Lifestyle guru Martha Stewart says she asked John F. Kennedy Jr., the son of President John F. Kennedy, whether he planned to fly with a copilot during a dinner four days before the 1999 crash that killed him, his wife and his sister-in-law — a story she had not told publicly before recounting it on the Season 16 premiere of Bravo’s “The Real Housewives of New York City” on Tuesday, September 8, 2026.
The revelation came early in the episode, during a cameo by the 85-year-old, who had dropped in on her longtime makeup artist Daisy Toye — one of the season’s new cast members — for a glam session. The two got to talking about “Love Story: John F. Kennedy Jr. & Carolyn Bessette,” the installment of Ryan Murphy’s anthology that FX launched February 12. From there, Stewart turned to a memory from July 1999.
“I was with him the Monday before the Friday he died,” Stewart told Toye.
She went on to explain that Kennedy telephoned her at a point when she was running Martha Stewart Living magazine. He told her he was in trouble, she said, and asked whether he could get her advice about what to do with George, the magazine he had founded. Stewart said she told him she would help with anything he wanted.
Kennedy, the publisher of the political magazine George, which he launched in 1995, then met Stewart one-on-one. She described a pleasant dinner and said that as it wound down she asked about his weekend plans; he answered that he was going to a wedding on Martha’s Vineyard, with his wife and her sister coming along.
Stewart said she pressed him on the arrangements. “I said, ‘Who’s flying?’ He said, ‘I’m flying.’ I said, ‘You have a copilot, right?’ He said, ‘No, I don’t need a copilot.'”
“I’ve thought about that so many times that I told him to get a copilot,” she said. “I feel sorry.”
The Flight Four Days Later
Kennedy, 38, was at the controls of a single-engine plane that left Essex County Airport in Caldwell, New Jersey, on Friday, July 16, 1999. With him were his wife, Carolyn Bessette-Kennedy, 33, and her sister, Lauren Bessette, 34. The plan was to drop Lauren Bessette at Martha’s Vineyard before the couple continued to Hyannis Port, Massachusetts, for the wedding of Kennedy’s cousin Rory Kennedy. Roughly a half-hour into the flight, the plane went down in the Atlantic Ocean several miles off the Vineyard, killing all three aboard.
Kennedy was a relatively new pilot. The National Transportation Safety Board (NTSB) determined that the probable cause was Kennedy losing control of the aircraft as he descended over the water after dark, a lapse the agency attributed to spatial disorientation. Conditions that night were hazy, with no visible horizon.
Investigators also documented a separate offer of help. According to the NTSB report, a certified flight instructor whose name was withheld talked with Kennedy the day the crash occurred and volunteered to accompany him in the cockpit. The instructor said Kennedy replied that “he wanted to do it alone.” The same instructor told investigators he would not have been comfortable with Kennedy flying at night on a route like the one flown, in weather like that of the accident night.
The Couple at the Center of the Series
Kennedy and Bessette met in the early 1990s, when she was working at Calvin Klein. They married in 1996 on Cumberland Island, Georgia, and she became known as Carolyn Bessette-Kennedy. Their romance, and its end, is the subject of the FX drama Stewart and Toye were discussing when the conversation turned personal.
Why Stewart Is on Bravo at All
Stewart is not a Housewife, and she has been clear about that. Bravo was reported to be interested in casting her in August 2025, and her representative, Susan Magrino, pushed back on the reports at the time. Stewart told TODAY in July 2026 that executive producer Andy Cohen had wanted her, and explained her decision plainly: “I’m not a housewife anymore.”
She agreed instead to appear alongside Toye, whose Bravo bio sets up a season built around a career that is straining her marriage and the question of whether she can have it all. Cohen, discussing the season trailer on his SiriusXM show, said simply: “And Martha Stewart’s in it several times.”
The franchise reworked its lineup after the Season 15 reunion wrapped in February 2025. Back again are Sai De Silva, Erin Lichy and Jessel Taank, alongside series veteran Carole Radziwill, who appeared in Seasons 5 through 10, and newcomers Hailey Glassman, Erika Hammond and Toye. Season 16 airs Tuesdays at 8 p.m. ET/PT on Bravo and streams Wednesdays on Peacock.