The first televised presidential debate in U.S. history took place in 1960 between then-Vice President Richard Nixon and a young, charismatic Senator named John F. Kennedy. You may have learned in high school that audiences who watched the debate on television thought JFK won, and audiences who listened on the radio thought Nixon won. But the truth is not quite that simple. To separate fact from fiction and chat about the legacy of the JFK-Nixon debate in U.S. politics, we’re joined by Craig LaMay, professor of U.S. and comparative media law at Northwestern University’s Medill School of Journalism and co-author of Inside the Presidential Debates: Their Improbable Past and Promising Future.

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To ring in the new year, we count down the 10 most important Kennedy moments of 2025, from government corruption to media scandals to tell-all memoirs to family feuds. Happy holidays!

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Today, we welcome back Rolling Stone features director Kate Storey to chat about her 2023 book White House by the Sea, a sprawling and meticulously researched history of the Kennedy Compound in Hyannis Port, MA. Kate walks us through the major historical moments, family events, and celebrity visits that took place in the Kennedys’ infamous vacation property, where they could be “the people we are when no one but the neighbors is looking.”

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America’s prince JFK Jr. and his wife Carolyn Bessette-Kennedy were ubiquitous in ’90s New York until their tragic death in a plane crash in the summer of 1999. “In the pages of the city tabloids during those few short years, Bessette was a daily soap opera, forced into the multitude of unforgiving tropes for public women. The scheming girlfriend; the coked-up vixen; the miserable spouse,” writes journalist and author Glynnis MacNicol in Town & Country. But little is known about what Carolyn was actually like. We’re joined by MacNicol to separate fact from fiction. NOTE: This episode originally aired July 14, 2025.

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From JFK’s allegedly hat-less inauguration to Jackie’s pillbox hats, the Kennedys have always had a distinct style. But the type of fashion they’re most known for is the “classic” New England look you’re already picturing. In a word: Preppiness. We’re joined by Avery Trufelman, the host of the podcast ‘Articles of Interest’ whose 2022 series ‘American Ivy’ explored the history of preppy fashion, to investigate.

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Today we’re taking a break from our regularly scheduled programming to talk about something in the news that caught our eye: JFK’s grandson Jack Schlossberg is running for congress in New York. Does he have what it takes to make an impact in an incredibly crowded race? And can he pivot from controversial social media star to respectable politician? Does he even want to? We’re joined by Washington Post political features writer Kara Voght to break it all down.

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After a string of serious episodes, we’re taking a movie break with something light… kind of. The House of Yes is a 1997 pitch-black Sundance comedy-turned-cult classic starring a who’s who of late-90s stars including Parker Posey, Freddie Prinze Jr, Tori Spelling, and Rachel Leigh Cook. We get into the movie’s iconic poster featuring Parker Posey in Jackie O’s pink Chanel suit, Tori Spelling’s acting chops, the role of the Kennedy assassination in pop culture, and why Entertainment Weekly called the film “a knowingly overripe… kitsch melodrama that dares to make incest sexy.”

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The Bay of Pigs invasion of 1961 was a covert plot to remove Fidel Castro from power in Cuba using a ragtag band of American-trained Cuban defectors. It ended up becoming one of the most humiliating episodes in American history — and a black eye for the Kennedy administration just four months into JFK’s presidency. We’re joined by Dr. Stephen Wilkinson, Chairman of the International Institute for the Study of Cuba at the University of Buckingham, to dive into how a plot dreamed up by the CIA and approved by two presidents failed so spectacularly, what it meant for JFK’s legacy, and how its impact reverberates in U.S.-Cuba relations to this day.

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