There were more intimate moments as well. In a February 1977 letter, Jackie sent John some newspaper clippings. In the letter, she worried a bit that she had become his “current events editor” but knew the articles could not be found in the Boston papers. She wrote that the “one nice thing” about having him grow older was that he would understand better what people he and his family knew were writing about in the newspaper. And then she was back to reminiscing about her baby boy. She wrote that she had been going through Caroline’s scrapbooks and found a picture of John’s first time on skis, on Easter 1964, when he was three years old. “In case the cold weather is getting you down, look how you went through it like a little chirping red bird 13 years ago,” she wrote. “Those huge instructors and that pained small creature—is that how you feel now, when your Math, Spanish teachers and Mr. Price loom over you[?]”
* * *
I REMEMBER ONCE GOING FOR A WALK with John around Rabbit Pond, behind our dorm, and out of the blue he asked me if I thought his father was a “good president.” We had never before broached the subject of his father—his mother and sister, yes—and needless to say I was quite surprised to hear him ask me about him. At seventeen, I was hardly in a position to answer the question with anything remotely akin to insight, and of course he must have known that. I think he just felt like talking about his father—the man he barely knew—if only for a moment. It was at once flattering—that he thought I might have something meaningful to say—and also shocking.
When I shared this story with Ed Hill many years later, he could barely contain himself. “Oh my God,” he said. “There you go. There you go. That’s pure John. What he was feeling, what he was asking, who he was asking, and why he was asking that guy, it’s all there. That’s what he was. You were senior to him in some perception that he had. You were more intellectually reliable than him, in his perception. You were better informed, in his perception. So just the whole nature of the inquiry and the vulnerability that it exposed, that was him.… That was it. That was him. That was the whole thing right there.” Had John, he said, then asked me to race him around Rabbit Pond to see who could get back to the dorm refrigerator first, the whole episode would have been a “crystalline” example of John’s personality.
Hill continued, “His father was murdered when he was three years old, and that was a subject that he never touched—never. That was the third rail of John’s existence. He did not touch the fucking assassination, which I learned for the first time at Andover, sitting on the steps on Samuel Phillips Hall, leafing through the pages of The Best of Life with John and Sasha and we hit the inevitable assassination chapter. And he almost tore the pages out of the book he flipped through them so—just quick. Then suddenly we’re on, like, the moon landing. He didn’t even look at those pictures.”
Hill said he always believed that John’s closest friends “all seem to have come from the Land of Misfit Toys”; this was the “interesting dichotomy” in John’s personality. “I think John understood and believed, as I did, that he would and should be the president of the United States, that he was born to it,” he said. “Everything about his personality and his life made it appropriate, and his commitment to do the right thing. It was all there. So you had that part of him that recognized his own ways in which he was extraordinary and competent, but I think there was a part that was horrible, too.”
It seems doubtful that John had figured out at Andover what was going to be expected of him—in terms of a political career, if any—but there was little question that his mother wanted him to have a variety of different physical and intellectual challenges, many of which were available only to him. It was as if Jackie was curating for John a series of experiences that together would force him to mature and to come to grips with his unique position in the world, while also giving him the chance to be a goofball, if that’s what he wanted to do.
After John’s first year at Andover, Jackie signed him up for an Outward Bound sailing trip in and around Hurricane Island, Maine. The monthlong trip, twelve miles off the Maine coast in Penobscot Bay, was a difficult seafaring adventure, featuring rowing and sailing small boats in weather that alternated between monsoonlike rains and pristine, warm sunny days. The crescendo of every Outward Bound trip is the “solo,” three days and nights alone, without any food, in the middle of nowhere. On his three-day solo, John was by himself on an uninhabited island in Machias Bay. He had a gallon of water and a tarp. His family insisted that the media keep its distance from him while he was on the solo. For his protection, Outward Bound stationed a small boat near the island in case its “famous charge” needed anything, the Boston Globe reported.
