PART ONE

Political Counsel in Plato’s Letters

It is natural for avid readers of Plato’s dialogues to approach the Letters with the following keen anticipation. Whereas in the dialogues Plato writes only in the voices of his characters and never in his own, we will now be hearing, for the first time, Plato speaking for himself. And since Letter Seven is famous for sections such as the Platonic autobiography and the philosophic digression, we seem to have here the promise of revelatory candor on the part of the great philosopher on a wide variety of interesting subjects. Yet a first reading of the Letters is apt to leave us with a sense of disappointment, as if some part of what we had hoped to find was strangely absent.

The missing element comes into focus when we consider the Letters’ strange treatment of Socrates. For Plato has given us his Socrates as the hero of the Platonic dialogues, as the peak of human virtue, and as setting the standard to which human intellect and character must be held. As students of those dialogues, we naturally come to the Letters hoping to see that when Plato at last emerges from behind the scenes, he is revealed to be the preeminent student of Socrates, who came to share his teacher’s peak virtues by doggedly following the course of Socratic education to its ultimate conclusion. What we find, however, is that the Letters not only highlights Plato’s catastrophic and all-too-human failure to serve the cause of philosophy in Sicily, but moreover that the great figure of Socrates is stunningly absent from the text (or nearly so). Plato appears to be no Socrates, and Socrates all but disappears. We are inclined to explain this by Plato’s famous claim in Letter Two that the writings attributed to him are not truly his, but are rather “of a Socrates become beautiful and new (kalou kai neou)” (314c1–4). By this, we are given to understand that the historical Socrates was less impressive, less dazzling than the Platonic reimagining of him as the star of the dialogues. Accordingly, it is only with puzzling brevity, in Letter Seven, that Plato ever mentions the role Socrates played in the story of his life, and there Plato speaks only of “a man who was my friend, the elderly Socrates” (324d8–e1)—in notable contrast to the description of the “new” or “young” (neos) Socrates of the dialogues. Moreover, while Plato lauds the “elderly” Socrates’s justice and piety, he makes no mention of his wisdom, or his philosophy, or his philosophic teaching. And this is to say nothing of the bizarrely banal passage in Letter Eleven, where it is said that Socrates (who in fact must be long dead) cannot travel to help in the founding of a colony because he is ill with strangury, a painful urinary infection (358d3–e1).

Thinking about Plato’s strange treatment of Socrates in the Letters thus helps us to clarify the sense that something important is disappointingly absent from the text. For we might well have hoped, in turning to the Letters, to gain assurance from Plato that the power of Socratic wisdom is as uncannily effective in guiding political action as it is in guiding the Platonic Socrates to dialectical victory in his refutations. Instead, the distance Plato puts between himself and his Socrates in the Letters provokes us to wonder whether Plato has misled us in the dialogues by giving to his Socrates an aura of infallibility, by exaggerating the power and sufficiency of Socratic philosophy to guide one’s life aright. If not by the light of Socratic wisdom, how did Plato think it best to approach and to manage practical and political affairs? Now, as our exploration of the text will reveal, the unifying theme of the Letters is the way in which Plato’s fame as a political philosopher brought with it some responsibility, and many opportunities, to provide political counsel to famous and powerful men across the Greek world of his day. Whatever disappointment the Letters may leave us with as regards Plato’s relation to Socrates and to Socratic education, we must welcome the prospect of learning how Plato brought his own wisdom to bear on actual political affairs. Let us begin, then, by asking: What kind of advice was Plato wont to give in his capacity as a political adviser?

Especially if we allow Letter Seven to loom over the Letters as we are led to do by its stature, one answer stands out as our clear starting point: Plato counsels the institution of philosophic rule, the capstone of the utopian regime made famous from his Republic. This is a highly consequential suggestion for our understanding of Platonic political philosophy. It implies that Plato wrote his Republic not merely as a thought experiment, nor as a defense of philosophy against its violent opponents, but as a vehicle for the promotion of his genuine political vision, for which he strove in his own lifetime, that philosophers might somewhere come to power as political rulers. By no means will this be our last word on what the Letters reveals about Plato’s promotion of philosophic rule. But before we can assess the suggestion that he seriously wished to establish such a regime, we must examine the manner in which this suggestion comes to light from a reading of Letter Seven, and especially of that letter’s first major section.

The Origin of the Idea of Philosophic Rule and the Intention of Dion

Letter Seven is addressed “to the intimates and comrades of Dion” in Syracuse; it belongs to the time following Dion’s assassination, and it is Plato’s response to a request from Dion’s posthumous supporters. The Dionean party in Syracuse is now mired in a bloody civil war without the vision and guidance of its illustrious leader, and its representatives have apparently appealed to Plato to provide help for their cause, “in deed and in speech” (324a1). The sense of this appeal is indicated by the fact that, in Plato’s restatement of their request, they have insisted that they are carrying on with the same “intention” (dianoian) that had animated Dion. Plato shows that he understands the significance of this claim: he strongly asserts that he knows precisely what Dion’s “intention and desire” had been, since it had been during the time of their first meeting—when Plato, at forty, first visited Syracuse and met a twenty-year-old Dion—that Dion “took hold” of the “opinion” that he “continued holding to the end.” It is only if Dion’s intimates and comrades prove to share Dion’s “opinion and desire,” says Plato, that he will grant their request for his partnership. Plato, for whom opinion or thought is primary, here acknowledges that Dion’s guiding opinion was formed as a result of his association with Plato. This, then, is the thrust of Dion’s followers’ request for help: it was Plato who inspired Dion with the dream he was pursuing; is it not incumbent on him, then, now that Dion lies dead, to help Dion’s supporters bring this dream to fulfillment?

The foundational and lifelong opinion Plato says Dion acquired during their first meeting was “that the Syracusans should be free, dwelling under the best laws” (324b1–2). It was a patriotic opinion, in the sense that it expressed Dion’s wish for the greatest well-being of his fatherland. Dion then apparently learned from Plato that civic well-being, or what makes life good for the citizens of a regime, consists of these two related components: freedom and good laws. That is, Dion learned to hold a certain high-minded political opinion, which we find expressed frequently in the history of political philosophy—namely, that genuine liberty is not equivalent to mere license or freedom from constraint. This view holds that human beings, in the absence of proper legal and customary constraints, naturally pursue ease and pleasure, shirk labor or responsibility, and, as a result, slump into a life devoid of the higher fulfillment available only to those who have cultivated good moral habits (see 334d5–335c2). Such a dissolute life could hardly be called “free,” since no one with a clear view of it would freely choose it; rather, those mired in it lack the moral and intellectual means to escape, and even the awareness needed to wish to escape (see 326b5–d6). Paradoxically, then, genuine liberty is achieved only through a specific kind of restraint imposed, in the best case, by law. The restraint cultivated by wise laws teaches the citizen by inculcating habits of serious devotion to one’s community, and thus prepares the citizen for profound fulfillment through just and virtuous activity (see 354d1–355c7).

The whole opening of Letter Seven, then, gives the strong impression that Plato and Dion shared this view of freedom or liberty, the view Plato has insisted Dion’s comrades must also hold as the condition of his coming to their aid. That impression is strengthened by a puzzling feature of the letter’s structure, which comes to sight in the following way. In this same opening section, Plato says it would be “in no way amazing if some one of the gods should” instill this same opinion of Dion’s in the mind of Dion’s successor, Hipparinus, who is now just at the same age Dion was when he met Plato. Thus we learn that Dion’s patriotic opinion, in Plato’s view, shares some kinship with those opinions reported by human beings as the content of divine revelation. It is of interest, then, that Plato next proposes to recount “the way of [Dion’s opinion’s] coming to be”—and yet what actually follows is a brief and famous section of Platonic auto biography, culminating in Plato’s development of the doctrine of philosophic rule. We learn that it was in the wake of that development that Plato first met Dion, and so we are given to understand that Dion’s patriotic opinion is somehow a reflection of his belief, learned from Plato, that the best regime would be the regime governed by philosophers. That is, Dion’s political career is presented as having been continuous with Plato’s own political philosophic project.

We gain greater clarity on the relationship between Plato’s political philosophy and Dion’s political agenda through observation of a few details from the famous autobiographical section itself. That section of Letter Seven begins, “When I was young, I underwent the same thing as many do: I supposed that, as soon as I should become my own master, I would engage straightaway in the common affairs of the city” (324b8–c1). What follows is the explanation of what came to dampen, even to extinguish, that youthful enthusiasm. This explanation features the only discussion in the Letters of Plato’s friendship with Socrates; but despite the fact that the transformation Plato describes culminates in his “praise of philosophy” in the form of the doctrine of philosophic rule, Plato nowhere describes Socrates as a teacher, either of Plato or of anyone else—or, for that matter, as a philosopher (cf. 325c1–2 with Apology of Socrates 24b6–c1). Instead, Plato’s account of his turn away from politics prominently features two famous instances of Socrates’s persecution by the Athenian regime. The first is the story of the Thirty Tyrants attempting to force Socrates “to carry off one of the citizens [Leon of Salamis] by force to be put to death, in order that [Socrates] should participate in their affairs whether he should wish to or not” (324e1–325a2; cf. Apology of Socrates 32c3–e1). The second is the trial and execution of Socrates, which was perpetrated by the restored Athenian democracy—to which, as Plato casts it, Socrates had been loyal in refusing to arrest the democrat Leon of Salamis.

It was in examining these things, as well as “the human beings who were doing the political things, and also the laws and customs,” that Plato became altogether disillusioned with the possibility of achieving anything in politics. In brief, Plato came to see that the corrupt condition of real cities, of their laws and customs, made them so profoundly resistant to genuine improvement that they were all but “incurable.” Only “friends and faithful comrades,” of a quality not easily to be found, working together in concert and employing “some amazing artifice,” could ever have any hope of success—and even then, the realization of their hope would be dependent on “fortune” (325c5–326a5). But this despair regarding political action did not stop Plato from continuing to examine (skopein) questions of better and worse with respect to laws and customs, “and moreover concerning the whole regime.” And now, at last, the theme of philosophy is introduced into Letter Seven:

And I was compelled to say, praising correct philosophy, that on the basis of this it is possible to see distinctly both the just political things and all in private matters; therefore the human tribes will not cease from evils until either the tribe of those philosophizing (correctly and truly, that is) should come into the positions of political rule, or that of those who are in power in the cities should, by some divine fate, really philosophize. (326a5–b4)

Thus do we have it that Plato’s story, not only of his abandonment of his own political aspirations, but of his abandonment of any hope of political efficacy anywhere, culminates with his praise of philosophy by way of his famous doctrine of philosophic rule. That is, this story proves to be the story of how Plato came to conceive of the crucial political-philosophic idea around which his Republic revolves.

