The route the Athenian fleet took to Sicily
Map of the siege showing walls and counter-walls
Disaster in Sicily
The last and most fateful chapter in Demosthenes’ career took place on the island of Sicily, and he himself was largely to blame for it. In 415, the Athenians sent a large fleet to Sicily and used it in the following summer to besiege Syracuse, the most powerful city on the island. This is not the place to discuss in detail the vagaries of what is known as the Sicilian Expedition, but it is necessary to describe the circumstances awaiting Demosthenes when he arrived at Syracuse with large reinforcements in 413.
Before Demosthenes’ arrival, the Athenians had won consecutive victories on land and sea against Syracuse, primarily under the leadership of their experienced general Nicias. They had occupied Plemmyrium at the entrance to the Great Harbor of Syracuse, built a wall that partially surrounded the city, and gained access to Epipolae (“Overtown”), a plateau overlooking Syracuse. To the Athenians’ disadvantage, however, the Syracusans had occupied Olympeium (a fort southwest of the Athenian camp in the harbor, north of River Anapos), recaptured a fort at Labdalum on the western Epipolae, and built a counter-wall that prevented the completion of the Athenian wall. In addition, the Spartan general Gylippus arrived to aid the Syracusans in the summer of 414 and won a first land victory against the Athenians. He then left to collect reinforcements and allies in Sicily. Twelve Peloponnesian ships also made it to Syracuse, representatives of a newly invigorated Spartan fleet.
At this juncture, Nicias sent a letter to Athens, drawing a gloomy picture of the Athenians’ situation and prospects. He asked to be relieved of his command for health reasons and offered two alternatives: recall the expedition or send large reinforcements to Syracuse. The Athenians chose the latter option. They appointed two commanders on the spot as Nicias’ colleagues and substitutes if he died, giving Demosthenes and the veteran general Eurymedon the command over the new armada. Eurymedon was one of the generals who opposed Demosthenes’ request to occupy Pylos, and in 424, he returned from campaigning in Sicily with nothing to show for it. Demosthenes also came back empty-handed from Boeotia in the same year. Yet, with the talented Alcibiades in exile, the general Lamachus dead (shortly before in Syracuse), and the ailing Nicias away, the inventory of accomplished Athenian commanders was fairly limited. On the positive side, both new generals could use their respective connections in Corcyra, western Greece, and Sicily to help with the campaign, while Demosthenes’ proven resourcefulness promised quick results.
Eurymedon left immediately for Sicily with money and a few ships, but Demosthenes waited until early spring of 413 before sailing with sixty-five ships, 1,200 Athenian hoplites, and an unknown number of allied troops. On the way to his first major stop in western Greece, he plundered Laconian land and participated in the fortification of a site on the Laconian coast across from the island of Cythera, intending to use it as a shelter for refugee helots and as a raiding base. It is unclear whether he initiated the project, but the similarity to his tactics at Pylos, noted by Thucydides, clearly suggests his endorsement. From thence Demosthenes sailed to Acarnanian and Ambraciot waters, collecting troops from allied cities on the islands and the mainland along the way, including his old friends in Acarnania and the Messenian Naupactus. It was there that he heard bad news from Eurymedon, who had returned from Sicily: the Syracusans had succeeded in capturing Plemmyrium on the mouth of the Great Harbor, where Athenian grain, goods, naval equipment, and personal belongings were stored. The loss also reduced the Athenians’ control over the land from which they could launch and protect ships or to which they could retreat from battle. Contributing to the Athenians’ distress and low morale were the Syracusans’ increased interceptions of provisions brought by sea to the Athenian camp.
