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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