America's Reluctant Prince

by Steven M. Gillon

  Neither of these initial ideas panned out, obviously, but over the next few years, the two of them toyed with other initiatives. The challenge was that both had day jobs—Michael at a public relations firm and John at the Manhattan DA’s office—so they met infrequently. Michael turned to his friend and publicist Nancy Haberman as an additional soundboard for ideas. In 1993, shortly after Arkansas governor Bill Clinton became president, Michael approached her with a new proposal. “I have this idea for a magazine that will be a mix of pop culture and politics. What do you think?” Nancy was initially unimpressed, but when Michael added that he intended to ask John to join the venture, she responded, “It just got a little better in my mind.”

  One evening over dinner, Michael pitched the idea to John, enticing him with the prospect of a multifaceted magazine integrating the popular with the political: “We could be what Rolling Stone is to music and Vogue to fashion.” Much of the motivation behind this vision had been inspired by the current political landscape. They agreed that the 1992 presidential race, especially Bill Clinton, had electrified nearly everyone they knew, even those who had been apolitical in the past. The excitement that the forty-six-year-old Clinton had been able to drum up reverberated with John, who had already been fascinated by the charismatic candidate. John admired politicians like his father, who could inspire and motivate people regardless of their political affiliation. In the 1980s, he admired President Reagan for many of the same reasons. Gary Ginsberg, who worked on the Clinton campaign, recalled John picking his brain about all aspects of the race.

  John saw obvious similarities between his father and Clinton. Both were engaging, young, and energetic. They offered a fresh alternative to a tired, old establishment figure. Clinton spoke often of how JFK had inspired him to pursue a life of public service, and his campaign never let pass an opportunity to show a 1963 photo of a sixteen-year-old Bill Clinton, who was in Washington as a delegate to Boys Nation, an American Legion program, shaking the president’s hand in the Rose Garden. One of Clinton’s themes from the start of his political career was to emulate JFK’s call for mutual responsibility, urging citizens to give back to their country. John’s mom, who usually avoided endorsing politicians other than family members, came to Clinton’s aid in the critical New York primary, where former California governor Jerry Brown was running a spirited campaign after having won the Connecticut primary two weeks earlier. Mrs. Onassis appeared at a public event and allowed the governor to claim himself as the rightful heir of the Camelot legacy. The day before his inauguration, Clinton traveled to Arlington National Cemetery to lay a wreath on the graves of JFK and Robert Kennedy, and once in office, he had photos of both men displayed prominently in the White House.

  Creating a new magazine, especially one that combined politics and popular culture, was risky. There had been a boom in new magazines over the previous two decades. Since the 1970s, celebrity magazines such as People had gained in popularity. Women’s magazines like Cosmopolitan and teen magazines like Seventeen also flourished, as did fashion publications, especially Vogue and Harper’s Bazaar. Each targeted a very specific audience, since magazines depended on advertising dollars to survive. In 1995 there were few gender-neutral magazines. Men flocked to Sports Illustrated and Car and Driver; women read Vanity Fair and Cosmopolitan. Fashion and cosmetics advertisers filled the pages of magazines focused on women, while car and alcohol ads flowed into men’s magazines. The conventional wisdom was that female readers did not read about politics, and without female readers, John’s proposed new magazine would not have a viable advertising base. Nina Link, who served as the CEO and president of the Magazine Publishers of America (MPA), noted that there was always risk in launching a magazine. “There was, however, a greater risk with George because it was creating a different category.”

  Despite the obvious challenges, they knew what they were getting into and were willing to take the plunge. John attended a two-day seminar called “How to Start Your Own Magazine.” On the first morning, the instructor cautioned the earnest faces before him that they could launch a successful magazine on any subject—except religion and politics. John then heard the statistics that seemed to doom his venture before it had even started: 90 percent of all start-up magazines fold, and no commercially viable political magazine had existed in the entire twentieth century. John left before the first coffee break. He and Berman decided to look on the bright side instead. “If everyone said that you can’t launch a successful political magazine, at least we won’t have any competition,” Berman said.

  In retrospect, they underestimated the depth of the problem and overestimated their ability to solve it. Some of the most experienced veterans in the magazine business had tried and failed to find ways of bridging the gap between male and female advertiser preferences. But John and Michael were two novices in the worlds of both publishing and business: neither had run a magazine before, let alone created one. But they did have a secret weapon in the power of John’s celebrity. Would his appeal transcend the gender divide and allow them to create a new genre of magazine publishing?

  I spoke with John several times about his ambitions for George, and my crystal ball was no clearer than his. What struck me was his willingness to take on such a risky venture, a quality that I had recognized years earlier when he was still a student. During his last semester at Brown, he chose to enroll in Mary Gluck’s extremely demanding course on European intellectual history, despite knowing full well that he was required to pass all his classes. Now, as he was starting his professional life, he resolved to do what no one else had accomplished: launch a successful political magazine designed to reach both men and women. Again, he seemed undaunted by the challenge. I remember thinking, “You can do anything. Why not take it step-by-step? Take a job at Rolling Stone, establish a reputation for being a good editor, learn about the business, and then launch your own magazine.” But I was always reluctant to offer John advice about anything other than history, because I knew that his life was often far too complicated for me to understand.