The worsening situation in Syracuse did not cause Demosthenes or Eurymedon to hurry there: they were busy drafting hoplites and light-armed troops in western Greece and southern Italy. Because the reported numbers of the new recruits are incomplete—we know only of 700 hoplites and 750 light infantry from Italy—they tell us little about the success of their recruiting. Yet their delayed arrival at Syracuse proved a costly risk, because it gave the Syracusans time to gain additional local allies, receive reinforcements from Greece and Sicily, and win a modest first victory over the Athenian navy in the harbor. Among their reasons for engaging the Athenian navy was their wish to forestall the arrival of the second armada. Demosthenes often relied for victory on his ability to predict and shape the enemy’s response to his actions. This time, his and Eurymedon’s calculated delay actually helped the enemy.
When the new Athenian fleet sailed into Syracuse harbor, however, it inspired disappointment, fear, and confusion in the enemy, and restored optimism and confidence to the Athenian camp. In his biography of Nicias, Plutarch describes Demosthenes’ showy entrance into the harbor:
Just then Demosthenes appeared off the harbors in a magnificent show of strength which dismayed the enemy. He had brought seventy-three ships, with 5,000 hoplites on board, and at least 3,000 others armed with javelins, bows, and slings. With his array of weaponry, with the figureheads on his ships, and the number of men employed in calling the time for the rowers and playing the pipes, he presented a fine display, designed to strike fear into the enemy.
Plutarch’s focus on Demosthenes is apt, because by all accounts he now dominated the scene. Thucydides ascribes to Demosthenes, not only an assessment of the situation when he arrived, but also a criticism of Nicias’ management of the war so far, although it is unclear if Demosthenes made it to Nicias’ face.56 He is depicted as almost a mirror image of the more cumbersome and passive Nicias, displaying decisiveness, a knowing-best attitude, and the confidence of a man who had a quick solution for the protracted campaign. In brief terms, his plan called for an attack against the Syracusans’ (third) counter-wall, which he identified as their weak spot. This was to be executed before the psychological impact of the fleet’s arrival wore off. Demosthenes is also said to have predicted two opposite outcomes of his plan: the fall of Syracuse or the Athenians’ withdrawal. That Syracuse did not fall and that the Athenians would withdraw only later and under worse conditions had much to do with the way he chose to implement his idea.
Nevertheless, the new vigor Demosthenes brought to the campaign appeared to have an effect. The Athenians descended on Syracusan lands around the River Anapos, and the enemy’s lack of response was optimistically interpreted as a yielding of control over land and sea to the Athenians. The next engagement was more sobering, however. Demosthenes used siege engines and frontal attacks against the Syracusan counter-wall but was repelled by the defenders. Under the largely self-induced pressure of having to take instant action, and with his colleagues’ consent, Demosthenes turned to his favorite modus operandi, a surprise attack.
He aimed to surprise the enemy on the Epipolae plateau by launching an attack from the relatively unexpected direction of the western and more accessible Euryalus Hill. More significantly, he took with him (according to one account) 10,000 hoplites and a greater number of light infantry for a full-scale night battle. There was no known precedent for fielding such a large force in a night combat, even in such bright moonlight as shone that night. The opposition consisted of a fort and sentries on the Euryalus, three fortified camps on the Epipolae, an advance guard of 600 men, and men in the city who could join the fighting. At first, everything seemed to go the attackers’ way. Led by Demosthenes and his colleague Menander, the Athenians went up the Euryalus, destroyed those they encountered, and took the fort there. Demosthenes, running ahead as at Megara, scattered the 600 advance guards who tried to oppose him. By now the surprise was gone, but Demosthenes and his men hurried on in order to exploit their momentum and to prevent the enemy from organizing a more effective defense. When the Syracusans’ commander Gylippus and his men came out of their camps, they were beaten back. In the meantime, other Athenian troops were busy tearing down the Syracusan counter-wall, whose guards fled. Yet the Athenian wave of attack collapsed entirely when it came up against its first stubborn opposition: a Boeotian unit that stood its ground and put the attackers to flight.
