One person who was not particularly supportive of this idea was John’s wife, Carolyn. She continued to shun the spotlight. “John knew that his wife had not fully adjusted to her new role,” Richard Blow wrote in Vanity Fair. “She was neither entirely comfortable nor entirely happy, and she certainly wasn’t sure what she wanted to do with herself beyond being John’s wife.”
But it was quickly a moot point. Hillary Clinton effectively thwarted John’s plan to run for Moynihan’s Senate seat by announcing that she was moving to New York and running for it. “John felt like he could not go against her because it would be too disruptive to the state Democratic Party,” Ginsberg said. “He would look disloyal and he felt like she just outranked him in the pecking order, and for his first campaign he did not want to go after a sitting First Lady. He thought that it would be too bruising, so he decided to drop it.” But he still had not abandoned the idea of entering politics. Instead, he just reoriented his thinking. Rather than running for the Senate, he decided he would challenge New York governor George Pataki in the 2002 gubernatorial election, an idea he discussed with his friends. “John recognized that he was a much more natural executive than he was a legislator,” Ginsberg said. “He talked about how boring the Senate was and how he wasn’t cut out to sit on a committee and listen to endless hours of testimony. He viewed himself much more as a chief executive and thought that his skill set was just much more suited to being a governor than it would being a senator.”
By then, Brian Steel, John’s friend from the Manhattan district attorney’s office, had moved to Washington to work in the White House. John had invited Steel to the White House Correspondents’ Dinner in April 1999, and the next day they worked out together, had lunch, and discussed his future. Steel drove John to the airport—he had flown down in the Saratoga—and on the way they discussed what he was planning to do about George and about a potential political career. “He was very concerned about all the people that worked at George,” Steel said. “He didn’t want to leave because he knew when he left that was it. He had that in the back of his mind.” He said he knew that Hillary Clinton had called up John and reiterated, “‘I’m going to run for Moynihan’s seat unless you want to run. If you want to run I’m not going to run.’ And John said, ‘I’m not going to run.’ John is telling me this story but then he said, ‘You know what? If I had to run for anything I want to run for governor. Listen, a lot of people from my family have run for office—I think that’s great—but no one’s been a governor. I like being the boss. I like being a CEO. I think I’m better suited to be governor.” The big unknown was what would happen with Carolyn. “She had to stabilize herself because she was pretty unstable at that point,” a close friend said.
During one of their many arguments, Carolyn had shared with John that she was still sleeping with Bergin. “She threw Michael Bergin in John’s face,” the Hollywood producer Clifford Streit told Vanity Fair. “I think she used Michael Bergin in any way she could to get whatever she wanted out of John. The only one in the world who thought Carolyn would choose Michael over John was John.” John wasn’t sure whether to believe her or not, but what with her mood swings, her drug use, and her extreme reticence, he wanted her to see a psychiatrist. She agreed. In March 1999, he agreed to join her at marriage counseling.
On July 12, Carolyn moved out of their bedroom into a spare room in their loft that John used to store his exercise equipment. John checked into the Stanhope Hotel, on Fifth Avenue. It was just down the street from where he grew up. His room overlooked the Met, where he used to play Frisbee and hang out as a kid. There were page proofs and cover mock-ups of the upcoming issue of George strewn around his hotel room. John spent a lot of time on the phone, contemplating with friends how things had spun so badly out of control. “It’s all falling apart,” he told one friend. “Everything is falling apart.” That afternoon, with his ankle still in a cast, he flew in his Saratoga with a copilot to Toronto to meet a second time with the Magna executives.
On July 14, Richard Blow was sitting in his office at George, which was near John’s, and he could hear John screaming through the closed doors. “In startling, staccato bursts of rage, John was yelling,” he recalled. “His yells would be followed by silences, then John’s fury would resume. At first I could not make out the words. Then, after a particularly long pause, I heard John shout, ‘Well, goddammit, Carolyn, you’re the reason I was up at three o’clock last night!’ The shouting lasted maybe five minutes, but John’s office door stayed shut for some time.” For lunch that day, John met Carolyn and her older sister, Lauren, an investment banker for Morgan Stanley, at the Stanhope Hotel. Carolyn’s sister thought the get-together would be a good idea to try to clear the air and get the marriage back on track.