  The greatest complication was that John felt he needed to prove himself—and fast. Most of us climb ladders in our careers: we start at the bottom and work our way up gradually. John had the means to start at the top, and he preferred it that way: hurrying and skipping steps that others lingered on. Perhaps it was the frequent comparisons with his father and what he had accomplished at a similar age that accounted for John’s rushed approach. Like many of his generation, John had enjoyed a prolonged adolescence. He spent three years at law school and another four years working in a field he knew he did not plan to pursue. Now in his midthirties, he felt the need to make a decisive career move. He wanted something identifiably his, a venture that he could own and expand into a successful business. He keenly understood his strengths and weaknesses, and he longed to be taken seriously for his own merits and not just because of his family name. If he launched a successful magazine, he could prove to the world that he was a man of substance.

  John’s lack of direction had troubled his mother, who’d asked her close friend Joe Armstrong to meet with him to discuss career options. Armstrong had been a successful magazine publisher who went on to work at ABC News. Joe recalled spending a week with Jackie on Martha’s Vineyard in the early 1990s, and she told him that John was bored working in the District Attorney’s Office and was restless; he knew he had no interest in practicing law, but he had no idea what he wanted to do next. “Joe,” she asked, “would you have lunch with John and just talk with him?”

  On this occasion and many others, John was not aware that his mother was reaching out to her vast network of friends to provide him with direction and opportunities. She was a “hidden-hand mother,” pulling strings behind the scenes, asking people to contact John and offer him plum summer jobs, internships, or, in the case with Armstrong, career guidance. She wanted John to think that he found these opportunities on his own, when, in fact, she had set t
hem up for him. “She often planted seeds for options to come his way,” Armstrong recalled. “She knew that he could be very casual about things.” He would forget to put in an application for school or a job. She, on the other hand, “was totally disciplined, and strategic, and such a responsible person.”

  Armstrong does not remember the details of what he and John discussed over a handful of lunches, but he had a vivid memory of the most telling comments that John made. He told Joe that the Clinton White House had offered him a Labor Department post organizing after-school programs for disadvantaged children. But he turned it down. “Joining the new administration is too predictable and what people would expect me to do,” John said. “I want to do something unexpected. All I know for certain is that I don’t want to do what people expect.”

  A year later, John called Joe to tell him that he and Michael Berman wanted to start a magazine. Armstrong, who had served as publisher for ten magazines, was just the right person to guide them. John explained the concept, then asked, “Is this viable?”

  Armstrong sincerely loved the idea and encouraged them to pursue it. “Joe was very kind at a time when most people we spoke with didn’t think we stood a chance,” Berman reflected in 2019. “He was a magazine insider and very well connected in the media world. He had a wide network that he was happy to introduce us to. He didn’t come from a large corporation like Time Inc. or Condé Nast or Hearst. He was more of a renegade and that appealed to us. He’d worked for start-ups like Texas Monthly, New York, and Rolling Stone—all scrappy, independent publications, working with small, smart staffs and limited budgets that somehow managed to break out and become important voices in the cultural zeitgeist. That’s what George aspired to be. And while he was soberingly realistic about the challenges we would face, not once did he say it couldn’t be done.”

  Armstrong also offered valuable advice. “First thing you do,” he said, “is to tell no one. Neither of you has any experience in magazine publishing, so people are not going to take you seriously until you prove yourself and prove that you know what you are doing.” He then asked a series of pointed questions: “What writers will you get to write for you? What kind of stories will you publish? How are you going to find your audience? How can you prove to potential investors that there will be interest and support for this magazine? How can you prove that there will be reader and advertiser support, so that investors will see solid evidence that the potential is real? What advertisers will be in the magazine, and how can you prove to them that they can’t find readers in other ways?

  “Political magazines have always had small audiences and small ad support,” he continued. “How can you give confidence that your publication will be the exception?”

  They could not answer a single question. “They knew nothing about publishing a magazine,” Armstrong recalled. “I told them again that their one chance would be destroyed if they didn’t keep this secret until they knew the answers to my questions, and until they could give potential investors confidence that they knew what they were doing, and until they could make a powerful case for a way to success.” Kennedy and Berman, he said in 2019, needed to prove that the business was viable and that they were smart enough to run it. “Otherwise the media would have torn them apart as unqualified and unprepared” and would destroy their ability to find investors.

