Pentos

The Valyrian Freehold founded Pentos as a forward trading post, and the city soon pushed its rule over the surrounding land. It came to hold nearly all of Andalos, from the Velvet Hills and the Little Rhoyne down to the coast, the ancestral Home of the Andals, now flying a Pentoshi flag.

Decades after the Doom of Valyria, Pentos took sides in a war against Volantis to defend Tyrosh, alongside House Durrandon and the cities of Lys and Myr.

The city sits on a bay off the Narrow Sea, ringed by square towers and brick buildings, and is larger even than Astapor. As the closest point in Essos to King's Landing, its ships cross to the Seven Kingdoms almost daily, and it trades as well with the Reach and with the Dothraki.

Its founders were mostly merchants and low-born traders, less protective of their Valyrian blood, and they mixed with the native Andals more freely than other Free Cities did, though their customs, despite that shared ancestry with Westeros, strike Westerosi visitors as strange. Pentoshi men are known for their oiled, tended beards, and the city holds a great red temple to R'hllor whose faithful keep growing.

The Prince of Pentos, chosen from among the forty great families, rules for life but keeps little beyond ceremony: he presides over feasts, travels by litter, and every new year deflowers two maidens to secure the land's and the sea's fortune. If the city loses a war or starves, he is sacrificed and another is chosen; real power lies with the council of magisters.

For centuries Pentoshi fleets were central to the slave trade, and that practice cost the city half a dozen wars with its northern neighbor Braavos over the last two hundred years, fights over fertile land and shared waters almost as much as over slaving itself.

Braavos won four of those wars. The last one broke Pentos so badly that within a single year the city chose and sacrificed four princes in a row; the fifth, Nevio Narratys, talked the magisters into suing for peace. The terms included abolishing slavery and the slave trade, capping the navy at twenty ships, and banning any army or hired sellswords beyond the city watch.

The law still stands, but it's bent more than kept: some Pentoshi ships still fly Lysene or Myrish colors to keep trading slaves, and tens of thousands of bondsmen live in the city wearing collars and brands much like the slaves of Myr, Lys, or Tyrosh. They're free under the law, yes, but bound by debts to their masters for life, since their labor is worth less than the food, clothing, and roof those masters provide.

In 40 AC, King Aenys I Targaryen stripped his brother Maegor of the office of Hand for taking a second wife, and banished him to Pentos for five years along with that wife, Alys Harroway. There, the Pentoshi beauty Tyanna of the Tower became his lover.

When Aenys died, the widowed Queen Visenya Targaryen flew across the Narrow Sea on her dragon Vhagar to bring her son Maegor home.

In 115 AC, Pentos was the first stop on the journey across Essos that Prince Daemon Targaryen and Lady Laena Velaryon took to mark their marriage, flying in on their dragons Caraxes and Vhagar. The Prince of Pentos received them with great honors: the Triarchy was growing in strength to the south, and Daemon could prove a valuable ally.

During the Dance of the Dragons, Prince Jacaerys Velaryon decided to place his half-brothers in the care of the Prince of Pentos while their mother, Queen Rhaenyra Targaryen, secured her hold on the Iron Throne. The two boys sailed late in 129 AC aboard the Pentoshi cog Gay Abandon. The ship never arrived.

In 262 AC, after executing the previous prince, the council of magisters chose a twenty-three-year-old for the post, a man the city would later know as the Tattered Prince. He fled Pentos rather than accept the title, and never came back.

By 298 AC, Viserys and Daenerys Targaryen had spent a long stretch in Pentos as guests of Magister Illyrio Mopatis. When the Dothraki khal Drogo arrived in the city with his khalasar, Illyrio tripled the city guard; not long after, Daenerys and Drogo were married outside the walls.

Later, Strong Belwas and his squire Arstan Whitebeard sought out Daenerys, meaning to bring her back to Pentos.

In time, Tyrion Lannister also washed up in the city after crossing the Narrow Sea, and stayed in that same mansion belonging to Illyrio Mopatis.