Siege of Astapor

"Astapor and Yunkai have stopped asking us for aid....The Masters have retaken both cities. Outside of Meereen, the whole of Slaver's Bay has returned to the slavers."

- Varys summarizes that the slave-masters have retaken Yunkai and now Astapor.

The Siege of Astapor is a battle that takes place during Daenerys Targaryen's campaign to liberate all of the slaves in Slaver's Bay.

Background
Daenerys Targaryen began her campaign of liberation in Slaver's Bay in the Sack of Astapor, in which she stole 8,000 Unsullied by commanding them to turn their spears against the Good Masters of the city who had been their owners moments before, and unleashing her juvenile dragons to support them with their flames. Daenerys and her new army then advanced north, defeating Yunkai and freeing its slaves, and finally advancing to Meereen, northernmost and largest of the three great city-states in Slaver's Bay, which Daenerys seized outright and began to rule as the city's new queen.

A few months later, however, without Daenerys's Unsullied army present anymore to enforce her rule, the southern two cities fell out of her control. In Yunkai, the Wise Masters retook control of the city from the freedmen she had left in charge - given that she had never totally crushed the Wise Masters but accepted their surrender. Meanwhile, the opposite occurred in Astapor: the ruling council of freedmen that Daenerys had established over the city when she left was overthrown by a former butcher of meat named Cleon who set himself up as despot of the city, and subsequently styled himself "His Imperial Majesty". In contrast to Yunkai, Cleon led an angry mob of former slaves, who wanted to be the new aristocrats ruling over the rest of the city.

Season6
With Daenerys Targaryen missing from Meereen after flying away on her uncontrollable dragon, her advisors are left to hold together rule over the city: Missandei, Grey Worm, and newcomers Tyrion Lannister and Varys. They convene in a meeting after the Sons of the Harpy succeed in burning Daenerys's captured Meereenese fleet in the port. No progress has been made on finding those responsible.

Tyrion asks if there is any actually good news, and Varys responds that Yunkai and Astapor are no longer asking for aid - because the slave-masters have outright retaken both cities. Presumably this meant that Cleon the butcher was killed when the old slave-masters retook the city. This leaves Meereen as the only part of Slaver's Bay the slave-masters have not regained control over, which means it is only a matter of time before they advance against it in force as well.

In the books
In A Song of Ice and Fire novels, Daenerys's navigation of the local politics in Slaver's Bay forms a running subplot - albeit much of it occurs "off-screen" or summarized in council discussions. The TV series heavily condensed the political maneuvering both within Meereen and with external powers: in Season 6's "Home", Varys simply gives a brief summation of what happened, though the general points seem the same.

As stated in Season 4, after Daenerys took her army north, the slave-masters reasserted themselves at Yunkai - unlike the other two cities she never even totally defeated them, but forced them to surrender their slaves and much of their wealth before moving on towards Yunkai. Meanwhile, a humble butcher of meat named Cleon overthrew the ruling council of freedmen she had left in charge. Cleon was a demagogue leading mobs of angry freedmen who wanted to punish the former slave-masters (the Good Masters and their families, a significant fraction of the city's population) even more than Daenerys had. Cleon did not want to abolish slavery, however: the roles reversed, with the city's former slaves led by Cleon as the new slave-masters and the former Good Masters as the slaves. Cleon also rounded up boys from all of the old slave-master families and had them castrated to begin training them as a new batch of Unsullied - though with only a few months to train these new Unsullied are considered to be little more than knock-offs and a joke compared to Daenerys's Unsullied, who were trained for years, their entire lives since birth.

After the initial shock wears off from Daenerys's initial campaign of liberation, however, the slave-masters begin to reform. While the former Great Masters of Meereen form the Sons of the Harpy insurgent movement inside that city, the Wise Masters reassert themselves at Yunkai, and start using what wealth they have left to hire numerous sellsword companies from as far afield as the Free Cities. The Yunkish also start forming alliances with other powers across Essos who are heavily involved in the slave trade, which was heavily disrupted when Daenerys began her campaign given that Slaver's Bay is the central hub of the industry, breeding and exporting slaves across the sea lanes. Yunkai forms an alliance with New Ghis, another large Ghiscari city-state somewhat father to the south, and also allies with Volantis (whose aristocrats rule over a large slave population, with five slaves to each free man in the city).

Daenerys tries to counter this growing new slaver alliance by making entreaties to Mantarys and Tolos to the west, but instead they outright join the slaver alliance. Qarth eventually joins the slavers as well. The most Daenerys can do is form an alliance with Lhazar on the other side of the mountain pass, which results in some food shipments reaching the city but otherwise the Lhazareen are not a martial people and they cannot offer signiicant military support.

Against this backdrop, "Cleon I, the Butcher King" sends frequent entreaties to Daenerys to marry her so they can unite the strength of the freedmen in Meereen and Astapor to strike back against Yunkai and its rebuilding strength. Daenerys repeatedly denies these requests, however: first, because she is having trouble enough holding Meereen itself against the insurgency and she fears that if her army leaves it will fall just like Yunkai did before, and second, because Cleon is little more than a despot and he doesn't want to abolish slavery like she does - he just wants to be one of the new slave-masters as a cycle of revenge continues.

The exact sequence of events occurs largely "off-screen" in the novels, but early in the fifth novel Cleon's envoys beg Daenerys to join his army in a pre-emptive attack against Yunkai - his army advancing from the south and hers from the north - and says that Cleon's army will be marching soon regardless of what she decides. Daenerys declines, however, not only because she fears leaving the city and detests Cleon, but because even she thinks his hastily trained new Unsullied are a joke, and his rabble of freedmen aren't much better to go on the offensive against the professional sellsword armies now employed by Yunkai. It is vaguely mentioned that at some point after this, Cleon's army met the Yunkish forces in a battle at the "Horns of Hazzat", where he suffered a crippling defeat (his army as weak as may assessed it to be) and barely fled back to Astapor with his life.

Soon after retreating back to Astapor Cleon was assassinated by his own men for his failure. At this point order in the city collapsed as one junta after another tried to seize power. After Cleon was assassinated, another man declared himself king of Astapor under the name "Cleon the Second" - he ruled for only eight days, however, before having his throat slit by a barber who declared himself king in turn, who due to the manner of his succession is referred to as "King Cuthroat". "Cleon II" still had many supporters, however, and they are rallied by his former concubine, who declares herself the new ruler of the city in opposition to King Cuthroat - she gets nicknamed "Queen Whore". The civil war between the two factions continued to rage through the streets of Astapor even as the city was outright encircled and besieged by Yunkai's new army. Starvation conditions and cannibalism soon set in within the besieged city, and then due to all of the refugees crammed inside the walls, a plague swept through the entire city (the bloody flux). Even the last of the outnumbered and poorly trained freedmen of the city were devastated by this: many killed by the disease and more too sick to fight.

Finally, some of the last healthy men in the city threw open the gates to try to escape before they also succumbed, but they were cut down by Yunkai's forces, which proceeded to enter and sack the city. What followed was not a battle but a massacre. Fires were set which ripped across the city from one side to the other, and sick men were cut apart by enemy soldiers and left rotting in the streets. Doran Martell's son Quentyn was passing through the city after joining one of the sellsword companies, and he described the fall of Astapor as the closest thing to hell he ever wished to experience.