Podcast Summary: The Realignment — Episode 581

Guest: Jeffrey Rosen
Hosts: Marshall Kosloff (A), with Saagar Enjeti referenced
Date: November 7, 2025
Episode Title: “Hamilton vs. Jefferson and the Battle Over Government Power in 21st Century America”

Episode Overview

This episode explores the enduring tension between Hamiltonian and Jeffersonian visions of American governance and their relevance to today’s political realignment. Marshall Kosloff and Jeffrey Rosen discuss Rosen’s new book, The Pursuit of Liberty: How Hamilton vs. Jefferson Ignited the Lasting Battle over Power in America, reflecting on the balance between national power and local autonomy, executive versus legislative authority, and the recurring debate over democracy versus elite rule. The episode contextualizes these foundational ideas within historic and current policy challenges, emphasizing why philosophical frameworks remain vital to understanding America’s political discourse.

Key Discussion Points & Insights

1. Why Hamilton vs. Jefferson Still Matters

• Philosophical Labels and Policy Debates

  • Marshall describes pushback he receives when discussing policy in Hamiltonian/Jeffersonian terms, with some accusing this approach of being “wonky” or elitist. He argues for the necessity of philosophical language in political debate.
  • Rosen responds:

    “The debate between Hamilton and Jefferson over national power versus states’ rights, and liberal versus strict construction of the Constitution... has defined all of American history.” (03:52)

• Recurring Historical Tensions

  • Rosen details how all major American turning points—founding, Civil War, Reconstruction, the New Deal—are refracted through these competing visions.
  • Anecdote: Hamilton’s admiration for Julius Caesar versus Jefferson’s celebration of Enlightenment thinkers.

2. Is One Side Right? Why the Tension Matters

• Balancing Instincts
  • Both hosts emphasize that American political development can’t be reduced to one “winner.” Rosen:

    “It’s far more illuminating to study the complexities of history and note how essential, inescapable each of them are than to try to pick sides.” (09:51)

  • Extremism, or complete rejection of the Hamilton-Jefferson framework (e.g., Calhoun’s celebration of slavery), is associated with the greatest dangers.

3. Who Won? Hamiltonian vs. Jeffersonian Legacies

• Rosen observes that, structurally, America became more Hamiltonian—urbanized, centralized, and industrial—but Jeffersonian rhetoric persists in American self-understanding and political culture.

  • On the cyclical popularity of each founder:

    “Who’s up and who’s down has as much to do with culture as politics... Hamilton and Jefferson are central to America not because of objective correspondence with their actual views, but because of the position they occupy in the American imagination.” (16:41)

• 21st Century Revivals

  • Lin-Manuel Miranda’s Hamilton musical redefined Hamilton as a multicultural icon—separate from renewed policy interest in Hamiltonian economics and reindustrialization.

4. Politicians as Historians: Then and Now

• Marshall laments that current politicians lack the historical depth of 19th/early 20th-century leaders (like Henry Cabot Lodge, Theodore Roosevelt, Woodrow Wilson).
  • Rosen agrees many 19th-century statesmen were historians but pushes back:

    “Certainly there are plenty of great enthusiasts of history in Congress today… Obama is absolutely as deeply rooted in the tradition of president historians as Henry Cabot Lodge and Theodore Roosevelt.” (26:09)

  • The current challenge isn’t a lack of intellectual interest but media and social attention spans discouraging complex debate.

5. The Dangers and Limits of “Scholar Presidents”

• Woodrow Wilson as Case Study
  • Marshall: “Wilson has the highest ratio of every single side of the aisle finding something truly abhorrent about that presidency.” (27:44)
  • Rosen: “The main objection to him… is not that he was a scholar, but that he was a virulent white supremacist.… He questioned the separation of powers… and advocated a form of British parliamentarianism.… So he’s really distasteful because he’s a centralizing pro-executive crypto-Caesar white supremacist.” (29:44)

6. Why Foundational Ideas Beat Policy Wonkery

• Marshall reflects that the more he tries to discuss policy in technical terms, the less resonant it is with real people.
  • “The more I transition from the wonky version and instead focus on the pursuit of liberty…the more it actually resonates and becomes just useful.” (35:17)
• Rosen:

  “It’s urgently important to learn about the big ideas of American history and the American idea: liberty, equality, government by consent… all these basic principles are essentially debated throughout history.” (37:30)

7. Refounding and Transformation in American Constitutional History

• Do We Need a “New Founding”?

