Podcast Summary: The Politics of Shakespeare, Part Two

Podcast: Hillsdale College Podcast Network Superfeed
Date: March 2, 2026
Host: Hugh Hewitt
Guest: Dr. Khalil Habib (Hillsdale College Professor of Political Theory)

Overview

This episode explores the political themes in Shakespeare’s history plays, especially focusing on Henry VI and Richard III. The discussion connects Shakespeare’s portrayals of monarchy, tyranny, and republicanism to Enlightenment political philosophy, particularly Montesquieu’s The Spirit of the Laws, and considers their resonance with the American founding and constitutional order. Dr. Khalil Habib dives into why these plays matter, Shakespeare’s critique of hereditary monarchs, Machiavellian politics, the interplay of morality and evil, and Shakespeare’s enduring influence on Western civic thought.

Key Discussion Points & Insights

1. Shakespeare’s Place at Hillsdale and the Neglect of the Henry VI Plays

• [01:01] Dr. Habib notes student enthusiasm for his Shakespeare course, specifically the Henry VI plays:

  “Shakespeare is beloved on our campus. Students absolutely love him. But no one's read the Henry VI plays...they're overshadowed by Hamlet and Romeo and Juliet.” (Dr. Khalil Habib)

• The plays are surprisingly in demand; students enjoy engaging with the lesser-known works.

2. Montesquieu, Liberty, and the English Constitution

• [01:59] Montesquieu saw the English constitution as a “republic hidden inside of a monarchy...”

  “Shakespeare is...tracing the emergence of a republican spirit within England. And it really does begin in these English history plays. And as the Plantagenets are escorted out the door, you see the rise of something like a modern state.” (Dr. Khalil Habib)

• Liberty is not just written law, but “the opinion of one's security”; true liberty requires separation of powers and institutional safeguards.

3. The Plantagenet Lineage and Their Legacy

• [04:00] The Plantagenets (from King John to Richard III) are described as “the bloodiest royal family” and central to Shakespeare’s critique of monarchy.

4. Richard III: Shakespeare’s Most Machiavellian Character

• [05:18] Richard III is unique among Shakespeare’s characters for openly embracing Machiavellian principles:

  “He’s the only character in all of Shakespeare’s work who identifies himself as Machiavelli. So it’s not a Straussian reading…It’s a play in which you find a lot of soliloquies. And there’s a simple reason why. He wishes to found alone.” (Dr. Khalil Habib)

• The play opens with a famous soliloquy, underlining Richard's isolation and cunning.

Memorable Story:

• [06:28] Hugh Hewitt shares Jon Voight’s impromptu Richard III performance on a turbulent flight—a testament to the enduring power of Shakespearean monologues.

5. The Political Failure of Henry VI and Rise of Richard III

• [06:59] Richard III’s ascent is a direct result of Henry VI’s inability to rule firmly:

  “Henry VI just couldn’t put his foot down...his father would have had no problem. Richard III is the direct result of Henry VI’s failures.” (Dr. Khalil Habib)

• Richard has a legitimate claim but is “misaligned”—he is the “devil incarnate,” courageous and cunning but evil for its own sake.

6. Richard III’s Crimes and Character

• [09:06] Richard’s villainy is comprehensive: he is implicated in the deaths of his brothers and the princes in the tower, reveling in murder.

  “He just has, as Nietzsche would say, a thrill for the knife.” (Dr. Khalil Habib)

7. Richard III’s Physical Deformity and Moral Evil

• [11:56] Discussion of the real Richard’s hunchback, confirmed by recent archeology.

  “He tells us...that his ugliness liberated him from the illusions of love so that he could just take advantage and exploit people...” (Dr. Khalil Habib)

• Richard’s “misshapenness” is symbolic and functional in the play.

8. Is Richard III Machiavelli?

• [13:23] Strong parallels between Machiavellian political theory and Richard’s methods.

  “Richard is presented in some ways as extraordinary and impressive...But there is, I believe, a critique.” (Dr. Khalil Habib)

• [14:30] Shakespeare critiques Machiavelli through Richmond’s victory, highlighting that love and justice can trump fear:

  “The pull to justice is always stronger than fear...Politics requires compromise and partnership and friendship. And so it begins with a soliloquy, and it ends with him dying like a dog in battle.” (Dr. Khalil Habib)

9. Catholicism, Religious Imagery, and English Identity

• [16:42] The plays’ references to Catholic practices are historically accurate:

  “These plays are set prior to the Reformation, and so it would be historically accurate to present them as Catholics.” (Dr. Khalil Habib)

• Catholicism serves a critical role in redeeming the nation from tyrannical dynasties.

10. Shakespeare, Regicide and the Foundations of Political Order

• [18:02] The deposing of Richard III aligns with Aquinas' teachings: tyranny may be lawfully overthrown, but only through proper institutions—not just any person.

  “It’s the proper people, through the proper institutional channels, essentially destroying Richard III and freeing England from tyranny…totally consistent with Aquinas on that score.” (Dr. Khalil Habib)

11. The Enduring Allure of Evil Characters

• [19:17]

  “There’s something seductive about him...But he does show you, at the end of the day, human beings do live in a moral order, and they do live in a political order. And man cannot live outside of the city...Richard tries to be a God, but he dies like a beast. Very Aristotelian.” (Dr. Khalil Habib)

• The plays reaffirm the necessity of virtue and justice, warning against the Machiavellian path.

