We’re taking a break this week, but here’s a sneak peek of what’s to come in the next ten episodes.

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On June 5, 1968, the day after winning the California Democratic primary for President, Robert F. Kennedy was shot and killed by a man named Sirhan Sirhan at the Ambassador Hotel in Los Angeles. As with most Kennedy tragedies, some people don’t buy the official narrative of how the events unfolded. Crimetown co-creator Zac Stuart-Pontier joins us to chat about going down the rabbit hole of RFK conspiracy theories for his acclaimed 2018 documentary series The RFK Tapes.

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“You’ll never believe how close we came.” That’s the tagline for this month’s film, the 2001 historical political thriller Thirteen Days. Kevin Costner stars as White House assistant Kenneth O’Donnell during the 1962 diplomatic standoff between the U.S. and the Soviet Union that became known as the Cuban Missile Crisis. The 2.5-hour slogfest has it all: unexamined Kennedy mythology, confounding music choices, dramatic black-and-white vignettes, and montages of atomic bomb explosions at seemingly random times. We discuss it all with open hearts and minds… sort of.

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The Kennedys are the most famous Catholic family in America, and their religious background shaped both their personal lives and their careers in politics. We’re joined by Matthew Sitman, co-host of the podcast Know Your Enemy, to chat about Joe Kennedy’s complicated relationship with the Catholic Church, anti-Catholic sentiment during JFK’s election, a Gary Wills book on the Kennedys we’ve been devouring, and more.

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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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