Hillsdale Dialogues — The Politics of Shakespeare, Part One

Podcast: Hillsdale Dialogues (Hillsdale College)
Host: Hugh Hewitt
Guest: Dr. Khalil Habib (Professor of Political Theory, Hillsdale College)
Date: February 23, 2026

Overview of the Episode

This episode kicks off a two-part exploration of the political themes in Shakespeare’s plays, focusing on the Henry VI trilogy and Richard III. With regular co-host Dr. Larry Arnn away, Hugh Hewitt welcomes Dr. Khalil Habib, who contextualizes Shakespeare’s works within political philosophy and English constitutional history. The dialogue draws connections between Straussian reading, the tradition of liberal education, and foundational questions surfaced in Shakespeare's history plays.

Key Discussion Points

Pathway to Political Theory and Hillsdale (00:29–04:29)

• Habib’s Academic Journey: Dr. Habib describes how studies at the University of Maine and mentorship from Straussian-influenced professors ignited his passion for political theory.
• Straussian Influence: Early exposure to Leo Strauss’s method of reading classic texts, especially Plato’s Republic, left a lasting intellectual impact.

“I never knew philosophy even existed until I got to University of Maine. And I don't know if you remember your first experience when you come into contact with a book that literally opens a lost world for you. It felt like Narnia to me.” — Dr. Khalil Habib (04:29)

What Is Straussianism? (06:39–10:40)

• Explaining Straussianism: Strauss’s approach values timelessness in great texts, treating them as living dialogues rather than relics.
• Self-Knowledge and Timelessness: The Straussian method exposes modern prejudices and guides students toward self-knowledge by reading works as mirrors to their own limitations.

“Once you’re bit by that, there’s no going back. … Primarily means looking at ideas as if they’re timeless and as a mirror to exposing one's own limitations. And so at the end of the day, its ultimate aim is self knowledge.” — Dr. Khalil Habib (09:26)

Education at Hillsdale and Strauss versus Historicism (12:56–16:01)

• Habib’s Openness: Dr. Habib shares why he is transparent with students about Straussian methods, aiming to replicate his own transformative experience.
• Jerusalem and Athens: Touches on Strauss’s motif of tension between faith (Jerusalem) and reason (Athens), impacting Habib’s own approach to education.

“He believed that philosophy means the autonomy of human reason, and faith would mean... taking a leap of faith in trust in God. And so that really made me want to turn to medieval thought.” — Dr. Khalil Habib (13:54)

Medievalism: History, Philosophy, and Tension (16:01–19:07)

• Medievalism in Political and Philosophical Terms: Differentiates between feudal decentralization (“medievalism” politically) and theological debate (“medievalism” philosophically).
• Straussian Tension: Strauss’s habit of posing sharp contrasts spurs critical thinking, mirroring Socratic and Platonic dialogic method.

“Almost everything Strauss touched always led to a Platonic end. There was always some kind of tension. Modernity is great, but it's in tension with the ancients.” — Dr. Khalil Habib (18:56)

Liberal Education and Teaching at Hillsdale (19:07–21:06)

• Curriculum at Hillsdale: Emphasis on primary texts and fostering a dialogue between conflicting ideas, regardless of chronological order.
• Goal of Liberal Education: Introducing students to challenging ideas, enabling pursuit of truth and moral seriousness.

“I always present the books, no matter what I'm teaching, as though they’re absolutely true. And I make sure that they all contradict each other, that there’s a debate, a dialogue going between them, between the authors…” — Dr. Khalil Habib (19:44)

Shakespeare’s History Plays: Henry VI and English Constitutional Identity (22:10–24:52)

• Why Henry VI Matters: Dr. Habib argues that these plays are central to understanding the evolution of the English-speaking peoples and their constitutional traditions.
• Shakespeare & America’s Intellectual Heritage: References to Tocqueville’s admiration for Americans’ appreciation of Shakespeare as a link to pre-Tudor English liberty.

“When you read them, it becomes very obvious that they share a lot of the same themes that are in the Federalist Papers. The cause of factions, religious persecution, conflicts between France and England, etc.” — Dr. Khalil Habib (24:24)

Henry VI: A Case Study in Political Misalignment (29:18–31:17)

• Henry VI’s Character: Portrayed as pious and ill-suited for kingship—a man better fit for religious life than rule.
• Problem of Hereditary Monarchy: Shakespeare uses Henry VI’s inadequacy to critique systems in which office and soul are misaligned, favoring merit over inheritance.

