Plato and the Tyrant by James Romm

Plato and the Tyrant:

The Fall of Greece’s Greatest Dynasty and the Making of a Philosophic Masterpiece

By James Romm

WW Norton 2025

For about twenty years in the 4th century BC, the Athenian philosopher Plato visited the royal court of Syracuse, mainly as intellectual ornament to the tyrant Dionysius II and mentor-guest to the tyrant’s uncle Dion. Dionysius II was a vain, stupid, incompetent despot, hated by his sycophants and distrusted by his own armed forces, and for most of the time that Plato was shuttling back and forth to his court of toadies, Plato was working on Republic, his famous treatise on rulership. As James Romm writes in his completely captivating new book Plato and the Tyrant, Plato “believed that an enlightened strongman, unconstrained by law or limits on power, could solve the world’s ills, which he otherwise deemed insoluble.”

Plato believed this despite the fact that it had never once been even remotely true in any of the history with which he was familiar, never once true the years of his own life, never once true in any of the history he didn’t know, and has never once been true in the two thousand years since Plato blathered himself into his grave. The dramatic tension of Plato’s interactions with Dionysius II is parallel to that of Plato’s disciple Aristotle’s interactions with Alexander the Great: can the airy discussion-topic principles of the Academy be applied to the real world? Can a good and just ruler be shaped by a philosopher out of the otherwise-unpromising clay of human nature?

That the answer is so crushingly, obviously “no” (this, too, has never once happened in human history) must have been clear to Plato, which has always given an extra charge to the question of what exactly was going on during those long stays in Syracuse?

Romm asks these kinds of questions at the start of his book:

Did Plato while extolling the Good as the source of transcendent joy, end up collaborating with evil? Had he sought benevolent ends by using unsavory means? How far had he bent the noble ideals of Republic – its unwavering commitment to justice – when he entered a world where injustice prevailed? Was it thinkable – the most troubling question of all – that he’d written Republic in part to explain his missteps in Syracuse, or to obscure them?

When it comes to ancient sources, the answers to these kinds of questions will come from in some parts from Plutarch and in some other parts from Diodorus Siculus but mostly from Plato himself, in the highly-contested body of his thirteen letters, most of which have been declared forgeries but two of which, the very long Seventh and the very personal Thirteenth, which breaks what Romm refers to as the “spell” of Plato “by showing Plato dealing with mundane matters – money he’s owed or needs to borrow, expenses he needs to meet – and working hand in glove with a notorious tyrant.”

This tone, knowledgeable but not servile, free of the “spell,” permeates Romm’s book, which is mercifully less about dissecting every nonexistent nuance of Republic and much more about reconstructing the extent and nature of Plato’s worldly hypocrisy. “In Syracuse Plato had made moral compromises, committed errors of judgment, and gotten into jams he nearly couldn’t get out of,” Romm writes, referring to the eye-opening experience he had when he first read the letters attributed to the philosopher. “He’d behaved like a real, and flawed, human being, not like the marmoreal figure I’d imagined up to that point.”

The Plato found in these pages, wonderfully evoked by Romm’s tense, insightful prose and massively substantiated by an extensive bibliography, is the very opposite of marmoreal in every way. In a world where a four billion dollar podcast-bro ecosystem worships the marmoreal on a daily, hourly basis, that alone makes the book extremely welcome.

 Steve Donoghue is a founding editor of Open Letters Monthly. His book criticism has appeared in The Washington Post, The American Conservative, The Spectator, The Wall Street Journal, The National, and the Daily Star. He has written regularly for The Boston Globe, the Vineyard Gazette, and the Christian Science Monitor and is the Books editor of Georgia’s Big Canoe News