The renewed interest in Sybil Hill comes after the premiere of Love Story: John F. Kennedy Jr. and Carolyn Bessette, which aired its first episode on February 12, 2026, on FX.
As the series revisits the life and marriage of Kennedy and his wife Carolyn Bessette-Kennedy, past relationships and long-rumored affairs have resurfaced in public discussion — including Hill’s claims about a nearly decade-long, on-and-off romance.
How Did Sybil Hill and John F. Kennedy Jr. Meet?
According to Hill, she first met Kennedy in January 1991 at a dinner in Manhattan. What began as a spontaneous introduction reportedly turned into a close personal relationship.
Hill, now 60, has described their connection as passionate and emotional. She claims the relationship continued on and off until Kennedy’s death in July 1999.
Kennedy, often labeled one of America’s most eligible bachelors in the 1990s, had a highly public love life. Hill alleges that despite other relationships, he repeatedly returned to her over the years.
The Nature of Their Relationship
Hill has shared that their bond grew through shared creative interests. Kennedy reportedly enjoyed painting, and Hill, a professional artist, says their artistic meet-ups often deepened their connection.
In a recent interview with RadarOnline.com, she spoke about the intensity of their time together and described the relationship as both romantic and complicated.
She also claimed they exchanged handwritten love notes. According to Hill, she later discovered that Kennedy had kept her letters.
What Happened After Carolyn Bessette Entered His Life?
Kennedy began dating Carolyn Bessette in the mid-1990s. The couple secretly married in 1996.
Hill claims their affair slowed when Kennedy became serious about Bessette. She recalls a final emotional meeting on February 7, 1998, when she realized he had chosen his wife.
However, Hill also alleges that Kennedy briefly reconnected with her in 1998 during a difficult period in his marriage. She says their last meeting took place in Aspen, Colorado.
Kennedy and Bessette later died in a plane crash off the coast of Martha’s Vineyard on July 16, 1999, along with Bessette’s sister, Lauren Bessette. Their deaths shocked the nation and marked the end of what many saw as an American dynasty chapter.
Who Is Sybil Hill Today?
Beyond the headlines, Sybil Hill has built a career as a painter. Now known as Sybil Hill Carter, she lives in Colorado.
Her artwork often features horses, American flags, and mixed-media elements that blend poetry and vintage materials. Over the past decade, she has reportedly sold hundreds of pieces to collectors in the U.S. and abroad.
Today, she continues painting while raising her family in the Colorado mountains and is known to donate her art to charitable causes.
Why This Story Is Back in the Spotlight
The FX miniseries has revived public curiosity about Kennedy’s personal life. As each episode explores different chapters of his marriage, former friends and acquaintances have shared new or revisited accounts.
Hill’s story adds another layer to the complex legacy of John F. Kennedy Jr., whose life often blurred the line between public image and private struggle.
Whether viewed as a romantic chapter or a controversial claim, the story continues to spark debate nearly 26 years after his death.
