When Plato first came ashore in Syracuse (in 388 BC), it seemed to him not so different from Athens: to him, it was “inevitable that these [two] cities will never cease to witness a succession of tyrants, oligarchs and democracies, and that their governors will barely tolerate hearing even the mention of a just and fair constitution” (VII letter, considered authentic by eminent scholars like Ulrich von Wilamowitz-Moellendorff, Giorgio Pasquali and Luciano Canfora). At that time the city was governed by Dionysius I, in the midst of a political career that would see him triumph in wars and in colonization, thus guaranteeing him a popularity that would only fade in the last years of his life. It appears that on this journey, the philosopher saw some glimmer of hope for Syracuse, due not so much to the establishment of the republic he theorized, but to a less hedonistic approach to philosophy and the exercise of power. His hope was embodied in Dion, the son of one of Syracuse’s wealthiest citizens and an advisor to Dionysius I, whom Plato held in high regard during that initial stay in the city.
It was this promising young man, a tutor of Dionysius II, who invited the philosopher to Syracuse in 367-366 BC, during the fraught period of succession to the throne. The feud that ensued inevitably generated new alliances and plans, and after three months, Dion was banished to Athens by Dionysius II, who took power and repudiated him as his tutor. Plato too was vilified; although he had interesting ideas, he was nonetheless an intellectual from the dangerous city that had laid siege to Syracuse fifty years earlier. The Athenian thus lived virtually as a hostage on Ortygia, and observed the shambles created by a tyrant he judged to be thoroughly unsuited to the practice of philosophy due to his unbridled ambition and alcoholic excesses. Taking advantage of a state of war, Plato managed to obtain permission to leave Syracuse and return to Athens, where he was reunited with Dion, who had begun to attend Plato’s Academy. During this period, the relationship between the Greek philosopher and the Syracusan aristocrat had an element of eros to it, according to fairly solid historical interpretations.
Plato’s third voyage to Syracuse (361-360 BC) came about at the insistent urging of Dionysius II, who claimed to have been converted to the master’s doctrine. Plato, however, refused to return to Syracuse without due guarantees regarding Dion’s fate. The philosopher’s mistrust was well-founded, and the journey ended in failure once again.