At the lunch, Lauren also convinced her sister to fly with John that Friday night up to Hyannis Port for the long-scheduled wedding of his cousin Rory Kennedy. In her fit of pique, Carolyn had decided she would not go to the wedding. But of course, her absence would be noticed and remarked upon. Even though their marriage was troubled, John wanted to avoid that at all costs and was desperate for Carolyn to agree to attend the wedding with him. In that regard, Lauren played a crucial role, convincing her sister not only to attend the wedding but also to fly up to Hyannis Port with John in the Saratoga. Lauren agreed to go with John and her sister, even though she was spending the weekend on Martha’s Vineyard, not in Hyannis Port. She convinced John to fly to Martha’s Vineyard, drop her off, then continue on to the wedding. “Come on,” she told them, “it’ll be fun.” John and Carolyn agreed to the proposal. “Great,” Lauren said. “Then I’ll see you guys at the airport.”
But John was still very unhappy. That night, from his room in the Stanhope, he was on the phone with a friend, unleashing on Carolyn. “I want to have kids, but whenever I raise the subject with Carolyn, she turns away and refuses to have sex with me,” he told his friend. “It’s not just about sex. It’s impossible to talk to Carolyn about anything. We’ve become like total strangers.… I’ve had it with her! It’s got to stop. Otherwise we’re headed for divorce.” He told the same friend he had even picked out a name for his son—Flynn.
The next morning, the New York Post ran a piece suggesting that Kliger and Hachette would “probably” pull the plug on George when the agreement was up with John at the end of 1999. “Though neither of us was at liberty to say so,” Richard Blow recalled, “Kliger and I both knew that the situation had progressed beyond ‘probably.’” Kliger had invited the staff of George to lunch at the Palm, on West 50th, that day as a way for him to get to know people better and vice versa. But John blew the lunch off. “His absence was a poorly hidden sign that John had other priorities,” Blow continued. After lunch, John called the George editorial staff together. First, he apologized for being a bit cranky and withdrawn of late. He said he’d been preoccupied by a “family problem” that “will be resolved soon.” He also wanted to assure people that George was in better shape than the tabloids would have everyone believe. George would carry on, either with Hachette or with a new partner. “Don’t worry,” he said. “We will all have our jobs at Christmas.” Later that afternoon, John conducted a similar meeting for the business side of the magazine. “As long as I’m alive,” John said, “this magazine will continue to publish.” He also made a stop that day to Lenox Hill Hospital to see his orthopedic surgeon, who removed the cast on his leg and told him to keep using crutches until his foot returned to full strength; it was still too weak to support his six-foot-one frame. The doctor also told him not to fly the Saratoga for at least ten more days, until the foot improved, since he needed his feet to fly the plane. But Ginsberg remembered how important it was for John to get back to flying after a six-week layoff. He had invited John to his son’s bris that morning, but John declined. It was either the bris or getting his cast removed. “If I don’t get my cast off then I can’t fly my plane and I really want to fly the plane,” John told him. “He hadn
’t flown in a couple of months, and he was really itching to get back up there.”
That night, after John had gotten his cast removed, John and Gary went together to the Yankees game. Ginsberg had also invited to the game James and Lachlan Murdoch, Rupert’s two sons. They all sat together in the box of George Steinbrenner, the Yankees’ owner. Part of the idea was to have John meet the Murdoch sons to see if there might be some interest in News Corporation replacing Hachette as John’s partner for George. Murdoch already owned one political magazine, the conservative (now defunct) Weekly Standard, and the more liberal George might be a way to balance out his holdings. Plus, unlike Hachette apparently, Murdoch was able to understand what it might mean to have John F. Kennedy Jr. as a publishing partner. They spent around eight hours together that night, talking about John’s future at George or in politics. “We had a full conversation about 2002 and there’s no doubt in my mind that he was going to run against Pataki,” Ginsberg said. After the game, Gary dropped John off at the Stanhope. A cover story was concocted for his friends about how John had lost his keys to the North Moore Street apartment and that he was working in the hotel on editorial spreads for the magazine—but the truth was obviously quite different.
