Gary Ginsberg said that for John, flying was a total and necessary release from the unending pressure on him. “He literally wanted an escape from being on the ground where the pressures on him were so immense,” he said. “The physical pressures on him in New York City, the constant attention—and the lack of any way to avoid it. Going up in the clouds in the sky was a really important physical escape for him. He talked about that. He talked about the solitude of being in the air. It gave him great comfort, which I think is as much a reason why he wanted to fly as wanting a way to get to the Vineyard. It was a psychological escape for him.” But Ginsberg worried about his friend flying and whether his mind was sufficiently logical to be a pilot. “He was the most non-linear thinker I knew,” he continued, “and to fly required an ability to think very logically and very linearly. You’ve got to go down a checklist essentially and that’s a physical checklist, and that was so not the way John approached problem solving. When he started flying I thought it was not the smartest thing he’d ever done because it was the last thing he should have been doing given his intellectual bent.”
A close friend also worried about what he called John’s “death wish.” He remembered having dinner one night with John and Carolyn during the summer of 1998. John had been out kayaking the night before in New York Harbor by the Statue of Liberty, and a huge boat had come bearing down on him. He barely escaped from being run over. “You definitely have a death wish,” he told John. “Carolyn said, ‘You definitely have a death wish, John,’ and he was like ‘Are you guys fucking mad? Stop! Stop!’ But we both agreed that he did because he just took too many crazy chances.”
* * *
JOHN SEEMED QUITE STYMIED by Carolyn and how poorly they were getting along. There was her drug use—cocaine mostly—as well as his gnawing suspicion that she was cheating on him—a suspicion that turned out to be true. He confided many of his concerns about his marriage to the private journals that his mother encouraged him to keep and that he seemed to write in frequently, and to his close friends. During the summer of 1998, John was having coffee at an outdoor café in Greenwich Village with one of his friends from Brown. John was writing furiously in his journal while his friend was reading the newspaper. When John got up to go to the bathroom, his friend couldn’t resist the temptation to see what he had written. “What happened to us, C?” he wrote. “What happened to our love?” He stopped reading when he sensed John coming back from the bathroom but asked him how he was doing. “Carolyn and I are fighting,” he said. “We’re not close anymore. We haven’t had sex in months. We’re not even sleeping in the same bed! One minute she’s up and happy and the next she’s mean and angry. Carolyn and her gay friends are snorting more and more cocaine, staying locked away in her room for hours at a time.… Some nights I stand by her bedside and stare at her as she sleeps. All I keep thinking is how much I want to lie beside her.” A few months later, when the same friend stopped by his North Moore Street apartment, he happened again on one of John’s journals on the coffee table. In it, John had written that he suspected Carolyn of having an affair with a friend who was a married antiques dealer. “I can’t believe she is doing this to me,” read the journal entry. John saw his friend reading the journal entry but didn’t seem upset. “My life is a mess and it’s all because of Carolyn,” he told his friend. “The only question is how do I get myself out of it.”
* * *
IN NOVEMBER 1998, on his annual out-of-town trip to avoid the news of his father’s assassination, John convinced Brian Steel to join him on a camping trip to Maine. Obviously camping in Maine in November is not exactly expected to be pleasant, given the cold temperatures. But Steel was game. With his new pilot’s license in hand, John convinced Steel to fly with him from Teterboro Airport, in New Jersey, to north of Bar Harbor, Maine. “Carolyn would call me up and she’d be like, ‘He’s dying to have you go in the plane,’” Steel said. “And I would say to Carolyn, ‘I’m not going to be the biggest footnote in aviation history.’ And then it became a joke between the three of us.” They spent the first two nights of the three-day weekend camping out. “It was twenty degrees and we’re in a tent freezing our asses off,” Steel recalled.
After two days of that, they decided to fly to Bar Harbor Airport, rent a car, drive to Acadia National Park, and hike around there. They arrived at Bar Harbor Airport at around nine forty-five at night. The rent-a-car agency was open until ten, and John urged Steel to run over to it and keep it open long enough for him to tie down the plane and join him at the rental counter. Steel got to the counter, and the clerk told him there were no cars for him to rent. But he kept delaying her long enough for John to arrive, after securing the plane. “John comes walking up,” he said. “She melted. We got a car. We got like the nicest car they had—‘Oh, do you want an upgrade?’ He knew he could pull that off. Unquestionably.” They got a motel room somewhere and the next morning got up early, had a big breakfast, and spent the next eight hours hiking around Acadia. “Keeping up with him was not easy,” he said. “I was in good shape for a whatever-year-old but John was like a panther, like he’s hopping all over the place.” They flew back together that night to Teterboro. “I like adventure,” Steel said, “but I don’t have any death wish: I would never have gotten in the plane if I thought I was at risk of dying. I just wouldn’t have. I’m essentially one of those guys that believes you’ve got maybe eighty years and you should try and make the best of it.”
