Podcast Summary: “Plato and the Tyrant” – James Romm on the New Books Network

Podcast: New Books Network
Host: Paul Sterman
Guest: James Romm (author, Professor of Classics at Bard College)
Episode Date: September 13, 2025

Episode Overview

This episode explores James Romm’s new book Plato and the Tyrant, which examines Plato’s journeys to Syracuse, his involvement with the city’s infamous tyrants, and how his personal encounters shaped both his political philosophy and his most influential works. Romm, building on rarely discussed Platonic letters, provides a rare biography of Plato as a complex, fallible human deeply enmeshed in efforts to influence—and possibly reform—the most powerful authoritarian regime of his day.

Main Discussion Points and Insights

1. The Forgotten Story: Plato’s Letters and Journeys to Syracuse

• Platonic Letters: Romm emphasizes the extraordinary value of five under-read letters attributed to Plato, which he regards as authentic and biographically revealing ([01:56]).

  • “They seem to me to be entirely genuine and incredibly revealing of Plato the man.” – James Romm [02:23]

• Historical Context of Syracuse:

  • Syracuse was the major Greek power in the west, surpassing even Athens and Sparta at times ([04:04]–[04:31]).
  • It faced existential threats from Carthage (modern Tunisia), paralleling the mainland Greek struggle with Persia ([05:18], [06:14]).

2. Plato’s Motivation: Tyranny, Power, and Philosophy

• Personal Background:
  • Plato, already a seasoned thinker at 40, was grappling with issues of tyranny, having witnessed the “Rule of the 30” in his youth ([10:06]).
• The Republic and Tyranny:
  • His philosophical inquiries into government coincided with his practical observation of Syracuse’s authoritarian rule ([09:03], [11:19]).
• Motivation for the Book:
  • Romm discovered these stories while researching another book, finding Plato’s Syracuse adventure “swept [him] off [his] feet” ([12:23]).

3. Contemporary Resonance of Tyranny

• Modern Parallels:
  • Romm acknowledges that Plato’s struggles with tyranny resonate today, with references to rising authoritarianism globally and in the US ([14:18], [15:07]).
    • “In an era when the lure of authoritarianism is stronger than ever, this story has resonance.” – James Romm [14:18]

4. The Psychology of Tyrants

• Character of Dionysius the Elder:

  • Dionysius favored the worst, rewarding toadies and enabling a culture of flattery out of self-preservation ([16:00]–[17:45]).
    • “[Dionysius] said … ‘I want there to be someone who's hated more than I am.’” – James Romm (quoting source) [15:57]

• Comic Shamelessness at Court:

  • Romm describes the antics and abasement of court flatterers, sometimes humorous but ultimately destructive ([18:07], [18:38]).
    • “It's a study in self-abasement that unfortunately has all too much resonance with things going on today.” – James Romm [18:07]

5. Plato’s Three Fateful Visits to Syracuse

First Visit: Naïveté in the Face of Power ([19:29]–[22:55])

• Plato attempts to advise Dionysius the Elder, ends up insulted and allegedly sold into slavery ([19:42]–[20:29]).
• “He blundered into situations that forced him to make terrible compromises, moral compromises, and actually endangered his life.” – James Romm [22:55]

Relationship with Dion

• Dion emerges as Plato’s “most promising, most rewarding acolyte ... abstemious and temperate in his own habits” ([24:59]).
• Romm notes their relationship was likely both pedagogic and romantic ([25:34]).

