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Timoleon was born into a noble Corinthian family. From an early age, he was marked out for leadership both in battle and in politics. Regardless of this early fame, he remained a modest and self-effacing man, as well as a great warrior. However, Timoleon had a brother - Timophenes - who was rash, impetuous and headstrong. He was also determined to become absolute ruler of Corinth, which had the reputation of having the most stable democracy in Greece. When Timoleon learned of this plot. He begged his brother to desist. When Timophenes refused, Timoleon killed him. While this act saved Corinthian democracy, it proved so emotionally jarring to Timoleon that he withdrew from public life for 20 years.

Timoleon returned to public life was brought about by a letter sent to Corinth from Sicily. At that time, Sicily was beset with internal and external enemies. The island had been ravaged, depopulated, and destabilized by the Pelopponesian War. The tyrant Dionysus ruled as an absolute monarch over the city-state of Syracuse. Other Sicilian cities were similarly dominated by tyrants and monarchs. Some Syracusans had looked to the Leothine king Hicates to drive out Dionysus. However, Hicates secretly allied himself with the Carthaginians who coveted the island. After the carthaginian navy appeared off the shores of Sicily, the desperate Sicilians wrote to Corinth asking for help in ridding their island of these menaces. The Sicilians wrote to the Corinthians because of the two lands' cultural affinities, the Corinthians' reputation for fighting wars of liberation, not conquest, and the Sicilians' belief that the Corinthian democracy would provide the most stable potential ally. It is telling that Athens, the so-called birthplace of democracy failed to meet any of these criteria.

At the meeting where the Corinthians discussed the response to the Sicilians' pleas, some unknown soul suggested Timoleon as the best person to save Sicily. It is not clear why the name of someone out of office for 20 years would be put forth for such a mission, but Timoleon accepted the post. He put together a small expedition comprising 1000 men and 10 ships and began crossing the Adriatic. While the Corinthian expedition had been putting to sea, Hicates and the Carthaginians had managed to defeat Dionysus in battle and had managed to besiege him in the impregnable Citadel of Syracuse, the symbol not only of the oppression of the Sicilians, but also the place that the Athenians had been unable to conquor during their own invasion of Sicily.

A Carthaginian fleet set sail on a bogus diplomatic mission to intercept the Corinthians at the town of Rhegium. Timoleon quickly realized that the Carthaginian diplomats were merely trying to delay him long enough to allow Hicates to extend his grip over Syracuse. Working with the Rhegians, Timoleon engaged in some fake diplomacy of his own. They convened a disputatious town hall meeting to "thoroughly discuss" the Carthaginian proposals. While the issues were debated at lengh, the Corinthians slipped out one by one, with Timoleon leaving last. They were safely at sea before the Carthaginians realized what had happened. Plutarch chortles a bit over Phoenicians complaining about being cheated!

Timoleon and his small force landed on a sliver of land where they made contact with some allies. Hicates marched to meet Timoleon's force, but Timoleon surprised them in their camp and put Hicates division to flight, leaving behind any stores and weapons. Dionysus was impressed enough by this that he secretly approached Timoleon and surrendered the Citadel to him. Thus, with a relative handful of men, Timoleon quickly found victory in battle, enough stores and allies to sustain his army, and possession of the impregnable Citadel (which remained besieged by Hicates). Timoleon sent dionysus into exile in Corinth, where he spent the remainder of his days living modestly (in glaring contrast to his ostentatious lifestyle as absolute monarch of Syracuse) and arguing vociferously with the Corinthians.

Hicates meanwhile began to rely more upon his powerful Carthaginan allies. He called in a force of ships commanded by Mago, which joined the siege of Syracuse. Mago's force was so large (60,000 troops, according to Plutarch) that the Sicilians saw this as the fatal hour when Sicily would fall to the barbarian hordes. A task force of Greeks from Rhegium and other greek colonies in Italy made their way over to Sicily, where they joined with Timoleon. with about 5,000 troops under his command, Timoleon marched to relieve the Citadel.

While Mago had superiority in numbers, he was a cowardly man and feared Timoleon's reputation as a warrior. During an eel fishing expedition outside Syracuse, Timoleon's men encountered some Greek mercenaries fighting for Mago. They asked how these men could fight for Mago, when they had to know Carthage would not be satsified with Sicily and would evventually look to conquor Greece. This set off enough tumult in Mago's camp that he became convinced his army was on the verge of mutiny. Mago simply packed up and left, taking his troops and his ships with him. When Timoleon and his army appeared in their battle array the next morning they simply laughed at the suddenly empty horizon, denuded of ships and men.

Hicates remained in his position beseiging the Citadel. Indeed, his position in Syracuse was nearly as impregnable as that of the Citadel. Timoleon divided his small force into three parts and carefully and systematically took down Hicates' defenses without any Corinthinans dying in action. Syracuse was finally liberated and Hicates escaped (Mago, for his part, was executed by the Carthaginians). The story of Timoleon's liberation of Sicily spread quickly through the Greek world, making him a legend in his own time.

having saved Sicily, Timoleon next set about restoring it to greatness. His first act was to destroy the Citadel which, for all its military utility, was also a symbol of the tyrannies that had bedeviled Sicily. Next, Timoleon sent out word to the greek world that Sicily was now a safe and welcoming place. Many Sicilians, especially Syracusians, had gone into exile, and many of these returned. Many other Greeks, attracted by the promise of bountiful farms and good trade also moved to Sicily. Within a year of the defeat of Hicates, Sicily was again a vibrant prosperous land with democracy, not tyranny as the ruling order.

The Carthaginians, however, made one last attempt at conquoring Sicily. Lacking a Greek ally, they simply landed a huge force of 70,000 men and began marching on Syracuse. Timoleon again had a small force - just 4,000! - to stop the invasion. Even his greatest admirers believed that timleon's famed luck had finally run out. It didn't help when Timoleon and his men encountered what they considered a bad portent - a mule train carrying parsley, of all things (a bad omen because parsley was used to adorn sepulchres). Nonetheless, Timoleon's luck was with him. He encountered the carthaginan army while it was crossing a river. timoleon attacked the smaller half, killing several thousand and putting the rest to flight. Timoleon again found himself in possession of an immense store of enemy booty.

Hicates and the remaining Sicilian tyrants, however, found common cause and joined with the remaining Carthaginians to defeat the Corinthians and the free Sicilians. This last alliance of tyranny failed to gain much traction. They were easily defeated piecemeal. The Carthaginians left Sicily for good. The local tyrants were deposed and either killed or sent into exile. The traitor Hicates was executed along with his entire family, including his wife and daughters (Plutarch identifies this as the one blot on Timoleon's career). With this, the era of war and tyranny in Sicily came to an end and a lengthy period of prosperity and political freedom began.

For his part, timoleon did not return to Corinth, but lived his remaining years out un Sicily. He did not seek any sort of official role, but lived in semi-retirement. But everywhere he went for the rest of his life, the Sicilians hailed him as their great hero and deliverer. His advice was eagerly sought out. He was always given seats of honor at banquets, the theater, or in the assembly. When his eyesight failed, Sicilians eagerly carried him about on a litter. When he died, his was a state funeral with the cortege passing over the former cite of the Citadel.