John and Caroline were as close as brother and sister could be, their bond forged by adversity. In personality and temperament, however, they could not have been more different. Caroline was reserved, distant, and protective of her privacy. For understandable reasons, she fretted that people used her family to sell books and magazines. She was also disciplined and focused, a first-rate student at both Harvard and Columbia Law School. Meanwhile, John managed to create a sphere of privacy while still remaining open and accessible. He had an outgoing and gregarious nature but lacked the discipline to be a good student. While much of the public attention focused on John, he always believed that Caroline faced a harder situation because Jackie insisted that her daughter be perfect in every way. She wanted her to wear designer clothes, maintain an ideal figure, and develop the same refined sensibility that she herself possessed.
Caroline was not interested in such frivolities. Like John, she was fiercely independent and wanted to craft her own identity. As a teen, she rebelled. She wore torn jeans and T-shirts, ate pizza, and enjoyed thick milkshakes. When Caroline was eighteen, Jackie sent her to London to study art history at the famous Sotheby’s auction house, but soon the British tabloids were filled with pictures of her late-night antics. John used to say that he felt sorry for his sister because everyone expected him to “be a fuckup,” while Caroline had to attain perfection.
After the wedding, the family and guests retreated to the compound, where a white tent large enough to accommodate a small circus covered the reception area for four hundred guests. John delivered a moving and heartfelt toast. “All my life, there has just been the three of us: Mummy, Caroline, and I,” he told an eclectic group of family, friends, and celebrities. Rob Littell remembered being “surprised at the depth of John’s emotions, because I hadn’t spent much time around him and his sister.”
Except for large family gatherings such as this one, John kept a healthy distance from most of his cousins, but he remained close with Tim Shriver, William Kennedy Smith, and Anthony Radziwill. In 1982, after graduating from Boston University with a degree in broadcast journalism, Anthony moved to New York, where he and John were now able to spend more time together. Over the next few years, while Anthony pursued a career as a television producer and John attended law school, the two men became constant companions, meeting for meals, playing sports, and traveling together. Most people who knew them remarked on the easy friendship they shared that allowed them to constantly needle each other. It was also clear, however, that they were bound together by mutual bonds of affection, respect, and trust. Anthony was perhaps the only person whom John trusted with his innermost secrets.
At the same time, John did not have much of a relationship with RFK’s children. In a sense, he was continuing the practice that his mother started after JFK’s assassination, when she moved her family to New York. She always worried that RFK’s unruly horde would leave a bad influence on John. Though John did not harbor the same worry, and empathized with his cousins’ struggle to emerge from their famous father’s shadow, their relationship was always complicated. He found them immature; they found him arrogant. He felt they wore their names and their privilege on their sleeves; they were jealous of the media attention he received. “Don’t tell me about the fucking family,” he occasionally complained.
Indeed, John resented being lumped together with his cousins. I always sensed that John thought of himself as the first among equals and that the Kennedy legacy was his by birthright. It should be passed to him. It bothered him that so many of his cousins were entering politics and running on the Kennedy name. RFK’s two oldest children had entered politics. Kathleen Kennedy Townsend had lost her bid for Congress in the Baltimore area (but went on to serve as lieutenant governor of Maryland for eight years), while Joseph Patrick Kennedy II overcame a troubled youth to win a House seat formerly occupied by John’s father—a seat he held for twelve years. Ted Kennedy’s youngest son, Patrick, was a state representative and, later, congressman from Rhode Island. Though not ready to throw his hat in the ring, John still resented his cousins for trying to seize control of a legacy he felt belonged to him.
John clashed occasionally with his aunt Ethel as well, who he felt intruded on his space in Hyannis and acted rudely to his girlfriends. In January 1987 John and Christina were scheduled to spend time at the family mansion in Palm Beach. He booked the house in advance through Joseph P. Kennedy Enterprises, which handled the family’s extensive investment portfolio. They spent the first night of their vacation at the Breakers Hotel because Ethel was using the house and asked to spend an extra night. But when they arrived the next day, his aunt was still there and occupying John’s favorite room near the pool. Although annoyed, John told the Irish housekeeper to bring his bags to his grandfather’s room. He and Christina then went to the beach for the afternoon. When they returned, they discovered that Ethel had moved Christina’s bags to his grandmother’s suite. John let it go. “She’s difficult, but she’s still my aunt,” he told her. But in the kitchen one morning, Ethel brought Christina to tears by refusing to acknowledge her presence. That coldness proved too much for John, who confronted his aunt and warned her that if she did not treat Christina with respect, he would ask her to leave.
His friendship with William Kennedy Smith was also put to the test after Smith was accused of raping a woman at the Palm Beach estate. On March 30, 1991—Good Friday—Smith and Senator Ted Kennedy, who had divorced his wife, Joan, in 1982 and was now single, picked up two women during a night of bar-hopping. Afterward, they returned to the Kennedy estate, where one of the women, Patricia Bowman, would accuse Smith of raping her. John demonstrated his loyalty to William in November 1991, when he joined his cousin in a West Palm Beach, Florida, courthouse for the jury selection. John sat on a wooden bench in the first row of the courtroom, directly behind Smith and his defense team, occasionally jotting on a legal pad. John denied any effort to influence the outcome of the trial. “William is my cousin, and we grew up together. . . . I thought I could at least come down and be with him during some difficult times.”
