Living in the long shadow of his father, JFK Jr. was struggling to make his own mark in the world, when a tragic plane crash cut his efforts short.

From the time he was born, just weeks after his father’s 1960 election, John F. Kennedy Jr. grew up under a relentless spotlight, privileged and burdened by the magnitude of his family mythology. After President Kennedy was assassinated at the age of 46, young John came to embody for many Americans the optimism and promise his father had brought to the nation. It was a promise he took seriously, and struggled to meet.

But in the last year of John Jr.’s own short life, things were anything but Camelot-like. His best friend, cousin Anthony Radziwill, was dying from cancer. His magazine George, which celebrated the intersection of politics and pop culture, was failing. His marriage to Carolyn Bessette, under the relentless glare of paparazzi cameras, was so rocky he had moved out of their Manhattan apartment. Even his bond with his sister Caroline had become deeply strained.

READ MORE: The Final Days of John F. Kennedy Jr. 

Historian and author Steven M. Gillon, author of America’s Reluctant Prince: The Life of John F. Kennedy, Jr., is uniquely positioned to go beyond the Kennedy mythology and reveal the full complexity of John’s story. Gillon knew JFK Jr. from the time they were at Brown University together in the early 1980s. He remained a friend, racquetball partner and an adviser and contributing editor to George until John’s premature death in a plane crash in July 1999. But Gillon, a professor at the University of Oklahoma focusing on modern American history and politics, has also put a scholar’s lens on the life story of one of the nation’s most beloved sons. He appeared in the BIOGRAPHY special JFK Jr.–The Final Year, and spoke with BIOGRAPHY about what it meant to be John F. Kennedy Jr.

You first met John under somewhat awkward circumstances—when you were a PhD student at Brown University, giving a lecture about his father to an undergraduate class in which he was enrolled. How did he react?

I gave a speech that was somewhat critical of John’s father’s handling of civil rights. That was in the spring of his sophomore year. Surprisingly, John came up to me after the class and thanked me for giving such a great lecture. John, I would later learn, had a fairly sophisticated understanding of the strengths and failings of his father’s presidency.

John F. Kennedy Jr., in cap and gown, chats with a classmate at his graduation ceremony at Brown University, where he received a Bachelor of Arts in History.

JFK Jr. at his Brown University graduation in June 1983. John earned his undergraduate degree in history.

How did your relationship develop after that?

In the fall of 1982, when he was a senior, we started seeing each other in the Brown weight room. We spotted for each other, and we’d talk. Then at some point, he came up to me in the main library on campus, and he said “Stevie, I need some cardio.” He wanted to play racquetball. So we got out the phone book and found this place in Seekonk, just over the border in Massachusetts. I didn’t have a car, so we would go in his blue Honda. We’d play, on average, one or two times a week. And after we played, we would go to Wendy’s. John never carried money, so I always ended up paying. That’s when we bonded, his senior year.

Did you have an opportunity to teach him after that first lecture?

I was getting my PhD in American civilization. As part of my training, I was assigned to run weekly discussion sections for a class in modern political history. John signed up for my section. When he showed up—which wasn’t often—I got to interact with him in a smaller setting.

What was that like?

There were 12, maybe 15 people. We were discussing modern American politics—including his father. John was passionate about certain topics, like the Supreme Court and race and civil rights. But he was very careful not to be intimidating. He always referred to his father as President Kennedy. I was surprised at how well read he was about his father’s presidency. He had a fairly sophisticated understanding of it, because it turned out he was tutored by people who were in the administration. I once had a debate with John about whether his father would have pulled out of Vietnam. The next day, he called me and said, “Stevie, I talked to Robert McNamara [the Kennedy administration secretary of defense] on the phone last night, and he said you’re wrong.”

President John F. Kennedy, perched on the edge of his desk in the Oval Office, plays in the Oval Office with his toddler son, John-John.

President John F. Kennedy playing with his son John-John in the Oval Office. Kennedy actively cultivated wholesome media images of his family in the White House, sometimes against the wishes of his wife Jackie, who jealously guarded their children's privacy.

John was arguably the most famous baby in the world. And with that image of him, a toddler, saluting his father’s coffin, the weight of the Kennedy legacy seemed to shift to him. How did he deal with that weight, and his fame, in his youth?

When he raised his right hand that day at age three (on his third birthday), all the hopes and unfulfilled expectations of his father’s presidency transferred to him. He was the heir apparent to Camelot, he was the one who was going to return America to the glory days of the early 1960s. That was a burden that would have crushed most people, but he carried it with remarkable grace. John always said he was two people: He was just John, a typical wealthy, privileged young man of his generation. But he also played a role, that of John Fitzgerald Kennedy Jr., son of the beloved slain president. Maybe that’s why he was so good at stage acting.

