Hillsdale Dialogues: The Politics of Shakespeare, Part Two

Podcast: Hillsdale Dialogues
Host: Hugh Hewitt
Guest: Dr. Khalil Habib (filling in for Dr. Larry P. Arnn)
Date: March 2, 2026

Episode Overview

In this episode, Hugh Hewitt and Dr. Khalil Habib continue their exploration of Shakespeare’s political thought, focusing on the English history plays—especially “Richard III”—and connecting Shakespeare’s themes to broader philosophical and political ideas. Dr. Habib discusses the interplay between Shakespeare, Montesquieu, Machiavelli, and the American founding, with insights on tyranny, the separation of powers, and the problem of evil in politics.

Key Discussion Points and Insights

The Appeal and Overlooked Riches of the Henry VI Plays

• Dr. Habib notes a surprising student enthusiasm for Shakespeare’s lesser-known works, especially the Henry VI plays, which were oversubscribed at Hillsdale.
  • “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, but this is the first time they're coming into contact with Henry VI. But they seem to be enjoying it.” (Dr. Habib, 01:01)

Montesquieu’s View on the English Constitution and Its Roots in Shakespeare

• Montesquieu admired the English constitutional order, describing England as a “republic hidden inside of a monarchy.” Dr. Habib suggests Montesquieu drew inspiration from Shakespeare’s history plays.
  • “...Shakespeare is in fact 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. Habib, 02:19)

Who Were the Plantagenets?

• Clarification on the Plantagenet royal line: They begin with King John (not Henry II) and were known as a “warrior family,” often embroiled in violence and political turmoil.

Richard III: Shakespeare’s Machiavellian Founder

• “Richard III is the only play in all of Shakespeare that actually begins with a soliloquy. And it's a play in which you find a lot of soliloquies. ...He's the only character in all of Shakespeare's work who identifies himself as Machiavelli.” (Dr. Habib, 05:18)
• The attraction of Richard III for actors is the opportunity to embody a character whose motivations and villainy are performed directly to the audience, without props or ensemble support.

The Roots and Results of Richard III’s Villainy

• Richard III’s rise is presented as a direct consequence of Henry VI’s inability to assert control and check destructive factions.
  • “Richard III is crucial because it is connected to, unfortunately, the failures of Henry VI. ...Richard does have his family anyway, has a legitimate claim to the throne. ...He is the devil incarnate, and he relishes that role.” (Dr. Habib, 06:59)

Shakespeare’s Critique of Hereditary Monarchy

• Shakespeare shows that both illegitimate kings (like Henry VI) and legitimate ones (like Richard III) can be disastrous if not aligned with the common good.
  • “You can have a legitimate king. You can have a legitimate claim to the throne. ...Richard III is courageous, he's a warrior. But he also is misaligned because he doesn't have the genuine concern with the common good. He kills for the sake of killing.” (Dr. Habib, 07:59)

The Nature and Consequences of Evil in Shakespeare’s Universe

• Richard III relishes evil for evil’s sake, taking pride in his own monstrous nature.
  • “He's just an evil, evil person and he loves it. He just has, as Nietzsche would say, a thrill for the knife.” (Dr. Habib, 09:06)

The Historical Accuracy of Richard III’s Deformity

• Recent archaeological discoveries confirmed that Richard III did have scoliosis, aligning with Shakespeare’s depiction.
  • “He actually was a hunchback, which he actually fixates on. He tells us at some point in the play that his ugliness liberated him from the illusions of love so that he could just take advantage and exploit people...” (Dr. Habib, 11:56)

Richard III as a Machiavellian Prince

• Shakespeare stages Richard III as an analysis—and critique—of Machiavellian principles: ruthless pursuit of power, preference for being feared over loved, and “founding alone.”
• Despite Machiavelli’s prescriptions, Richard ultimately fails because his cruelty and isolation alienate his supporters.
  • “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. And I think it's very appropriate.” (Dr. Habib, 14:22)

The Role of Religion and Justice in Richard III

• Richmond, Richard’s opponent, is beloved and victorious due to justice and alignment with Christian virtue, notably prayer and Marian devotion (rosary recitation in the play).
  • “Shakespeare introduces a character, Richmond, who actually is so beloved because of his commitment to justice and to England and to Christianity. ...People are willing to actually risk their life to side with justice.” (Dr. Habib, 14:30)
• Presence of Catholic ritual in the plays is partly historical accuracy, as they are set before the Reformation.
  • “These plays are set prior to the Reformation, and so it would be historically accurate to present them as Catholics. ...Catholicism and politics are not only compatible, they were instrumental in overturning this scourge...” (Dr. Habib, 16:42)

Tyranny, Regicide, and the Overthrow of Richard III

• The removal of Richard III is consistent with Aquinas’ views on dealing with tyranny: action through legitimate institutions, grounded in divine authority.
  • “...For Aquinas, it can't just be any Joe off the street. It has to be through the institutions which ultimately have their authority in God.” (Dr. Habib, 18:02)

The Allure and Limits of Evil Characters

• Richard III is irresistibly interesting as a character, but Shakespeare insists the moral order asserts itself: evil is ultimately self-destructive.
  • “Richard tries to be a God, but he dies like a beast. Very Aristotelian. ...Men like Richard simply will not get away with it, no matter how impressive they are. And I think the criticism is that Machiavelli is a dead end.” (Dr. Habib, 19:17)

