Although not apparent at the time, the same technology that Berman and Kennedy celebrated as the vehicle for mobilizing disenfranchised voters was also a double-edged sword. Radio did marshal voters, but it was not the apathetic liberals who responded to the agitation. In 1960 only two radio stations had talk formats. By 1995, there were 1,130. The most popular hosts were overwhelmingly men, and nearly 70 percent of listeners were conservative. By 1994, 20 million Americans were tuning in to hear right-wing conspiracy monger Rush Limbaugh on 659 radio stations. In addition, his late-night television show was syndicated to 225 stations, and his two books topped the bestseller list.
The optimistic ideas that informed George—that Bill Clinton’s campaign and election signaled the beginning of a new postpartisan age, and that the merger of politics and popular culture would lead to more educated and engaged voters who didn’t depend as much on parties for their political identity—were the product of America’s unique environment in the 1990s. Unfortunately, many of those assumptions would prove false.
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Berman and Kennedy labored quietly for two years, but the initiative picked up after Jackie’s death in May 1994. Since leaving the DA’s office earlier that year, John spent most of his time working out of Joseph P. Kennedy Enterprises on Forty-Second Street in Manhattan. He rode his bike from there to Michael’s Manhattan office a few times a week for meetings. The weekend after Jackie’s funeral, John called Berman and asked if he could move into Michael’s office. “I need to focus on this, and I can’t have everyone telling me how sorry they are every day,” he explained. “I can’t deal with the sympathy in the Kennedy office.”
Berman and a partner, Will Steere, had formed a public relations firm called PRNY, and Berman hired a tough-talking woman from the Bronx, RoseMarie Terenzio, as his assistant. Since they handled many celebrity clients, Rose was not surprised when John started showing up at the office. According to RoseMarie, by the spring of 1994, John, accompanied daily by Sam, his “slightly demented rescue dog,” visited the office every day. Michael never told Rose why John was coming to the office, but she did notice they had several “spirited” meetings during which John would gesticulate wildly. No one ever knew what they were talking about, and they always were careful to take whatever papers they had brought with them.
A few days after Mrs. Onassis’s burial, RoseMarie arrived at work only to find John and a stranger placing her possessions in a cardboard box and moving them out of her office. “What are you doing?” she shouted. John explained that Michael had offered Rose’s office to him. Rose shouted for Michael, who then explained to her that he and John were now working together. “Let’s be realistic,” he said. “You really think I’m going to give him the smaller office?
“You’re going to be just fine,” he added, reassuring her that her job was safe but that she simply was being dislodged from her office.
RoseMarie remained so angry that she ignored John every time he entered the office. He would greet her with a pleasant “good morning” as he walked past her small office, but she refused to reciprocate. On a few occasions when she heard him coming down the hall, she would pick up her phone and pretend to be talking. This act continued for about a month, until one day John decided to stick his head in her door and say, “Good morning, Rosie.” It marked the first time that he referred to her by name, and no one outside of her family ever referred to her as Rosie. He then stared at her to see how she would react. At first, she extended her middle finger but then started laughing. John’s gesture broke the ice. He did not know it at the time, but it would also gain him a trusted assistant and a dear, lifelong friend.
Over the next few months, each man spent $150,000 of his own money to hire consultants and develop business plans. During long, sometimes contentious sessions, and after conversations with dozens of consultants, paid and unpaid, they refined their vision for the magazine. Joe Armstrong convinced them that they would be in a better negotiating position with an investor or partner if they proved their concept through a direct mail campaign. “You buy ten thousand names from the mailing lists of fifteen magazines,” he told them, “and send out a mock-up of the magazine.” He hooked them up with George Lois, a legendary art director who’d produced iconic covers for Esquire, to help with the design. For every hundred samples sent out, the hope was to get 3.5 responses from random consumers who claimed they would pay for a $24 subscription. “George is to politics what Rolling Stone is to music. Forbes is to business. Allure is to beauty. Premiere is to films,” the editor’s letter read.
They mailed two test batches: one with John’s name on the masthead, and one without. “If the test without you is successful, then we have a business,” Berman told Kennedy. “Otherwise we have a business about you, and that’s not good for either of us.” The responses to both batches proved quite positive. Not surprisingly, they scored a 5.7 response rate with John’s name visible. But what was surprising was that the one without his name earned an impressive 5.1 response.
“This is a go,” they declared.
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John’s personal life was also in transition. In 1990, while still dating Daryl Hannah, John met Carolyn Bessette, a personal stylist catering to celebrity clients at the Calvin Klein store in Manhattan. Carolyn told model Michael Bergin, her boyfriend at the time, that she had originally been introduced to John at a charity event. Afterward, John visited the Calvin Klein store to purchase three suits and Carolyn served as his stylist. Although Carolyn admitted to Bergin that she knew John, she downplayed any hint of romance, telling him that she had been “under-impressed.” In reality, that first encounter led to a brief romance. In the summer of 1990, Carole Radziwill recalled staying at a house that John and Anthony shared in East Hampton, when Carolyn came bouncing out of John’s bedroom.
