America's Reluctant Prince

by Steven M. Gillon

  John, however, never revealed his inner doubts to his staff. It was not only his pride but also his future on the line. “This magazine has to be a success; otherwise I can’t move on to the next venture, whatever that may be,” he declared. He remained outwardly upbeat about George’s prospects, reassuring the staff, “We will find a new home.” Near the end of June, John gathered everyone into the conference room. He apologized for being withdrawn, confessing that he had been distracted by a personal issue, “a family problem.” It had consumed much of his time, he said, but that problem “will be resolved soon.” He also promised them that no matter what they read, George’s situation was not as bleak as naysayers claimed. Talk of the magazine closing was nonsense. George would persist, he guaranteed them. “Don’t worry,” John said. “We will all have our jobs at Christmas.” Still later in the afternoon, he met with the business staff. “As long as I’m alive,” John pledged, “this magazine will continue to publish.”

  RoseMarie had no doubt that John planned to stay at George until it was successful. “John was absolutely going to stick with George until it was a success on its own,” she reflected in 2019. He made her a promise: “I will not go do the next thing, whether it’s politics or something else, until this magazine is a success.”

  But the magazine, which was now almost four years old, was still trying to establish its identity. In addition to the internal challenges of articulating a consistent message, John worried that the media still focused too much on him and not enough on the product. Once again, John wanted to find a way to “sell George as George,” and not as John Kennedy’s magazine. In response, marketing director Michael Voss revamped the media kit, which hadn’t been reworked since the launch, and he met with companies that could help them to streamline their pitch to potential advertisers. One such company was Leifer-Stieffel, run by the husband-and-wife team of Cheryl Stieffel and Peter Leifer, who had developed an interactive computer program that would have allowed the magazine sales staff “to take people through a very dynamic presentation that showed the essence of the publication,” reflected Leifer. By hitting a few keys, the George reps could summon statistics, demographics, and other content that would be directly relevant to an advertiser. Their proposal highlighted George as a brand and made no mention of John. Unfortunately, Cheryl and Peter never had the chance to meet with John personally, and their proposal was still sitting on his desk when he left for Martha’s Vineyard on July 16.

  Along with finding another business partner and developing more sophisticated ways to describe George to advertisers, John began exploring whether to transform George into a web-based magazine—which in 1999 was considered cutting edge. He raised the idea with a number of people, including Rich Blow, who took over as editor after Biz Mitchell left. “Maybe we should just turn George into a website,” John suggested to him. “If we abolish the printed magazine, we would save on paper, printing, trucking, and mail costs.” Blow said he did not imagine George as a website, but John responded, “It would solve a lot of our problems.”

  Blow was not the only person with whom John was having this conversation. “I think he was interested in other alternatives and perhaps producing an online magazine,” recalled Jeffrey Sachs, who had helped John create Reaching Up. “He talked about turning it into an online magazine—an idea that was very much ahead of its time.” John was fascinated by how technology could potentially change the media landscape. The late nineties were an exciting time in the evolution of the internet. “This is the Kitty Hawk era of electronic commerce,” one internet entrepreneur boasted, referring to the site of the Wright brothers’ 1903 flight that marked the dawn of air travel. Although still primitive, the World Wide Web, as it was initially called, was the central character in a larger unfolding drama: the explosion in digital communications technology that made it possible to convert text, sound, graphics, and moving images into coded digital messages that would transform the way people worked and played.

  John recognized the potential of the internet, although he never anticipated how quickly or dramatically the media landscape would change. Voss recalled joining John on a trip to San Francisco and Seattle, where he met with people at Microsoft to discuss the future of technology. “John was very interested in what was happening online,” Voss recalled. “How should we be using the web to get more of our content out there and engaging better with our audience?” John asked.