Some of John’s closest friends were convinced the breach with Carolyn was irreparable. Chermayeff recalled, “He said to me one time, ‘Sasha, I think I’m finally ready for a real woman. I finally think I can handle a woman.’ I was like ‘Ah.’ That last year with Carolyn had been a disastrous year and he was really in pain about it. He was really in a tough way about it and really felt like it was over.… Anybody who knew them well knew how serious the problems were that last year. But he was always barking up the wrong tree when it came to women. He didn’t quite ever find a woman who was a whole [person], especially in his thirties with Daryl and Carolyn. He was ready finally at the end. He had chosen women who didn’t make him happy. He wasn’t happy with Daryl and then he wasn’t happy with Carolyn. Why? The different reasons that he was attracted to them to begin with then became the thing that he couldn’t be with. You know when you’re young the thing that makes you fall in love with a person, and then the thing that makes you fall out of love kind of thing. I think he was finally starting to feel that he was whole enough to find a really whole woman. I think he wanted to have children. He really did.”
There are others, including Rob Littell, who remained determined to perpetuate the notion that John and Carolyn were getting along just fine. It wouldn’t fit the gauzy narrative of America’s favorite son for their marriage to be failing. They were “two very passionate beings, and when their flames crossed, there were sparks,” Littell told People. If a breakup were even a possibility, “they would have made plans to go to a marriage counselor, to a priest at the church his mother went to. It wasn’t on the radar. John was very keen on the long term. He felt that Carolyn was his best shot at a successful marriage.” (Either Littell did not know that John and Carolyn had already sought the advice of a marriage counselor, or he was covering for them.) According to Littell, Carolyn’s ongoing affair with Bergin, her drug use, her maniacal fear of the press, and her refusal to have sex with John were just the adjustments she was making to being a newlywed, along the lines of “This is where my toothbrush goes,” he said. “Yeah, there was tension. But they were also just as passionate as the months before—and I’m talking right up to July of 1999.”
John also was having a difficult time getting along with his sister. He was never particularly close to Ed Schlossberg, Caroline’s husband, who he thought was arrogant, condescending, “and such a prick,” as a friend put it. “It would be hard if your one sibling after your mother died was married to someone that you just thought was an asshole. That would suck. And that’s what happened.” Occasionally, he would see Caroline and Ed in New York City, but he did not want to be in Martha’s Vineyard at the same time his sister and Ed were there—which was rare anyway since she had a home in the Hamptons, where she would go most weekends.
There was an ongoing dispute between John and Ed Schlossberg about what to do with the furniture and the significant family memorabilia at the Kennedy compound in Hyannis Port. “Ed became very obsessed with the value of the material at Hyannis Port because of what it was,” the friend said. “There was this battle over all this stuff, and John and Caroline didn’t actually speak for almost an entire year.” But that summer, with things between John and his wife becoming increasingly tense, he picked up the phone and called his sister. “They had this really, really good conversation,” the friend continued. “And I knew about it because he told me about it … and all I can say is fortunately for fucking her, because they hadn’t spoken for almost a year.” (Caroline Kennedy declined to be interviewed.)
With a cast off his leg for the first time since Memorial Day weekend, John was hobbling around the George office on Friday, July 16, on crutches. He met with Kliger, the Hachette magazine executive, to discuss ways to revitalize George. “He and I agreed that there had not been a well-thought-out business plan,” Kliger told the Times. “So we said, ‘Let’s figure out how to go forward.’” Kliger said John left the meeting feeling “fairly positive” about the outlook for George.
At around one o’clock, John spoke by phone with an employee at the airport hangar in New Jersey, where he kept his Piper Saratoga, confirming that he wanted to fly the plane later in the day and that he planned to get to the Essex County Airport between 5:30 and 6 p.m.