John was clearly smitten with Carolyn—and for understandable reasons. She was stunningly beautiful: tall (five feet, ten inches) and slender with long blonde hair, blue eyes, and broad shoulders. But it was not just her looks that John found attractive. When she wanted to be, Carolyn was also charming, engaging, almost mesmerizing. John preferred surrounding himself with friends—and girlfriends—who were not spellbound by his fame. He gravitated toward strong, independent-minded women who were not afraid to voice their opinions. “Most women sort of became tongue-tied around John,” said Brown fraternity brother Richard Wiese. “But not Carolyn. She was very strong-minded, knew what she wanted, and had absolutely no difficulty speaking her mind.” John once told Carole Radziwill that on one of their first dates he scored tickets to a play, but Carolyn got stuck at work and never showed up. (This happened before cell phones and instant messaging.) “John was shocked that she stood him up,” Carole recalled.
Carolyn Jeanne Bessette was born on January 7, 1966, in White Plains, New York, to kitchen designer William Bessette and public school administrator Ann. She had two twin sisters, Lisa and Lauren, who were older than her by two years. When Carolyn was six, her parents separated. Carolyn blamed her father for the breakup of their family and rarely spoke to him after that. In 1973, Ann married Dr. Richard Freeman, the chief of orthopedic surgery at a White Plains hospital, and the family moved to tony Greenwich, Connecticut.
Carolyn spent two years at Greenwich High School before transferring to St. Mary’s High School. She graduated in 1983, the same year that John finished at Brown. Her classmates voted her the “Ultimate Beautiful Person.” A story recounted by a fellow student offers evidence of why she received the honor. “When I was a freshman and she was a big senior, she was incredibly sweet to me,” recalled Claudia Slocum. “I remember I burst into the girls’ room one day, just sobbing, probably over some lip gloss that my friends had made fun of or something. And she was there with her friends. And she came right over. She dried my eyes and tucked my hair behind my ears and talked me up. And after that, she always smiled an
d said hi to me in the halls.”
That fall, Carolyn entered Boston University, where her reputation—unlike in high school—was less than stellar. No one at Boston would have voted her the “Ultimate Beautiful Person.” Friends attested that Carolyn did not join clubs or play any sports and never made the dean’s list. She did, however, enjoy an active social life, dating influential men on campus, attending parties, and going out to local clubs.
During this time, Carolyn worked at the Calvin Klein store in the Chestnut Hill Mall, near the Boston College campus. It was here, in 1988, that she met Grace (a student at Boston College who does not want her last name used), who was shopping for a dress when she struck up a conversation with Carolyn. They became fast friends. “We were interested in similar things such as fashion, art, and photography,” Grace told me in 2019. “We both liked the same designers.” During one of their chats, they shared their romantic fantasies. When Grace asked who Carolyn’s “dream guy” was, Carolyn responded, “John Kennedy Jr.” “I’m going to get him,” Carolyn insisted. “I’m going to move to New York and I’m going to get him.” Grace was shocked by the intensity of Carolyn’s focus on John. Carolyn’s comments suggest that her later encounter with John at a charity event may not have been by chance.
That obsession was not the only disturbing revelation about Carolyn. When Grace asked her what she wanted to do with her life, Carolyn stated, “I want to be famous. Maybe if I hook up with the right guy I will be famous.” Grace observed that Carolyn had a knack for getting to know the most important people on campus. “She had to be with the guy of the moment.” She dated fashion empire heir Alessandro Benetton, as well as John Cullen, a Canadian-born hockey star who later became a professional player for the Tampa Bay Lightning. Furthermore, it did not matter if the man she desired was already in a relationship. Another female classmate who wishes to remain anonymous recalled how Carolyn waged a campaign to steal her boyfriend, who was also a star hockey player. And yet another student told Christopher Andersen that “Carolyn was sort of known as the campus man-eater.”
In the end, Grace realized that even after spending months hanging out with Carolyn, “I did not know her true self. On one occasion, she would be stoic and reserved; on another, she would be wild and crazy. She would pretend to be humble and then turn around and be a complete snob when she was hanging out with fashion people. I felt that she was always acting.”
It took Carolyn an added semester to earn her degree in elementary childhood education at Boston University. After graduating, she continued to work at the Calvin Klein store while also doing marketing for That’s Entertainment, a company that owned a number of nightclubs in the area. Joe Verange, who hired her, remembered her as “a good schmoozer, a good networker,” capable of organizing parties at a variety of clubs. But Verange also told The Boston Globe that “she was obviously looking for more than a life of hanging out in nightclubs.”