  John and Michael took Armstrong’s lecture to heart and set out to answer the questions he’d asked. “They were determined and rolled up their sleeves and worked hard,” Armstrong recalled. Over the next year, Armstrong, in addition to helping them write a business plan, introduced them to the top magazine designers in the business and to circulation professionals, so that they could perform direct mail testing to prove their concept to investors. “I helped them create mock-ups as well as advertising and circulation and editorial plans,” Armstrong reflected. John and Michael did not always accept Joe’s advice, but they appreciated his enthusiasm and his encouragement.

  Armstrong wanted John to meet other people in the business, so he managed to get him a coveted seat at the 1994 Gridiron Club dinner, an annual event where the media performed satirical skits and the president was expected to engage in self-deprecating humor. “John,” Armstrong said, “would you like to go to the Gridiron dinner?” “What is that?” John asked. Armstrong was surprised that someone who was launching a political magazine had never heard of the event. “Well,” Joe told him, “you should think about going because you can see the whole Washington power structure. You can meet people at the cocktail hour. You can plant some seeds to build relationships.”

  As they settled into their seats, the emcee began the event by saying, “We have in the room today a man who every woman wants to have dress them: Ralph Lauren.” The fashion designer stood and welcomed the round of applause. “And,” he continued, “we also have in the room the man who every woman wishes would undress them: John Kennedy Jr.” As a spotlight shined on him, John sheepishly lifted himself from the chair, giving a brief wave before sitting down.

  The next day, Ralph Lauren offered to fly the two men back to New York in his private jet. He suggested they stop at his estate in Bedford, New York, for lunch, and then he would arrange for cars to take them into the city. “Let’s do it,” John said. He was curious to see Lauren’s famous mansion, but he was even more excited to ride in his private jet. John’s childhood fascination with the military had long since faded, but he never abandoned his love of flying, although the object of his affection was now planes, not helicopters. He spent the entire flight in the cockpit with the pilots. “That was when I realized how much he loved flying,” Armstrong recalled.

  As his first real professional project, John saw George as a way of forging a new identity. He’d spent his whole life up to now trapped by the image of himself bleakly saluting his father’s coffin. John longed for the public to recognize him for his accomplishments as an adult. Rather than conjuring up dusty images of a kid romping around the White House or bidding his father farewell, John hoped they would see an accomplished editor and a successful businessman.

  John also wanted to disprove the public perception that he was not bright. He had failed two bar exams. Being a district attorney should have put those concerns to rest, but no one could seem to forget John’s most publicized case, in which a man robbing a house fell asleep before escaping. He won, but how could anyone have lost? Now, at nearly thirty-four years old, he felt he lacked any professional accomplishment, and he feared any success he achieved would be attributed to luck. He told me that if he was appointed to a high-profile job, especially in politics, people would assume that his family connections had worked their magic. But founding and growing a business seemed different. He was convinced that if the business proved successful, no one could dismiss it as mere good fortune.

  By this point, all of us who knew John realized that he was gravitating toward a life in politics and envisioned George as his stepping-stone. While he had long avoided getting pulled into the family business, I began noticing a gradual change in his views. It became most obvious to me one night while dining together at the New York Athletic Club in downtown Manhattan. It was a moment so jarring that I can still recall John sipping from his bowl of steaming-hot tomato soup. He told me that he had spent the day ice-skating with underprivileged kids in Harlem. He noticed how excited they were to see him; how they clung to him as he circled around the rink.

  “What they need is hope,” he said. “They need to know that tomorrow will be better than today.” He then paused and put down his spoon. “I can do that. I can give them that hope.” I was stunned. Never had I heard him state so clearly his intent to enter the political arena. But he said that he had to make his magazine a success first, adding, “I can’t fuck this up.” Over the next few months, John and Michael engaged in long discussions, trying to articulate a clearer message and meaning for their vague concept. Together they produced an early working docu
ment that they planned to present to wealthy individuals and publishers to gauge interest.

  Both viewed Clinton’s election as a turning point in American history, like that of Franklin Roosevelt in 1932 and John F. Kennedy in 1960. Their own observations convinced them that the 1992 election was significant, and they turned to history to support their belief. They found useful evidence in a theory developed by famed historian Arthur Schlesinger Jr. The former Harvard professor and advisor to both JFK and RFK held that US politics was cyclical and repeated itself every thirty years. Each cycle allegedly began with a transfer of presidential power, which was animated by a desire for change and renewed public involvement in national affairs. Eventually that initial energy would fade and give way to a preoccupation with private affairs. Just as Roosevelt and Kennedy had inaugurated new eras in American life, so had Clinton’s election signaled the beginning of another. John and Michael pointed out that citizens turned out to vote in record numbers, including more than one million newly registered voters under twenty-five. Minority participation spiked despite the absence of a prominent black candidate on the ticket. The number of women voters also increased significantly. On election night, ABC, CBS, CNN, and NBC posted prime-time ratings that jumped from a 34.8 share in 1988 to 46.3. These figures, they argued, showed that voters “were once again wholly vested in the political process.”