Martha Stewart’s last conversation with JFK Jr. included a warning that became painfully significant days later. During Tuesday’s Season 16 premiere of The Real Housewives of New York City, Stewart said she advised John F. Kennedy Jr. to use a co-pilot before the flight that killed him, his wife and his sister-in-law in July 1999.

Stewart shared the story with her makeup artist and new cast member Daisy Toye. She said Kennedy contacted her on the Monday before the Friday crash because he wanted help with George, the political and lifestyle magazine he had launched four years earlier.

“I was with John-John the Monday before the Friday when they died. He called me,” Stewart said. “I was running Martha Stewart Living magazine. He called me and he said he’s in trouble.”

Her response was straightforward: “Of course, anything you want.” The two then met for what Stewart described as “a very nice dinner.” What followed was the sort of ordinary conversation that becomes much harder to hear in retrospect.

Why did Stewart tell Kennedy to get a co-pilot?

During dinner, Stewart asked Kennedy about his weekend plans. He told her he was attending a wedding and would be flying with Carolyn Bessette-Kennedy and her sister, Lauren Bessette.

“He said, ‘Oh, we’re going to a wedding in Martha’s Vineyard. And I’m taking my wife and her sister,’” Stewart recalled.

When Kennedy explained that he would pilot the plane himself, Stewart suggested bringing a co-pilot. According to her, he replied: “I don’t need a co-pilot.”

Stewart told Toye she has replayed that exchange repeatedly over the years.

“I’ve thought about that so many times, that I told him to get a co-pilot,” she said, adding, “Ugh, I feel sorry.”

Kennedy was 38 when he died. Carolyn was 33, and Lauren was 34. Stewart’s advice could not change what happened, of course, but memory is not especially interested in such practical limits.

What happened during the fatal 1999 flight?

On July 16, 1999, Kennedy took off from Essex County Airport in New Jersey in a red-and-white Piper Saratoga. The group planned to stop at Martha’s Vineyard to drop off Lauren before Kennedy and Carolyn continued to Hyannis Port for his cousin Rory Kennedy’s wedding.

Kennedy had relatively limited flying experience and was not qualified to fly solely by instruments. During the nighttime journey over the Atlantic, he became disoriented while descending toward Martha’s Vineyard. The aircraft entered a rapid descent and crashed into the ocean off the island’s coast.

The National Transportation Safety Board later concluded that Kennedy failed to maintain control of the plane during the descent, with spatial disorientation among the central factors. All three people aboard were killed.

Their bodies and parts of the aircraft were recovered several days later. The crash prompted intense public attention, both because Kennedy was the son of President John F. Kennedy and because he and Carolyn had become one of New York’s most closely watched couples.

How were the Kennedys connected to Stewart?

Before the crash, Kennedy and Carolyn moved within some of the same New York social circles as Stewart. Their connection was not limited to magazine advice and dinner conversation.

Elizabeth Beller’s 2024 biography, Once Upon a Time: The Captivating Life of Carolyn Bessette-Kennedy, said Carolyn had wanted to contact Stewart for cooking guidance. A 1996 report also said Carolyn called Stewart for help with food and decorating, an entirely reasonable use of Martha Stewart’s telephone number.

Kennedy and Carolyn’s relationship, along with the events surrounding the crash, was later examined in Hulu’s miniseries Love Story. The drama aired while the latest season of RHONY was filming earlier in 2026, bringing renewed attention to the couple’s private life and final months.

Stewart’s recollection added a personal detail to that familiar history. It was not a grand prediction, just practical advice offered over dinner. Nearly three decades later, she clearly has not forgotten that Kennedy declined it.

The Real Housewives of New York City airs Tuesdays at 8 p.m. ET on Bravo.