The Daily Stoic Podcast

Episode: Stephen Greenblatt: Why “This Time Is Different” Is Always Wrong

Host: Ryan Holiday
Guest: Stephen Greenblatt
Date: February 11, 2026

Episode Overview

In this richly insightful episode, Ryan Holiday sits down with acclaimed literary scholar and author Stephen Greenblatt to explore the continuing relevance of ancient wisdom, the recurring patterns in human nature, and why ideas from antiquity—especially those rediscovered in later eras—remain central to our moral and political thinking. The conversation weaves through topics like the survival of classical texts, how creatives navigated (and survived) repressive regimes, and the notion that “this time is different” is almost always proven wrong by history. Greenblatt, known for his Pulitzer Prize-winning book The Swerve, offers profound reflections on literature as rehearsal for human crises, the perils and creativity of constraint, and how both monstrous and likable geniuses shape culture.

Key Discussion Points & Insights

The Survival and Rediscovery of Ancient Texts

• Miraculous Transmission of Classics:
  • Ryan marvels at the “miracle” of ancient texts like Marcus Aurelius’ Meditations surviving the ravages of time, censorship, and destruction ([03:46]).
• The Swerve Defined:
  • Greenblatt’s The Swerve centers on the rediscovery of lost classical works that shifted the trajectory of Western thought, especially through the recovery of Lucretius’ On the Nature of Things ([05:01], [55:16]).

On Montaigne’s Timeless Relevance

• Montaigne’s Tolerance and Self-Exile:
  • Greenblatt expresses great admiration for Montaigne, positioning him as one of the most appealing thinkers for his embrace of intellectual humility and tolerance in intolerant times ([06:55]–[09:15]).
  • “He was determined to survive, but also to figure out how, while surviving, how he would—he wouldn't join one party or another.” —Stephen Greenblatt ([08:46])
• The Art of Being Likable (and Surviving):
  • Montaigne is contrasted with abrasive geniuses, exemplifying how agreeable personalities can exert influence and avoid making enemies ([11:34]).

Shakespeare, Political Dissent, and Dangerous Times

• Art Under Constraint:
  • Discussing Tyrant and Greenblatt's upcoming Dark Renaissance: Shakespeare’s England was "much more like North Korea than North Carolina” in terms of political danger ([15:01]).
  • Shakespeare, like Montaigne, was adept at voicing subversive ideas subtly enough to survive—unlike his risk-taking contemporary Christopher Marlowe, who was murdered at 29 ([15:56]).
• Coded Dissent:
  • Greenblatt cites lines from Shakespeare delivered by mad or marginal characters as examples of indirect social critique that would have been fatal if stated openly ([17:07]–[18:23]).
  • “In Shakespeare’s world, you could actually say things—but only in this special sphere [theater].” —Stephen Greenblatt ([18:46])

Creativity Born of Constraint

• Constraint as Spark:
  • Holiday invokes the Stoic Cleanthes, saying constraint (in poetry or life) is what “brings out the artistry”—but with high stakes in repressive societies ([21:44]).
  • Grossman’s Life and Fate as a 20th-century parallel: written under Stalinism, clandestinely smuggled out, illustrating both the imaginative surge and risk constraint can produce ([22:42]–[24:02]).

Genius and Tyranny in History

• Artists and Psychopaths:
  • Holiday shares a striking image of Da Vinci and Machiavelli working under Caesar Borgia, illustrating how transformative thinkers often served dangerously volatile patrons ([25:15]–[26:41]).
• Concentration of Power:
  • Discussion of how American constitutional innovation created separated powers partly by learning from classical accounts of tyranny, with ancient history feeling vividly real to Enlightenment thinkers ([27:10]–[30:10]).

Ancient Fiction as Moral Rehearsal

• Euripides’ Timeless Refugee Drama:
  • Holiday recounts reading Children of Hercules—a 2,500-year-old dialogue about refugees and national obligation: “It's, like, ripped from the headlines.” ([32:14]–[34:35])
• Literature’s Evolutionary Purpose:
  • Greenblatt posits that storytelling may have evolved as a rehearsal for dealing with critical real-world scenarios—a survival skill ([35:51]).

