I have heard it said that attempts have been made at staging productions of Plato’s dialogues, but that all have invariably flopped. I can’t vouch for the truth of that claim, but I can believe it. Intellectually, of course, Plato is gripping. And yet, as great a lover of Plato as I am, I fear that even I would fall asleep watching a dramatic reenactment of the Republic. Not enough “action,” in the conventional sense.

But did you know that there’s a ripping good yarn contained in the texts known as Plato’s “letters”? Therein, and especially in the longest and most famous Seventh Letter, Plato writes autobiographically of his political entanglements with Dionysius the Younger, the dissolute young tyrant of Syracuse. By accepting the invitation of his longtime friend and pupil, Dion of Syracuse, to realize the ideal of philosophic rule made famous in the Republic, Plato, by his own account, inadvertently precipitated the unravelling of the Syracusan regime, which finally plunged the city into a brutal civil war. In the pages of Plato’s letters, we find Plato the teacher, the counselor, the ally, the statesman; intrigue and faction in the court of a tyrant; grand political hopes dashed as famous utopian dreams become living nightmares—it is a stunningly dramatic and dynamic portrait of Plato and his philosophy.

And yet the experience of picking up and trying to read Plato’s letters tends to disorient the modern reader. For one thing, the political dynamics and major players of fourth-century BC Sicily are not very well remembered, which can make Plato’s narrative hard to follow. And to make matters worse, the authenticity and provenance of these letters have been the subject of fierce debate for centuries, which raises questions regarding their philosophic, historiographical, and biographical value. Thus, even though the skeleton of the story they contain is probably true, Plato’s letters suffer from an obscurity out of all proportion with their inherent interest.

The task of excavating the story of Plato’s political misadventures in Syracuse, of bringing it to life for a general audience of modern readers, is extremely complex. It requires extensive knowledge of classical Greek history, politics, culture, and philosophy, the ability to judge and to synthesize the accounts of varied and often conflicting historical sources, and, rarest of all, the discernment and literary talent to provide an education in the relevant background without sacrificing liveliness of storytelling. It is a great credit to James Romm that he was up to that task. In Plato and the Tyrant, Romm weaves together the threads of history, philology, philosophy, and archaeology with a deftness and erudition only a true classicist could possess. Historical details are illustrated by images of ancient Syracusan coins, vase paintings, and Sicilian ruins, the significance of Plato’s word choices are explicated by etymological lessons on the Greek roots of English words, complex scholarly arguments over fine points of historiography are distilled and clarified with admirable brevity, and all the while the reader is borne along on a journey of great historical and human interest. One senses from reading Romm’s work how lucky his students must count themselves for having found their way into his classroom.

In the long history of the study of Plato, there has never been widespread agreement about what Plato thought or how he meant to communicate it. It is inevitable that, as a scholar of Plato, I should have my disagreements with Professor Romm’s approach to the Platonic letters and what he does with them—especially since my most recent work culminated in a monograph on the subject, containing my own new English translation of the Letters and original interpretive essay. Romm will have no trouble finding supporters on those points where I will pick nits or bones; for the most part, he sides with the majority of scholars against my dissenting views. In particular, by assessing five of the thirteen letters in the collection as authentic works of Plato, dismissing one as spurious, and mostly leaving the others aside, he rejects effectively my heterodox contention that the Letters is actually a unified, semi-fictional work of Platonic philosophy, a one-sided epistolary novel in thirteen, artfully crafted and purposefully arranged parts. In a way, Romm recognizes the possibility of what I propose: he sees Letters Three, Four, Seven, and Eight as “open letters,” of which the salutation to one or more addressees is more literary device than real indication of Plato’s intended readers. But if that’s true, why couldn’t all the letters—indeed, the “Letters” as a whole—have been intended for broader dissemination? Had Romm given more weight, for instance, to the significance of Letter Two in the context of the whole Letters, he would have seen the importance of the claim there that “it is not possible for things written not to be exposed”: Plato writes nothing without anticipating that it will be published. In fact, the question of why Plato wrote as he did is a pervasive theme of the Letters—fitting for a text that, by its very form, emphasizes Plato’s role as author far more than anything else he wrote.