That’s a tough act to follow.

Later in life, people were constantly comparing him to his father. At one point, I think when John was getting a lot of heat about failing the New York State bar exam, people would say that, by the same age, his father had won a Pulitzer Prize. John would just say, “I’m not my father.”

READ MORE: How Jackie Kennedy Privately Unravelled Over JFK's Assassination

What kind of student was John?

It varied a lot. He made some mistakes and overreached early on. But by his senior year he was a solid B+ student. He excelled in his acting classes, which he loved. One theater professor at Brown told me John was the most talented actor he ever taught.

The most fundamental thing about John and his learning capability was that he had a really short attention span. He could be really well read and articulate about the things he cared about. But it was hard to get John to care about a lot of things. If he wasn’t interested in something, he could really tune it out.

JFK Jr. gives the peace sign as he enjoys Labor Day weekend at Hyannis Port on August 31, 1980

Privacy was not something John Jr. could ever count on. He was hounded by photographers wherever he went. 

You write in the book about his mother Jackie’s prickly relationship with the Secret Service, as she tried to balance her children’s safety and privacy. Your research led to a pile of long-buried documents related to this topic; what did they reveal?

I filed a FOIA (Freedom of Information Act) document request with the Secret Service and the FBI for all documents related to John. The response I got was that they had no documents, which was hard to believe because I had talked to agents who had worked on his detail, who talked about having to file regular reports. So I sued the agency. And ultimately, the Secret Service came up with 600 pages of documents. They covered a period starting just after he was born and going right up to when he was 16 years old.

READ MORE: Why Jacqueline Kennedy Didn't Take Off Her Pink Suit After JFK Was Assassinated

What were the big takeaways?

There were two main things. First was the profound tension between Jackie and the Secret Service as she tried to protect her children while also trying to give them as normal a life as possible. And second was the cocoon John grew up in. If he was going on a ski weekend, say, there were always these very detailed plans of where exactly they were going to go each day, where the agents were going to stay, on and on. Nothing was ever simple or spontaneous.

I understand why John always seemed so restless, why he wanted to just get on his bike and go wherever he wanted. He had lived in a total cocoon the first 16 years of his life.

What’s one of the most intense run-ins Jackie had with the Secret Service over her son?

The most dramatic one was in 1974, when John’s bike was stolen in Central Park. She wrote a scathing letter to the Secret Service accusing them of being incompetent. The most searing line: “If anything happens to John, I won’t be as nice to you as I was after Dallas.” It got to the point where the Secret Service asked her to decline protection because there was a question of whose authority supersedes—the mother’s or the agency’s? She put so many restrictions on what they could and couldn’t do: She didn’t want John to turn around and see a Secret Service agent. She didn’t want them to talk into their walkie-talkies around him. She didn’t want John to be constantly reminded of their presence. They told her they couldn’t guarantee his protection with those rules in place. So they asked her to decline Secret Service protection, which she refused. It was a difficult situation.

There was a period where it looked like John was pursuing a career in the law. How serious was he about that?

I think John didn’t know what he wanted to do. Law school is an easy thing for a lot of recent college graduates in his position. It kicks the can down the road. John never intended to practice law, but he wanted to get the degree. He failed the bar twice, and the third time they made a provision so he could take it by himself. It was such a circus the first two times he took it—all the media, this gauntlet of photographers outside, they were climbing up to take pictures of the test room from outside the windows. His PR representative, Michael Berman, had argued that the provision was necessary not so much for John, but for all the other people taking the test who would have to endure the aggressive paparazzi.

It can’t have been easy to have failed, repeatedly and so publicly.

John was devastated by failing, especially the second time. He felt he was letting people down—his family and people who he felt looked up to him. It was humiliating. But he wasn’t one to wallow in self-pity, so he picked himself back up again.

Growing up in the shadow of his iconic father, John seemed to be trying to make his own distinct mark in the world. How important to him was George, the magazine he started?

The whole time this is going on—when he goes to law school and he works in the district attorney’s office and he starts George, he’s trying to create an identity separate from his family’s identity. But he’s also laying the groundwork for some sort of career in politics, leaning into that legacy. He hadn’t fully made up his mind. That comes a couple of years later. I don’t think he had a plan to be an editor or a publisher for a long time. But he needed something, when he did finally go into politics, where he could show some accomplishment.

In the last year of John’s life, George was struggling financially, bleeding advertisers. You were a contributing editor for the magazine. What worked? And what didn’t?

