Martha Stewart has spent decades building a reputation as one of America’s most recognizable lifestyle and publishing figures, but one conversation from the summer of 1999 has never quite left her.
During the Season 16 premiere of The Real Housewives of New York City, Stewart recalled meeting John F. Kennedy Jr. only days before the plane crash that killed him, his wife Carolyn Bessette Kennedy and her sister Lauren Bessette.
According to Stewart’s account, Kennedy had reached out because he wanted her perspective on George, the political and lifestyle magazine he had co-founded. Stewart was then at the helm of her own rapidly expanding publishing operation, making her a natural person to approach for advice.
The two met for dinner and discussed the challenges Kennedy was facing with the publication. But it was a conversation about his upcoming weekend plans that Stewart would remember for decades.
Kennedy told her that he planned to fly with Carolyn and Lauren that weekend. Stewart asked about the flight and whether another pilot would be accompanying him.
She recalled encouraging Kennedy to have a copilot.
He ultimately made the trip without one.
On July 16, 1999, Kennedy took off in a single-engine Piper Saratoga with Carolyn and Lauren aboard. The aircraft crashed into the Atlantic Ocean near Martha’s Vineyard. All three were killed.
More than 27 years later, Stewart said she still thinks about the advice she gave Kennedy shortly before the tragedy.
Her recollection comes as another generation of television viewers is being introduced to the story of Kennedy and Bessette Kennedy. Their relationship has returned to the pop-culture spotlight through the FX series Love Story: John F. Kennedy Jr. & Carolyn Bessette.
That renewed attention has also intersected with the return of Carole Radziwill to the Real Housewives franchise. Radziwill’s late husband, Anthony Radziwill, was Kennedy’s first cousin. Anthony died from cancer only weeks after the 1999 plane crash.
For Stewart, however, the story is more than another chapter in America’s enduring fascination with the Kennedy family. It is the memory of an ordinary dinner that became extraordinary only in hindsight, and a piece of advice that has remained with her for more than a quarter-century.