* * *
IN APRIL, JOHN MADE THE FATEFUL decision to upgrade the single-engine Cessna 182 Skylane, which he had been flying in the two years since he obtained his provisional pilot’s license—a license that allowed him to fly by sight only, since he had not been sufficiently trained in instrument flying—for a more powerful 1996 Piper Saratoga II HP, a three-hundred-horsepower, single-engine six-seater. It cost John $300,000. Pilots compared the power of the Piper Saratoga to that of a sport utility vehicle—in other words, much more powerful than his Cessna. The Saratoga had state-of-the-art equipment, including automatic pilot, plus two fuel tanks that required the pilot to switch from one to the other as needed. There was a lot to do as the Saratoga’s pilot, and John was learning how to fly the plane thanks to a flight instructor who would accompany him and his passengers. By then, John had around two hundred hours of flight experience, “not a rookie, but not deeply experienced,” a pilot later told the Boston Globe.
Over Memorial Day weekend 1999, John and Carolyn went to Red Gate Farm in Martha’s Vineyard. They were joined by a number of John’s old friends, such as Rob Littell and Sasha Chermayeff, her husband, and their son, Phinny. Littell and his wife flew up with John and Carolyn in the new Saratoga, along with John’s flight instructor. John was in control the whole flight. “His landings were barely noticeable,” Littell recalled, “something he took pride in. None of us felt nervous about flying with John. He was the opposite of reckless, with the attitude of a cautious and serious pilot.”
At one point, as sunset was approaching on Saturday, John decided to go up in his Buckeye Dream Machine, the two-seater version of the flying parachute. John liked to fly the Dream Machine when he was up in Martha’s Vineyard. Some of his friends liked to join him, including Littell and Sasha’s husband; others, such as Brian Steel, refused. “I thought it was a death trap,” Steel said. John took off in the Dream Machine from the lawn of Red Gate Farm. “We were all watching,” Sasha said. They then were going to go to the beach and would meet John after he finished his flight. “He went up and we saw him have problems and then we saw him crash,” Sasha recalled. “When he crashed he went up and down and we all went running to him.” The Buckeye had hit a tree that John had tried to avoid, and crumpled to the ground. His foot had been bent backward, and the ligaments in his ankle shredded.
John was in considerable pain. “He put his arms around us and literally it was like ‘I think I hurt my leg,’” Sasha continued. “Yeah, I think I hurt my leg but I’m okay. But I’ve got to
go to the doctor.’” Sasha and her husband wrapped their arms around John, walking him up back to the house, dragging his leg behind him. “Then he went off to the hospital and came back with his cast on,” she said. Rob Littell had helped get John ready for the flight that day and remembered how things were fine until an unexpected gust of wind blew the Buckeye off course.
Two days later, back in New York City, John had surgery to put a metal plate in his leg. Littell urged John to “slow down”—to take the crash as a sign to cut back on his grueling work schedule and on the tough job of being him. John’s thyroid condition left him “lethargic, cranky, and frighteningly thin,” according to Gary Ginsberg. The winter before he had also hurt his hand on a broken champagne glass. Perhaps, Littell suggested, he was pushing himself too hard. “No shit,” John replied. His friend John Perry Barlow also told him the crash was “a sign” that he should chill. “I was afraid to fly that thing and I’m not afraid to fly much of anything, but that was a very treacherous aircraft,” said Barlow. “He was flying around up there by himself and Carolyn said, ‘He’s all alone up there. He couldn’t be happier.’”
John had decided to spend many of the following summer weekends in Martha’s Vineyard to be with his cousin—and best friend—Anthony Radziwill, who had been diagnosed with cancer and knew he was dying. John “wanted to help Anthony just relax that summer,” Sasha said. After John broke his ankle, which obviously put a serious damper on his mobility, he waxed philosophical about why he thought it had happened. “He was upset with himself,” Sasha said. “But he said he thinks it happened because he’s just meant to sit down in a rocking chair with Anthony and they could just spend the summer, the two of them, just sitting there and not being able to do anything while Anthony died. He kind of immediately saw the good side of that accident.”
John had also become increasingly protective of Ed Hill. Hill had a rough few years and John urged him to grow up, settle down, and mature. He approved of Hill’s decision to go to law school and then to practice law. When he met the woman whom Hill would eventually marry, John encouraged him to do so. “He never stopped trying to push me to straighten up and fly right,” Hill said. At one point during the spring of 1999, John asked Hill why he had not yet become engaged to Holly, his future wife. “I told him it was because I didn’t feel that I could afford an adequate wedding ring, which was true, because of course I wanted to go platinum and I wanted to go big because that’s the world I live in,” Hill said. “He looked at me. He was speechless. He was incredulous when I told him that. He almost stutters. He’s like, ‘Eddie, Eddie, your best friend’s mother’s boyfriend is the most powerful diamond merchant in the world, and you are worried about affording an adequate wedding ring?’ That was part of John. As silly and reckless as he liked to be, there was always the point where it was time for him to become the adult in the room, and by [this] time we had reached that point in life where that obligation arose on a daily basis and he wasn’t taking things as lightly anymore.” Hill, humbled, apologized to John for forgetting how helpful his friend could be. John talked to Tempelsman, who put John in touch with David Schwartz in his office, who agreed to help Hill. He ended up with a 50 percent discount on a $20,000 engagement ring. “That was all [John],” he said. “He might not have been able to clear that up when he was seventeen. He might have been too distracted at that time.” But by the time John was thirty-eight years old, he was able to deliver for Hill and not give it a second thought.
