Timoleon’s inextinguishable love for freedom


In the middle of the fourth century b.C. almost all the πόλεις in Sicily and Magna Graecia were experiencing grave political and economic crisis. Syracuse in particular, in those days the richest town of the Greek world, was slowly collapsing due to interminable internal struggles for the power. Dionysius, its former τύραννος exiled for ten years, leading an army of mercenaries, marched in town and in 347 b.C. re-established his domination worsened by his long wait for vengeance. Most of the population fled to Leontini asking for asylum to its tyrannos Hicetes, who was secretly conspiring with the Carthaginians, who already occupied Western Sicily, to extend their dominion over Eastern Sicily.



The Greeks felt the danger of the Carthaginians and sent a delegation to their metropolis Corinth to ask for aid. The Corinthians agreed to send armed forces in assistance of their colony Syracuse. The στρατηγός strategos (general) was Timoleon, a man in his sixties with a glorious military past. He had long retired from the political scene after being accused of the assassination of his brother Timophanes. He was hastily designated regardless he had been a solitary person for many years and had attempted suicide in the past.

Timoleon (411 – 336 b.C.) belonged to the Corinthian noble class and was renowned for his humility and love for democracy. In his youth he fought to defend his town and saved his brother’s life on the battlefield. Nevertheless, in the future he participated or witnessed to his brother murder, to prevent him to takeover the power and dominate Corinth. His guiltiness haunted him and he found refuge in the woods living like a hermit for twenty years.

Once appointed Timoleon was still reluctant to accept the assignment, but probably he accepted in order to redeem himself and convince the Corinthians he was not a fratricide, but the one who had killed a tyrant. Thus after he had recruited 1200 soldiers and consulted the oracle at Delphi he set sails on 10 τριήρεις towards Italy. When he reached Rhegium he apprehended that Hicetes with the help of Carthaginians had already defeated Dionysius and had taken over Syracuse; and a large fleet was barring his way to Sicily. Timoleon succeeded to elude the line of defence and repaired in Tauromentium, whose wise and composed monarch Andromachus, became soon his supporter, regardless the open menaces received from the Carthaginians. Consequently Tauromentium became his headquarter from which all the operations were organised. Meanwhile the situation in Syracuse was dreadful, since the citizens were trapped between the two Greek tyrants (Hicetes in the city and Dionysius in the citadel) and the Carthaginians in the port.

Timoleon modest troops were poorly equipped and tired and he could not recruit soldiers from other poleis who were disenchanted as to regain their freedom against tyranny. This notwithstanding, when the polis of Adranum called for help Timoleon marched with his 1200 soldiers taking Hicetes army (over 4500 soldiers) by surprise and obtained a glorious victory. When news reached Syracuse, Dionysius surrendered and determined to consign the castle, his mercenaries and equipments to Timoleon and exiled himself in Corinth. After this other success Timoleon increased consensus on the island and his army gained confidence and courage. The Carthaginians, summoned by Hicetes sent a large fleet and over 50 thousand soldiers and encamped in the bay of Syracuse, while Timoleon was besieged in the fortress. When the besieged were almost desperate, and only 2000 aiding soldiers were sent from Corinth to join Timoleon march on Syracuse, the 50000 Carthaginians who had institutional problems to solve in their own country and not trusting their own Greek mercenaries set sails towards Carthage leaving the battlefield to Hicetes with and his mercenaries who were easily defeated by Timoleon.

Being a true democracy believer, Timoleon, regardless the perfect conditions for him to become the total ruler of Syracuse, against any tyrannical intentions he demolished the castle and those monuments that could remind the gloomy latest years of regime and built courts of justice on the site. Moreover, since the population of Syracuse had decreased conspicuously, Timoleon asked to Corinth and the whole Greek world for more inhabitants; exiles from Syracuse and colonist from all over Greece, Southern Italy and Sicily joined the repopulation process; Corinth bore all the transportation expenses. Finally he redistributed the land to all the new citizens – about 60 thousand – and Syracuse regained its splendour. Nevertheless Timoleon was not satisfied, he kept travelling throughout Sicily banishing the tyrants from the island and forcing them to exile. After having freed two thirds of the island, Timoleon settled down in Syracuse and was the father of the new Constitution based on democratic principles.



Meanwhile the Carthaginians had arranged a new huge expedition aimed at conquering the Eastern territory of Sicily. Again Timoleon was meant to be the hero: he faced a more than ten times larger enemy army – and was not abated when many soldiers of his army deserted for the fear. He marched toward the Carthaginians’ encampment and saw them by the river Crimesus. He noted that they were too heavily equipped (swords, shields, armours etc.) and this could be turned into a noteworthy advantage for the Greeks. They started the battle very close to the banks where the Carthaginians could not move properly. In addition soon a real deluge began complicating even more the enemies’ manoeuvres. Now the problems originated by the river worsened because mire quickly formed all along the banks, obstructing their movements. Very many Carthaginians died under these horrendous circumstances, the rest of the army started an immediate and difficult retreat. Timoleon captured prisoners which were enslaved, and huge quantity of items and equipments were given to the temples of Syracuse.

The Carthaginians however tried again helped by Mamercus, the monarch of Catana (North of Syracuse) and Hicetes who was already marching to conquer himself Syracuse. Nonetheless Timoleon tackled Hicetes before he could reach the town and started a victorious fierce assault gloriously defeating the enemy. Hicetes was captured and sentenced to death by the citizens of Syracuse. Immediately afterward Timoleaon went after Mamercus and the Carthaginians who were in Catana, He defeated the Carthaginians and had them sign a treaty which bound them to leave Western Sicily for good and never interfere with any monarch in the future. To complete his rescue Timoleon marched towards Messena (North of Catana) where Mamercus had obtained asylum. Hippo, the tyrannos of Messena, was captured and put to death, while Mamercus was taken to Syracuse and sentenced to death by the citizens

Timoleon in 337 b.C. had completed his masterpiece: he had obliterated all forms of brutal government on the island. He had reinstated the government of the citizens, contributed to the new constitution. Syracuse and other cities regained their splendour and culture and fine arts started to develop again. People from all over the Greek world moved and settled down to Sicily.

Timoleon, sensibly did not return to his mother country, he feared he would have been victim of public jealousy, a deadly destiny that many famous Greeks generals had undergone Besides he had no interest in honours or power, thus he retired to live a quiet country-style life Syracuse. Nonetheless the citizens of Syracuse kept considering him as the father of the city and when some significant public issue was at stake they used to invite Timoleon – who with the age became also blind – to the assembly. He would listen to the questions and present his judgment, which the citizens would collectively approve, dismissing him with appreciation and blessings.



Timoleon was praised for his wisdom and braveness, although in his great modesty he himself credited all of his success just to good luck. He was warm and trustworthy to his associates, and astute and merciless against the tyrants and enemies. He should be remembered mainly for his political and social achievements, rather than for his battlefield victoriesWhen Timoleon died, people came from all Western Sicily to attend to his funeral crying genuine tears for the person who gave them back freedom. His ashes were stored into a special grave in the agora of Syracuse, with this epitaph:



“Drove away the tyrants,

won the barbarians, reinstated

the splendour of the devastated cities

and gave back to the Greeks of Sicily their laws”




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