Podcast Summary

Podcast: A Book with Legs
Episode: James Romm - Plato and the Tyrant
Date: August 18, 2025
Host: Cole Smead (CEO & Portfolio Manager, Smead Capital Management)
Guest: James Romm (Professor of Classics, Bard College; author, Plato and the Tyrant)

Episode Overview

This episode explores Plato's philosophy against the tumultuous backdrop of ancient Greek politics, focusing specifically on Plato’s interactions with the rulers of Syracuse—Dionysius the Elder and Younger—and the real-world attempts (and failures) to instantiate the "philosopher-king" ideal described in Plato’s Republic. Author and historian James Romm brings Plato out of the abstract and into the messiness of actual politics, drawing from letters, personal correspondences, and contextual history to illuminate the gap between Platonic ideals and lived reality. The discussion flows through lessons for leadership, virtue, and the perennial conflict between principle and pragmatism—parallels which still resonate in modern business and investing.

Key Discussion Points and Insights

1. Plato’s Relevance and the Genesis of the Book

[01:55] James Romm notes Plato’s central place in Western thought and cites Bertrand Russell:

"All subsequent philosophy are footnotes to Plato."
Despite Plato's foundational influence, the man himself is elusive; he rarely references his own times in the dialogues.
Romm’s interest was piqued by Plato’s Sicilian misadventures, as recounted in several letters believed to be authentic:

"That story showed more about Plato than all the dialogues put together."
—James Romm [02:50]

2. The Philosopher-King and Declining Democracy

[04:14] Plato, shaped by witnessing the fall and failings of Athenian democracy and the abuses of oligarchic rule (the Thirty Tyrants), posited a new standard: only those trained in philosophy and capable of "absolute justice" should rule.
Plato’s Academy sought to teach future leaders to apprehend "the forms":

"After decades, literally decades of that kind of training, a philosopher might be able to perceive what Plato called the forms...those would guide a ruler."
—James Romm [06:46]

3. Syracuse, Tyranny, and Plato’s Political Odyssey

[09:30] Dionysius the Elder seized power in Syracuse, founding a dynasty by clever use of mercenary forces and absolute control—a contrast to what Plato sought.
The ruler drew from models like Gelo and Hieron, earlier autocrats who maintained power with wealth and military might.

4. Criticism and Resistance: Lysias’s Olympic Stand

[12:30] Lysias, an Athenian with Syracusan roots, denounced Dionysius the Elder at the Olympics, likening him to Persia’s despotic king:

"He accused the tyrant of Syracuse of becoming a threat to all of Greece..."
—James Romm [13:06]
The crowd symbolically destroyed Dionysius’s pavilion—a potent act of political theater [13:54].

5. Tyranny, Wealth, and Mercenaries

[14:18] Dionysius’s absolute power rested on an unprecedented mercenary force:

"Perhaps 100,000 men...peoples from Iberia, from North Africa...not Greeks, but could be counted on for loyalty simply because he was paying their salaries."
—James Romm [14:18]

6. Ortygia: The Island Fortress

[16:14] The militarized, walled peninsula Ortygia functioned as an unassailable base, foiling siege attempts and tightening the tyrant’s grip.

7. Plato’s First Trip to Syracuse

[17:34] Plato visits Syracuse at Dion’s invitation, finds himself at odds with Dionysius the Elder (who craves flattery, not challenge), and is ultimately expelled—possibly sold into slavery:

"Plato was entirely too outspoken for the liking of this tyrant...perhaps the best evidence we have suggests that he was sold into slavery at the behest of the tyrant."
—James Romm [25:10]
Plato’s witty repartee with Dionysius:

"[Dionysius accused Plato of] 'elderizing,'...Plato snapped back...[that Dionysius was] 'tyrantizing.'"
—James Romm [26:13]

8. Founding the Academy

[26:45] After his ordeal, with a friend’s financial help, Plato purchases land outside Athens and starts the Academy—the West’s first higher learning institution devoted to philosophy.

9. Virtue, Temperance, and the Platonic Contrast

[18:37, 19:50, 20:42] The Dionysian (hedonistic) lifestyle of Syracuse stands in contrast to the more austere Doric traditions of Athens and Sparta. Plato viewed these excesses—drunkenness, sexual indulgence—as marks of unfit rulers.

10. Dynastic Schemes & Political Intrigue

[20:17–23:11] Dionysius’s polygamy, intended to produce more heirs and alliances, also introduced deadly rivalries.
Attempts to marry across maternal lines to unite the family led to internecine conflict.

11. Philosopher-Kings in Practice: Plato’s Sicilian Fiascos

[35:20] Despite past humiliations, Plato returns to Syracuse to instruct Dionysius the Younger, who is intellectually curious but poorly suited for philosophical rule. Dion’s (and possibly Plato’s) presence stirs jealousy and political exile.