Having articulated this “praise of philosophy,” Plato ambiguously says that it was with “this intention” in mind that he sailed over to Sicily for the first time. Plato devotes his account of the first portion of his arrival (before he entered Syracuse) to an impassioned denouncement of the hedonism he encountered among the Sicilian Greeks. No one raised among such customs, Plato insists, could ever become prudent, moderate, or virtuous in any way; nor could any city steeped in such customs ever be at peace “under any laws whatsoever,” but would instead cycle endlessly between tyranny, oligarchy, and democracy, as its rulers “won’t put up with hearing the name of a regime of justice and equality under the law” (isonomou; 326b6–d6). And it was in turn with all this in mind, in addition to the intention with which he began, that Plato says he entered Syracuse and met, for the first time, a young Dion, to whom he “reveal[ed] . . . through speeches the things that seemed to [Plato] to be best for human beings and counsel[ed] him to do them” (327a2–4). We can easily imagine how these revelations would have reflected Plato’s disapproval of the way of life of the Sicilian Greeks and how this critique would have led naturally to the patriotic opinion of which Dion then took hold. It is constraint by good and wise laws—precisely what is absent in the permissive culture of the Siceliotes—that inculcates the daily habits conducive to virtue, excellence, and happiness. Hence, Dion came to see the libertinism of his own culture as inimical to true liberty and came to long for a life of justice and virtue as a devoted member of a just and virtuous community.

Plato recounts that Dion thereafter wished “to live the rest of his life in a manner differing from the many Italiotes and Siceliotes, having come to cherish virtue more than pleasure and the rest of luxury; from which point he led his life until the event of Dionysius [the Elder’s] death in a manner that was rather aggravating to those living according to what is lawful convention in a tyranny” (327b1–6). Zealously devoted to Plato’s lofty political philosophy, holding the decadent lifestyle of his contemporaries in contempt, and sententiously insisting on his own (that is, Platonic) high moral principles, Dion understandably became unpopular and tiresome to the pleasure-loving Syracusan courtiers. This was the effect of Platonic philosophy, as taught by Plato himself—specifically, as we are invited to surmise, of the teaching of the Republic regarding philosophy’s power to resolve humanity’s deepest political problems—on a “good learner” who “hearkened keenly and intently such as none of the young [Plato had] ever met” (327a6–b1). Indeed, as Plato stresses, this was not the only effect, for Dion’s Platonic education turned out much later to be the cause of Dion’s deposing of Dionysius, and hence of the whole ongoing tragedy of the Syracusan civil war.

That Dion had learned from Plato to long for a regime of philosophic rule is evident from the terms in which he solicited Plato’s return upon the death of Dionysius the Elder. He sought Plato’s help in bringing the newly crowned Dionysius the Younger to the same “desire for the noblest and best life” to which Dion himself had been brought by Plato, in “great hopes of establishing, without slaughters, deaths, and the evils that have now come to be, a happy and true life throughout the whole land.” He considered the opportunity at hand to be the gift of “some divine fortune,” and told Plato that, “now if ever, there was every hope of bringing to completion the outcome that philosophers and rulers of great cities would be the same” (327d1–328b1). It is unambiguous that Dion, at least, had philosophic rule over Syracuse in mind as a serious possibility. Did Plato? He did, after all, accept Dion’s invitation. And the connection he has drawn in this letter between his claim about philosophic rule and his second venture to Sicily is plain to see. Moreover, when Plato recounts his inner deliberations about whether or not to accept Dion’s invitation, he reports resolving that, “if ever someone was going to undertake to bring these intentions concerning both laws and regime [or Laws and Regime] to completion, it must be attempted also now; for if I should sufficiently persuade just one, I would be achieving all good things,” and hence explains, “I set out from home . . . ashamed of myself in the highest degree lest I should ever seem to myself to be altogether, solely, and artlessly a certain speech, voluntarily taking hold of not one deed ever” (328b8–c7).

Whatever its purpose, there is no denying that the whole undertaking in Syracuse appears to have been a debacle. It would reflect poorly on Plato’s prudence, political wisdom, and foresight if his earnest hope in going was to bring the rule of philosophy, and with it the “cessation of evils” for humanity, at last into existence. But in fairness to Plato, there is ample evidence that he despaired from the start of any real success. Indeed, the statements just quoted in which Plato appears to indicate his intention to try for the rule of philosophy in Syracuse are directly interwoven with indications of other, less fanciful concerns and goals. Consideration of these other concerns will lead us toward a more grounded view of Plato’s political activity and ultimately to the concrete Platonic political counsel we are seeking. But in order to appreciate Plato’s articulations of these latter concerns in their context, we must first come to see why they sit directly alongside the other, misleading indications we have been reviewing. Specifically, we must gain some appreciation of why Plato allows himself to seem so similar to Dion in his opinion, desire, and intention throughout Letter Seven. For Dion, as we have seen, was keen to try for philosophic rule in Syracuse; the key to recognizing that Plato was not is to come to see the difference between the two men.

For this it becomes important to consider the literary character of the Letters. Plato speaks to us only indirectly in this work. Just as, in his dialogues, Plato allows us to observe his Socrates in a variety of specific circumstances, which give crucial context to whatever Socrates says, so in each letter we must consider the person or people to whom Plato addresses himself, and the circumstances that have called for his writing (see 363b4–5). It is not a coincidence that the only overt references to the doctrine of philosopher-kingship in the whole Letters occur in Letter Seven. The circumstances of this letter require that Plato eulogize Dion. He is writing to Dion’s “intimates and comrades” to discuss the legacy of their late, beloved leader, who has given his life, nobly, for his patriotic political dream (see 334d6–335c1, 351c6–e2; cf. 321b5–c1). If Plato had an unfavorable view of Dion or of his understanding of Platonic philosophy, he could hardly spotlight it in this letter.

As has been clear to many readers, however, Letter Seven has purposes beyond its officially stated one, just as it is addressed to audiences beyond the one identified in its opening salutation (cf. 323d7, 324b5–6, 330c3–8, 334c3–4, 338a2, 341e1–342a1, 344d3–4). Plato, we may surmise, thought of us, too, as prospective readers. What is more, if Letter Seven was never really intended as a letter to be sent to Dion’s friends and associates, if Plato wrote it as the centerpiece of this political philosophic book, then we are, in a sense, its primary intended readers. Yet we are to understand that Plato’s didactic method here is to let us see how he would have had to speak and write to the heirs of Dion’s political legacy. And because this letter is effectively an “open letter,” in that it is addressed indiscriminately to a somewhat ill-defined group of people, it is in fact in this letter above all that Plato demonstrates for us how he wrote to a broad audience in general. Viewing the letter in this light, then, we might even go so far as to interpret Plato’s choice of addressees for Letter Seven as indicating that whenever Plato wrote for broad publication and general consumption (see 314c1), he kept in mind the effect his writing would have on those whose impression of Platonic philosophy was akin to the one held and reproduced by Dion—on those “akin” to Dion (tois oikeiois; cf. 313c7–d3). But since, as we have said, these are not Plato’s only readers, he has found ways to indicate his true judgment of Dion in the same writings.

We must, therefore, examine the Letters with some care in order to grasp the crucial difference between Plato and Dion, so that we can better distinguish Plato’s motivation for going to Syracuse from Dion’s motivation for inviting him. We can begin to illuminate this difference by further considering what we have dubbed Dion’s “patriotic opinion,” which Plato said was the lifelong, abiding opinion by which Dion’s political aspirations were guided, and which Plato suggests Dion learned directly from him. The opinion, to restate it, was “that the Syracusans should be free, dwelling under the best laws,” and it reflected the noble equation of freedom and the yoke of law. Now, while Plato’s explicit articulation of this opinion occurs in the opening of Letter Seven, the same opinion is implicitly at the heart of Letter Eight, the companion to Seven. It is therefore worthwhile at this point to turn to a fuller examination of Letter Eight.

The Relationship of Freedom to Law in Letter Eight

Like Letter Seven, Letter Eight is addressed “to the intimates and comrades of Dion,” and purports to answer their request for Plato’s help. Unlike in Letter Seven, however, Plato here gets immediately to the matter at hand: after his characteristic salutation, “Do well!” he expresses his intention to “go through . . . as much as is in [his] power” what intentions the Syracusans should adopt in order “most of all really [to] ‘do well’” (352b4–5). The brevity of Letter Eight as compared with Letter Seven is further proof that Letter Seven has people and purposes in mind beyond Plato’s response to the request for help from Dion’s followers, since it is plain from Letter Eight that Plato is capable of responding to that request without anything so elaborate and complex as Letter Seven. Letter Eight, then, would appear to be the place in the Letters where Plato most directly provides what we are now seeking: his practical political counsel to real people in a real situation. And our expectation or hope for what this counsel will contain is only heightened by the fact that Plato indicates his intention to clarify the meaning of his characteristic salutation. For one might well think that to know what is required for one “really to do well” is to know the human good.

It turns out, however, that Letter Eight does not so clearly contain the practically useful advice it appears to promise. For Plato admits that the difficulty of fulfilling this promise, of providing genuinely good and usable counsel to one faction embroiled in a civil war, is nearly insurmountable. The difficulty is that it is not enough to counsel what seems “to the many” to be necessary, namely, whatever will produce “as many evils as possible for their adversaries in war and as many goods as possible for their friends,” because “it is in no way easy for one doing many evils to others not also to suffer many further evils himself” (352c8–d5). What is needed, then, is counsel that points to what is “either advantageous for all, both enemies and friends, or as little evil as possible for both” (352e3–4). But how likely is such a thing to be possible in the context of a civil war? Circumstances must dictate to a considerable extent how far it is possible for a given person genuinely to prosper or to “do well.” The more one is in a position to abstain from harming others, to avoid having enemies, the fewer the obstacles (consider Republic 335b2–336a8; Xenophon, Memorabilia 4.4.10–12). But in the case of Dion’s followers in Syracuse, real prosperity is almost certainly out of reach; Plato’s proposal in Letter Eight to counsel what is really advantageous for the Sicilians amounts to a promise to advise a course of action that will be almost impossible to follow. As Plato himself says in concluding his introductory remarks, “Such counsel and undertaking of speech resembles a prayer. Let it be altogether, then, a certain prayer—for one ought always to speak and think, in all things, beginning from the gods” (352e5–353a2). The plan Plato will here propose will depend on divine help for which one can only pray.

