It’s hard to believe it’s been 25 years since John F. Kennedy Jr, his wife Carolyn Bessette, and her sister Lauren Bessette died in a plane crash. On July 16, 1999, the plane, piloted by John, went down off the coast of Massachusetts, shocking the world. Just a few months prior, Katie sat down with John for what would be his last television interview. Now, for a special two-part remembrance, she reflects back on that fleeting moment in time when John and Carolyn captivated the public’s imagination and talks to the authors of two new books about them, contemplating their scrutinized lives, their fierce love, and their enduring legacy.

Below are some highlights from conversations with RoseMarie Terenzio and Liz McNeil, authors of JFK JR: An Intimate Oral Biography, and Elizabeth Beller, author of Once Upon a Time: The Captivating Life of Carolyn Bessette-Kennedy. Find out about the state of their marriage before their untimely deaths, whether they planned on starting a family, and more, and listen to the full podcast episodes below.

How Carolyn Bessette-Kennedy felt about the press scrutiny

Elizabeth Beller: She was terrified. Absolutely terrified. And they treated her differently when she was with John. If John was around, it was a little bit more of like, “Hi, how are you guys doing? Can you give us a smile?” You know, keeping a respectful distance. If she was on her own, they would often close in and yell out epithets to try to get a face of unhappiness, which they could then use to create the narrative that there was trouble in the marriage. She became further and further frightened. It was terrible… It ramped up after they got married, and that was exactly when they were expecting it to settle down. There was interest, and it was incoming, but once they got married, it went into overdrive. And I really don’t think there was any way to anticipate that it would be exactly like that. And I think John did try to sort of teach her. He was a gracious, kind man. 

What really happened before the plane crash

Elizabeth Beller: John was working that day. Carolyn, like any woman going to a summer wedding, went to get a pedicure, but she was not there for an elongated amount of time. In fact, the gentleman who initially said he saw her getting the pedicure did come back later to say, “I saw her leaving this salon no later than 5 o’clock,” and then they were all in cars at the same time, heading to the airport. Years later, there were a lot of books, some written by men, that really tried to place the blame on her and say it was her fault that they were late. That’s just not the case. They were all in the car at the same time, headed to the airport. It was a sticky, hot New York City Friday, as we know they can be. And sometimes, it feels like the city just doesn’t want to let you leave it. [There was] bumper-to-bumper traffic. And when people try to say John was careless or that he flew illegally, that’s not the case either. He was not careless with his life. Visual flight rules require 5 to 10 miles of visibility, and he checked the weather report in the afternoon before he went to the airport. He checked it again, and it said that there was that much visibility. Unfortunately, that can change very quickly over those islands. 

The state of their marriage at the time of the crash

Liz McNeil: Well, they were under an incredible amount of stress in those last few months. Anthony [Radziwill]’s impending death, difficulties at George trying to find funding, and difficulties in the marriage. And then John’s also thinking about politics at the same time. They were going through a difficult time. But you know what’s so interesting about them is that Carolyn gets on the plane, and she’s going to the family wedding with John, and makes this gesture of reconciliation…And that was very significant. 

RoseMarie Terenzio: I think they were having difficulties with all the things Liz mentioned. But they were looking for a house outside the city because they were talking about starting a family. The way I look at it, they had a couple of weeks of fighting and not being on the same page, but they were going to look at this house outside of New York, they still wanted that appointment with the real estate agent. And I think the fact that they decided to do marriage counseling was a sign that they wanted this to work. I don’t know that there’s a marriage that exists without difficulties, especially three years in with all of the pressures that they had, including how public their lives were. And I think they were trying to rein things in and get on the same page. But yeah, it was difficult. The last few weeks were tumultuous and difficult, but they were together. 

On the recent renewed interest in Carolyn Bessette-Kennedy as a style icon

Elizabeth Beller: I think it’s about that restraint. We’ve gone through a lot of years where it’s been about very revealing clothes and heavy, heavy makeup, contouring to make your face look like a completely different shape than it actually is. And I think, even though Carolyn had on the red lipstick and her hair might be back tight, she had a natural look. In an age where we’re saturated with images, I think that that becomes even more appealing… She had advised one young woman that she was friends with, “Just put your hair up when it’s wet, put on some lip gloss.” It was a very natural look, which is very appealing.