thumb|Coin of Timoleon (344–337 BC), with [[Zeus Eleutherios ('the liberator') and Pegasus]]
Timoleon (Greek: Τιμολέων), son of Timodemus, of Corinth (–337 BC) was a Greek statesman and general.
Timoleon is closely associated with the history of Sicily, particularly Syracuse, where he led campaigns against Carthaginian forces and local tyrants in the 4th century BC.
Early life
thumb|The assassination of [[Timophanes (Léon Comerre, 1874); Timoleon (at rear) covers his head with his cloak after having his own brother killed.]]
thumb|right|Timoleon sets sail for Sicily (as depicted in Children's Plutarch, 1900)
Timoleon was a member of the Corinthian oligarchy. In the mid 360s BC, Timophanes, the brother of Timoleon, took possession of the acropolis of Corinth and effectively made himself tyrant of the city. In response, Timoleon, who had earlier heroically saved his brother's life in battle, and after repeatedly pleading with him to desist, Most Corinthians approved his conduct as patriotic; however, the tragic occurrence, the actual fratricide, the curses of his mother, and the indignation of some of his fellow citizens, drove him into a self-imposed early withdrawal from politics and civic life for twenty years.
Sicily
Because of inner strife, the depredations and decline in Syracuse caused by the despots Dionysius I and his son who succeeded him, and because of the repeated conflicts with powerful Carthage, a group of Syracusans sent an appeal for help to Corinth, their mother city, which reached that city-state in 344 BC.
Corinth agreed to help, but her chief citizens declined to accept the seemingly hopeless task of establishing a stable government in tyrannical, fractious, insecure, and turbulent Syracuse.
Timoleon, being named by an unknown voice in the Corinthian popular assembly, was chosen by a unanimous vote to undertake the mission. He set sail for Sicily with seven ships, a few of the leading citizens of Corinth, and a small force of 700 Greek mercenaries. who was chosen annually by lot out of three clans, was invested with the chief magistracy. The impress of Timoleon's reforms seems to have lasted to the days of Augustus.
Hicetas persuaded Carthage to send (340–339 BC) a great army of 70,000 men, which landed at Lilybaeum (now Marsala). With a miscellaneous levy of about 12,000 men, most of them mercenaries, Timoleon marched westwards across the island to the neighbourhood of Selinus. Against all odds, after being deserted by a part of his army who believed that facing a foe six times as large as their own was hopeless, Timoleon, at the head of his infantry, won a great and decisive victory on the Crimissus. His victory was made possible by the fact that the Carthaginian army had not yet completed the river crossing, so his small force only had to fight the elite part of the Carthaginian force. He was also aided by a violent storm at the backs of his troops but blinding to the Carthaginians.
Later, Carthage dispatched mercenaries to prolong the conflict between Timoleon and the Greek tyrants. But this ended in the defeat of Hicetas, who was taken prisoner and put to death. A treaty in 338 BC was agreed upon, by which Carthage was confined in Sicily to the west of the Halycus (Platani) river and undertook to give no further help to Sicilian tyrants. Most of the remaining tyrants were killed or expelled. This treaty gave the Greeks of Sicily many years of peace, restored prosperity, rule of law, and safety from Carthage.
Ruler of Syracuse
Timoleon established a new Syracusan constitution, described at the time as democratic. For a short time he had wide powers equivalent to a supreme commander. He invited settlers from mainland Greece to assist in the re-population of Syracuse and other Sicilian cities. During this period, Greek Sicily enjoyed a recovery in its economy and culture. Peter Green views Timoleon as "no more than a benevolent tyrant" similar to Pisistratus. In Green's view, Timoleon merely posed as a democrat, and as such was using the methods of a tyrant. He also views that Timoleon tried to maintain the outward forms of democracy, yet reformed Syracuse in a democratic direction, and demolished the stronghold of the island that had been useful to tyrants in the past.
When taken to court on spurious grounds, Timoleon refused to be exempted, saying that this was the "precise purpose for which he had so long laboured and combated—in order that every Syracusan citizen might be enabled to appeal to the laws and exercise freely his legal rights."