Plato’s Last Word to Dionysius

By the time Plato departed the court of Dionysius the Younger in 361 BC, his relations with the Syracusan autocrat had turned frosty. Plato had spent many months at the court in Sicily over the course of two visits spaced six years apart. He had been pursuing a remarkable goal: to give a notorious tyrant, the most powerful ruler in the Greek world, a philosophic education. But the project had utterly failed and Plato had come to be seen as an enemy of the regime. Indeed, he was in mortal danger; only after a third party, the philosopher-statesman Archytas of Tarentum, had intervened from afar had he been given leave to return to Athens.

The final, tense meeting between the sage and the tyrant was steeped in animosity, to judge by the account in Plato’s Third Letter. Some scholars consider this epistle, addressed by Plato to Dionysius but clearly intended for wider circulation, to be a fake, concocted, perhaps, by a forger to sell to a library; others, including Robin Waterfield in his authoritative Plato of Athens (2023), take it to be genuine. The psychological depth of the letter’s account of this meeting, Plato’s last encounter with a debauched and alcoholic autocrat, is one good reason for doing so.

The meeting took place, according to the letter, on the grounds of ‘the acropolis’, a fortified castle that Dionysius used as both his palace and as the central command post for his mercenary army, a vast force recruited from various non-Greek peoples of Sicily, Italy, and the Iberian peninsula. On his earlier visit to Syracuse in 367, Plato, at that point Greece’s most renowned thinker, had been received in that fort with enormous fanfare, an honoured guest whose presence brought lustre to a widely mistrusted regime. But as his relations with the tyrant soured, Plato had been forced to relocate to poorer quarters, landing eventually near the barracks of the barbarian troops – some of whom thought he was seeking, as part of his reform programme, to get them dismissed, and therefore wanted him dead.

‘Do you remember when you first arrived here’, Dionysius asks Plato (according to the letter’s account of that colloquy), referring to Plato’s visit six years earlier, ‘you advised me to resettle the Greek cities?’ Part of Plato’s programme for reforming the regime had indeed involved resettling Greeks in Sicilian cities that had, over preceding decades, been abandoned or relinquished to non-Greeks. Syracuse, in Plato’s eyes, stood on the western frontier of Hellenism, and on the success or failure of its regime rested the future of the Greek West.

Plato acknowledges his advocacy of resettlement, but turns the conversation in a different direction: ‘Was that my only advice to you, or did I say anything in addition?’ His point is clear to Dionysius, who replies with a derisive laugh: ‘You told me to get educated first and then do these things, or else not do them.’ The course of instruction Plato had offered had started with reform of the tyrant’s habits; his drinking, feasting, and sexual dalliances had badly diminished his status. But this foundational lesson had not taken hold. The power of the ‘Syracusan tables’ – the phrase was proverbial in this era for riotous living – had been too strong for Plato to overcome, even with Dion, the ruler’s sober-minded brother-in-law, seconding his advice.

‘You have an excellent memory’, Plato replies, content at having set the record straight. But Dionysius is determined to keep the upper hand. ‘You meant, I suppose, I should learn geometry – or what?’ The sarcastic remark casts scorn on Plato and his Academy, an institution that prized geometry as a way to train the mind in abstractions. Plato had indeed brought this training programme to Dionysius’ palace; the air there, according to Plutarch’s Life of Dion, became thick with dust as courtiers traced polygons in the sand. But that early enthusiasm soon wore off, and Plato’s recondite teachings, and his close alliance with Dion, aroused mistrust. A faction at court that regarded the pair as a threat had begun mocking Plato and traducing Dion, finally bringing about the latter’s banishment from Syracuse.

‘There was much I could have said’ in response to this sneer, ‘but I did not say it’, Plato confides to Dionysius in the Third Letter, explaining some months later why at the time he had fallen silent and ended the conversation. His permission to leave Syracuse, he knew, could have been revoked had he spoken his mind.

Relations between the estranged teacher and student continued to deteriorate even after Plato’s departure. The Third Letter makes clear that Dionysius began using Plato as a scapegoat in subsequent months, blaming him for his own regime’s failure to repopulate Sicily’s cities. In a perverse twist of Plato’s insistence that self-reform should precede any other initiatives, Dionysius made the case, when speaking to visiting ambassadors, that he had wanted to restore the cities but Plato had prevented him. This effort at spin nettled Plato, who wrote the Third Letter partly in order to rebut it.

In addition to correcting the record of the past, Plato also looks ahead in the Third Letter to coming events that, he sensed, would allow him to have the last laugh. As he must have known when he wrote the letter, the exiled Dion was planning an armed invasion to drive Dionysius from power and take control of Syracuse. The prospect that Dion, Plato’s devoted student, might oust Dionysius evidently gave Plato satisfaction. In a comment in the Third Letter, Plato hints at this prospect in vainglorious tones: ‘What you mocked then’ – at the time of their last colloquy – ‘has proved a reality instead of a dream’, he tells Dionysius. Dion would in fact soon oust his brother-in-law, briefly putting Plato in the right; but factional differences split Dion’s ranks, an assassin ended his life, and Syracuse descended into chaos.

The complex relations between Dionysius and Plato are explored in several of Plato’s letters, especially the voluminous Seventh Letter. But in the Third Letter’s account of their parting words, we see that relationship vividly dramatised. Plato’s efforts to teach a tyrant had clearly not borne fruit, and disasters lay ahead for Syracuse.

James Romm is the author of Plato and the Tyrant: The Fall of Greece’s Greatest Dynasty and the Making of a Philosophic Masterpiece (W.W. Norton, 2025).