Because Demosthenes relied on surprise and speed for victory, he had to sacrifice order and effective communication with, and control over, units that were not in his vicinity. Poor visibility hampered his ability to respond to setbacks, while speed undermined the cohesion of his ranks. These conditions allowed an unyielding unit of defenders to repel the charge and caused the fleeing Athenians to sow confusion and uncertainty among their fellow combatants. According to Thucydides’ graphic account, the impaired visibility prevented the attackers from telling friends from foes, while those who kept arriving at the scene did not know where to join the battle. The only means of identification was the watchword, which the din of battle obscured, and which the enemy soon found out and used to its advantage. There were even incidents of Athenians’ dying from “friendly fire” and in near-clashes among fellow soldiers. Additional problems stood out because Demosthenes should have known better. At Acarnania, Sphacteria, and even Megara, he had won largely by his successful coordination of attacks from different quarters. On the Epipolae, there seemed to be no coordinated effort, only a rush forward to meet the enemy. At Acarnania, Demosthenes had used the Dorian-speaking Messenians to mislead the Ambraciots into believing that his troops were their allies. On the Epipolae, it was his own troops who fell victim to such confusion. Thucydides says that what confounded and terrified the Athenians most was the singing of Dorian paeans, because there were Dorian Greeks fighting on both sides. Finally, at Acarnania and Pylos, Demosthenes had made good use of local intelligence and the terrain to defeat the enemy. At Syracuse, those advantages worked in the enemy’s favor. Soldiers who had just arrived with Demosthenes were unfamiliar with the ground, lost their way, and were killed by the Syracusans even if they made it down from the plateau safely. In addition, the Athenians’ panicked retreat clogged the only narrow path down the Epipolae, and many of them fled their pursuers only to throw themselves off the high cliffs to their death. According to the sources, the Athenians lost between 2,000 and 2,500 men on and around the Epipolae. No other land battle during the Peloponnesian War resulted in so many casualties.
Like the plan of attacking Boeotia from different directions, the failure at Syracuse was not inevitable, but it could have been anticipated. Demosthenes took a gamble on surprise and lost disastrously, committing many men and assuming optimistically that shock and speed would compensate for the well-known difficulties of a night attack. His plan made it very difficult to direct the offensive and even the retreat.
The defeat had a significant impact on everyone involved, including Demosthenes. His arrival had caused fear among the Syracusans, which he wished to exploit, but now their fear changed into optimism and self-confidence, and they even used the victory to mobilize aid in Sicily. The defeated Athenians, who suffered also from unhealthy conditions in camp, grew despondent, and their leadership became divided. Demosthenes’ authority as the new commander who would change the course of the campaign suffered a devastating blow. When he recommended a return home, he was successfully opposed by Nicias, who had regained the prime leadership. It appears that the other Athenian generals also deemed Demosthenes’ solution of cutting their losses too radical, especially coming from the man who was responsible for the losses. Demosthenes then suggested evacuating the army to friendly Catana or Thapsus in Sicily, in order to raid enemy territory from there, or to fight at sea. Although his idea gained Eurymedon’s approval, Nicias successfully shot it down. Later the Athenians changed their minds about evacuation to Catana, but a lunar eclipse was interpreted as portending disaster, and no one could overturn Nicias’ decision to stay at Syracuse for twenty-seven days, as seers had prescribed. Because of my focus on Demosthenes’ generalship, I shall not dwell on the motives Thucydides attributes to Nicias on this and other occasions. The historian ascribes Nicias’ errors of judgment to his fear of the supernatural and of punishment at home if he returned, as well as to his belief that the Athenians could still take Syracuse. Whether Demosthenes’ suggestions were sound or not, his clouded reputation from the failed attack on the Epipolae forced him to defer to Nicias.