A first point I would make, then, is that we must be careful how we use the Letters. Romm mines the text for historical details of the story he wishes to tell, juxtaposing and triangulating with the versions given by later historians, biographers, and gossipmongers, to ascertain what “really happened” in Syracuse. But I would caution that even those Greek writers whom we now describe as “historians” were philosophers and teachers more intent on providing a profound education than on making a meticulous and comprehensive record of events. As for Plato’s activity in Syracuse, our primary source of information is Plato’s account in the Letters; details found in biographies written centuries later may, for all we know, have started as speculative rumors meant to fill gaps in Plato’s narrative. Just as the Peloponnesian War is not nearly so important an object of study in its own right as it is because a profound thinker, Thucydides, made it the canvas for his pedagogical masterpiece, the story of Plato in Syracuse, I would submit, should be of interest to us above all because Plato is its narrator.

But if Romm can interest a general audience in classics by bringing this Platonic drama to life—which I believe his book will and has—why rain on his parade by insisting that he has not adequately distinguished the forms and original purposes of his various classical sources? I would be less concerned about this if Romm had not taken on a weightier responsibility for his book than the recovery of a good story for the entertainment and edification of his readers. In his introduction, Romm recounts how the “spell” Plato had cast upon him as an undergraduate gradually lifted, how he had come to question Plato’s political philosophic wisdom, and how “the questions that first troubled [him] when the spell of Plato was broken” came to “trouble [him] even more when [he] came to the letters.” He articulates the possibility that Plato, the great moralist, wound up “collaborating with evil” in Syracuse, and that the Republic is meant to “obscure” his hypocrisy. He reports the famous judgment of Karl Popper that Plato’s Republic belongs to “the perennial attack on freedom and reason.” And he concludes his introduction by saying that his book will show us how “the wise can become more tyrannical by the company of tyrants.”

Romm thus suggests that Plato’s Syracusan story helps us to see a grave problem with Platonic philosophy, that we should not so much seek wisdom and understanding from the education Plato’s works provide as we should seek to learn an object lesson from them. We must not dodge this question. To put the matter bluntly, Plato’s political philosophy long predates, and so stands outside of, the liberal tradition upon which our civilization rests. If we have something of value to learn from Plato in our political moment, it will be no defense of liberalism per se—it will, in fact, appeal to pre-liberal and perhaps illiberal moral and political principles. This is not to say that Plato will counsel a break from liberalism. I, for one, see Platonic political philosophy pointing us to the preservation of liberal democracy through a reinvigoration of its noblest principles, guided by the Platonic virtue of moderation. Such a case can indeed be made on the basis of the Letters, where Plato repeatedly makes it clear—in letters of which Romm makes use as well as in some he doesn’t—that he never condoned the wholesale substitution of one form of regime for another, especially by violent revolution. In this, Romm sees a reflection of Plato’s Sparta-philia, a longing for permanence and stability in a Greek world plagued by war, stasis, and moral decay. He thus reduces Plato’s philosophic insight to his biographical circumstances. I believe that we do this to Plato at our own intellectual and cultural peril.

I don’t have the space here to remedy the excessive vagueness of the foregoing claims and critiques regarding Plato’s contemporary relevance. I will instead limit myself to describing one substantive disagreement I have with Professor Romm’s reading of Plato’s Letters, indicating how our evaluation of Plato might hang on such a point.

As messy and multipolar as the struggle for Syracuse became (elegantly clarified by Romm), Plato presents it as a battle between two factions: the tyrannical party of Dionysius and the anti-tyrannical party of Plato’s devoted acolyte, Dion. Throughout the Letters, Plato presents himself as having fundamentally, if moderately and contingently, supported Dion’s side in that conflict. Given the terms of Dion’s initial invitation to Plato, Romm naturally assumes that Plato hoped Dion might rule Syracuse as a philosopher king. This involves what I see as a critical error. Even though Dion himself is keen on the idea of bringing philosophic rule to Syracuse, Plato only ever represents him as having wished for Dionysius to be educated in philosophy for that purpose. It is surprising but undeniable upon reflection that Dion is never, in any of the Platonic letters, spoken of as having taken an interest in philosophic study himself. (Letter Ten shows how willing Plato was to endorse a view of philosophy among Dion’s circle that rested on a misapprehension of what the activity of philosophy is really like. Likewise, a careful study of Letter Eight shows that Plato and Dion do not have the same counsel for the Syracusans: Dion’s overly hopeful proposals must be compared with Plato’s much more practical, down-to-earth advice in Letter Seven.)

