Olynthos was the main city in the Chalkidian League and when Philip II conquered it in 348 BCE, it changed the course of history. While before Philip had focused on becoming master of Greece, afterwards he turned his eye to Asia. This is perhaps symbolized in the horse and rider’s change in direction on his staters from left to right.
Per mythology, the town was either founded by Olynthos, who was a son of Herakles, or the river god Strymon. During the invasion of Xerxes, the Persian king slaughtered all the inhabitants because he suspected they were disloyal.
In the Peloponnesian War, the city sided with Sparta against Athens and was for a time used as a base by the Spartan general Brasidas. Afterwards, the city gained in strength to such a degree that it at one time possessed Pella, which would eventually become the capital of Macedonia.
In the Social War, Olynthos first sided with Philip II, but when they suspected what his plans were, they joined Athens’ side and begged for assistance. Slowly Philip II cut them off by pealing away the other cities in the Chalkidian League until only Olynthos remained. He then bribed two of the leading men in the city into ensuring a quick siege, after which he sold the entire population into slavery, including the Athenians were were guarding it.
The city never fully recovered. The few left in 318 BCE were moved by Kassander to his new city of Kassandreia.
The ruins of the city have been found and may be visited.
The Persian general Artabazos captures Olynthos and kills its inhabitants.
Perdikkas II of Macedon convinces several towns to move their populations to Olynthos.
Amyntas III of Macedon transfers territory to Olynthos of the Chalkidian League.
Olynthos occupies the Macedonian city of Pella.
The Spartan king Agesipolis I, while undergoing operations against Olynthos, comes down with a fever and dies at the sanctuary to Dionysos at Aphytis.
The Spartans and Macedonians under Amyntas III destroy Olynthos after two initial defeats. Derdas II participates on the winning side.
Philip II conquers Olynthos and thus destroys the Chalkidian League.
Kassander forces the population of Olynthos to move to his new city of Kassandreia.