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When Good People Lose Themselves to Tyrants | James Romm (PT. 2)

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Aug 16, 2025

Guest

James Romm

James Romm, a Professor of Classics at Bard College, delves into the chaos of ancient Greece and Rome, focusing on philosophers like Plato and Seneca. Their intriguing discussions reveal the moral dilemmas faced by these thinkers when advising tyrants. Romm highlights how ambition can erode integrity and the struggles for self-respect amidst tyranny. They explore the psychological burden of political mistakes and draw parallels with contemporary governance, revealing timeless lessons about leadership, accountability, and the dangers of sycophancy.

54:48

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ANECDOTE

Visiting Plato's Humble Academy

Ryan Holiday describes visiting Plato's Academy in Athens and finding only a simple park and a hole in the ground.
He contrasts its modest preservation with abundant Greek sites and reflects on imagination's role in connecting to history.

insights

INSIGHT

Philosophy Can Become Complicit

James Romm asks whether Plato collaborated with evil by advising tyrants and whether Republic partly explains or obscures those mistakes.
That question reframes philosophy as potentially complicit when theory meets political practice.

question_answer

ANECDOTE

Plato's Second Trip To Syracuse

Romm recounts Plato returning to Syracuse despite a disastrous first stay and believing he could test Dionysius into virtue.
That replay shows Plato's naivete and human self-deception in thinking instruction can remake a tyrant.

Get the Snipd Podcast app to discover more snips from this episode

Philosophers and Tyrants: A Historical Reflection

01:59 • 13min

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Navigating Moral Compromise in Tyranny

14:33 • 5min

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Navigating Accountability in Political History

19:11 • 17min

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Treachery and Tyranny: A Tale from Herodotus

36:30 • 4min

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Running and Reflections on Nutrition and History

40:33 • 3min

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Philosophy and Personal Paradoxes

44:02 • 14min

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Philosophical Insights on Leadership and Morality

Travels with Herodotus

Ryszard Kapuscinski

#11960

• Mentioned in 3 episodes

Plato and the Tyrant

James Romm

#4419

• Mentioned in 7 episodes

How to be a leader

Donald R. Fessler

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• Mentioned in 6 episodes

THE LAST OF THE WINE

Mary Renault

The Last of the Wine is a historical novel by Mary Renault, published in 1956. It follows the life of Alexias, a young Athenian, as he navigates love, friendship, and the tumultuous political landscape of ancient Athens during the Peloponnesian War. The novel explores themes of love, friendship, and the pursuit of excellence, providing a rich portrayal of life in ancient Greece.

#12098

• Mentioned in 3 episodes

Letters of a Stoic

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Seneca the Younger

Seneca's "Letters from a Stoic" offers a personal and practical guide to Stoic philosophy. Through intimate letters to his friend Lucilius, Seneca explores various aspects of Stoic living, including managing emotions, dealing with adversity, and finding inner peace. The letters provide relatable examples and insights into Seneca's own life experiences. They offer a blend of philosophical reflection and practical advice, making them accessible and relevant to modern readers. The collection remains a timeless source of wisdom for those seeking self-improvement and a more fulfilling life.

• Mentioned in 769 episodes

Meditations

Marcus Aurelius

Meditations is a series of private writings composed by Marcus Aurelius, one of Rome's greatest emperors, as he struggled to understand himself and make sense of the universe. Written between 170 and 180 CE while on military campaigns, this work combines Stoic philosophy with personal observations on leadership, duty, mortality, and human nature. Through twelve books of intimate thoughts never intended for publication, Marcus Aurelius explores themes of self-improvement, resilience in the face of adversity, and living virtuously while accepting what cannot be changed.

#99

• Mentioned in 114 episodes

The great Gatsby

F. Scott Fitzgerald

Published in 1925, 'The Great Gatsby' is a tragic love story, a mystery, and a social commentary on American life during the Jazz Age. The novel is narrated by Nick Carraway, who moves to Long Island and becomes entangled in the lives of his wealthy and mysterious neighbor, Jay Gatsby, and Gatsby's obsession to win back his first love, Daisy Buchanan. The story delves into themes of honesty, the temptations of wealth, and the struggle to escape the past, ultimately reflecting on the disintegration of the American Dream.

#11416

• Mentioned in 3 episodes

Herodotus

G. C. Macaulay

Herodotus's Histories is considered a foundational work of history, offering a detailed account of the Greco-Persian Wars. It blends historical narrative with ethnographic observations, providing insights into the cultures and customs of various ancient societies. Herodotus's approach, often described as 'inquiry,' involved gathering information from diverse sources and presenting multiple perspectives. His work is celebrated for its vivid storytelling and enduring influence on historical writing. The Histories remains a valuable source for understanding the ancient world and the development of historical methodology.

#252

• Mentioned in 59 episodes

How Not to Die

Michael Greger

Gene Stone

In *How Not to Die*, Dr. Michael Greger examines the top 15 causes of premature death in America, including heart disease, various cancers, diabetes, Parkinson's, and high blood pressure. He explains how nutritional and lifestyle interventions can often be more effective than pharmaceutical and surgical approaches in preventing and reversing these diseases. The book includes Dr. Greger's Daily Dozen, a checklist of foods to consume daily for maximum health benefits, and is backed by extensive scientific research and evidence.

#1306

• Mentioned in 19 episodes

Dying Every Day

Seneca at the Court of Nero

James Romm

This book delves into the life of Seneca, a Stoic philosopher, as he navigated the complexities and dangers of serving as an advisor to the Roman Emperor Nero. It examines Seneca's philosophical writings and their relevance to his personal and political struggles, providing insights into the intersection of philosophy and politics in ancient Rome.

History has a way of looking calmer than it really was. In this PT. 2 episode, Ryan sits down with historian and author James Romm to talk about the messy, dangerous, and often absurd reality of life in ancient Greece and Rome, especially for the philosophers who tried to “advise” the powerful. From Plato’s naïve trips to Syracuse, to Seneca’s complicated dance with Nero, to Marcus Aurelius resisting the pull of corruption, they discuss the timeless tension between access and integrity.

James Romm is an author, reviewer, and a Professor of Classics at Bard College in Annandale, NY. He specializes in ancient Greek and Roman culture and civilization. His reviews and essays have appeared in the New Yorker, the Wall Street Journal, the London Review of Books, the Daily Beast, and other venues. He has held the Guggenheim Fellowship (1999-2000), the Birkelund Fellowship at the Dorothy and Lewis B. Cullman Center for Writers and Scholars at the New York Public Library (2010-11), and a Biography Fellowship at the Leon Levy Center of the City University of New York (2014-15).

Follow James on Instagram @James.Romm and check out more of his work at his website, www.jamesromm.com

📚 Get signed copies of James' latest book Plato and the Tyrant, and his other books Dying Every Day, How To Die, and How To Give, at The Painted Porch | https://www.thepaintedporch.com/

📚 View the full list of books mentioned in this episode here: https://www.thepaintedporch.com/collections/james-romm

🎥 Head to Ryan Holiday’s YouTube Channel to watch him give James Romm book recommendations at The Painted Porch: https://www.youtube.com/watch?v=iUuxMfJRc2c

🎙️ Listen to James Romm’s first episode on The Daily Stoic Podcast: https://dailystoic.com/romm/

📖 Preorder the final book in Ryan Holiday's The Stoic Virtues Series: "Wisdom Takes Work": https://store.dailystoic.com/pages/wisdom-takes-work

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