Subtexts, Art, and Unspoken Politics

• Seneca and Stoic Hypocrisy:
  • Holiday draws a connection between Seneca’s plays (under Nero’s regime) and Shakespeare, noting the indirect critique embedded in tragic drama ([36:32]).
• The Recurrence of the Monstrous Personality:
  • Both agree that insatiable, destructive power-seeking individuals are a perennial human type, as revealed via both ancient literature and primatology ([39:06]).

Progress, Endurance, and the Limits of Change

• No Progress in Human Nature?
  • Greenblatt is struck that art and philosophy show little “progress” compared to science; Paleolithic cave paintings show artistic brilliance undiminished across millennia ([45:59]–[48:36]).
  • Holiday tempers this with the reminder that, while certain human dilemmas repeat, many social conditions (like the eradication of slavery) have changed for the better ([49:09]).

The Allure and Limits of Lost Knowledge

• Dreaming of New Swerves:
  • The conversation concludes with enthusiasm for the high-tech possibility of reading carbonized scrolls from Herculaneum—wondering if undiscovered works by Epicurus or other ancients could cause another intellectual swerve, even if it might only awe the minority who care about such things ([60:21]–[63:53]).

Notable Quotes & Timestamps

• On Montaigne’s Tolerance:
  “That's exactly right. [Zweig’s] biography of Montaigne is I think fundamentally about how one remains tolerant in fundamentally intolerant time.”
  —Ryan Holiday ([08:35])

• On Surviving Repressive Regimes:
  “It’s much more like North Korea than North Carolina.”
  —Stephen Greenblatt ([15:01])

• Constraint Breeds Art:
  “The point of poetry is that the constraints are what bring out the artistry.”
  —Ryan Holiday ([21:44])

• Genius under Psychopaths:
  “If Picasso was attached to like the Gambino crime family”
  —Ryan Holiday ([26:46])

• On Fiction’s Purpose:
  “It must be that people very, very early on…tried to think of alternative scenarios for things...It must be something about our survival skill.”
  —Stephen Greenblatt ([35:51])

• On the Endless Return of Certain Problems:
  “There's no progress in all of this, which is very strange…there's no improvement in painting, as it were.”
  —Stephen Greenblatt ([45:59])

• On Awe and the Swerve:
  “I do think…what we are more likely to do is to feel the kind of awe, the catching one's breathing to discover that people have thought about the things we're worrying about for a very long time.”
  —Stephen Greenblatt ([62:05])

Timestamps for Key Segments

• [03:46]–[05:23] — Introduction to Greenblatt, his books, and the “miracle” of ancient works’ survival
• [06:55]–[11:23] — Montaigne’s approach to intolerance, and the art of likability
• [15:01]–[18:23] — Shakespeare, coded dissent, and the dangerous world of the Renaissance
• [21:44]–[24:37] — Artistic constraint, Grossman’s Life and Fate, and the creativity bred by repression
• [25:15]–[30:10] — Genius serving tyranny, American founders’ classical anxieties
• [32:14]–[34:35] — “Children of Hercules” and the untimeliness of ancient political dilemmas
• [36:32]–[39:06] — Subtext in Seneca’s plays, the enduring “monster” archetype
• [45:59]–[48:36] — The mystery of “progress” in art and human nature
• [55:16]–[58:23] — The atomic “swerve,” rediscovery, and why it mattered to Western thought
• [60:21]–[62:34] — The future of swerve: technology, recovered scrolls, and the allure of new ancient ideas

Memorable Moments

• The playful comparison of Da Vinci and Machiavelli working under a mafia-like tyrant ([25:15]).
• Greenblatt’s story of observing alpha male chimpanzees and seeing clear evolutionary roots for authoritarian dominance ([39:06]).
• The candid agreement that, for existential arguments about death and the afterlife, even the best philosophers seldom persuade emotionally ([59:22]–[60:01]).
• Shared awe at the possibility of uncovering unknown lost philosophical works thanks to modern technology ([62:34]–[63:53]).

Conclusion

This episode’s conversation is a compelling reminder that, from the Renaissance to the present, our perennial anxieties, ambitions, and moral dilemmas are far less “new” than we like to imagine. By drawing lines between ancient text recoveries, the strategies of historical creators under repression, and our own contemporary struggles, Greenblatt and Holiday illuminate the humbling, sometimes hopeful, and invariably fascinating continuity of human experience.