The Letters is about how Plato sought to present philosophy to the world, with the Republic as the centerpiece of his presentation. But even the Republic allows us to see that this presentation is steeped in paradox. Romm puzzles over the question of why Plato thinks the philosopher would return to politics, to “the cave,” after he has beheld the true world of the eternal “forms.” He fails to take note of the fact that, according to Plato’s Socrates, the philosophers have neither any obligation nor any desire to do so except in the ideal city he and his interlocutors have built in speech (cf. Letter Six). Only in that ideal city will the philosophers be compelled to administer the city as a just repayment for the regime’s cultivation of their philosophic natures. All this lends itself to the view that Plato did not really believe in the possibility of philosophic rule as presented in the Republic, which means that Plato and Dion were on drastically different pages. The distance that has grown between Plato and Dion by the time the latter is waging a war for Syracuse, which is made evident in Letter Four, is the fruit of Dion’s failure to grasp the meaning of Platonic philosophy.

In my book on the Letters, I share my own speculation as to why, if not to create philosophic rule, Plato went to Syracuse at all. In brief, I believe Plato’s literary project of defending philosophy in the wake of Socrates’s death achieved a kind of political success beyond even his own expectations, and that Dion’s zeal for philosophic rule put Plato in a bind. His decision to accept Dion’s invitation, as he makes clear in Letter Seven, had more to do with what the fallout would be for the reputation of Platonic philosophy if he should turn his back on this enthusiastic follower and benefactor than with anything he hoped to achieve politically in Syracuse. To be sure, that interpretation is itself up for debate. What is important for my purpose here is simply to emphasize that, unless we read the Letters closely as a work of Platonic political philosophy, we are prone to misunderstanding Plato’s intention and misjudging his character.

It must be said that Romm never really settles the question of whether the study of the Platonic letters issues in acquittal or condemnation of Plato. He comes back to it now and again—especially in his ninth chapter—indicating where a certain construal of the evidence might point to a harsher assessment of Plato’s thought and action than has been typical. But he tends to leave things at the level of suggestive “maybes” more than he draws conclusions or lays out a case of his own. If anything, the book ends with the suggestion that Plato stood above all for a government in which good rulers are constrained by good laws—a view with which I agree, and which I am glad Professor Romm has expressed. Yet I remain uncertain whether he has handled the matter in the most conscientious and responsible way. In his attempt to present the most entertaining and intriguing version of this tale, Romm often seems to seek out and present the theories that will most excite his audience. The possibility that Plato and Dion were lovers, which adds little to the substance of the story but to which Romm devotes considerable space, is probably the best example, but many other rumors and legends from sources of greatly varying reliability are sprinkled freely throughout the book. When Romm includes a vignette of lust, jealousy, and murder preserved by “Parthenius, a collector of salacious stories,” admitting that it is “impossible to confirm but too good not to tell,” he seems to describe what led him to include a great many of the episodes recounted in Plato and the Tyrant. Is it for this same reason that he has chosen to highlight the ways in which the story of Plato in Syracuse might be seen as evidence of Plato’s moral weakness or worse? Much as I am reluctant to make that accusation, I do wish Professor Romm had given more sustained and serious attention to the very serious question he chose to raise.

Updated, June 6^th, 2025: The original version of this review, posted on June 5^th, 2025, claimed that Dr. Romm accepts “five of the thirteen letters in the collection as authentic works of Plato and dismiss[es] the remainder as spurious.” That was erroneous. Only Letter One is dismissed by Romm as an “obvious fake”; otherwise, where he touches on the letters aside from the five he explicitly accepts as Platonic, Romm generally expresses openness to their possible authenticity.