Second Visit: The Philosopher’s Hope and Disappointment ([26:09]–[37:21])

• Trigger: 20 years later, Dion asks Plato to return to instruct Dionysius the Younger, described as a “blank slate” ([27:04], [27:21]).
• Plato hopes to realize the “Syracuse project”—to unite philosophy with absolute power ([28:13], [28:25]).
• Ultimately, court intrigue leads to Dion’s exile, and Plato is stranded, manipulated via Dion’s fortunes ([29:10]–[33:11]).
  • “The principal leverage ... was the fate of Dion.” – James Romm [31:50]

Third Visit: Final Disillusion and Rescue ([43:38]–[57:42])

• Older and warier, Plato returns, hoping to secure Dion’s restoration amid promises that are never kept by the tyrant ([44:06]–[45:34]).
• Tension erupts over Dion’s estate; Plato is moved out of the palace into a dangerous barracks ([50:08]–[52:54]).
• Plato is suspected of plotting a coup but presents himself as a cautious reformer, not a revolutionary ([53:11]–[54:18]).
  • “I don't think he meant to instigate a coup ... But I think he would have been happy if one took place.” – James Romm [54:47]
• Eventually, Plato is exfiltrated by philosopher-king Archytas of Tarentum, returning to Athens “very much in defeat” ([57:03]–[57:42]).

6. Aftermath and Influence

• Plato as Flesh-and-Blood Human:

  • Romm reflects on how the Syracuse adventures make Plato appear “much more human … not a marble bust any longer” ([34:01]–[35:03]).

• Tyranny as Contagion:

  • The “Syracuse model” is imitated across the Greek world ([47:09]–[48:00]).
    • “It is contagious, yes.” – James Romm [48:00]

• Learning and Adaptation:

  • Plato is influenced by alternative models like philosopher-king Archytas in Tarentum ([48:17]–[50:01]).
    • “He was learning by his own experience ... willing to have the world teach him.” – Paul Sterman [49:35]

Notable Quotes & Memorable Moments

• “We have this idealized image of Plato in the Western humanities … but his works give us no insight into who he was.” – James Romm [34:01]
• “Your administrators … are not telling you the truth … they're telling you what you want to hear and that's leading you into bad policy.” – James Romm (on Plato’s letter to Dionysius) [18:49]
• “He blundered into situations that forced him to make terrible compromises, moral compromises, and actually endangered his life.” – James Romm [22:55]
• “In an era when the lure of authoritarianism is stronger than ever, this story has resonance.” – James Romm [14:18]
• “It's a study in self-abasement that unfortunately has all too much resonance with things going on today.” – James Romm [18:07]
• “Plato was intensely concerned over Dion's fate. And the tyrant had the ability to either withhold Dion's entire estate, that is, impoverish him, or bring him back and reinstate him.” – James Romm [31:50]
• “We can't say that that's wrong … there are good reasons to think that Plato would have been very happy with that outcome and perhaps actually meant to bring it about.” – James Romm (on suspicions of plotting a coup) [54:18]

Timestamps for Key Segments

• [01:56] – Genesis of the book and discovery of the Platonic letters
• [04:04]–[05:18] – Explanation of Syracuse’s historical role
• [09:03]–[11:19] – Plato’s political philosophy and early development
• [14:18]–[15:10] – Contemporary echoes of Plato’s tyranny problem
• [15:57]–[18:07] – The psychology of tyrants and court flattery
• [19:42]–[22:55] – Plato’s first visit and experiences of failure
• [24:59] – Introduction and importance of Dion
• [27:04]–[29:10] – Second Syracuse attempt and the “blank slate” project
• [31:50] – Plato’s vulnerabilities and leverage during his exile
• [43:38]–[45:34] – The third visit and Plato’s waning hope
• [50:08]–[52:54] – Plato’s peril and political geography of Syracuse
• [53:11]–[54:18] – Motives and suspicions about Plato’s “plotting”

Conclusion

James Romm’s book and his conversation on the podcast paint a picture of Plato as deeply human, driven by idealistic hopes, personal attachments, and ultimately forced to wrestle with the gritty realities of political life. His repeated attempts to mold a tyrant into a philosopher-king—each time outmaneuvered, manipulated, or misunderstood—show the enduring tension between philosophical ideals and the brute facts of power. Romm’s work not only deepens our understanding of a “flesh-and-blood” Plato but also makes ancient debates on tyranny feel uncannily relevant for today.

Recommended for listeners interested in: Ancient history, political philosophy, the intersection of idealism and power, and contemporary reflections on authoritarianism.