JFK Jr.’s Alleged Affair With Sybil Hill: Intimate Details and Love Letters Resurface

John F. Kennedy Jr.’s romantic life, including his marriage to Carolyn Bessette Kennedy and long-rumored affairs, has regained global attention following the release of Ryan Murphy’s FX miniseries Love Story: John F. Kennedy Jr. and Carolyn Bessette, which premiered on February 12, 2026. Each episode delves into new chapters of the late couple’s tragic marriage, prompting friends and acquaintances to reveal fresh insights about Kennedy’s love life. Among those speaking out is Sybil Hill, who claims to have shared a deep and long-standing affair with the late political heir.

Long before the fatal plane crash off Martha’s Vineyard in 1999, Kennedy’s personal and public lives often intertwined. Nearly 26 years later, Hill revisits her alleged relationship with the so-called Camelot prince. Now 60, Hill recalls the passion she claims to have shared with Kennedy, calling it a defining connection amid his numerous romantic entanglements.

According to Hill, she and Kennedy first met in January 1991 at a Manhattan dinner. Their interaction soon evolved into an on-and-off relationship that allegedly lasted until Kennedy’s death in July 1999. “John liked to paint, and our painting sessions often turned into s– sessions,” she said, noting that their artistic meetings often became intimate, deepening both physical and emotional bonds.

The two reportedly exchanged handwritten love letters, some of which Kennedy kept. Hill recounted, “Once he asked me to go to his apartment and pick up some maps that he needed for an expedition overseas. He wanted me to take the maps to his mother… When I went into his apartment, my love letter was next to his bed.”

Hill said their affair gradually ended when Kennedy committed to Carolyn Bessette, whom he secretly married in 1996. She remembered a final intimate meeting on February 7, 1998: “I lit a fire in the fireplace… I teased him, ‘Are you like a sailor with a girl in every port?’ John gazed into my eyes and said, ‘No, Sybil, you’re the only one.’ But he obviously felt guilty… Finally, I put my hand over John’s heart and said, ‘You have to follow your heart.’ He dropped his head and said simply, ‘I’m sorry.'”

Hill also revealed that Kennedy briefly returned to her in 1998 during marital difficulties with Carolyn. Their final encounter took place in Aspen, Colorado, leaving Hill with unresolved questions. Tragically, Kennedy and Bessette, along with Carolyn’s sister Lauren Bessette, died in a plane crash on July 16, 1999.

Today, Sybil Hill, now Sybil Hill Carter, is a renowned painter based in Colorado. Her artworks, often depicting horses and American flags with abstract and poetic elements, have sold widely across the U.S. and internationally. She continues to create and donate art while raising her family in the Colorado mountains.