12. The Reality of Political Power

[39:17] Plato’s abstract program demanded decades of ascetic philosophical training; even he knew Dionysius the Younger would never become his ideal ruler:

"A young man of 30 who is already a debauched alcoholic was never going to get there."
—James Romm [39:17]

13. Syracusan Civil War: Revolution, Betrayal, and the Limits of Idealism

[46:01–54:13] The struggle for Syracuse becomes a complex web of betrayal, populist insurrection, and shifting alliances. The populace grows suspicious of Dion's real intent (is he liberator or just a new autocrat?), a tension inflamed by misleading letters.

14. Virtue and Friendship: The Damon and Pythias Legend

[54:56] Romm recounts the legendary loyalty between Damon and Pythias—Pythagorean exemplars who shock Dionysius the Younger with their steadfastness, refusing his offer of friendship:

"He threw his arms around the two of them, asked to be a third friend and a part of their company, to which they said, no way. You're not one of us."
—James Romm [56:04]

15. Allegory of the Cave and the Limits of Theory

[61:04] Dion, educated by Plato, finds himself unable to translate philosophical ideals into practical governance in a fractious, suspicious post-autocracy.
Cole Smead draws a parallel:

"In academia, there is no difference between the real world and academia. In the real world, there is."
—Cole Smead [61:31]

16. Plato's Spin and Legacy

[62:37] Plato’s Seventh Letter attempts to redeem Dion as a model of noble leadership (but is marked as “spin” by Romm), presenting an idealized version of events to protect Plato’s own reputation.

17. The Myth of Er and the Question of Death

[64:36] In the closing of the Republic, Plato turns to the myth of Er, imagining the afterlife as a moment of choice between philosophical virtue and tyrannical power:

"The task of the philosopher is to recover the visions that he has had before birth of this astral realm..."
—James Romm [64:49]

Notable Quotes and Memorable Moments

On Plato’s practical engagement with politics:

"He gives us very little access to his Persona, his inner life. Yet we do have a set of letters that seem to be by him and I argue are by him that show us the inner person and especially his misdoings or his grave mistakes on the island of Sicily..."
—James Romm [01:55]
On the gap between philosophy and reality:

"A young man of 30 who is already a debauched alcoholic was never going to get there."
—James Romm [39:17]
On academia vs. real world:

"In academia, there is no difference between the real world and academia. In the real world, there is."
—Cole Smead [61:31]
- Repeated for emphasis, capturing the chasm between philosophical theory and political practice.
On Damon and Pythias:

"He threw his arms around the two of them, asked to be a third friend and a part of their company, to which they said, no way. You're not one of us. And that was the end of that."
—James Romm [56:04]
On Plato’s self-interest as philosopher-king, via Karl Popper:

"When he talks about a philosopher king and someone trained in the kind of rigorous mathematical, abstract thinking that Plato's academy specialized in, he can only be talking about himself or at least his own class, the students of the academy."
—James Romm [47:31]
On Plato’s writing as an invitation:

"My book tries to give a basic introduction to the Republic along with this narrative...I hope it leads people to want to pick up the Republic and read the original text."
—James Romm [67:20]

Timestamps for Major Segments

| Timestamp | Segment/Topic | |-----------|-----------------------------------------------| | 01:55 | Why Romm wrote about Plato and the Tyrant | | 04:14 | Plato’s idea of the philosopher king | | 07:48 | The Thirty Tyrants and the fall of Athens | | 09:30 | Dionysius the Elder in Syracuse | | 12:30 | Lysias’s critique at the Olympics | | 14:18 | Mercenaries and autocracy in Syracuse | | 16:14 | The fortification of Ortygia | | 17:34 | Plato’s first visit, Dion’s invitation | | 25:10 | Plato and Dionysius’s confrontation | | 26:45 | Plato’s return to Athens and founding Academy | | 35:20 | Plato’s return to Syracuse under Dionysius Jr.| | 39:17 | The limits of education on tyrannical rulers | | 54:56 | Damon and Pythias, the ideal of virtue | | 61:04 | Dion as failed “philosopher king” | | 62:37 | Plato’s “spin” via the Seventh Letter | | 64:36 | The myth of Er and philosophical legacy | | 67:20 | Final thoughts: the enduring value of The Republic |

Takeaways For Investors and Thinkers

The search for wise, just leadership is ancient—and perpetually fraught with compromise.
Ideals are vital, but their implementation demands practical wisdom and an honest assessment of context and human nature.
Leadership (in business or politics) faces eternal temptations: tyranny, self-dealing, flattery, and short-term pragmatism.
Engaging with the classics, especially The Republic, remains crucial for understanding both personal and institutional ethics.