  Moving the magazine to the internet was not just a hypothetical question. John had also been having conversations with an old friend, Dan Samson, who had just sold a highly successful premium ice-cream company that he had created in Seattle in 1983. John respected Samson, admiring that he had built such a profitable business from scratch. Now he wanted to approach Dan about a new business venture. He began leaving voice messages for Samson, talking vaguely about “wrapping up conventional print, audio, and visual media concepts” and placing them on the internet. John revealed that he wanted a partner who could “mind the store” but not “some expert or big named person.” Rather, Samson recalled, “he just wanted someone that he knew he could trust to oversee the operations of the company.”

  In these conversations with Samson, it was unclear whether John had gone a step further with his dreams about George, imagining it could be interactive as well as online, or whether he had a completely different business in mind. John told Sasha Chermayeff that he was also considering going back to his original idea of mass-producing kayaks, which he and Michael Berman had investigated and dismissed before starting George. But the cryptic messages he left for Samson suggested that John was definitely focused on a venture that would involve tapping into the power of the still-nascent internet. On July 17 Samson was waiting at the airport to greet John in Hyannis. Afterward, they planned to go to the Vineyard “to spend two or three days hashing out his vision and developing the game plan.”

  * * *

  —

  I met Carolyn for the first time on May 19, 1999, at the Newman’s Own–George Awards ceremony. I had arrived in New York earlier that afternoon and called Rose to let her know I was in town. John got on the phone and told me that he was hosting a big event at the US Customs House Building downtown and wanted me to come. I tried to get out of it, insisting I had to prepare for my show, HistoryCenter, which I was filming two days later. But he refused to accept no for an answer. “Stevie, I better see you there,” he said.

  I tried to arrange a car service, but it was a rainy day, so I went outside and hailed a yellow taxi. As we made our way closer to the event, traffic started slowing down. When we were about three blocks away, I could see a line of black cars ahead of me, and after a few minutes, more limos appeared behind me. I decided to get out and walk the last few blocks, but security guards were patrolling the street. “Get back into the car,” one advised me. “You need to disembark at a special location.” Because it was a rainy day and John did not want paparazzi running around the area, George had created a tent by the building entrance. Each car needed to pull up directly in front of the tent so that photographers could take pictures of the guests. I sat helplessly in my taxi with my eyes transfixed on the meter as the cost of the trip seemed to increase by the second. Finally, I made it to the photographers’ tent. I was hoping that at least a few flashbulbs would go off, but as I exited the taxi, I heard one photographer ask, “Who is he?” to which another responded, “He’s nobody.”

  Dejected, I walked into the hall and stood alone in the reception area. Everybody seemed to know one another, but I knew no one. Finally, John and Carolyn arrived, holding hands and looking like the king and queen of the event. All eyes turned when they entered to a round of applause. I was taking in the moment, always marveling at the way people responded to John when he entered a room. He and Carolyn were making their way deeper into the reception area when John suddenly saw me standing alone and separate from the crowd. “Stevie!” he shouted. “You made it!” He rushed over
, put his arm around my shoulders, and escorted me into the dining area. It occurred to me that John was just as happy to see a friendly face as I was.

  I headed to my assigned table, but after a few minutes, John came over and asked me to join him at the head table with designer Kenneth Cole, actor Paul Newman, and his wife, actress Joanne Woodward. Several of his guests were arriving late, and he did not want the table to look empty. I became a seat warmer for Alfonse D’Amato, the recently retired New York senator, and Puff Daddy. I leaned into John’s ear and whispered, “Do I call him ‘Puff’ or ‘Mr. Daddy’?” John pushed me away. “Don’t embarrass me, Stevie.”

  John seated me next to Carolyn, who was stunningly beautiful, refined, and delicate. She was also aloof and guarded, qualities that were understandable, since she knew nothing about my relationship with John. At this point, I knew of their mercurial marriage from conversations with mutual friends and comments that John had made, but I did not really know what to expect. We made small talk, discussing the awful weather and a few other innocuous topics. Eventually the other guests arrived, so I went back to my regular table.

