In 344 the Syracusans, devastated by the civil wars and the near anarchy - and worried by the presence of a Carthaginian fleet - appealed to their mother-city, Corinth, for help (Diod. XVI 67). It seemed a hopeless appeal since Philip, the King of Macedonia, having just brought the Phocian War to an end, was busily tightening his grip in Greece (see chap. 18).Yet Corinth always took its maternal obligations seriously, and sent what it could: a thousand mercenaries under the command of the aristocrat Timoleon, who lived under a curious shadow in Corinth. He had slain a would-be tyrant (and so won his fellow citizens’ praise) who, however, was his own brother (and so incurred opprobrium as a slayer of kin). As Timoleon left Corinth, it was said that if his mission in the West prospered, then he would have slain a tyrant; but if it failed, then he would have murdered his brother (Diod. XVI 65).
With his modest troop of mercenaries, Timoleon set sail for the West. When he put in at Rhegium, he found both a Carthaginian fleet and envoys from a man called Hicetas waiting for him. Hicetas, having in the meantime gained control over Syracuse as tyrant and having shut Dionysius II up on the island of Ortygia, had reached an accommodation with the Carthaginians. So Timoleon was politely asked to return home. With equal politeness, Timoleon insisted on discussing matters in the Rhegine assembly. Here, with the Rhegines’ active connivance, Timoleon wasted both the envoys’ and the Carthaginian commanders’ time while his troops got his ships under sail. Timoleon himself left the assembly just in time to leap aboard the last ship - the Carthaginian commanders realized too late what had happened.
Timoleon next put in at Tauromenium. A civil war had broken out in the nearby Sicel town of Hadranum, and factions there appealed both to Hicetas and to Timoleon. Hicetas arrived first, but Timoleon on arrival caught Hicetas’ troops unawares and attacked them. With an easy victory behind him, Timoleon took control of Hadranum (Diod. XVI 68; Plut. Tim. 9-12). At this point Dionysius II, whose once mighty empire had shrunk to Ortygia, wearied of living trapped in the fortress there. He offered Ortygia to Timoleon in exchange for permission to go to Corinth to live out his days in peace. Timoleon acquiesced and thus gained Ortygia without the striking of a blow (Plut. Tim. 13; cf. Diod. XVI 70).
Hicetas still held Syracuse, but it was mostly thanks to Carthaginian support: 150 Carthaginian ships lay in the harbor and a Carthaginian force stood in the city itself (Plut. Tim. 13 and 16-17; otherwise Diod. XVI 68-69). However, whatever assignment the Carthaginian commander, Mago, did have, it was not to prop up Hicetas indefinitely. When Mago took his fleet back to Carthage, Hicetas lost control of Syracuse (Diod. XVI 69; cf. Plut. Tim. 18). Timoleon established democracy in the city, restored its population (depleted by the civil wars) by advertising for immigrants from mainland Greece, and suppressed tyrants in the other Greek cities on the island (Diod. XVI 70, 72-73; Plut. Tim. 22-24).
In 339 the Carthaginians finally invaded. They brought an army of (allegedly) 70,000 infantry and 10,000 cavalry to the island’s west (Diod. XVI 77; Plut. Tim. 25); against this host Timoleon could muster (allegedly) a mere 12,000, of whom a thousand shortly deserted anyway (Diod. XVI 78-79; Plut. Tim. 25, has even smaller numbers). That the numbers have been shaded a bit to emphasize the David-and-Goliath nature of the contest is eminently probable. The two armies met at the River Crimisus near Entella. As luck would have it, Timoleon’s troops caught the Carthaginians as they were crossing the river (Diod. XVI 79; Plut. Tim. 27). Initially the Greeks were winning, but as more and more Carthaginian troops reached the opposite bank, the latter gained momentum. Then a blinding rainstorm blew up - behind the Greeks and into the Carthaginians’ faces. Since the Carthaginians were wearing heavier armor, in the wet and mud they fought at a distinct disadvantage (Diod. XVI 80-81; Plut. Tim. 28). However much the story’s details may have been adjusted for dramatic effect, the fact remains that Timoleon returned victorious to Syracuse (Diod. XVI 81; Plut. Tim. 30).
He had to confront several tyrants again (including Hicetas who had set himself up in Leontini), but, as one might expect, defeated them. Peace was arranged with Carthage (Diod. XVI 82-83; Plut. Tim. 31-35), and Timoleon, to whom the Syracusans granted an estate near their city (Plut. Tim. 36), retired there and died in 337 (Diod. XVI 90).
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