General Demosthenes’ Night Of Madness At Syracuse


In 413 BCE, Demosthenes sailed to Sicily and arrived at the outskirts of Syracuse with around seventy-three ships and thousands of troops to reinforce the Athenian camp that was besieging the city. The fresh troops and ships were much appreciated, as the Syracusans had recently captured three Athenian forts, and ships from Syracuse had even forced the Athenian expedition fleet to retreat during a later sea battle. The Athenians had always considered themselves to be unbeatable at sea, so the naval defeat was extremely troubling. Yet, the arrival of Demosthenes with his ships and men gave the Athenians a much-needed boost in morale.

Demosthenes shared the command of the Athenian expeditionary force with two other generals, Eurymedon and Nicias. Now that the expedition force was replenished, the three generals decided that it was time to attack Syracuse. After assessing the local geography, Demosthenes decided that the best way to defeat Syracuse’s defenses was to occupy Epipolae, an elevated plateau that was defended by several Syracusan camps and forts, as well as a wall. First, the Athenians tried a direct attack, marching out with siege engines to capture the wall, but the engines were burned and the assault made little progress. Thwarted, Demosthenes began to think of an alternative way to capture Epipolae. As one of the most creative and unorthodox generals in the Athenian military, Demosthenes was adept at planning unusual and surprising methods of attack. During his career, Demosthenes’ creative style of leadership had led to miraculous victories; yet, his ideas were also known to sometimes go horribly awry.

Ultimately, Demosthenes decided to try a stealth attack after dark. Around midnight, Demosthenes led his army in a roundabout path and climbed up onto the plateau from the west. The Athenians successfully arrived at the first fort of Epipolae without having been discovered. With the first step complete, Demosthenes then attacked the unprepared Syracusans, catching the garrison inside completely off guard. The Athenian forces quickly defeated the surprised warriors and captured the fortification. The battle for the fort was a complete Athenian victory, yet the overarching battle for Epipolae was about to take a dramatic turn.

Although the Athenians had successfully taken the first fort of the plateau, survivors from the defeated garrison and the noise of battle had alerted the defenders of Syracuse to the attack. Waves of Syracusans began rushing toward the fort, and the first defenders to arrive were approximately 600 warriors from one of the other forward camps on the plateau. It was a sizable force, but not enough to defeat the army that Demosthenes had led into battle. The Athenians rushed against the new arrivals and easily cut them down. As the band of 600 Syracusans gave way, the Athenians pursued them deeper into Epipolae. Yet, in their pursuit, the Athenians began to lose their cohesion and discipline, a troubling occurrence for any battle, but especially deadly at night. Consequently, the Athenian forces were in a haphazard formation when the fully-mobilized army from Syracuse arrived to assist the forts and defend Epipolae.

Unorganized and surrounded by the dark of night, the Athenians reportedly bumbled into a band of Boeotians who, along with other Spartan-aligned Greeks, were fighting on the side of Syracuse. The Boeotians entered the battlefield with discipline and attacked as a whole against the jagged Athenian lines. The shock of the Boeotian charge sent the Athenians into a panic, and, to Demosthenes’ horror, his army began to scatter into the night.

Instead of conquering Epipolae, Demosthenes now had to gather his shattered army and herd them back to camp. It was reportedly a scene of utter confusion. Many Athenians, after running off, became lost in the dark—some were said to have run straight off the plateau cliffs. Others called out to humanoid shadows in the dark, asking for watchwords. Yet, before long, the Syracusans learned the Athenian watchword and used it to lure lost stragglers to captivity or death. Some stranded warriors from the Athenian side even tried singing battle songs and other tunes that were native to their homelands. Nevertheless, such eerie songs emanating from the darkness only added to the confusion, especially when the songs of friend and foe sounded similar.

Eventually, Demosthenes and the majority of his army escaped and safely returned to camp. Yet, many were missing. Apparently, the portion of the Athenian army that fared the worst was the new arrivals that had recently sailed in with Demosthenes. As they had not yet learned the local landscape, they were the most prone to losing their way in the Sicilian countryside or falling off a cliff in the dark of night.

Written by C. Keith Hansley.

Picture Attribution: (Darkened version of “Heroes of the Battle of Marathon”, painted by Georges Marie Rochegrosse (1859–1938), [Public Domain] via Creative Commons).


  • History of the Peloponnesian War by Thucydides, translated by Rex Warner and introduced by M. I. Finley. New York: Penguin Classics, 1972.

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