There is another important clue to the character of this “prayer,” which we discover in considering the structure of Letter Eight. About halfway through the letter, Plato makes a significant change. Saying that what he has so far laid out has been “natural,” Plato bids “the friends of Dion to explain” it “to all Syracusans,” calling it the “common counsel” of himself and Dion. That foregoing counsel is thus set apart from what is to follow, which Plato introduces by announcing that he will now “interpret” what Dion would say himself “if he were [still] breathing and capable of speaking” (355a1–7). This switch in authorship of the counsel is the primary reason for our present examination of Letter Eight: Letter Eight provides a rare opportunity to compare and contrast Plato’s and Dion’s ideas of sound political counsel. To be sure, we do not have here quite so direct a comparison and contrast as we might wish, since we are not contrasting the counsel that Plato says Dion would give by himself to the counsel that Plato says he would give by himself, but rather to their “common counsel”—a phrase that seems to indicate that the first half of the letter represents counsel that is given by Plato and Dion in partnership. It is perhaps best to imagine this joint counsel as exemplifying that strain of Platonic exhortation and counsel that most of all charmed and captivated Dion and animated his political activity. The very fact that this joint counsel is acknowledged to be a prayer, however, shows Plato qualifying the practicality of the joint counsel—by contrast, Plato’s qualifying influence is notably absent from the second half of the letter. To oversimplify slightly, we can say that the first half of the letter gives us the nuanced view Plato presented to Dion, winning his endorsement, while the second half shows the partial and therefore distorted version of that view Dion himself took away from Plato’s presentation and proceeded himself to proselytize. Consider, for instance, that the “common counsel,” which more fully reflects Plato’s own thought, begins with the imperative “think” (noēsate), as he bids his readers to think about what he might mean (352c4). Plato even says, toward the end of this section of his counsel, that he will “converse” as an “arbiter” with each of the two parties, namely, “those who tyrannized and those who were tyrannized,” as though each party were a single individual (354a3–5). Plato thus effectively acknowledges that the counsel he is providing is better suited to dialogue with one or two interlocutors than to the persuasion of a multitude. By contrast, Dion’s counsel is presented as an oratorical address to the Syracusans, and, in parallel to Plato’s imperative “think,” begins with the direction to “accept” (dexasthe) such laws as he prescribes for them (355a8).

Letter Eight is therefore immensely valuable to our understanding of the relation in which Dion stands to his teacher, and we will have more than one occasion to revisit it for that reason. Lest the present digression lose track of its purpose, however, we will focus now only on the element of this letter that illuminates the difference between Plato and Dion regarding Dion’s patriotic opinion, and specifically regarding his understanding of freedom. In the latter half of the letter, wherein Plato “interprets” Dion’s would-be advice to the Syracusans, Dion insists above all that the city’s inhabitants must accept laws that “make the virtue of the soul most honored” (355b3–4). Those living properly under such laws, says Dion, will achieve their full and completed potential as “really happy” human beings (355c2). This will amount, it seems, to “freedom under kingly rule” for the subjects and “accountable” “kingly rule” for the rulers, “with laws as masters both of the other citizens and of the kings themselves in case they should do anything illegal” (355d8–e3). That is, Plato here has Dion affirm the view that the citizens’ life of subjection to genuinely good laws is a life of happiness and freedom—even if Dion is somewhat loose in his application of the word “freedom”: he also speaks of himself, his father, and the young Hipparinus, each in his time, as having “freed” the Syracusans from the oppression of barbarians or tyrants, though without having established the rule of law he continues to extol (355e6–356a7, 357a7–b1). All of this must be compared to Plato’s usage when speaking, not for Dion, but in his own name (or that of his and Dion’s “common counsel”). Plato appears willing to agree that the deposition or circumvention of a tyrannical power amounts to an act of liberation or “freeing” (see 333b4, 334a2, 336a3, 7; cf. 329b4). But neither here in Letter Eight nor anywhere else in the Letters does Plato himself ever assert that lawfulness is equivalent to, or even compatible with, freedom. Precisely to the contrary, Plato is consistent—in both Letters Seven and Eight—in characterizing the subjection to law needed by the Syracusans as a form of slavery (334c6–7, 337a2–8, 354c3–6). Plato’s Dion comes closest to this, as we have seen, when he speaks of “laws as masters both of the other citizens and of the kings” (emphasis added), but this comes in the same breath as his speaking of “freedom under kingly rule.” Nowhere does Dion speak so frankly as Plato does of enslavement to laws and even to “kingly laws.”

In fact, at the center of Letter Eight, just before Plato transitions from his and Dion’s “common counsel” to his interpretation of Dion’s own counsel, Plato directly addresses the opposition of slavery and freedom in one of the richest and most intriguing formulations in the Letters. First, he criticizes the bygone Syracusans who lived in the democracy preceding the rule of Dionysius the Elder. Plato says that they suffered from a “disease” “because of the excessive anarchy, making use of an unmeasured passionate love (erōti) of freedom”; the Syracusans of his own day, says Plato, must beware of this disease, lest they contract it “out of insatiability for a certain unpropitious freedom” (354d2–5). For it was in the throes of that love of freedom that the Syracusan democrats illegally executed their ruling generals, “in order that they should in no way be enslaved with either justice or law as a master, but be altogether free in every way; hence did the tyrannies over them come to be” (354d8–e3). Passionate or “erotic” love of freedom, which makes slavery to “justice or law” seem as repugnant as slavery to a tyrant, is disastrous and must be warded off like a disease—needless to say, the Letters nowhere indicates that Dion ever acknowledged such a limitation on the goodness of freedom. (Where Dion speaks of eros in this letter, it is in reference to the tyrannical party’s passionate desire to rule [355d5].)

It is here that Plato makes his rich and cryptic pronouncement “For slavery and freedom are each, if excessive, altogether bad, but if [each] is in measure, altogether good; and slavery to a god is measured, to human beings unmeasured; and law is a god to moderate human beings, pleasure [a god] to the imprudent” (354e–355a). Imagining again that this proclamation belongs to the presentation of his political philosophy by which Plato won Dion over, we can easily understand how Dion would have heard it, or rather misheard it. That is, one can briefly articulate the superficial and edifying gist of the statement, without attending to its nuanced complexity, as follows. To mistake the unobstructed and unmitigated pursuit of pleasure for true freedom is imprudent and altogether bad; it is no better in fact than slavery. What is genuinely good for human beings requires moderation, which in turn points to faithful obedience to the law. To the truly wise, happiness, the good, all human fulfillment, are seen clearly to lie along the path of moderation, piety, and lawfulness. But this path can only be open in a regime of laws: tyranny must be replaced with something like kingship so that slavery to human beings can be replaced by fulfillment, and true freedom, through obedient lawfulness.

But a close and unprejudiced reading of the passage does not so clearly articulate this view and may in fact raise more questions than it provides answers. Most obviously, there is the following paradox. Plato says that slavery “in measure” is “altogether good” and that slavery to a god is measured—slavery to human beings, of course, is “unmeasured,” and presumably, therefore, “altogether bad.” But in what he says next, Plato does not contrast slavery under divine masters to slavery under human masters. He identifies instead two different gods to whom one might be enslaved: law, god of the moderate or sound-minded (sōphrosi); and pleasure, god of the imprudent or mindless (aphrosi). A stubbornly literal reading would force us to conclude that, for the mindless, slavery to pleasure is altogether good. The strangeness of this proposal prompts us to correct our reading by inferring that the mindless, as such, worship a false god, and that only the sound-minded know the true god, law. But even with this correction, Plato’s statement is not as clear-cut as we might think. For Plato has spoken of the total badness of slavery under human beings, but has said nothing of slavery to false gods. He has, in fact, given no explicit assessment of slavery to pleasure; we may only infer what may be implied by saying that it is slavery to the god of the foolish. Moreover, even what he says about being a slave to the law is problematic. Does his claim (that the moderate or sound-minded have law as a god) mean that this is the only or ultimate god to whom the wise bow? Even, say, if there is a conflict between the law of the city and what the gods demand, such as we know from, for example, Sophocles’s Antigone? But as almost any sensible person knows, the law as one finds it in one’s political community is liable to be seriously defective precisely because it is not of divine origin, is not “a god,” but human (consider Statesman 293e7ff. and Xenophon, Memorabilia 1.2.40–46 and 4.4.7–25).

What, then, can Plato mean by saying that the moderate are measured in enslaving themselves to their god, Law? Either he means by “law” only such law as the wise would obey, in which case the “moderate” do not enslave themselves to any set of real, existing laws, but evaluate the laws under which they find themselves and obey them only insofar as they are in accordance with what we might call the “true” law (as in the regime of Plato’s Laws); or Plato here means by “moderate” something narrowly political or otherwise qualified, so that in speaking of “the moderate,” he does not designate simply “the wise”—but in that case, a question arises as to how much more the god of the “moderate” is to be revered than that of the imprudent, and we are left to wonder to what extent the god of the wise may align in the end with pleasure just as well as law. Or, indeed, perhaps Plato is quite serious in saying that moderation indicates the necessity of enslaving oneself to the law as one finds it in one’s political community and of avoiding the enthralling power of pleasure, and yet does not mean that this is the whole of what guides the wise person’s activity. For what one might easily miss in this complex Platonic pronouncement is that, though he begins by saying that both slavery and freedom are altogether good only when they are in measure, he goes on to identify only the measured and unmeasured versions of slavery. This provokes the question, in what does measured freedom consist for the moderate and wise? Consider that, at the beginning of Letter Two, Plato claims that he himself is “great” because he makes himself “a follower,” not of the law, nor indeed of pleasure, but of his “own reason”; in the same moment, he bemoans the truth of Dionysius’s allegation that Dion, who is in the process of raising an army to march on Syracuse, is not likewise ruled by Plato’s reason (310c1–6). Dion and Plato do not take their bearings alike, in political action at least.

We may summarize the upshot of our consideration of Letter Eight as follows: Dion’s opinion that freedom was simply compatible with obedience to the law constituted a misunderstanding of Plato, one that reflected Dion’s own native hopes and prejudices. Plato himself speaks only of slavery to the law and is more careful than Dion was in his use of the word “freedom.” Apart from his references to the liberation of a city from the yoke of tyranny, then, in what manner does Plato himself, in contrast to Dion, employ the word “freedom”?

