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Hellenistic Period
There is considerable information about Miletus of the 3rd and 2nd century BC thanks to a series of inscriptions discovered in the early 20th century at Delphinium, the official archives of the city.
When Alexander died, Miletus came under the control of the satrap of Caria Asandrus, who had become autonomous. Antigonus I Monopthalmus (One-Eyed) sent Docimus and Medeius in 312 BC to free the city and grant autonomy.  Moreover, the democratic patrimonial regime was restored. Miletus remained under Antigonus until he was killed in the Battle of Ipsus in 301 BC. After that, the city seems to have maintained good relations with all the Successors: Seleucus I Nicator made substantial donations to the sanctuary of Didyma and returned the statue of Apollo, which had been stolen by the Persians in 494 BC. In 295 BC Demetrius Poliorcetes, son of Antigonus, was the eponymous archon (stephanephorus) in the city. Then the city allied with Ptolemy I, while Lysimachus must have assumed power in the region. In general, he adopted a strict policy towards the Greek cities by imposing high taxes. In order to cope with them Miletus resorted to lending. Around 287/286 BC Demetrius returned but failed to maintain his possessions and was imprisoned in Syria. Nicocles of Sido, the commander of the fleet of Demetrius, surrendered the city. Lysimachus dominated until 281 BC, when he was defeated by Seleucus. In 280/279 BC the Milesians adopted a new chronological system, the Seleucid period. The first eponymous archon of the period (stephanephorus) was Antiochus I, the successor of Seleucus. The following year, Ptolemy II made a large donation of land to the city, while some years later he was honoured through a resolution, which stated his friendship and alliance with the city. Miletus remained in the league of the Ptolemies until the end of the century. In 262 BC Antigonus II Gonatas, the King of Macedonia, who coveted Caria, unsuccessfully tried to detach the city from the Ptolemies.
The next year (261/260 BC) the regent of Ptolemy II in Asia Minor, his son Ptolemy III, who was settled in Ephesus and Miletus, revolted with the help of Timarchus, an Aetolian war lord, who managed to impose tyranny on Miletus. Finally, Ptolemy was assassinated by his mercenaries. The Seleucids controlled Miletus again, while Antiochus II was offered divine honours because he was considered to have restored freedom and democracy by expelling the tyrant Timarchus.
Miletus supported Seleucus II in the conflict among the successors of Antiochus II, who died mysteriously in 246 BC. However, the city came soon under Ptolemaic influence thanks to the expedition of Ptolemy III to Asia (246-245 BC). In the same period, the city signed an immunity treaty with the Koinon of Aetolians aiming to avoid being attacked by Aetolian pirates.
Miletus in the second half of the 3rd century BC adopted a policy of military colonisation of its wider region thanks to the settlement of Cretan mercenaries in a series of fortresses. At the same time, the city wanted to consolidate its relations with other, not immediately neighbouring, Asia Minor cities: treaties of egalitarianism were signed with Tralles / Seleuceia (218/217 BC), Mylasa (215/214 BC) and Antioch ad Maeandrum.
In 201 BC Philip V of Macedonia managed to capture Miletus because the Milesians had been impressed by his victory in the naval battle of Lade. The Macedonian king detached the territories of Myous from Miletus and gave them to neighbouring Magnesia ad Maeandrum. Nothing is known about Miletus during the extensive operation of Antiochus III in Asia Minor in 197/196 BC. During the war between Antiochus III and the Romans (190 BC), the Milesians allied with the latter and, what is more, provisioned the Roman fleet. The victory of the Romans offered Miletus a new list of eponymous stephanephoroi archons. Under the Peace of Apamea in 188 BC, the city reoccupied the territories of Apollo Terbintheus in Myous, which had been detached by Philip. In the immediately following period the external policy of Miletus was actually controlled by Rhodes. The city signed a series of treaties in the 180s BC: a) a confederation treaty with Pidasa (188/187 BC) – it was actually a concealed annexation of Pidasa to the state of Miletus –, b) a treaty of alliance with Heraclea by Latmus (185/184 BC) and c) a peace treaty with Magnesia ad Maeandrum (between 185 and 180 BC), following a war between Miletus and Heraclea on the one side and Magnesia and Priene on the other side. Throughout the Hellenistic history of Miletus, Priene was hostile towards the city: inscriptions of Priene refer to clashes, truces and arbitrations dating from the 3rd century BC, circa 200 BC, until the 1st century BC.
After Rhodes was punished by Rome because of its wavering attitude in the third Macedonian War, Miletus came under the influence of the Attalids. Eirenias, the Milesian ambassador in the Attalid court, worked so that both sides would benefit from this relationship: Eumenes II benefited the city, which in turn honoured him even after his death. In the same period the city was benefited by the Seleucid ruler Antiochus IV, who is considered to have dedicated, through his court, the bouleuterion of the city. After 129 BC and the formation of the province of Asia, Miletus must have remained free, although historians believe that the Romans controlled even the regime by appointing a body of 50 archons. Large families of merchants (negotiatores), such as the Gessi and the Clodii, moved their businesses to the city. At the same time, throughout the 2nd century BC Miletus maintained its preferential relations with its alleged metropolis Athens, by the Milesians participating in the Panathenaea and other Athenian festivals.
In the decade of 90 BC the Roman Senate settled border disputes among Miletus, Magnesia and Priene, which had put forward claims over the plain of Maeander. Accordingly, Miletus together with other cities of Asia Minor, such as Mylasa and Erythrae, were often summoned to act as arbitrators between cities of Crete and the Peloponnese. This proves that Miletus was a free city even in the 1st century BC.
In the Mithradatic War Miletus encountered serious difficulties between 89 and 81 BC – as indicated by the fact that the god Apollo was chosen four times as the eponymous stephanephorus archon. After 81 BC the city did not face similar difficulties, although the initial alliance with the King of Pontus resulted in the city losing its freedom. In 83 BC the city was compelled by Lucius Licinius Murena to send a naval force of 10 ships so that the war against Mithradates could be continued. In the end, one of the ships was occupied by Verres, an action considered piratic by the Milesians.
This attempt must have delivered the decisive blow to the once mighty naval force: while Julius Caesar was sailing to Rhodes in 75-74 BC, he was captured by pirates in Farmakoussa, off the coast of Miletus. The city had to pay the ransom the pirates were asking. In the same period some Milesians under Alexander of Miletus (Polyhistor) managed to be awarded the Roman citizenship. Finally, the city became autonomous in 38 BC, in the years of Mark Antony.
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