Shortly thereafter, Blow popped into John’s office and asked him if he wanted to grab lunch. “Sure,” he said. “I’m starved.” It was obvious to Blow that John’s ankle was still tender, and that he was using the crutches to judge how much weight, if any, he could put on his leg. “With every step, John looked as if he was assessing how much pain his ankle caused,” Blow recalled. They went off to Trionfo, a small Italian restaurant near the George offices. The owners loved it when John came in, and quickly ushered him and Blow to a private room in the back of the restaurant where John wouldn’t be bothered. “John was in a contemplative mood,” Blow remembered. “We spoke about the magazine’s future, and he sounded confident and upbeat.” John told Blow that, following their meeting at the Yankees game the night before, Lachlan Murdoch had called Gary Ginsberg asking about George’s circulation and “how involved John was” in the day-to-day operations of the magazine. They spoke about whether there would be staff changes if George changed publishers. John said there would be. “You know,” John told Blow, “for a while I hired people because I found them entertaining.” That had made the office fun, John continued, “but it hadn’t always helped the magazine.” That would have to change.
As they headed back up to George’s forty-first-floor offices, Blow asked John what he was doing for the weekend. He said he was flying up to Hyannis Port for his cousin Rory’s wedding. “I glanced at John’s foot—even the short walk from the restaurant had tired him—then gave him a skeptical look,” Blow recalled.
“Don’t worry,” John told him. “I’m flying with an instructor.”
“Just don’t crash, O.K.?” Blow replied. “Because if you do, that speech about all of us having jobs at Christmas goes right out the window.”
“Not to worry,” John said. “I’ll be fine.”
At around 4 p.m., John popped into Blow’s office to ask him his opinion about the possibility of publishing a poem by Jack Kerouac. But they both agreed the poem wasn’t much good. They passed on it, and John returned to his office to write a rejection letter. Five minutes later, he sent an email to his friend John Perry Barlow. Barlow’s mother had just died. He commended Barlow for being at his mother’s side. He knew something about that kind of loss, too. “I will never forget when it happened to me,” John wrote, “and it was not something that was all that macabre.… Let’s spend some time together this summer and sort things out.” Barlow did not open the email until later the next day.
John’s initial plan to get to the Essex C
ounty Airport by around 6 p.m. was, of course, foiled and he ended up leaving 1633 Broadway at around 6:40 p.m., along with Lauren Bessette, who had put in a full day at Morgan Stanley; together he and Lauren would drive in John’s white Hyundai convertible to the airport, near Caldwell, New Jersey. Normally, the trip from Midtown Manhattan to the small airport could be accomplished in around forty minutes. But not on a warm summer Friday. John and Lauren left the George offices and encountered heavy traffic along the way, especially as they made their way through the Lincoln Tunnel. At 8:10 p.m., with the light beginning to fade, John and Lauren pulled into the West Essex Sunoco gas station across the street from the airport. Wearing a light-gray T-shirt, John went into the store and bought a banana, a bottle of water, and six AA batteries. When they arrived at the airport a few minutes later, Carolyn was not there. By prior arrangement, she was to come to the airport separately in a black sedan.
Where was Carolyn? Following her sister’s intervention at the Stanhope two days earlier, Carolyn had reluctantly resolved to join John at Rory’s wedding in Hyannis Port. On Friday afternoon, she went to designer boutiques on the third floor of Saks Fifth Avenue to find a dress that she could wear for the wedding the next day. For $1,640, she found what she wanted: a short black dress by designer Alber Elbaz. From there, Carolyn decided to get a pedicure. According to Colin Lively, a haircolorist and stylist, “it was late at the end of the day on Friday, and Carolyn Bessette Kennedy was right next to me, sitting in the same line of people getting pedicures. She had a little piece of sheer fabric—about three inches square, almost white with a hint of lavender—and she wanted her toenail polish to match the swatch. The pedicurist would apply the polish, and Carolyn would go to the window and put her foot up and put the fabric next to it. Meanwhile, her cell phone kept ringing, and she kept answering it. ‘What?’ she said impatiently into the phone. ‘I told you—I’m getting a pedicure.’ She made the pedicurist re-do her toenails, and the phone rang again, and she said, ‘The more times you call me, the longer it’s going to take!’” She had the pedicurist do it three times. “She wasn’t overtly bitchy,” Lively said. “But she was so self-involved. If this was a key to her personality, then I would say she was obsessive about a lot of things.” Carolyn’s phone rang a third time. It was her driver. “If you can’t park, circle the block,” she told him. “I’ll be down in a few minutes.”
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