Demosthenes appears only sporadically in Thucydides’ narrative of the ensuing events. He is not mentioned among the generals who participated in the next naval battle in the harbor, though he may have fought in it. This engagement cost the Athenians their general Eurymedon, about 2,000 men, and at least eighteen ships, though they did repel a Syracusan attack on the Athenian walls. Thucydides suggests that the Athenian defeat at sea changed the Syracusan definition of victory from driving the invaders away to preventing them from escaping to a friendly base, and that they accordingly blocked the entrance to the harbor with a boom. In response, the Athenians set their slender hopes on an all-out naval battle, which, if successful, would allow them to sail out of the harbor, and if a failure, would compel them to march by land to a friendly place. They also limited their control over land to a small, fortified space next to the ships, which was easier to defend and allowed them to free troops to man the ships. The man in charge was Nicias, according to Thucydides, who credits him with a pre-battle exhortatory speech and with individual appeals to the ship commanders. Plutarch even suggests that Nicias refused to yield to the Athenians’ demand to retreat by land and insisted on a naval battle.
But Demosthenes’ possible contribution to the Athenian plan, or at least his support of it, can be gleaned from the fact that he was one of the generals who commanded the huge Athenian fleet of about 110 ships, as well as from the tactics chosen. Victory hinged on the Athenians’ numerical superiority (about 110 ships to 76) and their ability to convert the fighting into something like a land battle. The plan called for the light infantry on deck to shoot arrows and javelins at the enemy while the marines used grappling irons to prevent the enemy ships from backing away, finally boarding them to kill those on deck. Thucydides specifically mentions Demosthenes’ Acarnanian recruits among the light-armed troops who fought at the harbor. Demosthenes had little experience in maritime warfare, if any, but the kind of naval battle sought by the Athenians was as close as possible to the land fighting he was familiar with. In addition, the Athenians’ use of land forces on ships copied the Syracusans’ tactics, and Demosthenes had shown in the past his ability to learn from the enemy.
To judge by Thucydides’ description of the battle, the generals played only a limited role in it. The Athenians succeeded in breaking the barrier at the harbor mouth, but once the Syracusans joined battle, the fighting consisted largely of individual conflicts, with the generals mainly watching lest ships back away unforced from the fray. The Syracusans won because they made the Athenians fight a traditional naval battle in which the Syracusan lighter vessels enjoyed an advantage, destroying about fifty ships and losing only about twenty-five. Fear now dominated the Athenian camp. The troops were so desperate to leave by land that very night that they were willing to give up collecting their dead. But Demosthenes approached Nicias with a different plan, which illustrated the essence of his generalship. The general, who recommended surprise attack as the preferred solution for most military problems, suggested that they board the remaining triremes straightway and attack the enemy unexpectedly. One may admire Demosthenes’ resourcefulness in the face of adversity and his unconventional thinking, but his idea was unworkable for two reasons. The Athenians had lost faith in their ability to win at sea—understandably, in light of their two recent, consecutive defeats in the harbor. Moreover, they had only sixty ships left and about 40,000 people in camp, which meant that even a victory would give them little chance of evacuating so many people by sea, rather than by marching on land.
In the end, the Athenians waited two days before starting their march away from the harbor and generally north toward Catana. They were despondent, hungry, and full of guilt for leaving the wounded and dead behind. Thucydides’ emotive description of their retreat and tragic end is unsurpassed. Reduced to factual terms, it tells us that the Athenians formed a hollow square, Nicias leading the van and Demosthenes bringing up the rear, with the rest of the marchers in the middle. Their pace was slow and grew increasingly slower, largely because of their short supplies and the Syracusan opposition. Intentionally or not, Thucydides’ narrative of the Athenians in retreat evokes memories of the Spartans on Sphacteria, who were similarly harassed by elusive light infantry. With distress growing, the leading generals approved what would be Demosthenes’ last attempt at outwitting the enemy. The Athenians lighted many fires, as if camping for the night, but left under cover of darkness, changing direction toward the southwest, away from their Syracusan pursuers and toward the sea and friendly locals. The tactic won them freedom from pursuit only till the middle of the next day. They became disoriented and very fearful, and a gap was created between the van under Nicias and the larger rear under Demosthenes. Thucydides notes that Nicias’ men marched together and in good order, while Demosthenes’ troops moved more slowly and in disarray. It was as if a circle closed in Demosthenes’ career: his last retreat resembled his first one in Aetolia where his troops fled in disorder and suffered losses. In fairness to Demosthenes, we should note that the Syracusans attacked his men with greater frequency than they did Nicias’ division. Demosthenes arrayed his troops for battle in an enclosure, but the Syracusans did not take the bait: it was easier and safer to bombard the enemy with missiles from a distance. At the end of that day, exhaustion, hunger, thirst, and many injuries led Demosthenes to surrender with 6,000 of his troops on the condition that no one would be killed. Nicias capitulated two days later after losing many more men, a carnage that justified Demosthenes’ decision to spare his followers’ lives.