Plato’s View of Freedom and Dion’s View of Philosophy

There is one place in Letter Seven where Plato rather plainly criticizes Dion, though not harshly, and it is in this same place that he indicates his own understanding of what constitutes genuine liberty. Dion’s assassination, says Plato, was facilitated and partly perpetrated by a pair of Athenian brothers in whom Dion had imprudently placed his trust. The mistake in Dion’s judgment stemmed from the fact that he trusted in a kind of “promiscuous comradeship belonging to most friends, which they work out through hosting someone as a guest-friend (xenizein) or through initiation into the lesser and greater mysteries,” as distinguished from such bonds as are formed “from philosophy” (333e1–4). In defense of the reputation of Athens and its citizens, whose virtue and trustworthiness might seem to have been tarnished by the actions of the Athenian brothers who betrayed Dion, Plato points out that he, an Athenian himself, remained true to Dion despite all he might have gained from doing otherwise, attributing this to the fact that his own bond with Dion came to be “not through vulgar friendship, but through partnership in liberal education.” “In this alone,” he concludes, “ought one who possesses mind to trust, more than in kinship of souls and of bodies” (334b3–7; emphasis added). Plato thus juxtaposes Dion’s catastrophic error in judgment with what is rare in the Letters, a statement about liberty made in Plato’s own name—indeed, a statement that identifies a form of liberty worth exalting above all else. It is the liberty of “liberal education” (eleutheras paideias), that is, such education as befits a truly free human being, or rather, and more to the point, such education as can make one truly free. Freedom means above all freedom of the mind. This explains why and how it can be said that a soul cannot be free if it lacks the habits of moral virtue and self-restraint—since it will be unable to recognize and thus to choose a life worth having; and also why Plato cannot fully endorse the idea of freedom under the law, even under good laws that would inculcate those virtuous habits—for genuine freedom of the mind cannot rest satisfied with the authoritative and peremptory manner in which even the best code of laws necessarily articulates and insists on its vision of virtue and the human good. Philosophy’s demand for unfettered questioning—“measured” freedom in the view of the wise—puts philosophy in tension with the spirit of law as such (cf. Republic 537e1–541b5).

There is a paradox, however, in what Plato implies about his relationship with Dion here. For Plato claims he was loyal to Dion on account of their “partnership in liberal education”; but was that loyalty not to some extent misplaced, given that Dion himself erred so badly in his own judgment by trusting those who became his assassins? More to the point, can the supreme trustworthiness of friendship through liberal education or philosophy really be maintained if that education does not itself impart or include firm knowledge of the very fact that, and the reason why, other so-called friendships cannot be trusted—that is, precisely the knowledge Dion lacked? In short, what good is Plato’s “trustworthy” friendship with Dion based on liberal education, if Dion cannot be trusted to be prudent in his own choice of friends? The resolution to this paradox is to be found by taking account of the decorum Plato observes in his writing, and particularly in this letter, in his critique of Dion’s judgment. In criticizing Dion’s failure to recognize the untrustworthiness of “vulgar friendship,” Plato shows us a glimmer of the truth amid the eulogistically exaggerated terms in which he otherwise describes the strength of his own friendship with Dion. In other words, Dion must not have obtained so complete and transformative a “liberal education” as Plato tactfully implies that he did in writing to the late Dion’s distraught and grief-stricken followers. Yet to say that Plato judged Dion to have been deficient in his pursuit of education is itself paradoxical in view of the general impression given by the Letters. Was Dion not a zealous devotee of Platonic philosophy? Was he not persuaded that philosophy provided the best life for a human being? Was his own plan in taking over the rule of Syracuse from Dionysius not to lead the city as a philosopher-king?

It is the last of these questions that first opens our eyes to the unexpectedly limited character of Dion’s relationship to philosophy. Over the course of his counsel to Dion’s followers in Letter Seven (334c3–337e2), Plato makes it clear that the plan he and Dion jointly had for the education of Dionysius was distinct from the plans that both he and Dion developed in the wake of that first plan’s ultimate failure. Dionysius’s failure as a ruler, says Plato, was due to his “having been in no way willing to make use of justice throughout his whole rule” or “empire”; but, “had philosophy and power really come to be” in the same ruler of that empire, Plato continues, the “true opinion” regarding the key to political and individual happiness, “shining out among all human beings, both Greek and barbarian,” would consequently have been “sufficiently set down in everyone.” That is, it would have meant the “cessation of evils” for humanity, and it is in this sense that Dionysius, in his failure, “inflicted the greatest harms,” not only on Plato, but “on all other human beings” (335c4–e1). These goals, says Plato, “common goods for all,” were sought “first”; what Dion undertook, together with Plato, “meaning well toward the Syracusans” (but not necessarily “for all”), was “second” (337d5–8). Had Dion secured his rule over Syracuse, says Plato, he would have made the city “free,” “adorned the citizens with the proper and best laws,” and then “striven eagerly . . . to recolonize all Sicily and make it free from the barbarians, casting some out and subduing others” (335e3–336a8); the goods achieved by this “Plan B,” as we may call it, do not extend to the barbarians, as did “Plan A,” involving Dionysius himself. We cannot help but think of the relation between these two plans as at least parallel to that of the regime of the Republic (the best imaginable city, in which justice is secured by the absolute rule of benevolent philosophers) to the regime of the Laws (the best practicable city, from which philosophy is generally absent, but wisely given and carefully guarded laws ensure a just political order).

We may summarize our conclusions regarding Dion’s relationship to philosophy as follows. Dion had hoped above all for Plato to educate Dionysius toward philosophy, believing that the manifest, perfect justice of genuine philosophic rule would shine as a beacon to the rest of the world and herald a new age of happiness for humanity; when this failed, Dion attempted (coordinating to some extent with Plato—see sumpraxai at 337d6; but cf. 321a5–b5) to conquer Syracuse in order both to free it and to establish a rule of new, wise laws throughout Sicily. But this was not to be the rule of philosophy, as indeed Dion never thought of himself as a potential philosopher-ruler. The closest that Plato ever comes to suggesting that Dion was involved with the activity of philosophy is in this same section of Letter Seven: imagining a scenario in which Dion’s plan had been successful, Plato extrapolates, “And had these things in turn come to pass through a man who was just and courageous, moderate, and philosophic, then the very same opinion concerning virtue would have come to be among the many that, if Dionysius had been persuaded, would have come to be among, so to speak, all human beings and saved them” (336a8–b4; emphasis added). The grammar of this sentence makes it ambiguous whether Plato is affirming that Dion himself would have been such a man or not. But in the context of Letter Seven, addressed as it is to the followers of Dion still mourning his loss, this ambiguity comes awfully close to damning with faint praise. Likewise, by replacing the cardinal Platonic virtue of being “wise” with being “philosophic” in this enumeration, Plato implies that Dion lacked wisdom. Had Dion succeeded in giving good laws to the Syracusans, his reputation of being associated with philosophy, more than any ability to govern wisely himself, would have benefited the reputation of philosophy in turn.

Indeed, it seems Dion was widely known for his connection to Platonic philosophy. But when we attempt to reconstruct, from the Letters, the real substance of his involvement in philosophy, we find, in confirmation of the impression we have just now been forming, that it was shallow in some critical respects. Dion certainly admired Platonic philosophy for what he believed to be the clarity with which Plato had revealed to him the true aspect and requirements of human happiness. Above all, he was powerfully impressed by Plato’s identification of moral virtue as a sine qua non of such happiness, both for the individual and for the political community. Dion therefore loved and exalted philosophy as a means for identifying and pursuing the requirements of a good life, which he saw as characterized above all by the virtuous self-restraint and devotion to a higher cause that give justice, courage, and moderation their essential nobility. The promotion of moral virtue was therefore, to Dion, the real purpose of philosophy, and the establishment of the perfectly just political order its highest and ultimate task. But it seems he believed in the possibility of all this on trust, thanks to the persuasive power of Plato’s speeches. For nowhere is it ever suggested that Dion himself pursued philosophy as an activity.

Much of the Letters may be said to abstract from the genuine activity of philosophy, from the philosophic life. This is partly because the Letters is a book Plato wrote to be published, and Letter Seven shows us that when Plato wrote so as to be widely read he minimized the profound difference between himself and Dion as much as the subject matter would allow. Neither the Academy nor Plato’s activity as a teacher in it is ever mentioned in the Letters. The opening words of the whole text refer to the inordinate time Plato spent, or wasted, in the Syracusan court: “After I had been occupied for such a long time with you” (diatripsas egō par’ humin chronon tosouton). He refers exceedingly rarely to his own “not indecorous” occupations (tas emautou diatribas ousas ouk aschēmonas), which he left behind in Athens during that time (329b1–2). But the Letters is not entirely without reference to the content of genuine philosophic thinking, thanks to the fact that not Dion but Dionysius appears to have pursued the study of philosophy somewhat seriously for some period of time. The two parallel passages in which Dionysius’s involvement with philosophy is most directly treated help to bring out by contrast the emptiness of Dion’s involvement with philosophy. Letter Two contains the only passage in the Platonic corpus in which Plato himself explicitly undertakes to teach someone the highest principles of his philosophy: he explains to Dionysius, albeit through all but impenetrable “riddles” in case the letter should fall into the wrong hands, his view of what he calls the “nature of the first.” In Letter Seven, in response to the rumor that Dionysius has written a handbook purporting to explain the principles of Platonic philosophy, Plato gives an account of the nature of knowledge and of reality that explains why no one with a correct grasp of these things would ever attempt to put this into writing (and therefore why any such attempt on Dionysius’s part would only reveal his ignorance of Platonic philosophy as well as his lack of self-knowledge).

Without ever becoming perfectly explicit about Plato’s thought, then, these two passages nonetheless indicate the subject matter treated by Plato’s most “serious” philosophic activity. “The nature of the first,” and “the highest and first things concerning nature,” suggest questions of cosmology, ontology, metaphysics, and epistemology. It is true, Plato indicates that these same subjects are connected somehow to his moral and political philosophy. But nowhere in the Letters is there the slightest indication that Dion, for his part, ever showed any interest, ever spent any time, in the pursuit of these more theoretical philosophic questions. Perhaps the greatest proof of this is given by the shortest letter in the collection, Letter Ten. In this letter, written to a comrade of Dion whom Plato has not met—but who, Plato hears, is the most highly reputed for wisdom of all Dion’s friends—Plato says that “it is the steadfast, and faithful, and healthy” that Plato himself claims “is the true philosophy,” dismissing all “the other wisdoms and clevernesses, which extend to other things” as mere “nice-ties” (358c3–6). Not only does Plato thus abstract completely from any suggestion that philosophy is an inquiry into nature, he denies that philosophy is an activity at all. This means that, as far as Plato is concerned, anyone who, like this Aristodorus, has come to learn about philosophy through Dion must think that philosophy is above all a tool for bringing about political harmony through justice and virtue, or that philosophy is nothing but the soil upon which civic friendship and patriotic loyalty can flourish—and Plato is perfectly happy to leave such a person with such a distorted view.

