This rare gold coin was struck in support of Corinthian general Timoleon and his Peloponnesian mercenaries as they campaigned on behalf of the Syracusans, who were experiencing difficult times. In 345 BC, the Syracusans sought to expel their tyrant, Dionysius II, initially seeking help from Hicetas, the tyrant of Leontini. However, Hicetas aimed to seize control of Syracuse himself, aspiring to dominate Greek Sicily. Concurrently, there was growing concern that Carthage might exploit the instability in Syracuse to mount an offensive that could overwhelm the island’s Greek cities. Pressed by these threats, the Syracusans urgently requested assistance from Corinth, their mother city. Corinth responded by sending Timoleon and a substantial force of mercenaries to restore order.

In 344 BC, Timoleon defeated Hicetas at the Battle of Adranon, and in the following year, he negotiated Dionysius II’s surrender in exchange for safe passage to Corinth. With these immediate threats removed, Timoleon restored Syracuse’s democracy (the city’s third after periods of tyranny) and increased its population. However, the looming threat of Carthage persisted. In 339/8 BC, Carthage launched a large-scale offensive, deploying an army of around 70,000 to overpower Sicily’s Greek cities. Timoleon, with his smaller mercenary force, met the Carthaginians at the Krimissos River and achieved a decisive victory.
This defeat forced Carthage to renegotiate boundaries, reaffirming the Halycus River as the divide between Punic and Greek territories. Shortly after securing both Syracuse and Greek Sicily, Timoleon was compelled to retire in 337 BC due to blindness and passed away shortly thereafter.
The imagery on this coin reflects the impact of Timoleon and his Peloponnesian mercenaries. The obverse displays the head of Zeus Eleutherios—Zeus of Freedom—invoked to symbolize Timoleon’s mission to free the Syracusans from tyranny. The same head, along with a full Greek inscription, also appears on bronze coins minted in Syracuse under Timoleon’s governance. The reverse, featuring Pegasus, draws from Corinthian coins where Pegasus was a standard emblem of the city.