  A few weeks later, John had just returned from a long trip and asked me to have dinner with him at his favorite local restaurant, Odeon. The dinner was uneventful, but John seemed tired, which I assumed was the result of jet lag. I realized something was wrong when halfway through the meal he still had not made fun of me. “John, are you feeling okay?” I asked. “You are unusually subdued and uncharacteristically respectful.” I hoped to elicit a laugh, but instead he spoke in subdued tones about contentious negotiations with Hachette. He had come home to a nasty letter that day and wanted a fresh pair of eyes to read it and give him an opinion. While I was a contributing editor at George, I did not work there and wasn’t embroiled in office politics, so I agreed.

  It was now obvious that he had invited me to dinner to discuss the letter and to suggest that I come to his apartment to read it. It would be my first time at his Tribeca apartment. We walked down a busy street, populated with countless bars and restaurants, onto a dark side street with only one dimly lit streetlamp. “Why would John live here?” I thought, as I scanned a neighborhood full of old, abandoned warehouses. His building looked like an outdated industrial factory. We approached the front door, which John opened with a key. We entered a small, nondescript lobby with linoleum floors. No doorman. No security. He used another key to call the elevator. John’s apartment was on the top floor of a nine-story building. The apartment was dark, so I did not get to see much other than some mismatched furniture. Somehow I’d imagined John living in a fancy high-rise with a doorman and dramatic floor-to-ceiling windows. But John was always the rustic type. He would have been perfectly comfortable living in a tent in Central Park.

  As we walked in, John told Carolyn that he had brought a friend over to read “the letter.” Carolyn, whom I had met just a few weeks earlier at the awards ceremony, was wearing an oversized Columbia University sweatshirt. It was probably ten o’clock, and she looked exhausted. We went into a tiny kitchen with a small counter. John handed me the letter, and as I pulled it out of the envelope, John nervously lit a cigarette, and the two passed it back and forth. I was somewhat surprised—I knew that John smoked cigarettes occasionally and that he enjoyed pot, but he had never smoked either in front of me.

  I cannot recall who wrote the letter, or the specific language, but I do remember it being an unrelenting assault on John’s stewardship of the magazine, essentially attacking him for being both lazy and stupid. I told him that this letter would almost definitely serve as Hachette’s defense for refusing to renew the contract with Random Ventures. It represented a clear warning shot, putting John on notice that if he protested, they would go after him personally.

  At this point, Carolyn jumped into the discussion, enraged. I knew that she was fiercely protective of him, but I never expected what followed: a string of expletives like I had never heard before. “John, they are trying to fuck you!” she shouted. “Everybody fucks you, John, and you just take it! You let everybody fuck you, John. When are you going to grow some balls and start fighting back? You need to start fucking people back, John.”

  “Was this the same person I had met at the dinner?” I asked myself. She was seething with anger that seemed directed more at John than at the business partner who was about to abandon him. That night, I got a glimpse of John’s troubled marriage, along with his struggling magazine, and had the clear sense that both were coming to an end. Until then, I knew the magazine was limping along and that John and Carolyn, like most married couples, had problems. But not until I witnessed both firsthand—Hachette’s blistering letter and Carolyn’s rage and anger toward John—did I understand that both had become untenable.

  John solemnly guided me out of their apartment. He said he needed to clear his head. When we got to the curb, I shook his hand and turned right toward civilization. John turned left down the dark street. After taking a few steps, I turned around and saw his silhouette, head down and hands in his pockets. It was the last time I would ever see him.

  * * *

  —

  As if things were not bad enough in John’s life, he was also feuding with his sister, Caroline. They had been so close growing up and shared countless memories, but tragically, they were barely on speaking terms in the final months of John’s life. The two had great affection for each other, but they were very different people, and their lives had taken divergent paths. She was disciplined, focused, and book smart, while John was laid-back and mellow, relying more on his charm than his brains. Caroline had always been dismissive of George, believing that John was wasting his time when he should have been forging a real career path. On several occasions, she even visited the George offices and shared her concerns with John’s coworkers. “He’s irresponsible,” one staff member recalled her saying. “Can’t he keep his shirt on?”

