Herakleia Trachinia was founded by Spartan settlers in 426 BCE at the behest of the locals, who were suffering from raids from the mountains. The city was not far from the famed Thermopylae.
Unfortunately, the city never did get along well with it’s neighbors. First came the Thessalians, who weren’t fond of a Spartan outpost in their midst. Several times the city fell, only to be regained by Sparta. Next up were the Thebans, who again captured the city.
Jason of Pherae was next up, and he destroyed the city walls since he felt the presence of a fortified city at Herakleia would prevent him from attacking Greece.
In 280 BCE, the city was taken by the Aetolians, and that was when this coin was minted. Clearly it follows a similar pattern to other Aetolian coins and only the city name is different.
Thebes takes Herakleia Trachineia from Sparta and installs the Trachinians and Oetaians.