Of John’s many bespoke experiences, nothing he did ever inspired me personally as did that Outward Bound trip to Hurricane Island. I can’t say exactly how or why this happened, but there was something about John’s trip and his unique combination of privilege and a certain common touch that made me feel that if he could survive such an ordeal, so could I. Moreover, I felt that the time had come for me—at age eighteen—to overcome my fears and give it a try. So I went on an Outward Bound trip to the Gila Wilderness in New Mexico, a decision that changed my life. The monthlong experience was beyond exhilarating, and gave me a sense of well-being and confidence—akin to what I imagine a huge shot of adrenaline might do—that I have rarely experienced since. John also inspired Ed Hill to go on Outward Bound—to Hurricane Island, during the summer of 1979. “Whether he was inspiring me to do that or whether he was holding me accountable for a poorly founded opinion or statement, that was a big part of who he was,” Hill said. “It was a great thing about him.” But, he added, “Sadly, he would cross a line repeatedly in his own life, where he would move beyond invaluable inspiration to outright recklessness.”
* * *
DURING HIS SENIOR YEAR AT ANDOVER, John roomed with John Pucillo, a middle-class kid from Boston. His mother had died when he was three years old, which gave him and John something in common. That year at school Pucillo and John also had girlfriends—John had started dating Lydia Hatton, a classmate from Grand Haven, Michigan—and they both had parental permission to smoke cigarettes in their dorm room. “We had people coming in and out of the room,” Pucillo remembered, “smoking up a storm, playing Bruce Springsteen’s Born to Run—we probably played that thing a hundred times a month, simulating the guitar.” The roommates signaled to each other when one’s girlfriend was over so they knew to keep out of the room. “There was a little bit of negotiating,” Pucillo said. According to Chermayeff, Hatton “loved partying and really loved New York City partying” especially at Studio 54. “She loved that, and John had so much access to that.” Chermayeff remembered partying in New York City with John while they were all at Andover as “insane—we would be ushered into the Studio when there was like a thousand people outside, ushered in to do coke with Steve Rubell.” (Hatton declined to be interviewed about her relationship with John.)
Pucillo found himself in a bit of a difficult position, rooming with John. He had resolved at the start of his Upper year that he was going to buckle down, study hard, and avoid breaking any rules—at least while on the Andover campus. He also was elected the cluster president of Rabbit Pond, which put him squarely in between his classmates and the Andover disciplinary system. In the nicest way, John Kennedy, of course, had pretty much figured out that these rules did not apply to him, or if they did, there always seemed to be an intervention at the highest levels to make sure that any rule he happened to violate—should he be caught—would be dealt with through compromise. While it was fine for others to be dismissed from Andover for breaking the rules—and several of John’s best friends were, such as Wilson McCray, his former Collegiate classmate, and Ed Hill—it was an unwritten rule that John F. Kennedy Jr. would not be tossed out of Andover for smoking pot or for drinking or for being with a girl after hours. As Bruce MacWilliams discovered—when he was the Rabbit Pond cluster president before Pucillo—John’s infracti
ons could be dealt with quietly and efficiently, giving everyone a way to save face and to avoid the unwanted publicity of John leaving the school. During John’s senior year, the rule breaking continued, of course, but his roommate, Pucillo, was now the cluster president and in a position to make sure the unwritten rules about John were followed to everyone’s benefit. “We had the perfect cover for everybody to come smoke pot because we got that smoking permission,” Pucillo remembered. “You would light up a cigarette. They’d light up a bong, put the bong smoke through a wet towel to decrease the smoke, get a couple of cigarettes going and no smell of pot, and put the bong away.”
Pucillo wasn’t abstemious, just careful not to break any of the rules while he was on Andover’s campus. He and John would go drinking in New York or in Cambridge. “On a lot of weekends, we would take a bus into the Sevens [Ale House] on Charles Street,” he said. “At that point, if you were sixteen and you had a fake ID and [looked] reasonably official, they’d let you in.” He also took John around Boston’s notorious Combat Zone. Going out with John in Boston could be riotous. Once, I remember, he and I went to The Black Rose, a classic Irish bar on State Street. Pictures of John’s father were everywhere, of course, and John, immediately recognized, was treated, appropriately, as royalty. There was no question of whether he was old enough to drink—he wasn’t—or whether I was—I wasn’t—but we were served plentifully. I don’t think we had to pay.