Podcast Summary

Episode Overview

Key Discussion Points and Insights

1. Plato’s Relevance and the Genesis of the Book

[01:55] James Romm notes Plato’s central place in Western thought and cites Bertrand Russell:

"All subsequent philosophy are footnotes to Plato."
Despite Plato's foundational influence, the man himself is elusive; he rarely references his own times in the dialogues.
Romm’s interest was piqued by Plato’s Sicilian misadventures, as recounted in several letters believed to be authentic:

"That story showed more about Plato than all the dialogues put together."
—James Romm [02:50]

2. The Philosopher-King and Declining Democracy

[04:14] Plato, shaped by witnessing the fall and failings of Athenian democracy and the abuses of oligarchic rule (the Thirty Tyrants), posited a new standard: only those trained in philosophy and capable of "absolute justice" should rule.
Plato’s Academy sought to teach future leaders to apprehend "the forms":

"After decades, literally decades of that kind of training, a philosopher might be able to perceive what Plato called the forms...those would guide a ruler."
—James Romm [06:46]

3. Syracuse, Tyranny, and Plato’s Political Odyssey

[09:30] Dionysius the Elder seized power in Syracuse, founding a dynasty by clever use of mercenary forces and absolute control—a contrast to what Plato sought.
The ruler drew from models like Gelo and Hieron, earlier autocrats who maintained power with wealth and military might.

4. Criticism and Resistance: Lysias’s Olympic Stand

[12:30] Lysias, an Athenian with Syracusan roots, denounced Dionysius the Elder at the Olympics, likening him to Persia’s despotic king:

"He accused the tyrant of Syracuse of becoming a threat to all of Greece..."
—James Romm [13:06]
The crowd symbolically destroyed Dionysius’s pavilion—a potent act of political theater [13:54].

5. Tyranny, Wealth, and Mercenaries

[14:18] Dionysius’s absolute power rested on an unprecedented mercenary force:

"Perhaps 100,000 men...peoples from Iberia, from North Africa...not Greeks, but could be counted on for loyalty simply because he was paying their salaries."
—James Romm [14:18]

6. Ortygia: The Island Fortress

[16:14] The militarized, walled peninsula Ortygia functioned as an unassailable base, foiling siege attempts and tightening the tyrant’s grip.

7. Plato’s First Trip to Syracuse

[17:34] Plato visits Syracuse at Dion’s invitation, finds himself at odds with Dionysius the Elder (who craves flattery, not challenge), and is ultimately expelled—possibly sold into slavery:

"Plato was entirely too outspoken for the liking of this tyrant...perhaps the best evidence we have suggests that he was sold into slavery at the behest of the tyrant."
—James Romm [25:10]
Plato’s witty repartee with Dionysius:

"[Dionysius accused Plato of] 'elderizing,'...Plato snapped back...[that Dionysius was] 'tyrantizing.'"
—James Romm [26:13]

8. Founding the Academy

[26:45] After his ordeal, with a friend’s financial help, Plato purchases land outside Athens and starts the Academy—the West’s first higher learning institution devoted to philosophy.

9. Virtue, Temperance, and the Platonic Contrast

[18:37, 19:50, 20:42] The Dionysian (hedonistic) lifestyle of Syracuse stands in contrast to the more austere Doric traditions of Athens and Sparta. Plato viewed these excesses—drunkenness, sexual indulgence—as marks of unfit rulers.

10. Dynastic Schemes & Political Intrigue

[20:17–23:11] Dionysius’s polygamy, intended to produce more heirs and alliances, also introduced deadly rivalries.
Attempts to marry across maternal lines to unite the family led to internecine conflict.

11. Philosopher-Kings in Practice: Plato’s Sicilian Fiascos

[35:20] Despite past humiliations, Plato returns to Syracuse to instruct Dionysius the Younger, who is intellectually curious but poorly suited for philosophical rule. Dion’s (and possibly Plato’s) presence stirs jealousy and political exile.

12. The Reality of Political Power

[39:17] Plato’s abstract program demanded decades of ascetic philosophical training; even he knew Dionysius the Younger would never become his ideal ruler:

"A young man of 30 who is already a debauched alcoholic was never going to get there."
—James Romm [39:17]

13. Syracusan Civil War: Revolution, Betrayal, and the Limits of Idealism

[46:01–54:13] The struggle for Syracuse becomes a complex web of betrayal, populist insurrection, and shifting alliances. The populace grows suspicious of Dion's real intent (is he liberator or just a new autocrat?), a tension inflamed by misleading letters.

