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.”See omnystudio.com/listener for privacy information.

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. See omnystudio.com/listener for privacy information.

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.See omnystudio.com/listener for privacy information.

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.See omnystudio.com/listener for privacy information.

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.”See omnystudio.com/listener for privacy information.

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.See omnystudio.com/listener for privacy information.

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.See omnystudio.com/listener for privacy information.

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.See omnystudio.com/listener for privacy information.

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.See omnystudio.com/listener for privacy information.

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.See omnystudio.com/listener for privacy information.

“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. See omnystudio.com/listener for privacy information.

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.See omnystudio.com/listener for privacy information.

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.See omnystudio.com/listener for privacy information.

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.See omnystudio.com/listener for privacy information.

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.See omnystudio.com/listener for privacy information.

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.See omnystudio.com/listener for privacy information.

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?”See omnystudio.com/listener for privacy information.

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.See omnystudio.com/listener for privacy information.

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.See omnystudio.com/listener for privacy information.

You may have seen JFK’s 32-year-old grandson Jack Schlossberg command a crowd at the DNC or present the JFK Profile in Courage Award. You may also have seen him on your feed dancing shirtless while singing “Ticket to Ride” or railing about his hatred of restaurants. We’re joined by William Cohan, co-founder of Puck and author of the Town & Country article “You Don’t Know Jack,” to explore the most famous millennial Kennedy’s unlikely path to social media stardom.See omnystudio.com/listener for privacy information.

Jackie Kennedy was only 34 years old when JFK was assassinated. She was suddenly a single mother of two — and one of the most famous women in the world. We’re joined by J. Randy Taraborrelli, author of the bestselling biography ‘Jackie: Public, Private, Secret’ and the just-released ‘JFK: Public, Private, Secret’, to talk about the relationships that defined Jackie’s post-White House life.See omnystudio.com/listener for privacy information.

In 1918, Joe and Rose Kennedy had their first daughter, Rosemary. She experienced developmental difficulties as a child and had trouble keeping up in school. When she was 23, her father arranged for her to undergo a lobotomy, which left her profoundly handicapped for the rest of her life. The truth about Rosemary was kept hidden for decades. We’re joined by historian Kate Clifford Larson, author of the New York Times bestseller ‘Rosemary: The Hidden Kennedy Daughter,’ to discuss Rosemary’s life and legacy.See omnystudio.com/listener for privacy information.

For our first edition of Kennedy Film of the Month, we dive into Oliver Stone’s 1991 political thriller opus ‘JFK’. While nominated for 8 Oscars including Best Picture, it was also roundly condemned in the press for popularizing the theory that there was a government conspiracy to assassinate JFK. Los Angeles Times film critic and co-host of the Unspooled podcast, Amy Nicholson, joins us to unpack the film’s legacy.See omnystudio.com/listener for privacy information.

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.See omnystudio.com/listener for privacy information.

In 1969, a young Ted Kennedy drove his car off a bridge on Chappaquiddick Island in Massachusetts. He managed to get out of the car and survive, but the 28-year-old woman in the passenger seat did not. Kennedy fled the scene and didn’t report the incident until the following morning. As with all Kennedy scandals, conflicting reports of what exactly happened led to enduring conspiracy theories. We’re joined by Liz McNeil, editor-at-large at PEOPLE, author of JFK Jr.: An Intimate Oral Biography, and host of the Chappaquiddick podcast COVER-UP, to discuss what we know about that night — and what we don’t.See omnystudio.com/listener for privacy information.

Joe Kennedy, the patriarch of the Kennedy family, lived out the American dream. He amassed a fortune and gave his children a launching pad to political and cultural dominance. Lyra and George introduce themselves, the show, and the cast of characters who will be featured throughout.See omnystudio.com/listener for privacy information.

See omnystudio.com/listener for privacy information.