George was ahead of its time in anticipating the merger of politics and popular culture, but it struggled to find the sweet spot where the two came together. There was also a struggle over John's role. The publisher, Hachette, wanted him to be more visible in the magazine; John simply planned to be an editor and allow the magazine to speak through the talented voices of its writers. What was most memorable about George were not the stories, but the covers, especially when John had someone—I think it was Drew Barrymore—dress like Marilyn Monroe when she sang “Happy Birthday, Mr. President.”

READ MORE: The Story Behind Marilyn Monroe's 'Happy Birthday, Mr. President'

John F. Kennedy Jr., son of the late President Kennedy speaking at the 1988 Democratic National Convention. John was introducing his uncle, Senator Edward Kennedy.

John Jr. giving a speech at the 1988 Democratic National Convention, introducing his uncle, Senator Edward Kennedy.

Toward the end of his life, it seemed like John was getting more comfortable with the idea of running for office. What was his thought process?

The first big opportunity came when Daniel Patrick Moynihan [the longtime United States senator from New York] retired, leaving his seat open for 2000. John was considering it. But ultimately he didn’t feel he was ready. And he didn’t think Carolyn was ready for the strains of a campaign. What many people don’t know—I spoke with Hillary Clinton’s campaign manager, and they said that if John had declared his candidacy for Moynihan’s seat, Hillary was not going to run. They didn’t think they could beat John in a primary.

In the documentary you mention that he actually had been eyeing a governorship.

He didn’t like the idea of being a legislator. He saw how miserable and frustrated so many of his family members were, serving as legislators. John saw himself as an executive, someone who made decisions.

During your research, you dug up tape of John practicing for his speech at the 1988 Democratic National Convention, when he introduced his uncle Ted. What did you see in that transformation he made between rough practice and the final speech?

The tape was John’s first practice session, and he’s understandably struggling. He’s reading from a teleprompter for the first time. It’s really difficult, especially if you’re going from one prompter to another. What it shows is that John was able to transform himself. He always rose to the occasion, and he rose to the occasion in that convention hall. That was the moment for millions of Americans who were watching—the moment they were waiting for. They had watched him grow up, but most had never heard his voice before. They see him up there, he’s so strikingly handsome. He was that little boy, but all grown up.

Talk about his relationship with his cousin Anthony Radziwill.

Anthony was the brother John never had. They had a bond that went back to when they were little children. They poked fun at each other. Anthony’s wife, Carole, compared them to the odd couple: Anthony was always neat and proper and John was always perpetually a slob. John loved Anthony and showed him a lot of respect for the courage he showed in facing his illness. That Anthony was dying of cancer devastated John.

John F. Kennedy Jr. and his wife Carolyn after the 1998 funeral of his cousin Michael Kennedy, who died in a skiing accident.

John F. Kennedy Jr. and his wife Carolyn at the 1998 funeral of his cousin Michael Kennedy, who died in a skiing accident.

There were a lot of stressors on his marriage with Carolyn. What was the state of their relationship before their fateful plane ride?

The main problem was that they believed that once he was married, the paparazzi would leave them alone. It was the opposite. They were vicious with Carolyn. And while he was used to it, she wasn’t. He needed to support her more. It created a lot of tension in their relationship, to the point where he would act out and she would act out. That last week before he died, he had moved in to the Stanhope Hotel. He had told friends they might separate.

Was there stress, too, over the topic of starting a family?

John wanted to have kids. Carolyn, for understandable reasons, wasn’t ready. She said how can we bring up John III in this type of environment? Your best friend is dying, your magazine is dying, the paparazzi are making my life miserable—and you want to bring kids into this?

His sister Caroline had always been a rock in his life, but you write there was stress there as well.

They had been very close. But in the years before John’s death, there were a lot of problems in his relationship with his sister. He thought she was dismissive of him as the family screw-up. One big problem was her husband, Ed Schlossberg. John didn’t like it when Ed got so involved in the liquidation of Jackie’s estate, of her home and belongings. He thought those decisions should only be made by blood family. John wanted to have a silent auction, which he thought would be low-key. Ed wanted a public auction, which he thought would draw more attention and more money. The day before John died, he called his sister, and they agreed to work on their relationship.

That’s a lot to deal with.

It was. But in the last month of his life, it seems like he was really trying to turn things around. For George, he had ideas to save it by making it into an online magazine and cutting costs that way. Carolyn, by flying with John to Hyannis that weekend to his cousin Rory’s wedding, was showing that maybe she was going to give this marriage a chance. And then reaching out to his sister, he was hoping to turn that relationship around. He was hopeful. But tragically, he ran out of time.