Hillsdale Dialogues – The Politics of Shakespeare, Part Three

Date: March 9, 2026
Host: Hugh Hewitt
Guests: Larry P. Arnn (brief intro), Professor Khalil Habib

Episode Overview

This episode of the Hillsdale Dialogues continues a multi-week exploration of Shakespeare’s history plays, focusing especially on their political lessons and their unique place in the English tradition. Hugh Hewitt and Professor Khalil Habib delve into why Shakespeare wrote the history plays, what they teach about monarchy and republicanism, and the evolution of English identity and government. The episode is particularly centered around Shakespeare’s King John as the entry point to the English history cycle and compares England’s political development to that of other European nations and ancient Rome.

Key Discussion Points and Insights

1. Shakespeare’s History Plays: An Educational Rarity

• Neglected Texts: Professor Habib points out that plays like King John, the Henry VI plays, and Henry VIII are seldom taught, despite being crucial to understanding the evolution of English politics.

  “Even if you’re familiar with Shakespeare, you’re usually not going to get too many English history plays in classes. You might get Henry V, you might get Richard III. But to the best of my knowledge, hardly anyone teaches King John or the Henry VI plays or Henry VIII. And it’s really too bad.” – Prof. Habib (01:33)

2. Why King John? The Bookends of English Transformation

• Beginning and End: Shakespeare’s history play sequence begins with King John and ends with Henry VIII, tracing England’s movement from a feudal Catholic state to an independent, Protestant nation.
• Central Theme: The struggle between monarchy and church (e.g., John’s battle with the Papacy) is emblematic of England’s gradual separation from medieval Christendom and rise of national identity.

  “What he’s tracing in these plays is the transformation of England as part of medieval Christendom and... eventually becoming its own unique English nation.” – Prof. Habib (03:42)

3. Monarchy, Republicanism, and Montesquieu’s Influence

• Shakespeare’s Political Vision: The plays demonstrate the gradual attenuation of aristocratic and ecclesiastic power, clearing the path toward a 'mixed regime'—part monarchy, part republic.

  “What you witness in these plays, I think, is Shakespeare teaching thinkers like Montesquieu how to look at England as kind of a mixed regime. ... There is a certain kind of republican spirit that emerges.” – Prof. Habib (07:13)

• Republican Seeds: Passages like Henry V’s St. Crispin’s speech and the role of the Bastard in King John are cited as anticipatory of English republicanism, despite their “man out of time” status.

4. Succession, Legitimacy, and Family Dynamics in King John

• Inheritance Crisis: The episode unpacks the convoluted royal succession at the heart of King John:
  • The Bastard (Philip Faulconbridge) is the illegitimate son of Richard I;
  • Arthur is the son of John’s older brother and has the stronger legal claim to the throne.
• Power vs. Legitimacy: This conflict is dramatized through Eleanor of Aquitaine’s candid admission to John:

  “He says, ‘I do hold this throne legitimately through both legitimacy and power’. And she said, ‘No, unfortunately, just power. You’re not legitimate.’” – Prof. Habib (09:59)

5. Comparative Politics: Why England Evolves While Europe Revolts

• Geography and Governance: Montesquieu’s argument explained: small, insular countries with a shared history (like England) are less conducive to centralized autocracy.

  “There’s hardly an English history play where you don’t see somebody, some character, mentioning how proud they are that they’re an island, that they’re small, that they’re homogenous, that they have a shared history.” – Prof. Habib (15:22)

• American Founding: Shakespeare’s portrayal of English constitutional evolution influenced American founders—including in the Federalist Papers.

  “Tocqueville mentions how every cabin he came across in his journey throughout America seemed to have a complete copy of Shakespeare’s plays.” – Prof. Habib (17:42)

6. Locke vs. Montesquieu in the American Context

• Locke as Ideal, Montesquieu as Implementation:

  “I think Locke is the language of natural right, and Montesquieu is the engineering of how to secure them.” – Prof. Habib (18:58)

• Montesquieu’s model of separated powers (rather than Locke’s) is the one the Constitution adopts explicitly.

