government of their own.

That government fell to an Archon, drawn from a council of magisters, and the city still runs that way today. Tyrosh sits north of the Stepstones, a scatter of small, much-fought-over islands, and it's bigger than its spot on the map would suggest — bigger, in fact, than Sunspear.

In the harbor stands the Bleeding Tower, the first thing anyone arriving by sea sees. Nearby runs the Fountain of the Drunken God, and outside the Temple of the Trios a huge statue of the three-headed god that gives the place its name waits for visitors.

The Tyroshi have a reputation for greed and for living in permanent disorder; the city itself gets called boisterous to the point of chaos. They fight constantly over scraps of the Stepstones and the Disputed Lands, a low-grade war that never quite seems to end.

They love loud colors enough to dye their hair and beards with them, and their craftsmen have a somewhat twisted talent: helms with beaks and bird's claws, studded with precious metals, and torture devices dreamed up with unsettling imagination. They speak their own dialect, descended from High Valyrian.

The city also lives off selling what others would rather not: slavery is common there, and it's a good place to hire sellswords. Its pear brandy is known by name across the rest of Essos.

During the Century of Blood, the turbulent stretch that followed Valyria's fall, Tyrosh didn't escape the appetite of its neighbors. Volantis tried to bring it to heel and add it to its holdings, though the attempt never quite took.

In time Tyrosh entered an alliance with Myr and Lys known as the Triarchy, run by a High Council shared between the three cities. When the Dance of the Dragons broke out, the Triarchy sided with the Greens.

Its ships fought in the Battle of the Gullet, a naval clash as bloody as anything the dragons themselves fought. The alliance, though, didn't survive the peace well: by the year 130 after the Conquest it was already coming apart.

The Band of Nine — pirates, sellswords and traders who had seized the Disputed Lands — ended up marching on Tyrosh too and taking it. They didn't stay to rule it: they sat a wealthy merchant of the city, Alequo Adarys, on the throne and moved on to other business.

The rest of what the Band had conquered slipped from their grasp shortly after Maelys Blackfyre died in the War of the Ninepenny Kings. Alequo, though, held the throne for six more years before he was deposed.

Around the time Westeros was bleeding through its own civil war, Tyrosh was one step from declaring its own against Lys.

Not long after, Tyrosh and Lys joined forces to threaten Myr with war. Word went around that the Archon had offered Lys peace, ready to finally close a trade dispute that had been wearing down all three cities.