Just when the conclusion that Plato and his followers had hoped for seemed to have been achieved, Dion the devoted disciple of Plato was murdered and the comedy became a tragedy. What was worse, the mastermind of the assassination was Callippus, an alumnus of the Academy and a former colleague of Dion, now turned traitor. Was the Academy, the alleged beacon of enlightenment and social progress, just a den of cutthroats and scoundrels after all?
Whereas Dion was apparently laying the groundwork for a constitutional government, Callippus made himself tyrant without any idealistic pretenses and managed to rule for thirteen months. At that point, Hipparinus, son of Dionysius I and half-brother of Dionysius II, launched a surprise attack on Syracuse while Callippus was away, and succeeded in making himself tyrant. Two years later, Hipparinus’ brother Nysaeus usurped the throne and ruled for five years.[20] In 346 (after the death of Plato), Dionysius II usurped power again in the ongoing game of thrones.[21] The Syracusans finally appealed to their mother city Corinth for help. The Corinthians sent a retired military man, Timoleon, with dark past, accompanied by a small force in ten ships.[22] Meanwhile, Hicetas, a Syracusan operating from Leontini, managed to defeat the mercenary army of Dionysius and kill 3,000 of them. He captured the city of Syracuse, leaving Dionysius again besieged in the fortress of Ortygia. He made an alliance with the Carthaginians and now, revealing his own ambitions, called on their fleet to block the expedition of Timoleon.[23]
Timoleon managed to evade the blockade and sailed to Tauromenium, where he gained some reinforcements and defeated an army of Hicetas on the slopes of Mt. Etna. He then moved quickly south to Syracuse, where he occupied part of the city. At the same time, Hicetas held the eastern quarter known as Achradina, and his allies the Carthaginians occupied the Great Harbor with 150 galleys, while Dionysius held the fortress of Ortygia.[24] Now Dionysius, cut off from all support and surrounded by two enemy forces, negotiated secretly with Timoleon. In accordance with their agreement, Timoleon took over the fortress at Ortygia and allowed Dionysius to go into exile in Corinth, while Dionysius’ 2,000 mercenaries joined Timoleon’s army. Dionysius secretly sailed away on a small freighter with only a few friends and a small treasure.[25]
Now a power struggle emerged between Hicetas, bolstered by a barbarian army and navy, and Timoleon, the liberator sent by Corinth. The danger was that a victory by Hicetas might mean subjection to a foreign power, Carthage, with its vast reserves of manpower and materiel—and traditions of autocracy. In the long run, the Carthaginian general became suspicious of the loyalty of his Greek mercenaries, and sailed away with his fleet to north Africa. Timoleon attacked Hicetas’ troops and captured the rest of Syracuse. [26] He then did what a good liberator should do, and had his troops destroy the fortress of Ortygia which had been the stronghold of those who would oppress Syracuse and Sicily. He also instituted democratic reforms in the government of the city.[27] Timoleon had freed Syracuse against the odds, and he continued to campaign against Hicetas on the one hand and the Carthaginian empire on the other, until he defeated Hicetas and forced the Carthaginians to sue for peace, in 339/8 BCE.[28] The liberation of Sicily, counting from Dion’s incursion, took almost two decades and untold blood, toil, tears, and sweat to complete.
In the end, the fate of Syracuse and Sicily was decided not by philosophical ideals and political theories but by armies, navies, mercenary forces, alliances, foreign expeditions, barbarian invasions, palace coups, would-be tyrants, ex-tyrants, would-be liberators, and one liberator who, happily, acted with altruistic motives. Dion himself had been moved by Platonic ideals, but he seems to have been insensitive to the desires of the people, aloof and cold among his peers, and too permissive with rebellious subordinates. His efforts were subverted and ultimately undone by those closest to him. And, to Plato’s chagrin, a colleague from the Academy played Judas in the hour of Dion’s triumph. Plato’s dream of a philosophical republic would never be realized. The divide between Realpolitik and the ivory tower was never greater than in Plato’s lifetime.
[20] Diodorus 16.36.5. On the genealogy of the family, see Diodorus 16.6.2-3, Plutarch Dion 3; 6.1.
[21] Plutarch Timoleon 1.
[22] Plutarch Timoleon 2-8. Timoleon had stood by while his brother was killed by Timoleon’s colleagues; the brother had launched a tyranny in Corinth: was Timoleon a virtuous tyrannicide or a despicable fratricide? Timoleon himself was deeply troubled by his own responsibility: Timoleon 4-5; 7.2.
[23] Diodorus 16.68.1-5; Plutarch Timoleon 1.6; 2.
[24] Diodorus 16.68.6-11; 16.69.3.
[25] Plutarch Timoleon 13.
[26] Plutarch Timoleon 18, 20-21.
[27] Plutarch Timoleon 22.1-3; Diodorus 16.70.4-5.
[28] Diodorus 16.82.2-83.1.