Mary Kate Cary is a former White House speechwriter for President George H. W. Bush and a lecturer at the University of Virginia, where she teaches Democracy Out Loud a course on great American speeches. In this episode, Cary explores the long, complicated friendship and rivalry between Thomas Jefferson and John Adams, tracing their relationship in three acts—from collaborators on independence, to bitter political opponents, to reconciled friends through letters late in life. She reflects on how their disagreement shaped America’s two-party system and the tradition of peaceful transfer of power. Drawing on her own career as a bipartisan commentator and teacher, Cary argues that principled disagreement—rather than hostility—is essential to a healthy democracy.

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Jordan Pace represents District 117 in the South Carolina House of Representatives and serves as Chairman of the House Freedom Caucus. Pace recounts how his political conversion—from an ardent pro–Bush-Cheney neoconservative teenager to a libertarian-leaning Ron Paul disciple— was sparked by an unexpected conversation with Paul himself. Reflecting on that moment, Pace discusses the power of genuine dialogue to reshape convictions, the enduring tension between government power and personal liberty, and why he believes our polarized culture desperately needs more real debate and less echo-chamber shouting. It’s a candid story of ideological transformation and quiet persuasion.

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Lara Schwartz, author of Try to Love the Questions, argues that our disagreements get stuck when we reduce them to binary yes/no battles. Instead, she calls for “lovable questions”—open-ended inquiries that push us beyond entrenched positions and into shared exploration. From campus debates over AI to national fights about free speech, Schwartz shows how the real challenge is deciding which questions remain open and which society has already answered. She makes the case that disagreement is a skill we can all practice—and that doing so helps us find common ground without forcing false compromises.

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Former Congressman Joe Cunningham shares the story of how he broke ranks with his own party by calling on President Biden not to seek reelection—and the backlash that followed. From being the first Democrat in 2022 to publicly urge generational change, to his later role with the No Labels movement, Cunningham reflects on the costs of speaking out against political orthodoxy. His story raises big questions about loyalty, party power, and the limits of disagreement inside America’s two-party system.

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Ben Klutsey, executive director of the Mercatus Center whose work to bridge political differences is showcased in the documentary Undivide Us, shares a formative story of encountering racism as a child visiting Germany—a moment of unprovoked hostility that deeply shaped his outlook. Years later, after leaving Ghana and arriving in Appleton, Wisconsin for college, he was met with unexpected warmth, an experience he describes as a healing contrast that sparked his lifelong commitment to what he calls pluralist points. For Klutsey, pluralism means more than diversity—it’s about engaging across difference with tolerance, humility, and patience.

When We Disagree returns for season 3 in October 2025.

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Kurt Gray, a psychology professor and the author of Outraged: Why We Fight about Morality and Politics and How to Find Common Ground, discusses leaning into curiosity, asking questions and fostering understanding when political conversations veer into controversial territory. He emphasizes that persuasion begins with empathy, not facts, and argues that deep listening is essential in rebuilding relationships fractured by politics. For Gray, genuine dialogue means recognizing shared moral motivations, even when beliefs differ starkly.

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Jermaine Johnson, a South Carolina state representative and former pro basketball player, shares his frustration with the legislative process, revealing how performative politics often masks real, behind-closed-doors power plays. In his push to reform outdated laws, he’s faced fierce resistance rooted not just in political ideology, but in the weight of our shared history. For Johnson, the real battle isn’t left versus right; it’s past versus present. Still, his fight is fueled by hope—for his grandchildren to live in a world that finally catches up to its ideals.

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Kathryn Joyce, a philosopher and civil discourse director at Ohio State University, recalls a memorable clash with a college professor over unfair tests—an early lesson in the challenges of pushing back against authority. Now an educator herself, she teaches students to hold powerful people accountable with humility and care. For Joyce, civil discourse isn’t about winning arguments. It’s about fostering fairness, connection, and dialogue, especially across power divides. Still, she cautions: not every conversation is worth having—discernment matters just as much as empathy.

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