Plato, then, is not being candid when he says that he shared with Dion the firm, supremely trustworthy friendship that can only be founded on liberal education and philosophy, because Dion did not really understand what philosophy means for Plato. Perhaps this is indicated above all in Letter Six. In this letter, Plato attempts to forge a new friendship between his three addressees: Hermias, the monarchical ruler of Atarneus in Asia Minor, and Erastus and Coriscus, two men who had spent considerable time studying with Plato in Athens. The steadfastness of this friendship is to be assured by the trio’s communal practice of philosophy. But here, Plato is blunt in disclosing the fact that the two Platonists—they who have spent their time acquiring “this beautiful wisdom of the Forms”—are completely inept when it comes to practical political affairs. It is they who need to take shelter under Hermias’s “defensive power,” under his “wisdom that guards against the wicked and unjust,” since they themselves are “inexperienced” on account of having lived so long with Plato and his companions. They require safety provided by one who knows how to fend off political dangers, “lest they be compelled to be careless of the true wisdom in order to take care over the human and compulsory [wisdom] more than they need to” (322d4–e5). Whatever the reason, then, that two philosophers may trust each other so much more surely than those whose friendships are founded on other bases, this steadfastness is not essentially useful when it comes to the challenges of political action. Letter Six thus reveals that philosophy is not—contrary to the primary impression that Plato gives—the solution it seems to be to the problems that turned Plato away from politics in his youth (see 325d1–2).

In Letter Seven, Plato gives us some help in understanding the nature of Dion’s deep misunderstanding of the meaning and import of Platonic philosophy. Twice in that letter’s philosophic digression, Plato discusses ways in which his readers or pupils might misunderstand his teaching; both times, Plato seems to include a veiled pointer to Dion. First, when Plato explains how he himself would undertake to communicate the content of his most serious philosophic thought, he says that his account would fill some “with a lofty and empty hope as though they had learned some august things” (341e5–6); and when he later considers the reasons why someone, having been exposed to Platonic philosophy, might not continue to pursue it, he says that his hearer might consider the things he heard “beyond him” or “not on his level” (ou kath’ hauton), as “greater” than him; and Plato indicates that such a person might doubt his own ability to live “while taking care of practical wisdom and virtue,” but would see the great themes of Platonic philosophy as “worthy with a view to the education of a free soul” and would honor his teacher on that account (345b3–c2). Of Dion it may be said that he revered Plato and his philosophy, that he believed the Platonic claim that philosophy is the key to the resolution of humanity’s political woes; but he could not claim to understand how exactly that is true because he considered the actual practice of philosophy “beyond him,” and so did not really grasp what philosophy entails.

Plato’s Concern for the Reputation of Philosophy

Dion was wrong ever to believe that Plato’s description of philosophic rule in the Republic was a blueprint for political action. He never seems to have considered, for example, Plato’s indications both that philosophers will not wish to rule (Republic 499a11–c5, 519c4–521b6; cf. Letters 357e4–358a2) and, compounding the problem significantly, that the people will be profoundly resistant to being ruled by philosophers (Republic 487e1–489c9, 501c4–502a4). In saying this about the Republic, of course, we risk plunging ourselves into the weeds of a very old debate, which we could hardly hope to resolve to the satisfaction of all. Simpler than tackling the whole meaning of the Republic is to point out that Dion was wildly optimistic to think he could ever bring about philosophic rule in Syracuse. Plato’s excoriation of the Syracusan regime in Letter Seven, in which he says precisely that its licentiousness and lawlessness are such that no good regime could ever take root there, disqualifies it as a candidate for becoming the regime of the Republic, which can only arise in a city where a vanishingly rare attachment to virtue has been carefully cultivated by its lawgiver (Republic 497b1–d2). Otherwise, it seems the philosophers would have to begin by exiling every citizen over the age of ten (540d1–541b5), whereas Dion believed that a life of “indomitable bliss” for all the Syracusans could be achieved without bloodshed (Letters 327b6–d7). By the same token, Dion’s overestimation of Dionysius’s philosophic potential was itself likely a necessary result of Dion’s failure properly to understand the substance, and hence the requirements, of philosophy. With respect to the possibility of rulers coming to philosophize, Plato says there would be need of “some divine fate” (326b3–4; see also 326a5), whereas Dion appears to have thought that all the requisite divine help had already been proffered by the time he invited Plato to Syracuse (327e4–5).

The remaining difficulty for our view—that only Dion’s misunderstanding of Platonic philosophy could have led him to believe in the possibility of anything like the regime of the Republic in Syracuse—is Plato’s own apparent endorsement of philosophic rule in Letter Seven itself. But here, if we attend carefully to the text, we will find not only that Plato never claims to have hoped for success in Syracuse, but that he never even claims to think that philosophic rule is possible. What he says is that, in light of his observations of the treatment of Socrates and of other political matters, he was compelled to say something in praise of philosophy—namely, that human beings would not be free from evils until philosophy and political power should coincide. But it is perfectly possible to understand Plato as saying that he was compelled to promote a certain portrayal of philosophy, to bolster its reputation by praising it—we may even grant that he thinks it would be a great common good for human beings if philosophic rule could ever emerge—without insisting that he believed in that regime’s possibility.

There is substantial evidence, then, that Plato must have considered the idea of philosophic rule in Syracuse a nonstarter. Thus we have come to recognize a significant gulf separating Plato’s and Dion’s understandings of the meaning of the doctrine of philosopher-kingship. The effect of this recognition, however, is to intensify the basic question as to why Plato accepted Dion’s invitation at all. What did he hope to accomplish in Syracuse that was worth taking such grave risks as were evidently involved? This question is put into particularly stark relief when we consider Letter Eleven, in which Plato is responding to a man named Laodamas, who has invited Plato to come lend his expertise in the founding of a new colony. Plato declines the invitation with the following rationale: “It would be indecorous (aschēmon) if, having arrived there, I should not accomplish the very things for the purpose of which you are calling upon me. But I do not have much hope that these things would come to be . . . and at the same time, I, because of my age, am not in a sufficient bodily condition to be wandering and undergoing dangers” (358e2–6). But all of this could just as well have been said in response to Dion’s invitation—indeed, all the more so with respect to Plato’s third and final visit, from which Plato indeed says he tried to beg off by making pretext of his old age (317c5–8, 338c3–5). The question of why Plato went back to Syracuse for the second and third times, the journeys on which he tried to provide Dionysius with an education in philosophy, represents the major puzzle of the Letters’ whole drama. Indeed, even those letters that do not deal with Plato’s activity in Syracuse, nay, especially those letters (Five, Six, and Eleven) intensify that puzzle.

We come back at last, then, to Plato’s account in Letter Seven of his private deliberations about whether to accept Dion’s first invitation to return to Sicily. Now, there are some parts of this passage in which Plato seems to indicate he was serious about some kind of political undertaking. For example, he says that he would have been ashamed to have to see himself as being, so to speak, “all talk and no action” on account of never having voluntarily undertaken any serious deed (328c4–8). In the same breath, however, he gives another pair of important considerations. First, he insists on the religious duty he had toward Dion under the Greek custom of xenia, guest-friendship: having been a xenos, a guest, of Dion, Plato had received favors from him—on his first visit to Syracuse and perhaps over the following two decades—the repayment of which was now Plato’s religious obligation (328c7–d1; see also 329b1–2). Of course, we must recognize that a shadow is cast on this argument by Plato’s later denigration, which we have already discussed, of friendships founded on xenia.

But the reason for which Plato says his loyalty to Dion had become an urgent matter takes us, in an unexpected way, to the second reason for his departure. The urgency of Plato’s need to help Dion is indicated by Plato’s saying that Dion “had really come to be in no small dangers” (328d1–2). In Plato’s preceding description of Dion’s invitation itself, by contrast, all had been excitement and enthusiasm. Nowhere did we get any sense that Dion himself recognized he was in grave danger. This would seem to be of a piece with the unpopular haughtiness Dion assumed after his first encounter with Plato; his zeal for Plato’s hyper-moral philosophy, his hopeful faith in the promise of philosophic rule, all brings with it a certain obtuseness regarding the impression he must make on those around him who remain unpersuaded of his vision. Indeed, Letter Four, the only letter addressed directly to Dion himself, concludes with this warning from Plato: “Take to heart . . . that you seem to some to be rather lacking in the proper courtesy. Let it not escape your notice that it is through being agreeable to human beings that it is possible to act, but stubbornness dwells with loneliness” (321b5–c1). Dion never understood or cared about the animosity he aroused in Syracuse with his rigid, moralistic preaching about philosophy. Plato, for his part, makes the angry popular resistance to philosopher-rulers a major theme of the Republic (see 473e6–474a4ff., 487b1–d5ff., 499d8–502a4),

So Plato saw, as Dion did not, that Dion was getting himself into serious trouble. And in deliberating about whether to accept Dion’s invitation, the decisive consideration appears to have come out of Plato’s thinking through what would happen if he should decline the invitation, and Dion, without the benefit of Plato’s awareness and counsel, should be sent into exile. Plato imagines the exiled Dion arriving at his doorstep in Athens with the following accusation: the harm suffered by Dion is a minor thing compared with what Plato, by his inaction, has done to “philosophy, which,” as Plato’s imagined Dion puts it, “you always extol and which you claim is held in dishonor by the rest of human beings—how has it not been betrayed at this point, together with me, insofar as a part of what has come to pass was up to you?” (328e3–5). “If these things had been said,” Plato concludes, “what decorous answer would I have to them? There isn’t [one]” (329a5–7). Thus, when in summary Plato describes his departure for Syracuse, he says, “In going, I both acquitted myself in relation to Zeus Xenios and rendered the philosopher’s part unimpeachable—it would have come to be a matter of reproach had I participated in shamefulness and vice by in any way becoming soft and being cowardly” (329b3–7). From all this it is clear that Plato’s concern for the reputation of philosophy was the preeminent reason for his agreeing to go to Syracuse to become the philosophic tutor of Dionysius the Younger (see also 347e6–7).

This conclusion is corroborated by an important statement in Letter Two, the only place in the Letters where Plato provides a simple, concise answer to the question of why he went to Syracuse to meet Dionysius the Younger. He says there, addressing himself directly to Dionysius, “I myself came to Sicily with a reputation of being quite distinguished among those in philosophy; and I wished, by coming to Syracuse, to get you as a fellow-witness in order that, through me, philosophy would be honored even among the multitude” (311e5–312a2). Now this is not identical to what he says in Letter Seven. The statement in Letter Two identifies the positive goal of establishing a good reputation for philosophy by winning over the young tyrant; the indications in Letter Seven point to the damage that philosophy’s reputation would sustain if Plato declined Dion’s invitation. But there is an obvious consistency between the two accounts, in that they both stress the reputation of philosophy as Plato’s primary concern. And when we consider the interpretive suggestion we have already advanced, that the whole doctrine of philosopher-kingship, and in this sense the whole Republic, were conceived out of a necessity Plato felt to praise philosophy in light of his observations of political life, we begin to see that Plato’s journeys to Syracuse, too, fit into the great motif that plays through virtually every one of Plato’s writings: the tension between philosophy and the city as represented by the Athenians’ persecution of the quintessential philosopher, Socrates. This is not the place to dilate further on that important theme. But we are now in a position to see that the Letters points us toward an interpretation of the whole doctrine of philosopher-kingship as primarily intended to bolster the public image of philosophy.