“His wife says he should have been a pope. He himself says he wishes he could have been a priest. … I think the greater sort of framework of this whole series of plays is the problem with it, with hereditary monarchy.” — Dr. Khalil Habib (29:41)

The Structure and Failure of Hereditary Monarchy (31:17–33:25)

• Shakespeare’s Republican Leanings: Asserts the plays show the flaws of hereditary rule, pointing toward republican ideas.
• Support Networks and Abdication: Henry VI’s reliance on others, particularly Gloucester and his wife, highlights his unsuitability for leadership.

“By the time you're done with this play, you're struck by how you can only conclude that there's something fundamentally flawed. With a hereditary monarchy… Shakespeare forces you to consider that maybe merit, rather than birth, should determine somebody's role in office.” — Dr. Khalil Habib (32:57)

France, Joan of Arc, and Englishness in the Plays (33:25–34:38)

• Contrasts of Centralization and Decentralization: Explains why France needs Joan of Arc (centralized monarchy and emasculated aristocracy) and England produces figures like Talbot (decentralization creating strong military leaders).
• Political Regimes Shape Characters: The differences in national character are products of their respective regimes, according to Shakespeare’s depiction.

“...It's so deeply decentralized that it unfortunately leads to factions, but it also leads to extraordinary military men like Henry V himself, Talbot and others. And that's a nice pairing that Shakespeare does…” — Dr. Khalil Habib (33:55)

Shakespeare’s Intentions and Catholicism (34:38–36:36)

• Did Shakespeare Offend with the Henry Plays?: Habib believes not, arguing that the plays ultimately vindicate the Tudor dynasty.
• Was Shakespeare Catholic?: Views the evidence as ambiguous and dependent on interpretation; the plays’ main critique is of hereditary monarchy, not Christianity per se.

“There is no conflict between Christianity and politics. What you have in those plays is an examination of the problems that are inherent in hereditary monarchy, not in Christianity…” — Dr. Khalil Habib (35:44)

Notable Quotes & Memorable Moments

• On First Encounter with Great Books
  “It felt like Narnia to me. I just couldn’t believe what I was reading.” — Dr. Khalil Habib (04:29)

• On Straussian Reading
  “We place ourselves in a position of moral and intellectual superiority without knowing the roots of our own beliefs and our prejudices.” — Dr. Khalil Habib (08:13)

• On the Goal of Liberal Education
  “The best thing you could do for them is to show them the many paths that they can take to pursue something that they’re genuinely interested in.” — Dr. Khalil Habib (21:00)

• On the Political Message of Henry VI
  “Henry VI is the most pious of the English kings... He’s really not fit for the task of a monarch.” — Dr. Khalil Habib (29:41)

• On Shakespeare and Republicanism
  “It's pretty clear he has a lot of republican leanings... I think what Shakespeare is really trying to show us in these plays is... How do you avoid [misalignment in monarchy]? And the problem is, you can't avoid it.” — Dr. Khalil Habib (31:24)

Important Segment Timestamps

• 00:29 — Introduction, Dr. Habib’s educational background
• 04:29 — Discovery of Straussian thought
• 07:26 — Explaining Straussianism to newcomers
• 13:39 — Frankfurt to Claremont: Strauss’s influence and liberal education
• 22:10 — Why and how to read the Henry VI plays
• 29:41 — Dr. Habib’s interpretation of Henry VI’s character
• 33:32 — Joan of Arc, Talbot, and regime differences
• 34:47 — Shakespeare’s intentions and the Tudors
• 35:30 — Was Shakespeare Catholic?

Conclusion

Part one of this two-part series lays a rich philosophical and historical foundation for reading Shakespeare’s English history plays, using the lens of political theory to uncover questions of governance, legitimacy, and national character. Dr. Habib argues that Shakespeare’s depiction of monarchy is informed by republican sympathies, and he adeptly weaves together classical thought, medieval theology, and English constitutional development. The stage is set for an even deeper dive into Richard III in the next episode.