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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As a senator and later as JFK’s attorney general, one of Bobby Kennedy’s signature causes was taking on organized crime. And his Public Enemy No. 1 was always Teamster President Jimmy Hoffa. But the years-long feud between Kennedy and Hoffa was not just about politics — it was personal. And it haunted the Kennedys for decades. To help us unpack it all, we’re joined by Dan O’Sullivan, co-host of The Outfit, a podcast about the mafia’s surprising role in our society.

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Since we started this podcast, one member of the Kennedy family has been in the news most consistently. Trump’s Secretary of Health & Human Services, RFK Jr., has been the elephant in the room during any conversation we’ve had about the Kennedy family. Today, we take a break from our regularly scheduled programming to chat with Julie Rovner, Chief Washington Correspondent for KFF Health News, about RFK and Trump’s much-covered “autism announcement” last week and RFK’s role in the anti-vax movement.

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In 1991, JFK’s 30-year-old nephew, William Kennedy Smith, was accused of raping a woman named Patricia Bowman at the Kennedy estate in Palm Beach. The ensuing trial coincided with the birth of CourtTV, and its “gavel-to-gavel” television coverage changed the media landscape forever. We’re joined by Dr. Paul Thaler, author of The Watchful Eye: American Justice in the Age of the Television Trial and The Spectacle: Media and the Making of the OJ Simpson Story, to talk about the ethics of cameras in the courtroom, the legacy of the William Kennedy Smith trial, and our current true crime landscape.

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In 1969, a young Ted Kennedy drove his car off a bridge on Chappaquiddick Island in Massachusetts, leading to the death of a young woman in the passenger seat named Mary Jo Kopechne. For this month’s Kennedy movie episode, we’re joined by Jason Concepcion, co-host of the X-Ray Vision podcast, to talk about the baffling 2018 film ‘Chappaquiddick,’ which attempts to depict the infamous incident and its aftermath — with mixed results.

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Bravo fanatics know Carole Radziwill as the “voice of reason” during her time on the Real Housewives of New York. But before answering that call from Andy Cohen, Radziwill was an Emmy-winning journalist and a New York Times bestselling author. She was also married to Jackie O’s nephew Anthony Radziwill and was close friends with his cousin JFK Jr. and his wife Carolyn Bessette. We’re joined by Vulture writer and Real Housewives anthropologist Brian Moylan to break down Carole’s Kennedy connections and chat about her triumphant years in the Real Housewives universe.

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In 1995, JFK Jr. and PR executive Michael Berman started a new magazine focused on the intersection of politics and culture. Today we’re joined by Rolling Stone features editor Kate Storey to talk about her 2019 Esquire article about the history of George Magazine, from infamous covers to notable contributors including Al Franken and Kellyanne Conway. As Storey writes, George Magazine “covered politics like it was pop culture. Was it folly — or a glimpse of the Trumpian future?”

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Taylor Swift’s fascination with the Kennedys is well documented, but it really reached a fever pitch in the summer of 2012 when she briefly dated RFK Jr’s son Conor Kennedy. Today, we’re joined by Vulture staff writer and Taylor Swift historian Fran Hoepfner to break down Taylor’s top Kennedy moments, from an infamous paparazzi scandal to a mysterious real estate purchase.

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Pablo Larrain’s ‘Jackie’ stars Natalie Portman as Jackie Kennedy in the moments before, during, and after her husband’s assassination. The film landed Portman an Oscar nomination and jumpstarted Larrain’s trilogy of films about misunderstood 20th-century women. We’re joined by ‘Jackie’ superfan Hunter Harris to chat about the film’s depiction of grief, how Larrain subverts biopic tropes, and which actors’ Boston accents could have used a bit more work.

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