That opportunity for a wider life came when Susan Sokol, president of Calvin Klein’s women’s collection, spotted Carolyn while visiting the Boston store. She was impressed by Carolyn’s looks and style and invited her to move to New York, where she would have a job accommodating celebrity clients. “She wasn’t intimidated,” Sokol recalled. “She had a wonderful ease about her. She was comfortable with anyone, and she had a lot of self-confidence, aside from looking great.”
With that new job, Carolyn finally landed in John’s orbit. But their brief romance ended when Daryl Hannah moved to New York to try to mend her relationship with John. Carolyn continued dating Michael Bergin. John, however, made sure to keep tabs on her. He would always inquire about her from mutual friends. “It was often the first question out of his mouth,” recalled one friend. According to Carole Radziwill, “He always had one eye on her.”
By the time Jackie died in 1994, John had already been planning to ditch Daryl. He started seeing Julie Baker, whom he had dated briefly before meeting Daryl. But Carolyn still lingered in his mind. Although she had clearly made it her goal to be with John, Carolyn now played hard to get. If John did something to upset her—like canceling dinner at the last minute—she would scream at him, “Fuck you! I’m going off with Michael!” She would claim to mutual friends that she was not going to wait for John, but she would actually remain home and listen for the phone to ring.
Even as he pursued their relationship, John tried to gather more information about Carolyn from others. He had heard rumors that Carolyn liked to party, so he asked a friend who had connections in the Manhattan nightclub scene to investigate and report back to him. The friend, who wishes to remain anonymous, recalled that he did not deliver a “flattering” report. “She does a lot of blow, she stays out late, she knows how to reel in guys and play guys, she dated the star football player in high school, the captain of the hockey team in college. Be careful.” John not only ignored this advice, he also told Carolyn everything he’d heard. She never forgave the friend.
Yet for now, John tried to keep his relationship with Carolyn under the radar, partly because most of his time was occupied by the launch of his new magazine.
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Over the next eighteen months, the two partners arranged meetings with wealthy investors, many of them friends of John’s mom, along with a handful of publishing houses. “Every door was open to them,” said a friend of John’s. “But that was good news and bad news. Did these people believe, or did they just want to meet John?” At one point, John and Michael joked that they could fund the magazine simply by charging people $1 million to meet with John.
Their initial meetings did not go well. Even if Michael and John attended a meeting together, it would become clear that everyone wanted to see and hear from John. The two men were invited to make a presentation to a large publishing house. Michael did all the talking, and John sat largely silent. When the publishing executives were asked afterward how the meeting went, one said, “We were pissed. We had no intention of giving them any money. We just wanted to hear from John, and all we got was Berman. We could not kick them out of the office fast enough.”
Some potential investors found them unprepared and unfocused. One of those they approached described it as “very much amateur hour.” The president of a small publishing company said that John came to him with only a vague idea about his magazine’s direction. “He gave me his feelings about the marketplace, that young people are interested in politics, but we don’t realize it and it doesn’t show up in the stats,” he recalled John explaining. He then asked John about a magazine article suggesting that only 15 percent of any generation find government or public affairs interesting, but John dismissed the observation. “It was the worst presentation I have seen in my business life,” the executive stated. “He was like, ‘I’m JFK, so there you go.’ He just knew he had this perfect idea; he was so worked up.”
Even close friends of the family rejected him, including Jann Wenner, whose negative response especially disappointed John. He initially thought that Wenner, the founder of Rolling Stone magazine, would at least offer constructive comments. Instead, John complained afterward, “He shit all over it.” “Politics doesn’t sell,” Jann told him bluntly. “It’s not commercial.” He then proceeded to offer John a job at Rolling Stone. John suspected that Wenner simply did not want the competition. “John was hurt and felt betrayed by Jann,” a colleague recalled.
They also set up a meeting with David Koch, an oil billionaire from Wichita, Kansas, who donated heavily to both the Republican and Libertarian Parties. But Koch seemed less interested in buying the magazine than he did in purchasing Mrs. Onassis’s apartment, which he’d seen and wanted a second look at even though potential buyers were allowed only one visit. “I am planning to get married, and I’m looking at your mother’s apartment,” he told John. “Your mama was a lot like mine. Neither one of them likes spending a penny. That apartment is a mess.” John was taken aback by Koch’
s bluntness and his lack of interest in the real purpose of the meeting, but he arranged for the billionaire to see the apartment again, and Koch eventually bought it. “We received no investment from him,” Berman recalled with a laugh. “But John got $9.5 million.”
John and Michael did manage to snare about a dozen investors, mostly Europeans, who were willing to offer between $500,000 and $1 million each. The total sum added up to roughly $10 million, which fell well short of the $20 million they needed to launch. A large portion of the money needed to be directed toward circulation, publication, and sales, three essential elements that a publishing company would already have in place. But no publishers expressed interest. Worse still, John and Berman feared that many of those who put up money did so for the wrong reason: they just wanted to be in business with JFK Jr. “It was like buying a racehorse,” Berman claimed.
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