7. Religion and Politics: The Catholic Question

• The conflict between church and state in the history plays is re-examined in light of later Catholic teaching:

  “If you read the papal encyclical Rerum Novarum by Pope Leo XIII, he shows you that the Catholic Church is completely compatible with... liberalism...” – Prof. Habib (20:24)

• But these reconciliations are “pretty late in the day,” after America’s political settlement (20:57).

8. Rome as Foil to England: Shakespeare’s Roman Plays

• Roman Decline vs. English Adaptation:
  • In the Roman plays, Shakespeare contrasts the fleeting success of Roman republicanism with the English capacity for adaptation and constitutionalism.
• Imperial Temptations:

  “He never presents England resembling anything like Rome with respect to its expansion. ... England is a little bit different. The plays ... present England moving from a feudal medieval nation... to something like an independent state under Henry VIII.” – Prof. Habib (25:17)

9. Educational Standards: The Decline and Recovery of Shakespeare in Education

• A Lost Generation: Both Hewitt and Habib lament having to “rummage” for Shakespeare in their own educations, blaming an academic hostility to the Western canon.

  “But now you’re starting to see more and more charter schools pop up... Hillsdale has really set an example... of how to deliver a curriculum that gives you a coherent path to read Shakespeare’s history plays.” – Prof. Habib (30:57)

10. How to Read the History Plays: Chronology Over Composition

• Follow the Historical Line:

  “The better way to do it, rather than lining them up based on the year they were performed or written, is to just let Shakespeare guide you. There’s a historical chronology that he begins with. He begins with King John, then he goes to Richard II, and so on. And if you do it that way, you can actually see a coherent history.” – Prof. Habib (32:32)

11. Monarchy’s Flaws: Legitimacy, Divine Right, and Human Necessity

• Each Play as a Case Study:
  • King John: The crisis of legitimacy during dynastic conflict.
  • Richard II: The problems of divine right without merit.
  • Henry IV: The crises resulting from usurpation.
• Why No Abdications?:

  “Sometimes politics is like riding a tiger. If you let go, you’re going to get mauled... you’re compelled to remain in that position.” – Prof. Habib (35:33)

Notable Quotes & Memorable Moments

• On Shakespeare’s Unusual Kings:

  “King John was the most excommunicated king in all of England. ... His name was so bad, so stained by his reputation, that nobody named their son John after him. So there’s only John the First, there’s no John II or the third.” – Prof. Habib (03:01)

• On England’s Unique Evolution:

  “England has an evolution.” – Prof. Habib (15:22)

• On the Difference Between Rome and England:

  “I just don’t think Shakespeare thought that the English people were like the Romans. ... They never had this divine mandate to conquer the world.” – Prof. Habib (25:17)

• On Mixed Regimes:

  “Shakespeare [is] teaching thinkers like Montesquieu how to look at England as kind of a mixed regime. ... There is a certain kind of republican spirit that emerges.” – Prof. Habib (07:13)

Timestamps for Key Segments

• [01:33] Why the history plays matter – teaching and neglect
• [03:01–04:45] Why Shakespeare starts with King John
• [06:53–09:30] Shakespeare and the nature of monarchy; Montesquieu’s influence
• [09:31–10:25] The succession controversy in King John
• [15:22–17:42] Comparative government: England vs. Russia, France; influence on American Founding
• [18:53–20:08] Locke (idealism) vs. Montesquieu (system) in Anglo-American political tradition
• [22:18–26:19] Shakespeare’s Roman plays as a foil to the English history cycle
• [29:06–31:51] Shakespeare in education: why he disappeared, and how Hillsdale aims to restore
• [32:32–35:19] How and why to read the history plays in chronological order
• [35:33] The rarity of abdication and inherent flaws in hereditary monarchy

Final Thoughts

This episode sets up a deep dive into King John and the Plantagenet lineage for the next Hillsdale Dialogue, while offering a sweeping view of Shakespeare’s political insights and their resonance in Western and American traditions. Professor Habib’s comparative method—pairing Shakespeare’s plays with political philosophers and contrasting England’s gradual constitutionalism with Rome’s and Europe’s violent disruptions—makes this an illuminating and accessible guide for listeners seeking to grasp not just Shakespeare, but the historical roots of modern politics.