This in turn means that Dion’s misunderstanding of philosophy and of the doctrine of philosophic rule was not unintended by Plato. Dion was a member, albeit of special importance and impressive character, of the “multitude” that Plato sought to win over toward a gentler disposition to philosophy. And so in Dion’s zealous love of Platonic philosophy as the truest foundation of justice and virtue, we see something of what Plato hoped people would think and say about philosophy on the basis of his work. Recall that Plato never even tried to determine whether Aristodorus, to whom Letter Ten is addressed, may have had a more sensitive awareness of the genuine character of philosophy than Dion himself. When dealing with the “comrades of Dion,” Plato promotes the view of philosophy as the instrument of utopian politics: “true philosophy” as “the steadfast, faithful, and healthy.”

Plato’s Reticence to Provide Political Counsel

We began by asking what kind of advice Plato was wont to give in his capacity as a political adviser. The first possibility we had to consider was that Plato counseled the establishment of a regime ruled by philosophers, since his account in Letter Seven gives the impression that he and Dion shared this goal for Syracuse. We have now arrived at the conclusion that Plato’s purpose in Syracuse was to do with the public defense and promotion of philosophy and was not a serious attempt to bring about a cessation of evils for humanity by establishing a regime of philosophic rule. But this should not be the end of our investigation of Plato’s practical political counsel. The Letters portrays Plato engaged in political activity, and so it is here more than anywhere else in the Platonic corpus that we may hope to find Plato showing how his political-philosophic wisdom may actually illuminate the political world and usefully direct the actions of someone seeking to navigate it. Yet such lessons are surprisingly difficult to find in the Letters. We might be tempted to say that Plato’s purpose in the Letters is to dispel the notion that he possessed any practically useful political knowledge. In order to give the proper context and qualification to such political counsel as Plato does give in the Letters, then, we must first show how Plato’s reticence to reveal it actually forms the unifying impression of the text as a whole.

To begin with, it seems that whatever political acumen Plato may possess does not issue in any clear or immediate way from his philosophy per se. For whenever Plato discusses or presents philosophy in the Letters with any semblance of its true proportions and concerns, it appears to stand at some remove from politics. In the “philosophical” passages in Letters Two and Seven, political philosophy is mostly left behind in favor of what seem like abstruse cosmological and epistemological subjects; in Letter Six, Plato associates “this beautiful wisdom of the Forms” with total ineptitude in practical affairs and separates “the true wisdom” from “the human and compulsory” wisdom; and this separation accords with Plato’s claim in Letter Two that “by nature, practical wisdom and great power come together in the same place, and they always pursue and seek each other and come to be together” (310e5–6)—for this obviously does not mean that rulers naturally become philosophers or vice versa, but rather that wisdom and power seek each other out because, as Plato’s list of examples suggests (311a1–b4), each lacks something it hopes the other can provide. Plato repeatedly indicates a disjunction between the study of Platonic philosophy, on one hand, and the development of insight and ability useful for the pursuit of political goals, on the other. Yet as the Letters makes clear, Plato was frequently sought out for his political wisdom, perhaps especially because of his reputation as author of the Republic. So we continue to press the question: What does Plato say, what does he do, when called upon to give political counsel?

In general, it seems that Plato responds to requests for counsel by declining to provide any advice at all. When Plato digresses from the narrative account of his Sicilian engagements in Letter Seven to address Dion’s associates’ request for help—the first of Letter Seven’s two major excursuses—he begins by stating the principled reason for his policy of turning away so many who come seeking his guidance. He begins by laying out the prerequisite conditions of his willingness to provide anyone with personal or political counsel, using the analogy of a doctor who is called upon to counsel someone living a life of unhealthy habits. Plato says that the courageous way to respond to such a request is to make certain that the patient is willing to reform his way of life, and otherwise to refuse to give any counsel at all. That is, the patient must pledge to obey the doctor’s orders, which will be directed not only at curing the painful symptoms, but at developing a new, healthy, holistic daily regimen. Likewise, then, if someone with power in a city comes to Plato to ask for counsel, but the city is “deviating altogether from the correct regime and in no way willing to go in its tracks,” and if moreover Plato is warned that, as a counselor, he is to let the regime remain as it is on penalty of death, then the courageous thing for him to do is to walk away and deny them any counsel (330e2–331a5). Plato will only counsel individuals or cities who request his help if they agree to cede him the ultimate authority over any decisions bearing on their adherence to the way of the “correct” regimen or regime.

Plato’s application of this principle is on display in Letter Three. Letter Three contains Plato’s twofold defense against what he claims are slanderous accusations, some of them being propagated by Dionysius himself, regarding the influence Plato exerted as a political adviser at Syracuse. In response to the allegation that Plato prevented Dionysius from pursuing his ambitious vision for a Sicilian empire, Plato clarifies that he did support the tyrant’s plan to recolonize the island’s Greek cities, but not until Dionysius had been educated (319a2–c4). Admittedly, this was a point of some confusion for Dionysius—who responded to the effect of, “Educated in what? Geometry?!”—which response, however, may be said to give credence to our sense that education in Platonic philosophy points elsewhere than toward expertise in practical political affairs. In any case, Plato here was apparently true to his word, in that he would not counsel political action until the advisee had first completed the necessary transformation.

Likewise in Letter Eleven, Plato declines the invitation from Laodamas to participate in the founding of a new colony, explaining that he does not believe his contribution would be likely to assure the success of the undertaking. But the advice he gives to Laodamas in place of his partnership goes even further in emphasizing Plato’s pessimism regarding the efficacy of wisdom as a guide to political action. No act of lawgiving, Plato warns, can be sufficient to establish a city well unless someone is present who can oversee the daily regimen of all the inhabitants as a “sovereign authority,” so as to ensure that they are being instilled appropriately with moderation and courage. If no one present is up to that task, says Plato, then the situation is irremediable: for there will be no one present capable of educating anyone to become such a “sovereign authority,” nor will there be anyone capable of learning what must be taught (359a2–b3). “What remains” in that case, says Plato, is “to pray to the gods.” In the absence of anyone willing and able to serve as a wise sovereign, the success of the regime—even if the lawgiver was wise—will depend on such strokes of fortune as could only be controlled by divine power. Plato thus denies that any political counsel is sufficient for the guidance of a city lacking the means to establish and to maintain virtuous habits or the appropriate combination of moderation and courage among the inhabitants. In what we are compelled to suggest is the vast majority of cases, even the most elevated and developed prudence is inadequate on its own to ensure the success of major political undertakings. Divine assistance or fortune, for which one can only pray, is needed as a supplement to ensure that the political health of the city is sustained.

But Plato’s policy regarding political counsel is still more restrictive than we have recognized so far. For in Letter Seven’s first digression, Plato explains that, unless he is asked directly, he will not even consider providing personal advice, on his own initiative, to any individual, nor would he ever use force to compel anyone to take counsel they do not wish to accept. Even if the individual in question should be his own son, says Plato, he would let the matter lie rather than use force—and if it should be his own mother or father, the use of force would be downright impious “unless they are out of their senses due to illness” (331b4–c2). From this solemn injunction against compelling one’s mother or father, Plato at last extrapolates to conclude that one must be wary, too, of offering political counsel even to one’s fatherland: “If [one’s city] does not appear to him to be nobly governed,” “he should speak” only “if he is neither going to be talking in vain nor put to death for speaking; but he should not bring force against a fatherland to produce a change of regime when it is not possible for it to come to be best without exile and slaughter of men; rather, he should keep quiet and pray for the good things for both himself and his city” (331c7–d5; emphasis added). Unless one can transform one’s political community into the best regime—however that ambiguous phrase is to be understood—and without recourse to exile or killing, one should not offer counsel at all, but “keep quiet and pray.”

As it happens, Plato has occasion in the Letters to explain how he applied this principle in his own life at Athens. At the end of Letter Five, Plato imagines and addresses the following accusation against himself, reminiscent of the Apology of Socrates: “Plato, it is likely, pretends to know what things are advantageous to a democracy, but when it was possible to speak in the demos and to counsel the things best for it, he never went up to utter a sound” (322a4–7; cf. Apology 31c6ff.). The answer Plato wishes to promote is as follows:

Plato was born late in [the life of] the fatherland and came upon the demos already elderly and habituated by those who came before to do many things unlike to his own counsel—since, of all things, it would be most pleasant for him to give it counsel as to a father, if he didn’t suppose that he would be taking risks in vain and doing nothing more. (322a8–b4)

Again, the Letters indicates that Plato lived his life true to the principle he lays out in Letter Seven; he never brought his political counsel to bear on the affairs of his fellow Athenians, as they were not in a condition to accept it. The letter closes with an implication that the Athenians were in “an incurable state” (322b5–c1). By avoiding participation in political deliberation that could only have served to endanger him, Plato chose the artful and manly course.

But we must also put this statement from Letter Five in its proper context: this Platonic apologia occurs because Letter Five is one place in the Letters where Plato actually claims to possess, and offers to share, some useful political knowledge. He writes to a young Perdiccas, ruler of Macedon, to say that he is sending along an associate of his, a man named Euphraeus, to serve as Perdiccas’s political adviser. Euphraeus will be useful, says Plato, because he possesses a certain rare understanding especially helpful to a young ruler. Plato says that each type of regime—democracy, oligarchy, and monarchy are the ones he names—has a distinctive “voice,” like an animal. Regimes flourish if they use their proper voice in addressing themselves “both to gods and to human beings,” and if their actions accord with their voices; but those regimes that try to imitate the voice of another are ruined. Euphraeus, says Plato, can help Perdiccas “in finding out the speeches befitting monarchy” (321d2–322a2). It is because he has thus revealed his own possession of this knowledge that Plato feels compelled to conclude the letter, as we have just seen, by defending his failure to employ that knowledge for the benefit of the democracy of his own Athenian fatherland. Thus Plato at least clarifies what he would have counseled to the Athenians had he encountered them at a more propitious time—and, presumably, what he would counsel to any city with ears to hear him. Of course, what this counsel really urges—that each regime must be sure to speak only in its own voice—is quite consistent with Plato’s caution against trying to bring about a change of regime in one’s own community. In fact, Plato’s insistence that a regime strive to remain what it is must strike any would-be reformers as stiflingly conservative. It seems, for example, that Plato would never counsel a monarchy to turn itself into a democracy: for either the monarchy is healthy (or willing to become healthy), in which case one should help it become the best monarchy it can be with no admixture of democracy, or else it is stubbornly unhealthy, in which case Plato offers no counsel but to pray for good fortune. His answer to the important question whether he would support the transition from a tyranny to a kingship is obscured by his choice of words in Letter Five.