Hill also got another unexpected gift from John, who had decided to get custom-made suits through a service that arranged to have a tailor come to the office and take measurements, supposedly making the process easier for busy executives. “He was measured for four suits, a silly sort of pleated-pants, three-button-jacket style that was pure late 1990s,” Hill said. “They set him back $400 or $500 apiece.” But somehow the measurements for the suit jackets were wrong. “They didn’t fit right,” Hill said. “So what did he do? What does this prince of a guy do? Rather than rat out [the sales rep] and get her in trouble with the company, he paid the bill, put them in a garment bag, and gave them to me with a note that he had scribbled in an orange highlighter that simply says, ‘Cosmo, the clothes make the man.’” He reveled in the memory. “There’s so many things that are indicated by every aspect of that story, the ring and the suits, of what he was capable of at that stage of his life, the generosity, the kindness, the sense of propriety, the need to get the fucking shit together because there are no rehearsals anymore,” Hill said. “We’re in our late thirties.”
* * *
JOHN’S LEG INJURY IRRITATED him to no end. He was a guy who hated to miss a single workout. With a cast on his leg, he was sidelined for much of the summer. “It’s an emotional thing,” Chermayeff said. “You break your leg. It’s the beginning of the summer. It’s sort of like a symbolic, just, everything’s broken down.” He was not happy. “When he returned to the office, hobbling on crutches with his lower left leg encased in a cast, John was in a foul mood,” recalled Richard Blow. “His ankle sent shooting pains up his leg, and the painkillers he took were making him woozy. To keep his leg elevated, John had to recline in a long black lounge chair, only inches off the floor, his head about knee-high. He was embarrassed by the accident and quickly tired of people asking what had happened. He even gave different versions, telling some people that he had hit a stone wall while landing and others that he had hurt himself Rollerblading.”
John was also struggling with the realities of running George with a financial partner—Hachette—that understandably demanded a return on its investment. Frustration was building on both sides. “He had been told that Hachette was going to basically pull back on its funding,” recalled Gary Ginsberg. “It was up to him now to keep it alive.” Audited circulation for George for the last six months of 1998 had fallen to around 403,000, slightly above the guaranteed circulation of 400,000 that George had promised advertisers. The plan had been to get to a circulation of half a million by 2000, a goal that looked increasingly elusive but was key to the magazine breaking even. Ad pages for the first half of 1999 had fallen 30 percent. George was expected to lose $10 million for the year. “We were still successful in the sense that we could keep the lights on,” Ginsberg said, “but we had fallen from those early highs and fallen so dramatically that it felt deflating, and I think Hachette at a certain point just wasn’t willing to invest the dollars because they didn’t see any big return.”
In May, John had fired George’s publisher and associate publisher—both of whom had been appointed by Pecker—and was looking to replace them with a publisher of his own choosing who might be more amenable to leaving the Hachette fold if it came to that. On June 1, Jack Kliger replaced David Pecker as Hachette Filipacchi’s CEO. Kliger gave permission for John to explore finding new investors who could inject fresh capital into George. He told John that Hachette wanted to retain its 50 percent stake in George; any new capital, which was much needed, would have to come from third parties. (Although initially John and Michael Berman had put their own money into developing the magazine, John had still not invested any equity capital into George in exchange for his ownership stake and had no intention of doing so. That meant that a new investor would be diluting John’s ownership.) John made some discreet inquiries. He had lunch at San Domenico with Steve Florio, then the president and CEO of Condé Nast. On July 11, John and his flight instructor flew the Saratoga to Toronto to talk to the executives of Magna International, a Canadian auto-parts company, and also reportedly spoke with Paul Tudor Jones, the hedge-fund manager and driving force behind the Robin Hood Foundation, where John was on the board.
John still had a hankering for politics, beyond just editing a magazine about it. In November 1998, Senator Daniel Patrick Moynihan announced that he would retire from the Senate at the end of his term, meaning that a US Senate seat from New York was up for grabs. Many people urged John to run for it. “John immediately started exploring
his viability,” Ginsberg said. He and Ginsberg spoke sporadically about the possibility of John running for the Senate and studying the numbers to see if it might work. Ginsberg, who had recently left George to be the head of public relations at News Corporation, introduced John to Roger Ailes, the onetime political operative who had created Fox News. “He and I spent a long time with Roger discussing whether he would be viable and how he would put together a candidacy or campaign,” Ginsberg said. “And Roger was very supportive.”
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