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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On October 31, 1975, 15-year-old Martha Moxley’s body was found under a tree in her family’s backyard in a wealthy enclave of Greenwich, CT. Nearly 25 years later, after countless false starts, someone was finally charged with Moxley’s murder: Michael Skakel, a former neighbor and classmate of Martha’s — and Bobby Kennedy’s nephew. The story only gets weirder from there. And with new revelations coming to light just last week, it’s still not over.

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Kathleen “Kick” Kennedy was the fourth child and second daughter of Joseph and Rose Kennedy. Always her father’s favorite, Kick spent her adolescence in London while he served as Ambassador to the United Kingdom. She quickly became a society it-girl and eventually married one of the most eligible bachelors in England — much to the chagrin of her very Catholic mother. We’re joined by Paula Byrne, author of Kick: The True Story of JFK's Sister and the Heir to Chatsworth, to discuss Kick’s life and tragic death, her twin-like relationship with JFK, and her complicated legacy.

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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. The 2006 film Bobby, written and directed by Emilio Estevez, tells the interconnected stories of a group of fictional characters staying at the Ambassador Hotel the day Bobby was shot. The star-studded ensemble cast includes everyone from Anthony Hopkins and Demi Moore to Lindsay Lohan and Nick Cannon. We’re joined by comedian, Crooked Media writer, and Bobby Kennedy aficionado Julia Claire to discuss the highs and lows of one of the most confounding wannabe Oscar movies of the aughts.

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60 years after he was arrested for killing President John F. Kennedy, Lee Harvey Oswald remains one of the most enigmatic figures of the 20th century — and a lightning rod for conspiracy theorists everywhere. Today, we’re joined by Peter Savodnik, author of the book The Interloper: Lee Harvey Oswald Inside of the Soviet Union, to unpack Oswald’s tumultuous life and legacy.

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“A gothic tale of wealth and rebellion in East Hampton.” That’s how New York magazine described the plight of Jackie O’s aunt Edith Bouvier Beale and her daughter Little Edie Bouvier Beale in a 1972 cover story about their life together in a dilapidated mansion on Long Island. Four years later, Big Edie and Little Edie were immortalized on the big screen in the cult classic documentary Grey Gardens. Olivia Aylmer, senior editor at The Slowdown (slowdown.media), joins us to break down Big Edie and Little Edie’s enduring appeal — and to give us an on-the-ground report of this month’s 50th-anniversary screening of the film at New York’s Paris Theater featuring Julia Fox. 

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