Plato’s Reluctant and Qualified Proposal of Oligarchy and the Problem of Foundings

It seems Plato’s considered view is that, in most cases, more will be lost in the attempt at significant political reform than one can reasonably expect to gain, especially given the part that chance must play. Yet we would wish to hear what Plato had to say in more difficult, more pressing circumstances, in which some positive course of action must be chosen. What about a case in which it is patently obvious that the status quo, or the likely outcome of inaction, is unlivable (see 358b1–3; Republic 347a10–c5)? What if there is a genuine crisis, a situation in which the city must either change or perish? In such a situation, there would be no question of aiming at “the best” regime—certainly not the best imaginable regime or the rule of philosophy, nor even the best regime one could reasonably hope to attain by incremental improvement if the city were basically sound. If Plato were compelled to provide counsel in such circumstances, he would have to bend from his habitual insistence on aiming at the ideal by instead pointing to what he saw as the best available, pursuable course of action—however low that bar might prove to be. But since Plato says that all the cities in his time were “governed [so] badly” as to be “nearly incurable” (326a3–4), his counsel in a situation like this would shed some light on a vast region of ordinary political reality regarding which he tends not to offer any advice.

Of course, it is precisely such a situation that hangs over Letters Seven and Eight, and therefore over the whole Letters, giving to the work its urgency and dramatic tension. For the context of these two letters, both addressed “to the intimates and comrades of Dion” in the wake of Dion’s assassination, is the ongoing civil war between those in Syracuse seeking to reinstate the monarchy and the addressees, who wish to overthrow the tyrants in the name of freedom. The city is in need of some means of escape from its terrible and bloody civil strife—for which, we must not forget, Plato has admitted some responsibility: it was Plato’s initial influence on Dion decades ago that set the Sicilian tragedy in motion; so it falls upon Plato now to offer some guidance to the Syracusans as to their best available course of action. It is at the end of the first digression in Letter Seven, after he has elaborately detailed his policy regarding requests for counsel and the manner in which he has followed this policy at Syracuse so far, that Plato at last relents in his resistance to providing counsel and suggests what he thinks should be done—as opposed to his advice in Letter Eight, which, as we have seen, was merely a “prayer.”

Plato leaves no doubt that the rule of philosophers is not an option for the Syracusans in their present circumstances. Even the hopes that Dion himself had cherished of establishing philosophic rule in his city had depended upon the philosophic education of Dionysius, the attempt at which, Plato stresses, has been a failure (335c2–e1). Plato goes on to suggest that, had Dion in turn succeeded in his own campaign to take over the city and to reform it, he would have implemented a somewhat different, second-best regime (337d4–6)—a suggestion that accords with our assessment that Dion himself did not partake in the activity of philosophy. Dion, Plato reiterates, intended to make Syracuse a city of freedom, adorned by the best laws (335e3–336b4). He counsels Dion’s followers to continue to emulate their fallen leader, making patriotism and temperance the touchstones of their daily lives and attempting to build a Sicilian empire of equality under the laws (336c2–d7). And yet, Plato finally concedes, “if it should be that these counsels have come too late, since the many and varied conflicts naturally growing each day among the factions are pressing upon you,” there must be recourse to some other strategy (336d7–e2). The dreams of Dion must be set aside, and something must be done to end the terrible hostility between the parties. A third-best and more practicable option—some “Plan C”—must be pursued.

What follows is therefore Plato’s counsel for those who live in a regime riven and convulsed by the worst kind of factional strife. The principle underlying this counsel is that there will be no cessation of these evils until both factions put aside their grudges (336e2–337b3). As we know from Letter Eight, it is the refusal of either faction to settle for less than total victory that endlessly prolongs the conflict: one party may gain the upper hand for a time, but eventually the tides will turn, and the recently oppressed will seek to exact vengeance on their oppressors (353c8–354a3). Letter Seven accords with Letter Eight in stressing the need for the Syracusans to escape this deadly cycle and, moreover, in advising that this is to be accomplished by the institution of a new set of laws, which, crucially, must apply equally to all who live under them. Thus Plato here advises members of the victorious party to impress their superiority upon the defeated precisely by demonstrating that they are “more willing and capable of being slaves to the laws” (337a6–8).

But here in Letter Seven, in contrast to Letter Eight, Plato takes up explicitly and in detail the question of where this new and impartial legislation is to come from. Plato says the victorious party must call in a great council of legislators, dozens of men from all over Greece who meet the following qualifications: they must be old, they must be patriarchs of great families of well-known and respected lineage, and they must be relatively wealthy. The Syracusans are to beg these eminent Greeks to come by promising them the greatest possible honors in the city, in exchange for which the legislators must swear oaths to favor neither the victors nor the vanquished in their lawgiving (337b3–c7). Apart from this, Plato gives no prescription as to the content of the law or the form of the regime; Plato himself in no way offers to take up the task of lawgiving. He leaves this entirely to the respectable gentlemen who will be called in to rewrite the Syracusan constitution.

What form of regime is likely to emerge from the adoption of Plato’s proposals? Though Plato provides no specific guidance as to the structure or appointment of political offices, one arrangement is suggested more than any other by the details of his counsel. By urging the Syracusans to reserve the city’s highest honors for the legislators (337c2–3), Plato intimates that these legislators should be invited to occupy the ruling offices themselves. Moreover, the suggestion that Plato is thinking of the legislators as a potential ruling class is corroborated by his strange specification that “as a number, fifty such are sufficient for a city of ten thousand men” (337c1–2). Plato thus indicates that the number of legislators should be proportionate to the size of the city. But why would a larger city require more legislators? Will not the increase in quantity likely dilute the quality? It seems rather that Plato is arranging for the members of this constitutional convention to transition easily to becoming a new class of citizen rulers—at least for a time (cf. Laws 681c7–d5).

Thus, in this particular situation, Plato invites the establishment of an elevated kind of oligarchy at least as much, and probably more, than any other form of government: the law will be laid down by, and the highest honors reserved for, a group of elderly, prestigious, and wealthy gentlemen representing about half of 1 percent of the citizen population. We are reluctant to call the regime an aristocracy, since Plato in his Republic reserves that term for the ideal version of rule of the few, literally the rule of “the best” (445d3–6; cf. 544c1–3, 545b3–7). Plato gives the Syracusans no direction as to how they might vet their legislators for any particular traits of character: not only will they not be philosophers, Plato has explicitly included neither wisdom, nor justice, nor any moral or intellectual virtue among their necessary qualifications. To be sure, the Syracusans would do best to choose the most virtuous and competent legislators they can get, and Plato has done what he can to direct the Syracusans toward well-qualified candidates by describing the social class or station from which the legislators should be sought. We can say that Plato aims for the type of regime that, in the best case, comes to be called “aristocracy,” and comes to be viewed as worthy of approbation by its citizens and posterity. Even the best real aristocracies are, after all, oligarchic in some measure at least: in practice, aristocracy is the rule of the few and rich, who, over generations, are vulnerable to being led astray from their political responsibilities by concern for their own wealth (cf. Aristotle, Politics 5.7). But in the best case, at which Plato is aiming, wherein the rulers are governed by a concern to preserve the honor belonging to their offices and their lineages, there is reasonable hope for decent, equitable rule.

We may go so far as to speculate that Plato’s recommendation of this elevated oligarchy, this realistic form of aristocracy, as a third-best but achievable option has a certain resonance with his presentation of the devolution of regimes presented in book 8 of the Republic. Let us presume that the golden regime, the rule of philosophy, is but “a prayer”; consider then that the silver regime, for which Plato must invent the name “timarchy,” which is after all a “middle” between the imaginary “golden” regime from which it emerges and the oligarchy that will follow (547c6–7), is in any case only possible in the rarest of circumstances—only Lycurgus’s founding of Sparta might be said to fit the bill; then oligarchy itself, the bronze regime, is, in the best case, the highest regime for which one might realistically aim or for which there is any encouraging precedent. However that may be, it seems that this form of rule, not by philosophers or wise men but merely those of good repute among the Greeks, is what Plato considers the best realistic solution to the Syracusans’ need for a new regime to restore peace and order to their city.

It would hardly be surprising for a student of Platonic political philosophy to register a sense of disappointment at this conclusion. When finally pressed, the great champion of philosophic utopia counsels the adoption of an imperfect and mundane form of government. It is therefore worthwhile to conclude our exploration of this theme by returning to Letter Eight. For Letter Eight as a whole, as we have seen, purports to do again precisely the same thing that we have been discussing Plato doing at the very center of the Letters, that is, at the end of Letter Seven’s first digression: to provide practical political counsel to the Syracusans in the midst of their mortal dilemma. But as we have also seen, Plato does not make the move in Letter Eight, which he does in Letter Seven, of counseling on the presumption that circumstances have foreclosed the possibility of truly following in Dion’s footsteps. On the contrary, the counsel of Letter Eight is suffused with the spirit of Dion, the first half presenting the “common counsel” of both him and Plato, and the second half presenting Plato’s “interpretation” of what Dion himself would counsel if he were still alive. By carefully comparing the political counsel of Letter Eight, then, with his advising toward oligarchy in Letter Seven, we can appreciate more fully why Plato considered the loftier Dionean alternative to be basically misguided, and hence why he found it necessary to promote a more mundane course of political action when circumstances finally required real, practical advice.

Letter Eight is consistent in directing the Syracusans to transform their regime into a kingship. Kingship here must be distinguished from monarchy: Plato’s Dion ultimately recommends a system of three kings so as to satisfy the varied existing claims to political honor and power in Syracuse (356a7ff.). We begin by noting, however, that Plato himself leaves quite unclear whether the transformation of Syracusan tyranny into a kingship is even possible—a fact that bears some relevance to his characterization of the counsel contained in the letter as a “prayer.” When Plato first proposes this transformation into a kingship, he adds the qualification “if it should be possible” (354a7–b1). Now, although he proceeds to affirm that “it is possible, as Lycurgus,” “a wise and good man,” “showed by deed” (354b1–2; emphasis added), his subsequent explanation of this proof of concept is problematic. For one thing, his story of Lycurgus being provoked by the degradation of Argos and Messene occurs nowhere else in extant accounts—including Plato’s Laws, in which the case of Sparta is compared with those two cities, but the history presented is altogether different (690d1–692b1). More importantly, however, the example Plato cites does not prove his point: Lycurgus preserved a kingship in danger of devolving into tyranny as the kingships of Argos and Messene had done. But Plato here asks the Syracusans to transform their tyranny—which has been a tyranny since the regime’s inception (353b3–4)—into a kingship.

