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The Siege of Kephaloidion occurred from 398 to 397 BC when the Sicilian Greek armies of Syracuse besieged the Hellenized Sicel town of Kephlaoidion (Cefalu) amid the Syracusan-Agyrian War. The Syracusans besieged an equally-strong garrison in the port town, maintaining their siege in the face of attrition, before decisively defeating an Agyrian sortie in the winter of 397 BC. In the aftermath of the failed sortie, the Agyrian archon Hermokrates escaped by ship to Messina, and Kephaloidion was taken by storm in the spring of 398 BC.

History[]

In 399 BC, the Syracusan tyrant Dionysius I launched a surprise invasion of the rival city-state of Agyrion in northeastern Sicily, capturing Catania with light casualties before joining forces with his general Hipparinus to take Agyrion itself by storm in the winter of early 398 BC. After replenishing their ranks, the Syracusan armies pursued the fleeing Agyrian armies of Hermokrates and Philippos north to the port town of Kephaloidion (Cefalu), skirmishing with Philippos' cavalry bodyguards along the way. Upon reaching Kephaloidion, the Syracusans found that the port was well-defended, and that it had enough supplies to hold out for two and a half years. Rather than risk a disastrous assault on the walls, Dionysius decided to besiege Kephaloidion and maintain the siege until the city was starved into surrender.

In the winter of early 397 BC, however, the Agyrian general Philippos and his cavalry bodyguards attacked the Syracusan armies in conjunction with a major sortie by Kephlaoidion's defenders. In the ensuing battle, Dionysius and Hipparinus' armies joined forces and formed a "V"-shape, with the combined Agyrian forces advancing into the gap between the two Syracusan forces. This enabled the Syracusan slingers and archers to inflict heavy losses on the Agyrian flanks and advance units, causing the Agyrian skirmishers and militia on their flanks to retreat. The Syracusans proceeded to attack the trapped Agyrian army, and the combat turned into a battle of phalanxes. The Syracusans were able to outflank the Agyrian army and destroy its phalanxes piecemeal; the Syracusan cavalry rode down the Agyrian archers and slingers, allowing for the Syracusan horsemen to charge the Agyrian phalanxes from the rear. The Syracusans forced the Agyrians to flee back into their city, losing 1,012 troops and inflicting 1,791 losses on the Agyrians. Because of the Syracusans' heavy losses, the Agyrians were able to resist the siege for another season. However, the Syracusans soon replenished their losses by recruiting mercenaries, and their combined assault on Kephaloidion in the spring of 397 BC led to the city's fall; 374 Syracusans and 1,130 Agyrians were killed, and Agyrion's main army was destroyed. Hermokrates fled by ship to Messini (Messina), where he would make his last stand in 396 BC; after the fall of Messini to Syracuse in 396 BC, Syracuse came to rule over all of eastern Sicily.

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