GLOBE: JFK Jr.’s early years had profound sadness between longing for his dad when he was alive, to growing up fatherless after his death.
RMT: In the Collegiate [the NYC private school Kennedy attended] chapter of the book, especially the story of football legend Rosey Grier accompanying him on Parents’ Night when he’s in sixth-grade — it’s then that John understands he doesn’t have a father. He also has all these people around him who have memories, images, affection, and emotional connection to his father, but unfortunately John doesn’t. That’s where I saw the searching, the seeking, the trying to uncover as much information as possible about his father in John.
LM: Rose told me Rosey Grier would call the George office like once a week to check on John, right?
RMT: Yeah, John and Rosey talked all the time. And John always took Rosey’s calls. I remember Rosey came up to the office and he was massive, I mean he was huge. And Rosey was the sweetest, kindest man — so gentle. They had a real connection and affection for one another.
GLOBE: President Kennedy is often credited for his civil rights work, so it seems natural that JFK Jr. would have such diverse friendships. But it’s also pleasantly surprising because privileged or not, it’s very easy to stay in similar racial, socio-economic friend groups.
RMT: Not only did John have this diverse friend group but many of these people, who went all the way back to grade school, were still friends of his literally until the day he died. His friends say John touched and changed their lives, but I think it was the other way around. Each of these people left their mark on John as well.
GLOBE: During his bachelor days the media depicted him as a real ladies’ man, linked to celebrities including Madonna and Sarah Jessica Parker, but you found that he was a serial monogamist and a one-woman kind of guy. Why do you think the press got that aspect of his life wrong?
RMT: Because he was PEOPLE’s Sexiest Man Alive! John was young and handsome and from a prominent family. But if you think about who raised him, it was a mom and a sister that he had a beautiful close relationship with, and he had a lot of respect for women.
GLOBE: George Magazine, which launched in 1995, mixed politics and celebrity in an eclectic way. In hindsight it was a publication ahead of its time. RoseMarie, you worked there. Had John lived, do you think George would still be around?
RMT: I do, and I think so because John had ideas for George that went beyond the magazine. He understood the whole idea of taking it online, he was already thinking about how to merge entertainment and politics in an online version. If you look at what’s on the internet, George was the first iteration of The Huffington Post, The Daily Beast, Politico, and Axios is now.
LM: Back then we probably thought George was unusual. As a journalist, I was really interested in the types of people John was interviewing for George. A lot of subjects were connected to his father; like George Wallace, who challenged his dad, and Gerald Ford, who at the time was the last living member of the Warren Commission. As Rose mentioned, we’re now reading the outlet descendants of George every day.
GLOBE: Based on your interviews do you think the Kennedy legacy weighed heavily on John’s life and career choices?
RMT: Knowing and working with him every day I can say John really didn’t see it that way. When asked that question, he used to say, ‘I don’t see it as a legacy, to me it’s just my family.’ He felt there was a lot more privilege than burden that came with it, and a sense of responsibility.
LM: I’m reminded of something Steve Gillon, John’s friend from Brown, said. Steve also wrote a biography on John and knew him well. Steve said John said, “I don’t want to do what people expect me to do.” Steve said around the time that John’s life ended it looked like he might want to do the thing that people expected him to do — which was enter the world of politics. But John had to figure that out and come to that conclusion himself.
GLOBE: The Carolyn Bessette and JFK Jr. courtship seemed like a fairy tale. Did it appear that way from your perspective?
RMT: It was more than this fantastical fairy-tale romance, they had a friendship — they were buddies. They talked, gossiped together. They had this connection that was like best friends. They shared a sense of humor, teasing with jokes back and forth.
LM: From a journalist perspective they were a magical couple. They had that New York, downtown kind of element to them. You could sort of relate to them. We were entranced by them.
GLOBE: The marriage was a fairy tale, until it wasn’t. They had issues that partially stemmed from his fame overshadowing her existence. How much did the press pursuit of them contribute to the challenges in their relationship?
RMT: They needed more time. They were thinking about starting a family, and looking at houses outside the city. We also include [in the book] them meeting with a security firm. Because I think Carolyn was fearful of having a baby in the city and walking around where paparazzi could jump out and try to get photos.
GLOBE: Kennedy often took the subway to work. Even boxing heavyweight champion Mike Tyson advised him to get a security team, but early on John didn’t want one.
LM: Right. A lot of famous people have lots of layers, layers, and layers of protection around them. John didn’t have any. Instead, there was this trust and good will he built up. The reporters and photographers were always there from the beginning. I can’t imagine what it would be like to marry into something like that. It makes you realize how vulnerable Carolyn was.
GLOBE: On July 16, 1999, John piloted a single-engine Piper Saratoga plane with plans to drop off his sister-in-law Lauren in Martha’s Vineyard and then continue to Hyannis Port with Carolyn to attend his cousin Rory Kennedy’s wedding. But the plane crashed, killing them all. How hard was it revisiting their deaths for the book?
RMT: It was terrifying. When I read about it, talk about it I still feel a little bit of a knot in my stomach. And it’s not that I haven’t accepted it, but it’s that feeling — that physical gut feeling of discomfort, shock, fear, it being scary. All those things.
LM: There was disbelief. You feel like you lost something. There are a lot of people you report on at PEOPLE, but I certainly didn’t see them Rollerblading from time to time. I remember seeing John and Carolyn out in the East Village. So, there’s a real sadness. Your heart breaks all over again.
GLOBE: If JFK Jr. had lived, he would have been 64 years old this year. What would he be doing now? Would he be president? His impressive introduction of his Uncle Ted Kennedy at the 1988 Democratic National Convention made it seem possible.
RMT: That’s a tough one. I don’t like making those predictions, because I’m not a clairvoyant. But, I believe he could have been president if he wanted to. I also think the world and political climate would have been different [if he lived]. As I said before, people seem to behave better when John was in the world.
LM: John represented a lot of hope for people, and his parents represented a lot of hope. In the world we live in now, that almost feels like a foreign idea, especially with the headlines we read every day. I liked writing this part of the book because I thought, “It’s possible, you can bring people together in politics.” John really represented that. Maybe we can all be inspired by that a little bit.
GLOBE: What is John’s legacy, what can be learned from his life?
RMT: His legacy is really George Magazine. And the notion that different ideas, sides of the political spectrum and the social spectrum can co-exist and have meaningful relationships and dialogue. That’s a lesson we can all learn from John.
LM: I think his friends and friendships were his legacy. He really had a gift for friendship and deep relationships with people. I like to think that’s part of his legacy, too.
Ronke Idowu Reeves is the Globe’s SEO Editor, and a contributor to the books Vibe’s “Hip Hop Divas” and “Oprah: A Celebration at 70.”
