Suddenly the great city of Syracuse, the largest and most powerful city in the Hellenic world, was free from the tyranny that had oppressed it for some fifty years.[5] A half century of pent-up frustration was loosed, and hopes were bright for the future. But the struggle was not over yet. The hated tyrant was just outside the gates of the city, in the mighty fortress his father had built to intimidate foreigners and citizens alike, along with warships and an army of mercenaries, as well as a group of experienced and loyal commanders. More ships and soldiers were on their way with the admiral Philistus. So the future of Syracuse was anything but secure.
From the fortress of Ortygia, Dionysius tried to negotiate with Dion, but Dion replied to his messengers that he should apply to the government of the now independent city. While Dionysius was communicating with the city, he planned a surprise attack against it. The following morning, his mercenaries attacked the siege wall the Syracusans had built to keep Dionysius’ troops away from the city. The siege wall was hastily built and presumably easy to breach, and Dionysius’ troops broke through to attack the city. The Syracusans had to rally their forces and counterattack. In the confusion, Dion himself led an attack on Dionysius’s troops and drove them back. Finally the Syracusans defeated the enemy and patched the siege wall.[6]
Now a new figure appeared into the harbor, Heraclides. Nominally an ally of Dion’s, he had sailed in support of Dion’s invasion but been delayed by storms from arriving in time to participate in the liberation of Syracuse. He now arrived with seven galleys and three transport ships, or, by another account, twenty galleys and fifteen hundred soldiers.[7] He immediately addressed the assembly of Syracuse and got himself elected admiral and commander of the naval forces of Syracuse. Dion, who had already been made general with emergency powers, pointed out that only he could appoint Heraclides admiral. After annulling the election, he himself appointed Heraclides to the same post, preserving a chain of command with himself at the top. Heraclides deferred to Dion publicly but privately began a campaign to undermine the general’s power.[8]
Dionysius’s admiral Philistus now arrived from Rhegium with a sizable fleet, carrying more than five hundred cavalry and two thousand infantry.[9] Soon after, the two sides fought a naval battle in which each side committed about sixty galleys. In the battle, Philistus, whose ship had fought bravely, was surrounded and captured. Philistus died in the fight, either by his own hand or by enemy action. His body was mutilated and dragged around the city in a gruesome vendetta. At this point Dionysius was defeated, outnumbered, and outmaneuvered. The siege was taking its toll, and the outlook was bleak for the former tyrant. He turned over the care of the fortress to his son Apollocrates and fled by ship to Italy.[10]
[5] Diodorus 16.11.2; Plutarch Dion 28.4 counts 48 years.
[6] Diodorus 16.11-12; Plutarch Dion 30.
[7] Seven galleys: Plutarch Dion 32.3-4; twenty galleys: Diodorus 16.16.2. On Dion’s association with Heraclides, see Cornelius Nepos Dion 5.
[8] Plutarch Dion 33; Nepos Dion 6.3-4.
[9] Diodorus 16.16.1.
[10] Diodorus 16.16.3-16.17.2; Plutarch Dion 35.2-7, 37.1-4.