  • Discussion of the French “fifth republic” vs. the American historical transformation.
  • Rosen: Accepts Keith Whittington’s argument for five constitutionally transformative presidents (Jefferson, Jackson, Lincoln, FDR, Reagan)—but whether these eras are truly “foundings” is opinion, not settled fact.

• Debate: Does the New Deal/Ronald Reagan/Trump Era Count as a New Founding?

  • Marshall: Argues in favor of New Deal as a “founding” moment.
  • Rosen: “I would side with those who say that the founding and Reconstruction were the two moments where the transformed understanding culminated [in] amendments. And that sets them apart…” (46:46)
  • Marshall: Suggests a Reagan-Trump continuity in constitutional transformation, particularly focused on the administrative state.
  • Rosen: “[Trump’s] using executive power... would have made even Hamilton blanche…” (49:43)

Notable Quotes & Memorable Moments

• On the use of Hamiltonian/Jeffersonian language:

  “Anyone who loves American history, and I know everyone listening to this podcast does, can view Hamilton and Jefferson as golden and silver threads woven throughout the tapestry of American history. Sometimes they clash, sometimes they cross, sometimes they almost snap apart. But it’s the productive tension… that has sustained the republic…” (07:52)

• On the tension balancing the republic:

  “It’s on the rare occasions that extremists have rejected the Hamilton and Jefferson framework entirely that the shooting begins. That was John Calhoun… or similarly with extremists on the right and the left today who want to tear down the founders…” (10:06)

• On contemporary resonance:

  “It’s not like there’s a clear answer to them, but it’s the details of the debates themselves that are necessary to understand the American idea.” (37:46)

• Rosen on politicians as historians:

  “We are not returning to the primary sources… on a mass level, there’s plenty of deep reading and engagement… But in a world of Instagram posts… you can’t make the complicated arguments that history requires.” (26:19)

Key Timestamps for Important Segments

• [03:52] — Jeffrey Rosen explains why Hamiltonian and Jeffersonian labels remain vital, not just ‘wonky’.
• [08:25] — Rosen on why he refuses to pick sides in the Hamilton vs. Jefferson debate, and why the tension is productive.
• [12:05] — Discussion of how the country has moved in a Hamiltonian direction, culturally and structurally.
• [16:41] — The cyclical rise and fall of Hamilton’s and Jefferson’s reputations in culture and politics.
• [21:34] — The lost tradition of historian-politicians and reflections on why deep historical knowledge once mattered more in politics.
• [26:09] — Rosen defends the tradition of presidential historical engagement into the present day.
• [29:44] — Limitations of the “scholar president” with Woodrow Wilson as a negative example.
• [35:17] — Host reflects on the value of motivating political action with foundational ideas rather than policy details.
• [37:30] — Rosen on the importance of learning big constitutional ideas for civic engagement.
• [41:07] — The right and left debate the idea of “refounding” the country; five transformative presidencies listed.
• [45:38] — Rosen and Marshall debate the New Deal, Reagan, and Trump eras as transformative periods in constitutional history.
• [49:43] — Rosen parses how Trump’s executive overreach fits into the Hamiltonian/Jeffersonian continuum.
• [53:44] — Rosen teases the next book in his trilogy, “The Pursuit of a Union”.

Overall Tone

Engaged, historically rich, and nonpartisan with good-natured, intellectual disagreement. Marshall is candid about his evolving views, while Rosen offers a broad, nuanced, and educational perspective.

For Listeners New to the Topic

This episode deepens understanding of how America’s political divides are rooted in the tension between the urge to build, centralize, and innovate (Hamiltonian) versus the drive to preserve local autonomy, limit power, and protect individual liberty (Jeffersonian). The ongoing dance between these forces shapes not just past events, but how Americans conceptualize change, policy, and the purpose of government even today.