In 345/4 BC the citizens of Syracuse had sent envoys to the mother city Corinth to plead for assistance against Dionysius. The Corinthians chose Timoleon, who so hated tyranny that in c.365 BC he had consented to the murder of his brother Timophanes when he tried to make himself tyrant in Corinth.
In 344 BC Timoleon set sail from Leucas with ten ships and seven hundred mercenaries. He eluded a Carthaginian squadron at Rhegium and landed at Tauromenium. Hicetas had already arrived with a much larger force at Adranum to the south. Timoleon, suspecting Hicetas to be a would-be tyrant, marched on Adranum and caught him off guard, killing hundreds of his troops and capturing many more. With Hicetas’ troops in disarray, Timoleon marched on to Syracuse and made himself master of the northern part of the city (Epipolae and Tyche). Hicetas retained Neapolis and Achradina; Dionysius remained blockaded in the island citadel Ortygia.
Timoleon’s success prompted neighbouring cities to seek his friendship and offer their services. Mamercus, tyrant of Catana, proposed an alliance and Dionysius, at last, sent a message offering to deliver himself and the citadel to the Corinthians. Timoleon immediately dispatched two of his captains with four hundred men to seize the citadel, where they found a magnificent supply of horses, war-engines, weapons and armour. Dionysius quietly slipped away and sailed to Timoleon’s camp at Catana from where he was soon dispatched to Corinth with a small sum of money.
Hicetas continued his blockade of Ortygia. He asked the Carthaginians for assistance, and in 343 BC Mago (4) arrived in the Great Harbour with one hundred and sixty ships and fifty thousand men. As Timoleon had sent supplies to Ortygia, Hicetas and Mago set off to attack his base at Catana. Noting their departure, Neon, the Corinthian commander at Ortygia, made a surprise attack and captured Achradina.
Daunted by this setback and suspecting treachery Mago sailed away with all his forces to Carthage, where he was censored by his government and committed suicide. Meanwhile, Timoleon with reinforcements from Corinth had taken Messina. He then went on to Syracuse where Hicetas, his forces now insufficient to hold his part of the city, withdrew to Leontini leaving Timoleon in sole command of all Syracuse.
Timoleon’s first act was to demolish the defences on Ortygia, a fortress long used as a base by the tyrants. Next he established democratic laws and popular courts. He then re-peopled the city, which had whole streets without inhabitants, with restored exiles and new colonists in their tens of thousands from Corinth, Italy and Sicily.
In 339 BC the Carthaginian generals Hasdrubal (2) and Hamilcar (2) landed an army of seventy thousand troops at Lilybaeum but while it was crossing the Crimissus River near Segesta, Timoleon’s force of only twelve thousand men with the help of a flooding of the river defeated it, inflicting heavy losses. The Carthaginian survivors retreated back across the Crimissus to Lilybaeum and later returned to Carthage.
After this defeat the Carthaginians formed an alliance with Mamercus and Hicetas, and in c.339 BC they sent Gisco with seventy ships. Joining forces in the territory of Messana they at a place called Hieras ambushed and killed four hundred of Timoleon’s mercenaries under Euthymus of Leucas. In c.338 BC Timoleon defeated Hicetas at the Damyrias River (probably near Camarina). Soon after the battle Timoleon captured Hicetas with his entire family and put them all to death. He followed this up with a victory over Mamercus near the Abolas River. Mamercus was eventually captured and killed. The Carthaginians asked for peace, and the Halycus River was again stipulated as the boundary. Warfare continued until 337 BC when the last of the tyrants were suppressed. Timoleon, his task completed, retired to private life.
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