* * *
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In 1984 John accepted a $20,000-a-year position in the Office of Business Development for New York City. Here he would meet Michael Berman—an encounter that would change the directions of both their lives. Berman, who grew up in an affluent family in Princeton, New Jersey, was three years older than Kennedy. In 1979, after graduating from Lafayette College, Michael settled in New York, where he took a job working for a division of a global advertising company. He quickly became disenchanted working in a large corporate environment and decided to explore his entrepreneurial instincts. Over the next few years, he formed a number of companies in marketing and communication and started handling several big clients, including Pfizer, Hallmark, and Johnson & Johnson.
At the request of a client, Berman volunteered to work pro bono at the Office of Business Development. One day he arrived at the office and was introduced to its newest employee: John Kennedy Jr. Shortly afterward, John invited Michael to a small birthday party of “close friends and family” at his mother’s apartment. Instead of finding an intimate formal dinner, he walked into what appeared to be “a glorified frat party in one of the most rarefied apartment buildings in Manhattan.” A few weeks later, John asked Michael to join him at a small music club in Manhattan to watch one of his favorite bands. Over the next few years, John would introduce Michael to his eclectic musical taste, inviting him to concerts by Sinéad O’Connor, Bruce Springsteen, the Rolling Stones, and Patti LaBelle.
After a few months, John invited Berman to lunch. He revealed that his uncle Teddy was pressuring him to participate in a few events that would involve talking with reporters. John expressed ambivalence. “I’m willing to do it if I can set some parameters,” he told Michael. “I don’t want to talk about myself personally, I don’t want to talk about my family legacy, and I certainly won’t talk about my fa
ther.” Michael’s advice was simple: “Then stay home.”
But John continued to struggle with either alternative, so Michael asked why he was reluctant. “That’s a good question,” John responded. “It makes me uncomfortable. I just don’t want to.” Berman explained that it was possible to grant interviews “without giving away your deepest, most personal feelings.” He told John that he could merely give them a glimpse of himself. “When you speak to a reporter, you need to tell the truth, but you don’t have to tell your entire truth,” he said.
John asked Michael to serve as his informal publicist. Berman was surprised that John was coming to him with this request, since they hadn’t known each other very long. He assumed his family had already set him up with a team of advisors. But instead, it just seemed like he was sent out without a net; he had no professional support group. John also had never really had much formal media training. “His default position had always been to say no,” said Berman. There was no handler, no fixer, no strategist. And there was certainly no tutorial for being John F. Kennedy Jr.
The two men quickly bonded, forming a close friendship and a mutually respectful professional relationship. “When I watched John and Michael, it was more like watching siblings than watching friends,” recalled Nancy Haberman, a powerful public relations expert who had been friends with Michael for many years and would later serve as the publicist at George. Both were quick witted and shared a similar sense of humor. Haberman remembered being with them one evening and telling John that he had almost single-handedly transformed Brown University into a hot college, noting that nearly half of her daughter’s high school graduating class of 105 had applied for admission there. John responded in a voice loud enough to get Michael’s attention, “How many applied to Lafayette?” But it was also their differences that contributed to the special alchemy that created their friendship. John could bring attention to any issue with his high-powered celebrity, and it was not lost on Michael that being associated with John helped his business. Furthermore, where John was scattered and unfocused, Michael was disciplined and detail oriented. John trusted Michael, convinced that he would respect his privacy.
John relied on Berman to handle his public image and empowered him to negotiate all his media appearances. From Michael’s perspective, it seemed obvious that John, who had always protected his privacy, was inching into the public realm. He would show up at Michael’s apartment with lists of topics he wanted to cover at his media appearances. He constantly received requests for interviews from local tabloids and occasionally The New York Times. If John held a dinner party, reporters would call Michael and ask for the guest list. Berman also had the unenviable job of managing bad press. John was photographed more than once buying pot on a street corner. Berman would implore reporters not to print the pictures, emphasizing that John was a private person, and the pictures would “ruin his life.” Surprisingly, reporters acquiesced.
In 1988 Teddy Kennedy asked John to introduce him at the Democratic National Convention in Atlanta. John was apprehensive but could not say no, so Berman enlisted a media coach named Michael Sheehan to train John for his brief speech. Sheehan recalled seeing John enter the media training room escorted by Teddy, and he was stunned by how handsome John was. “I said, ‘Just go out there and look up. The rest will be easy.’” Sheehan realized the minute he saw him that, with his good looks and his association with his father, there would be an automatic emotional bonding between John and the audience. “He’s going to get more applause than you are, so don’t be disappointed,” Sheehan joked to the senator.
