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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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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