Memnon of Rhodes
Spartan control of Eresos ended in 389 when the Athenian commander Thrasybulus retook the city. In 377 Eresos is recorded as a member of the Second Athenian League. About 371, Theophrastus, remembered as the "father of botany", was born at Eresos; he spent hs entire career at Athens, where he succeeded Aristotle as head of the Peripatetic school. From 377 down to 332, the chronology of Eresian politics is difficult to establish with any certainty. Phaenias of Eresus was also a native of the town. Athens is thought to have lost control of Eresos following the Social War (357–355 BC), after which its power in the Aegean waned. It was perhaps at this point that the tyranny of Apollodorus and his brothers took power. This family and their descendants remained in power until 336, when Attalus and Parmenion campaigned in the region against the Persians at the behest of Philip II of Macedon. It is assumed that a democracy was set up at Eresos and the city enrolled in the League of Corinth. In 335, Memnon of Rhodes retook this region for the Persian Empire and re-installed the tyranny of Apollodorus and his brothers. In spring 334, Alexander the Great invaded Asia Minor, and it is assumed that the cities of Lesbos (including Eresos) went over to the Macedonian forces soon after his victory at the Battle of the Granicus in May 334; again, the tyrants will have been expelled and the Eresian democrats re-installed. In 333, the admiral Memnon of Rhodes again attacked the island of Lesbos: he seized all the cities except for Mytilene and installed a new pair of tyrants at Eresos, Eurysilaus and Agonippus. A long inscription later set up at Eresos c. 306-301 by the Eresian democrats claims (not without partisan intent) that the tyrants committed many crimes, including expelling the men from the city, holding their women hostage on the acropolis, and exacting large sums of money from the populace, as well as helping the Persians commit piracy against Greek shipping.