  Her constant needling bothered John, because he felt judged, even for his passion. “She loved him, and they loved each other, but she was always making fun of him,” recalled Sasha. What John could tolerate even less, however, were her friends, who he thought did not respect him at all. While Caroline dismissed John and his friends as “potheads,” John described Caroline’s friends as “entitled snobs” and “know-it-alls.” John would often scoff at their pretentious conversations. “No, no, no,” he said in a mocking voice, “that was not who translated Freud.” He interpreted their attitude as, “Look, Caroline, there’s your cute, dumb brother.” After their mom died, John and Caroline would often find themselves on Martha’s Vineyard together, but they rarely interacted when they were with their spouses or friends. “John’s and Caroline’s friends never crossed over,” recalled Sasha, who spent considerable time with John at the Vineyard. “We stayed separate. She didn’t think much of his friends, and he didn’t think much of her friends, but I always felt there was an old closeness between the two of them. They really loved each other.”

  Their respective marriages further strained their relationship. Edwin Schlossberg, who was fifteen years John’s senior, made a genuine effort to reach out to John after marrying Caroline in 1986. But John found him to be just as pretentious and arrogant as the other people in Caroline’s life. “John just never liked Ed,” recalled Sasha. When asked what Ed did for a living, John responded, “You tell me!” According to a close friend, John regularly referred to his brother-in-law as “Ed the dickhead” and dismissed his art as drivel. “He hated the guy,” said one of John’s close friends. Carolyn also added a new element to the combustible mix. She repeatedly told John that his sister and brother-in-law treated him “like shit” and that they viewed him as the “family fuckup.” John, Noonan said, initially ignored her comments, but he eventually started to take them seriously. “When it’s just Caroline and me, we’re fine,” John reflected, but “add a spouse and look out.”

  Tensions between John and Ed escalated f
urther during the auction of Mrs. Onassis’s estate, which unfolded over the course of four days beginning on April 23, 1996. The auction consisted of six thousand items from Jackie’s homes. She wished for John and Caroline to sell most of her belongings, saying, “Sell them! Tell them it was from Jackie’s love nest.” Jackie left all her tangible property to John and Caroline, asking them to donate items of historical significance to the Kennedy Library. The library received thirty-eight thousand pages of documents, thousands of photographs, and around two hundred artifacts. John and Caroline could then keep what they wanted and sell everything else. Even Caroline’s rocking horse and John’s high chair were auctioned off. Sotheby’s calculated a conservative presale estimate of around $5 million for the entire auction.

  An estate sale is always stressful for a family, but John seemed to blame Ed—often unfairly—for making the whole affair more difficult than it should have been. “What I understood from John was that Ed was such a prick [about selling memorabilia],” a close Kennedy confidant recalled. “Ed insisted that they divide up the estate and sell items that had great sentimental value to John, including his father’s rocking chair.” Caroline and Ed rarely went to Hyannis Port, while John and Carolyn made regular trips during the summer. John resented how Ed and his sister “plundered” the house for auction items, dividing everything in half, including plates, glass, and silverware. Ed also insisted on a public auction that would garner maximum attention and profits. John pleaded for a private auction, where the estate could be sold discreetly and largely out of the public eye.

  In reality, Ed and Caroline were probably right. Everyone agreed that it was important to keep the Martha’s Vineyard home, but they needed to raise lots of money from the estate sale to pay for the taxes. They were more likely to raise the sum of money needed from a public auction. Also, John and Caroline were required to tag and declare all the items in the Hyannis Port house. Whatever items they decided to keep would be charged to them and deducted from the money they received at the end of the sale.