If the Lycurgus example does not prove that such a transformation is possible, then we are left without resolution to the doubt Plato initially casts on its possibility. We may characterize the difficulty in the following way. “Kingly rule” is here explained as rule in which “law [is] a sovereign king over human beings,” and “human beings [are not] tyrants over laws” (354b8–c2). Now Lycurgus is thought to have preserved the king-ship of Sparta by establishing two new political institutions to counterbalance the kingly power and thus to maintain the rule of law. But in Syracuse there is no living history of lawful or kingly rule—even the democratic regime preceding the tyranny of Dionysius the Elder and Hipparinus was “anarchic,” the people ruling “luxuriously” over their rulers, judging their superiors “in no way . . . according to law, in order that they should in no way be enslaved with either justice or law as a master.” This indeed, says Plato, was the source of the tyranny (354d4–e3). There is no doubt but that—to say nothing of the difficulty of changing the “form” of regime in a city (eidos at 354c5; see 321d4–e6)—a new act of lawgiving will be required if a kingship is to be established.

Plato, for his part, gives no sign that he ever held out hope for a legislator to refound Syracuse as a kingship. It is clear that, in Plato’s view, the establishment of an excellent legal order is a matter not only of tremendous difficulty but also of chance—indeed, this was the specific and explicit conclusion of the series of observations that led Plato to withdraw from politics according to Letter Seven (326a1–5). But Plato makes it equally clear that Dion, for his part, failed to appreciate the monumental difficulty of bringing about “freedom under kingly rule” (355d8–e1). Accordingly, in Letter Four (which belongs to the critical time following Dion’s initial triumph over Dionysius), Plato advises Dion that he must be prepared to outdo even Lycurgus and Cyrus (320d5–8)—a task to which, as it would turn out, Dion was not equal. We must recognize that, in attempting to provide useful advice to the Syracusans—that is, in Letter Seven, which proves to be a franker and more practicable version than Letter Eight—Plato’s primary concern was to contrive some means for generating new laws for the Syracusans: laws devised and laid down not by lawgivers who are rare paragons of wisdom or virtue, but by lawgivers who are conventionally respectable and therefore practically obtainable Greek gentlemen. One cannot produce a Lycurgus at will, but one may hope to construct a stable and benign oligarchy (consider Laws 710e5–7), which will be vastly preferable to the ravages of civil war.

Plato’s counsel to Dion’s comrades thus expresses a kind of political realism not usually associated with Platonic political philosophy. This strain of Platonic realism helps us to identify, by contrast, the major defect in Dion’s own political idealism. The counsel Plato offers the Syracusans in Letter Seven is focused almost exclusively on the need to find a legislative mechanism by which to obtain a new and stable Syracusan constitution. The Platonically reanimated Dion of Letter Eight, however, is singularly insensitive to the need for such a mechanism. This imagined Dion begins his address to the Syracusans with the injunction that they must accept the right kind of laws—laws that accurately reflect the Platonic denigration of pleasure and money, and the Platonic exaltation of care for the soul (355a8–c6). This beginning is crucially flawed: Dion here gives no explanation of where these laws will come from. Moreover, he concludes this initial injunction by insisting thus: “That these things I encourage are true, you will recognize by deed if you shall taste the things now being said concerning laws, which seems to come to be the truest test concerning all things” (355c5–8). Does not the metaphor of taste suggest that the Syracusans must experience life under such laws as Dion describes? In other words, the Syracusans cannot be persuaded to accept Dion’s recommendation until they have already accepted it and “tasted” its fruit firsthand. To his credit, Dion does at least seem aware that the Syracusans are not likely to be persuaded as he himself was by the force of Plato’s persuasive rhetoric alone. But he seems to overlook the fact that, if the Gordian knot he has unwittingly described is to be split, the Syracusans must be forced to “taste” the laws they will ultimately learn to love. It is no use merely to direct them to “accept” such laws in speech.

Dion is perfectly clear that it is after their “having accepted such laws” (355c8) that he would have the Syracusans attend to the form of the regime. It is at this moment that he reckons with the “danger” that “has taken hold of Sicily,” and thereby recognizes the need to accommodate both of its rival factions under the new regime and its laws—to “cut down the middle,” as he puts it, by establishing three kings, including representatives of both factions. That is, it is only after the Syracusans’ acceptance of the initial laws, of unexplained provenance, that Dion will deal with those exigent circumstances that in Plato’s view called for the abandonment of the Dionean course altogether. Plato saw that it would be extremely difficult to get the dominant faction at any given time to prefer compromise to the hope of annihilating the enemy; and then, in the unlikely case that one faction should choose compromise, Plato knows that the only hope of obtaining legislation that will be viewed as impartial is to invite lawgivers from outside the city—and even then the vanquished party must be cowed into submission “by means of a pair of compulsions, awe and fear” (337a3–5). Dion is stunningly inattentive to this whole cluster of obstacles and concerns. It is as if he hopes or expects that the new laws, to be accepted spontaneously by all the Syracusans in common, are to arrive via some deus ex machina.

Dion’s whole counsel proves to be pervaded by this same grave difficulty. The first order of business for the three kings, who are to be established only after the Syracusans have accepted good laws, will be to “set down laws and the sort of regime in which it is consonant for kings to come to be sovereign authorities,” and so on (356c8–d2). The circularity of this procedure is a result of the key failing of Dion’s political thought: he has not given sufficient attention to the difficult problem of political foundings. It seems he recoils instinctively from the ugly business of “laying down the law” for a new regime. It is in the nature of such a task that it take place in a context of political and legal flux, and, as Machiavelli’s intensive treatment of the theme infamously makes clear, even the noblest political undertakings require some not altogether noble beginning. Plato’s counsel to bring in respectable Greeks to found the new Syracusan regime would seem merely to point to the gentlest possible version of such a beginning.

Even more than in Letter Seven, Plato shows his awareness of the true dimensions of the problem of political founding in Letter Eleven, where he responds to a request for his help in the founding of a new colony. Plato warns that the colonists’ attempt at founding will fail without a properly educated sovereign to oversee the daily life of the city’s inhabitants—in the absence of such a sovereign, nothing would remain for the colonists to do but “to pray to the gods” (359b3). But, Plato continues, “the earlier cities too were established in nearly this way and were well managed thereafter, under the coming-to-be of conjunctions of great affairs, both in war and in the other actions—whenever, at the propitious moments, a man both noble and good came about having great power” (359b4–8). There is an ambiguity here: Does Plato intend for his account of the origin of “the earlier cities” to lend support to his paradigm of a colony overseen by a wise sovereign authority? Or is this account rather supposed to encourage Laodamas and the colonists, to make them more hopeful, in the event they find themselves lacking such a sovereign authority and forced to resort to prayer? That is, is the “noble and good” man who exercises his “great power” for the sake of the city meant as a model of the educated sovereign? Or is his appearance, together with the “conjunctions of great affairs,” an example of the alternative to such a sovereign, which benevolent gods might provide?

On one hand, Plato concludes by stressing to Laodamas the necessity of remaining eager and thoughtfully prepared for the emergence of the right opportunity, whether “in war” or “in the other actions,” and ends the letter with the word eutuchei, “good luck” (359b8–c3)—the same word with which he ends all of the letters (or portions of letters; see 337e1) most fully devoted to providing political counsel (321c1, 322c1, 357d2). Plato evidently counsels Laodamas, then, to be ready to intervene as a “noble and good man” himself, should the opportune moment arise. On the other hand, it is unlikely that Plato considers Laodamas a candidate to be the sovereign overseer described earlier in the letter—otherwise, there would have been no need for Plato to raise the question whether anyone qualified for the office existed among the colonists. It seems, then, that we must distinguish the case of the wise sovereign who actively upholds the courageous and moderate ways of life in the city from the case of the noble and good man who seizes power at a critical moment. For the latter case, which Plato claims has generally obtained in successfully established cities, Plato indicates a need both for divine providence—it is a case for which the colonists should pray—and for vigilance and decisive action on the part of the founder, combined with “good luck.”

There is a difficulty, however, in which Plato becomes involved by offering counsel to the prospective founder: the good fortune for which Laodamas and the colonists should pray, and the propitious moment that the founder must seize, is a moment of grave crisis for the city, a “conjunction of great affairs, both in war and the other actions.” His phrase here is reminiscent of a passage in the Laws, where the Athenian Stranger claims that the great innovations or revolutions in laws and regimes are always prompted by “chances and misfortunes of every sort,” such as “war,” “harsh poverty,” “plagues,” and prolonged periods of inhospitable weather. The Stranger takes this as evidence that “no mortal ever legislates anything,” since “almost all human matters belong to chance,” before adding that the same thing may just as well be said thus: “In all things a god—and together with a god, chance and a propitious moment—pilots all the human things” (709a1–b8). The Stranger’s equivocation as to whether human affairs are determined providentially or purely accidentally has a parallel in Plato’s telling Laodamas both that he must resign himself to prayer and that he must prepare himself to seize decisively upon a moment of “good luck” when it arises. There are, however, the following differences. The Stranger, who has decided to devote a great deal of energy to helping his interlocutors in the founding of their new colony, is quite explicit in his enumeration of the varieties of catastrophe that decide the course of human affairs. Plato, who leaves Laodamas on his own in the founding of his colony, providing only so much advice as can fit into a very brief letter, speaks vaguely about the “propitious moments” for which Laodamas must be prepared. By referring to Laodamas’s model as a gentleman, a “noble and good man” (kalos te kai agathos), Plato emphasizes the difficult but noble end at which the founder aims; he directs the reader’s gaze as much as possible away from the observation that the insight about the “propitious moments” for the founding of cities could equally be exploited by an aspiring tyrant. Machiavelli, by contrast, is much less cautious in his counsel to princes. This difference in degree of cautiousness is reflected also by the fact that Plato declines in this context to make the Machiavellian suggestion that human virtue might substitute for fortune or divine favor (cf. 353b4–7). Plato is much less willing than Machiavelli to encourage the prospective founder to discard his belief in divine providence as a determining factor in political affairs.

Does the Letters suggest in any consistent manner that Platonic philosophy issues in concrete political guidance? More than anything else, the Letters suggests that political affairs belong too much to the realm of flux and chance to be mastered or that great political undertakings require more good fortune than one can reasonably hope for. The possibility that the vicissitudes of fortune may be subject to the wills of providential deities does little to alter this dim evaluation of human efficacy: prayer, as anyone can observe, offers no guarantee of good fortune (Second Alcibiades 138a7–b4). But our portrait of Plato, resigned to the indomitability of political affairs and thus reluctant to provide political counsel, remains woefully incomplete without the identification of the alternative to political striving that he would direct us to choose in its place. We have already recognized that the whole Platonic Syracusan project was driven to a great extent by concern for the reputation of philosophy. It is devotion to philosophy that appears to hold the highest place in Plato’s economy of concerns, higher certainly than political activity in itself, and it seems to be only this end that can draw him into political activities to which he would otherwise be totally averse. To go to such great lengths for such a cause, however, indeed to risk the kind of danger and destruction that were consequent to Plato’s dealings in Syracuse, calls for some explanation. What is the character and import of this philosophic activity, for the sake of which Plato was willing to go so far and at such a great cost?