Machiavellian “Virtu” Versus Political Virtue

• Hewitt and Habib discuss Machiavelli’s concept of “virtu”—self-reliance and willpower. Richard III represents a Machiavellian founder who tries to rely on himself alone, whereas Henry V’s character is more ambiguous.
  • “If you're biblically informed. But Machiavelli basically just said relying on God, you might as well just be rolling the dice. You should always have virtue and go it alone. Hence, Richard is presented.” (Dr. Habib, 20:37)

The Problem of Evil and the Political Order

• Students are struck by the direct engagement with evil and the supernatural, including demonic forces, in Shakespeare’s plays—so different from today’s secular political lens.
  • “There's a lot of evil and flirtation with Satanism, actually in these plays... they're really struck by that because we're so conditioned to thinking of politics in purely secular terms.” (Dr. Habib, 24:09)

Shakespeare’s Authorial Genius and Political Sympathies

• Dr. Habib leans toward the belief that Shakespeare’s coherent vision is the work of a single author.
• He also suggests Shakespeare was sympathetic to republican ideals, often portraying figures like Julius Caesar in a surprisingly negative light, perhaps as a “closet Republican.”
  • “I think Shakespeare is a closet Republican and I didn't know this. I didn't catch it until I teach Julius Caesar, actually, every summer.... And I was struck by how incredible Julius Caesar himself is.... the only thing I can attribute that to is that Shakespeare presents Coriolanus sympathetically... He's a republican through and through.” (Dr. Habib, 27:12)

Montesquieu and the American Founding

• Montesquieu’s “Spirit of the Laws” was foundational for the American Founders, particularly his model of the separation of powers.
  • “He published a work called the Spirit of the Laws. It came out in 1748, and he is the second most quoted authority among the American founders.... And the American founders drew our separation of powers from Montesquieu and not from Locke.” (Dr. Habib, 29:32)
• The American solution to factionalism, drawn from Montesquieu and Hume, was a confederated republic—a large, federated system to dilute and manage factions.
  • “...the way to deal with [factions] is not to deprive human beings of the right to associate... They decide to go and adopt what they call a Confederated republic, which is to say a large country made up of various states... where the federal government would be something like a monarchical power...” (Dr. Habib, 30:23)

Why Separation of Powers Matters

• The ongoing “anxiety” in American politics is a feature, not a bug: it keeps citizens vigilant and liberty intact.
  • “Montesquieu thought, your liberty is destroyed the moment you become complacent. And what the separation of powers does is it gives the illusion... that at any moment you could lose the liberty that you have.... They'll remain politically active and avert the problem that luxury and complacency can create.” (Dr. Habib, 33:02)

Churchill and Shakespeare

• Winston Churchill was shaped by Shakespeare’s English history plays, knowing their lines by heart and frequently attending performances.
  • “Churchill would show up whenever an English history play was being performed and the people would report that he would actually mouth all of the lines sitting there as the actors were acting.... He loved the English history plays.” (Dr. Habib, 34:54)

Notable Quotes & Memorable Moments

• On student engagement with Henry VI:

  • “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, but this is the first time they're coming into contact with Henry vi. But they seem to be enjoying it.” (Dr. Habib, 01:01)

• On Richard III as Machiavellian:

  • “He's the only character in all of Shakespeare's work who identifies himself as Machiavelli.” (Dr. Habib, 05:18)

• On the limits of Machiavellian principles:

  • “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. Habib, 14:22)

• On religion in Shakespeare’s plays:

  • “It's a classic example where Catholicism and politics are not only compatible, they were instrumental in overturning this scourge...” (Dr. Habib, 16:42)

• On Shakespeare’s view of evil and politics:

  • “They're really struck by that because we're so conditioned to thinking of politics in purely secular terms. ...Shakespeare, these specific plays really remind you that where you have that kind of ambition, you will always have temptations that are no different than the temptations you find from the fall.” (Dr. Habib, 24:09)

Timestamps for Important Segments

• 01:01 – Student enthusiasm for Shakespeare at Hillsdale; introduction to Henry VI plays
• 02:19 – Montesquieu and the English constitution; Shakespeare’s republican themes
• 05:18 – Richard III as Shakespeare’s Machiavellian character
• 06:59 – Richard III as the product of Henry VI’s failures
• 09:06 – The violence and thrill-seeking of Richard III
• 11:56 – Archaeological confirmation of Richard III’s hunchback
• 14:22 – Shakespeare’s critique of Machiavelli and political isolation
• 16:42 – Catholic rituals and their political meaning in Shakespeare
• 18:02 – Aquinas, tyranny, and regicide in the plays
• 19:17 – The moral order and ultimate fate of evil in Shakespeare
• 20:37 – Machiavellian “virtu” vs. Henry V’s ambiguous virtue
• 24:09 – The confrontation with evil in Shakespeare’s politics
• 27:12 – Shakespeare as a “closet Republican” and his portrayal of Caesar
• 29:32–33:02 – Montesquieu’s influence on the American founders and the separation of powers
• 34:54 – Churchill’s love of the history plays and Shakespeare’s influence on his worldview

Conclusion

This episode connects literary analysis with enduring political questions, showing how Shakespeare’s historical dramas offer profound insights about legitimacy, tyranny, virtue, and the structure of free government. Dr. Habib’s erudition and enthusiasm invite listeners to see Shakespeare as not just a poet and playwright, but as a formative political thinker. Through the lens of thinkers like Montesquieu and Machiavelli, the dialogues reveal the continuing importance of Shakespeare’s moral and political vision for understanding both history and the present.