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The Sicilian Expedition was an Athenian expedition to Sicily from 415 BC to 413 BC, during the Peloponnesian War. The expedition was hampered from the outset by uncertainty in its purpose and command structure—political maneuvering in Athens swelled a lightweight force of twenty ships into a massive armada, and the expedition's primary proponent, Alcibiades, was recalled from command to stand trial before the fleet even reached Sicily—but still achieved early successes. Syracuse, the most powerful state on Sicily, responded exceptionally slowly to the Athenian threat, and as a result was almost completely invested before the arrival of a Spartan general, Gylippus, galvanized its inhabitants into action. From that point forward, however, as the Athenians ceded the initiative to their newly energized opponents, the tide of the conflict shifted. A massive reinforcing armada from Athens briefly gave the Athenians the upper hand once more, but a disastrous failed assault on a strategic high point and several crippling naval defeats damaged the besiegers' fighting capacity and morale, and the Athenians were eventually forced to attempt a desperate overland escape from the city they had hoped to conquer. That last measure, too, failed, and nearly the entire expedition surrendered or was destroyed in the Sicilian interior.

The impact of the defeat was immense. Two hundred ships and thousands of soldiers, an appreciable portion of the city's total manpower, were lost in a single stroke. Athens' enemies on the mainland and in Persia were encouraged to take action, and rebellions broke out in the Aegean. The defeat proved to be the crucial turning point in the Peloponnesian War, though Athens struggled on for another decade. Thucydides observed that contemporary Greeks were shocked not that Athens eventually fell after the defeat, but rather that it fought on for as long as it did, so devastating were the losses suffered.