14. Virtue and Friendship: The Damon and Pythias Legend

[54:56] Romm recounts the legendary loyalty between Damon and Pythias—Pythagorean exemplars who shock Dionysius the Younger with their steadfastness, refusing his offer of friendship:

"He threw his arms around the two of them, asked to be a third friend and a part of their company, to which they said, no way. You're not one of us."
—James Romm [56:04]

15. Allegory of the Cave and the Limits of Theory

[61:04] Dion, educated by Plato, finds himself unable to translate philosophical ideals into practical governance in a fractious, suspicious post-autocracy.
Cole Smead draws a parallel:

"In academia, there is no difference between the real world and academia. In the real world, there is."
—Cole Smead [61:31]

16. Plato's Spin and Legacy

[62:37] Plato’s Seventh Letter attempts to redeem Dion as a model of noble leadership (but is marked as “spin” by Romm), presenting an idealized version of events to protect Plato’s own reputation.

17. The Myth of Er and the Question of Death

[64:36] In the closing of the Republic, Plato turns to the myth of Er, imagining the afterlife as a moment of choice between philosophical virtue and tyrannical power:

"The task of the philosopher is to recover the visions that he has had before birth of this astral realm..."
—James Romm [64:49]

Notable Quotes and Memorable Moments

On Plato’s practical engagement with politics:

"He gives us very little access to his Persona, his inner life. Yet we do have a set of letters that seem to be by him and I argue are by him that show us the inner person and especially his misdoings or his grave mistakes on the island of Sicily..."
—James Romm [01:55]
On the gap between philosophy and reality:

"A young man of 30 who is already a debauched alcoholic was never going to get there."
—James Romm [39:17]
On academia vs. real world:

"In academia, there is no difference between the real world and academia. In the real world, there is."
—Cole Smead [61:31]
- Repeated for emphasis, capturing the chasm between philosophical theory and political practice.
On Damon and Pythias:

"He threw his arms around the two of them, asked to be a third friend and a part of their company, to which they said, no way. You're not one of us. And that was the end of that."
—James Romm [56:04]
On Plato’s self-interest as philosopher-king, via Karl Popper:

"When he talks about a philosopher king and someone trained in the kind of rigorous mathematical, abstract thinking that Plato's academy specialized in, he can only be talking about himself or at least his own class, the students of the academy."
—James Romm [47:31]
On Plato’s writing as an invitation:

"My book tries to give a basic introduction to the Republic along with this narrative...I hope it leads people to want to pick up the Republic and read the original text."
—James Romm [67:20]

Timestamps for Major Segments

Takeaways For Investors and Thinkers

The search for wise, just leadership is ancient—and perpetually fraught with compromise.
Ideals are vital, but their implementation demands practical wisdom and an honest assessment of context and human nature.
Leadership (in business or politics) faces eternal temptations: tyranny, self-dealing, flattery, and short-term pragmatism.
Engaging with the classics, especially The Republic, remains crucial for understanding both personal and institutional ethics.

James Romm - Plato and the Tyrant

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Summary

Podcast Summary

Episode Overview

Key Discussion Points and Insights

1. Plato’s Relevance and the Genesis of the Book

2. The Philosopher-King and Declining Democracy

3. Syracuse, Tyranny, and Plato’s Political Odyssey

4. Criticism and Resistance: Lysias’s Olympic Stand

5. Tyranny, Wealth, and Mercenaries

6. Ortygia: The Island Fortress

7. Plato’s First Trip to Syracuse

8. Founding the Academy

9. Virtue, Temperance, and the Platonic Contrast

10. Dynastic Schemes & Political Intrigue

11. Philosopher-Kings in Practice: Plato’s Sicilian Fiascos

12. The Reality of Political Power

13. Syracusan Civil War: Revolution, Betrayal, and the Limits of Idealism

14. Virtue and Friendship: The Damon and Pythias Legend

15. Allegory of the Cave and the Limits of Theory

16. Plato's Spin and Legacy

17. The Myth of Er and the Question of Death

Notable Quotes and Memorable Moments

Timestamps for Major Segments

Takeaways For Investors and Thinkers

Further Reading & Resources

Summary

Podcast Summary

Episode Overview

Key Discussion Points and Insights

1. Plato’s Relevance and the Genesis of the Book

2. The Philosopher-King and Declining Democracy

3. Syracuse, Tyranny, and Plato’s Political Odyssey

4. Criticism and Resistance: Lysias’s Olympic Stand

5. Tyranny, Wealth, and Mercenaries

6. Ortygia: The Island Fortress

7. Plato’s First Trip to Syracuse

8. Founding the Academy

9. Virtue, Temperance, and the Platonic Contrast

10. Dynastic Schemes & Political Intrigue

11. Philosopher-Kings in Practice: Plato’s Sicilian Fiascos

12. The Reality of Political Power

13. Syracusan Civil War: Revolution, Betrayal, and the Limits of Idealism

14. Virtue and Friendship: The Damon and Pythias Legend

15. Allegory of the Cave and the Limits of Theory

16. Plato's Spin and Legacy

17. The Myth of Er and the Question of Death

Notable Quotes and Memorable Moments

Timestamps for Major Segments

Takeaways For Investors and Thinkers

Further Reading & Resources