The sources are divided about Demosthenes’ fate. Thucydides, our most authoritative informant, says that the Spartan general Gylippus wished to bring both Demosthenes and Nicias to Sparta as living trophies, but the Syracusans “cut their throats.” Other sources mention a debate in the Syracusan assembly over their fate that ended with the same result. We are even told that Demosthenes tried unsuccessfully to kill himself when surrounded by the enemy, and that later, when he and Nicias learned in prison of their imminent execution, they took their own lives. Their bodies were then exposed to public display.
Pausanias, the Greek traveler of the Roman era, cites an Athenian inscription that commemorated the war dead, including those killed in Sicily, along with its interpretation by the Sicilian historian Philistus (c. 430–356):
The names of the generals are inscribed with the exception of Nicias, and among the private soldiers are included the Plataeans along with the Athenians. This is the reason why Nicias was passed over, and my account is identical with that of Philistus, who says that while Demosthenes made a truce for the others and excluded himself, attempting to commit suicide when taken prisoner, Nicias voluntarily submitted to the surrender. For this reason Nicias had not his name inscribed on the slab, being condemned as a voluntary prisoner and an unworthy soldier.
We don’t really know why Nicias’ name was not inscribed, but the contrast drawn between him and Demosthenes is surely unfair. Some scholars think that Thucydides is equally unfair in eulogizing Nicias as the man who, of all the Greeks of his age, least deserved his misfortune, saying nothing comparable about Demosthenes. Clearly, the last chapter of any commander’s career should not dominate the assessment of his entire generalship, but it is equally wrong to ignore it. Demosthenes was neither a hero nor a failure, but both, or one of these historical actors who do not easily fit a single category. He demonstrated original thinking and good planning skills in each of his campaigns. He was chiefly known for his victories at Pylos and Sphacteria and for establishing a permanent base in enemy territory. His success encouraged imitations as early as the year he captured Pylos (425), when the Athenians set up a post near Epidaurus to raid the adjacent territory. By 413, when the Spartans similarly occupied Decelea in Attica, and when Demosthenes himself fortified a site in Laconia opposite Cythera, such projects had become quite common. Demosthenes therefore deserves credit for coming up with a plan that was adopted by both his city and its enemy, although it is ironic that the Spartans made more effective use of it at Decelea than the Athenians did anywhere. In some of Demosthenes’ campaigns, he used military intelligence and light infantry very effectively, although Greek antecedents of such uses suggest that he was not their originator. He was a gambler who enjoyed good luck in some of his operations and suffered losses in others. He was a firm believer in surprise and deception as the best means of accomplishing his goals. His personality well suited these qualities: he was ambitious, aggressive, self-confident, daring, and a risk-taker, but also someone who tended to take failure as an endpoint instead of as a temporary setback. His impatience, however, was not as disastrous as his preference for a quick solution in the form of surprise attack, even when conditions disfavored it. With its share of successes and disappointments, Demosthenes’ career shows the benefits and pitfalls of having such a general in command.