12. Virtù: The Machiavellian Standard

• [20:37] On Machiavelli’s “virtù”:

  “Virtue and a prince [means] relying on one’s own arms...Richard is presented [as such]. Now, Henry V is a different animal…Shakespeare himself makes Richard III explicitly that [Machiavellian character].” (Dr. Khalil Habib)

13. Shakespeare, Evil, and Political Temptation

• [23:54] Students are struck by the overt treatment of evil and the demonic in the plays, challenging purely secular readings of politics.

  “There’s a lot of evil and flirtation with Satanism actually in these plays. Joan is working with the demonic...a part of their ambition and their desire to disrupt the political order.” (Dr. Khalil Habib)

14. Shakespeare’s Authorship and Mastery

• [25:13]

  “My experience on committees makes me doubt that more than one person could have produced something that coherent...[Shakespeare’s works] are just too interconnected.” (Dr. Khalil Habib)

15. Shakespeare’s Republican Sympathies

• [26:57] Shakespeare presents Caesar as frail compared to real historic accounts—possibly as a “closet Republican.”

  “I think Shakespeare is a Closet Republican...sympathetically, even though...he’s a true aristocrat.” (Dr. Khalil Habib)

16. Who Was Montesquieu and Why Does He Matter?

• [29:17] Montesquieu’s The Spirit of the Laws was crucial for the U.S. founding:

  “He is the second most quoted authority among the American founders...They take Montesquieu’s path...the way to deal with [factions] is not to deprive people of liberty, but to create a confederated republic...” (Dr. Khalil Habib)

• American separation of powers and federalism owe much to Montesquieu’s design.

17. Montesquieu and the American Political Anxiety

• [32:47] Montesquieu saw political anxiety—not complacency—as essential for liberty:

  “This kind of anxiety...is actually not a bug. It’s a feature of the separation of powers. Because Montesquieu thought, your liberty is destroyed the moment you become complacent.” (Dr. Khalil Habib)

18. Churchill and Shakespeare’s History Plays

• [34:39] Churchill was deeply influenced by the English history plays, often attending performances and even mouthing the lines.

  “He loved the English history plays...Churchill himself wrote a history of the English speaking peoples. And I think he was absolutely educated and formed by Shakespeare.” (Dr. Khalil Habib)

Notable Quotes & Memorable Moments

• Richard III as Machiavelli:

  “He’s the only character in all of Shakespeare’s work who identifies himself as Machiavelli…he wishes to found alone…”
  (Dr. Khalil Habib, 05:18)

• On the Allure and Downfall of Richard III:

  “Richard tries to be a God, but he dies like a beast. Very Aristotelian.”
  (Dr. Khalil Habib, 19:17)

• On Political Liberty and Montesquieu:

  “Liberty, as Montesquieu describes it, is the opinion of one’s security that nobody has to fear the arbitrary harm from a fellow, whether it’s from a ruler, a representative or a fellow citizen.”
  (Dr. Khalil Habib, 02:59)

• On Shakespeare and Evil:

  “They are quite satisfied and happy to see somebody take seriously evil and say it’s evil...It’s the first time they see somebody of the magnitude of Shakespeare presenting politics with that lens of looking at the world in terms of good and evil.”
  (Dr. Khalil Habib, 23:54)

Timestamps for Important Segments

• [01:01] Student interest in Shakespeare’s lesser-known plays
• [01:59] Montesquieu on the English constitution and liberty
• [05:18] Richard III as Shakespeare’s Machiavellian villain
• [09:06] Richard’s crimes and evil nature
• [11:56] Richard III’s physical deformity and moral character
• [13:23] Richard III vs. Machiavelli – Shakespeare’s critique
• [16:42] Catholic imagery and politics in Shakespeare
• [18:02] Regicide, legitimacy, and overthrowing tyranny
• [19:17] The seductive power and ultimate fate of evil
• [20:37] On Machiavelli’s “virtù” and Henry V vs. Richard III
• [23:54] The theme of evil and the demonic in Shakespeare
• [25:13] Shakespeare’s authorship and artistic coherence
• [26:57] Shakespeare’s republican leanings and portrayal of Caesar
• [29:17] Montesquieu’s impact on the American founding
• [32:47] The productive anxiety of the separation of powers
• [34:39] Churchill’s passion for Shakespeare’s history plays

Tone and Style

The conversation is learned and spirited but accessible, blending scholarly analysis with personal anecdotes and broader cultural references. Dr. Habib’s explanations are rich but never condescending, inviting listeners to see Shakespeare as both political commentator and timeless dramatist.

Conclusion

This episode masterfully connects Shakespeare’s history plays with foundational concepts in Western political thought. Dr. Habib and Hugh Hewitt show how characters like Richard III and the fate of the Plantagenets illuminate issues of liberty, tyranny, virtue, and the very mechanisms that underpin constitutional government—in Shakespeare's England and in America’s founding vision. The dialogue encourages a robust appreciation of literature’s role in understanding the perennial questions of political order and justice.