Sheehan described John as cooperative and eager to learn but not especially happy to be present. “It was like he had to ski down a very dangerous hill,” Sheehan reflected. “He did not want to be there, but he did not want to disappoint his uncle.” Giving a speech in a convention hall had numerous challenges. “They have to get used to the size of the room, the noise, and the visual input, which is overwhelming.” The trickiest part was using the teleprompters, one placed on either side of the podium. Without a center prompter, speakers needed to learn how to move back and forth so as not to get stuck reading from one prompter. Despite these difficulties, Sheehan gave John rave reviews. “He was the best person I ever worked with. He had every justification to be a jerk. But he was unfailingly kind and gracious. I would want my sons to grow up to be like him.”
The Democratic Convention, held in Atlanta from July 18 to July 21, ended up being a fairly dull event, as the party rallied around its nominee, Massachusetts governor Michael Dukakis, and his running mate, Senator Lloyd Bentsen of Texas. Dukakis, who lacked both a governing philosophy and passion, had secured the nomination after front-runner Gary Hart, who had so fascinated John back in 1984, was caught allegedly having an affair and withdrew from the race.
On the day of his speech, John was pacing around backstage with Andrew Cuomo, the thirty-year-old son of the governor of New York, Mario Cuomo, and his friend Jeffrey Sachs. Both were helping him with his delivery. John was supposed to cut his long hair before appearing on national television, but he was so nervous that he and Cuomo went running on the roof of the convention center in hundred-degree heat. By the time he returned, no time remained for him to get his hair cut.
John ascended the podium at 9:10 P.M. on the second day of the convention. The crowd roared and sprang to its feet, giving him an ovation that lasted longer than a minute. As he tried to speak, delegates gathered near the podium to take his picture. “Over a quarter of a century ago, my father stood before you to accept the nomination for the presidency of the United States,” he said in a voice that bore little resemblance to either his father’s or his uncle’s. “So many of you came into public service because of him, and in a very real sense, because of you he is with us still.” He continued, “I’m not a political leader, but I can speak for those of my age who have been inspired by Teddy to give their energy and their ideas to their community and not just to themselves. . . . He has shown that our hope is not lost idealism but a realistic possibility.” The thunderous applause nearly drowned out his introduction of Uncle Ted.
John’s appearance marked one of the most passionate moments of a largely passionless convention. UPI noted that John drew “misty eyes from a charmed” crowd. Conservative activist Richard Viguerie commented, “I can’t remember a word of the speech, but I do remember a good delivery. I think it was a plus for the Democrats and the boy. He is strikingly handsome.” All the reports about John’s appearance referred to the famous image of him saluting his father’s coffin. Maureen Dowd, writing in The New York Times, noted that the “little boy whose picture saluting his father’s funeral cortege was seared into America’s consciousness 25 years ago” was now grown up. Indeed, the nation could remember him in almost no other way. This moment marked the first time many saw him again, especially in such an overtly political environment. His image had appeared in magazines for years, but there was no matching the power of television. “I remember his speech at the Atlanta Democratic Convention in 1988,” said William Schneider, a political analyst at the conservative think tank the American Enterprise Institute. “It was a success the minute he showed up onstage. There was an audible gasp. I’m not sure anyone remembers one word of what he said.”
Inevitably, speculation arose, much of it encouraged by Senator Kennedy and his staff, that John’s appearance signaled a new desire to get involved in politics. “It’s his debut before the party,” claimed a Kennedy spokesman. Teddy told reporters that he believed John would be involved in public affairs. “Not necessarily running for office but trying to make some sort of contribution.” Cousin Bobby Kennedy Jr., Robert and Ethel’s third oldest, also echoed Teddy: “He has a tremendous sense of duty and responsibility. Whenever any of the cousins need help on one of their [charity] projects, John always participates.”
The convention speech signaled a turning point for John. With Berman as his guide, John sta
rted assuming a bigger public profile. “He went from ignoring requests to controlling them,” Berman recalled. “He liked participating in things every once in a while, but on his own terms. I think the understanding that he could take control is what freed him to be able to participate more. At first, he was tortured by it all, and would often agree to things and then cancel at the last minute. But once he became more comfortable with the process, it was easier for him. It became yet another sport.”
As a child, John felt trapped by the constant presence of the Secret Service; now, as a young adult, he needed to gain greater control over how the public would see him. He used to complain often, “Don’t box me in.” He liked to do the unexpected. For instance, he once posed for an Annie Leibovitz photo in Vogue, which “was one of the last places you’d expect to see him, but it seemed like an easy way to promote a project for the John F. Kennedy School of Government at Harvard University he was working on,” said Berman. “He hosted a six-part documentary, Heart of the City, on New York City’s unsung heroes, and while he basically had an open invitation to appear on network TV any time he’d like, he opted for the local PBS station instead. It was his way of giving back to his adopted city.” The documentary served two purposes: it allowed John to brag about the city he loved while also gaining more experience in front of the camera. In November 1989 a division of Random House released an audiobook of John reading his father’s Profiles in Courage, which earned him a Grammy nomination. He also appeared one Christmas on Good Morning America to read a book to a gathering of children.
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