The fact was, nobody wanted to read a newspaper story about John leaving Andover before graduating. According to C. David Heymann, in his book American Legacy, an Andover security guard once caught John smoking pot in the men’s room of the Oliver Wendell Holmes Library but did not report him. Another time he was caught getting high, at night, on a ball field. He got off with only a warning. “I was in a number of situations where I had to exercise, I would say, the best political skills I could have, I guess, considering that it was my roommate,” Pucillo said. “So trying to present it in somewhat of a nonbiased way or objective way.… But also truthful. The kid, he was a good guy.… I protected him a lot. I was always vouching for him and positioning him in a positive way.”
Sometimes, his friends called John out for his bad behavior. Once, one recalled, he and John were met at Andover by a couple of John’s friends from Boston and they all drove together to a party about an hour away. They were drinking beers and getting stoned in the car when at one point John finished a beer and then threw the empty beer bottle out the window onto the street. “No one else in that car would have possibly done that even if they were really stoned,” recalled one of the people in the car that night. “Why did he do it? He almost didn’t realize that that was a big deal. [Was he too] sheltered? I don’t know. He was isolated.” His friends in the car got really pissed at him. And he was contrite. “He got it,” this person recalled. “He actually really apologized at some point, but it was interesting.”
There were plenty more innocent high school shenanigans. For some reason, John had more than his share of adolescent body odors, and one time in particular he had a medical problem with his feet that made them stink more than usual. Pucillo remembered he was getting some treatment for the problem. “It was like fucking disgusting,” he said. “So we’re all just saying, ‘John, that’s fucking disgusting.’ He decided to have fun with it.” Pucillo got back to the dorm one night, got into bed, and noticed a funny smell emanating from his pillow. “He put two of his fucking socks in my pillow,” he said. “I had to throw the fucking pillow out and get a new pillow.”
On another occasion, when Pucillo was visiting John in Hyannis Port, John suggested they take the family’s fifteen-foot Chris-Craft motorboat over to Martha’s Vineyard for a visit. It was the same boat the two Johns used to drive to take Jackie waterskiing. “She loved to water-ski,” Pucillo said. The trip was to take about ninety minutes, each way. They went to Martha’s Vineyard and then headed back to Hyannis Port. When they were about halfway home, the boat ran out of gas. “We’re fucking stranded in the middle of the fucking ocean,” Pucillo said. John called the Coast Guard on the boat’s radio. From the call letters, the Coast Guard knew immediately that it was a Kennedy boat. They waited about twenty minutes, bobbing up and down, in the Atlantic Ocean between Hyannis Port and Martha’s Vineyard for the Coast Guard to bring John enough gas to get back to the dock. “I knew him enough that that wasn’t a big shock to me and it was just part of the adventure, I guess,” he said.
* * *
AT SOME POINT EARLY IN HIS SENIOR YEAR, it was obvious to the Andover administration and to Jackie that John’s ongoing struggles with math were not going to be resolved easily. He also had a problem in English—there had been “a question” about a paper he wrote, Pucillo said. Andover made the decision that John should not graduate in June 1978 with his class but rather stay at Andover for another year, a postgraduate year of sorts, to see if he could his act together. “In a way it’s nice not having to think about colleges this year,” John wrote a former girlfriend, Meg Azzoni, that fall, “but in the long run next year here will probably suck. They’re cracking down even more. How long can I last?” In truth, John was upset with the decision. “We had been seniors together, right?” Pucillo said. It also wasn’t a private embarrassment. The news made the National Enquirer. The newspaper reported that John was “such a poor student” that he had to repeat his senior year “at the posh prep school that he attends.” The paper somehow tracked him down at Andover by telephone and asked him if he were a “poor student,” prompting him to answer, “Well I don’t know. It depends what you call a poor student.”
John started dating Jenny Christian, an Andover senior from Englewood, New Jersey. Her father was a doctor. Jenny and her older sister, Vicky, were legendary at Andover for their combination of beauty and intelligence. They attended the premiere of Saturday Night Fever together over Christmas 1977 and managed to upstage John Travolta, the star of the film, leaving him alone on the red carpet as photographers and fans rushed to John’s side. As with many of his other Andover relationships, things with Jenny eventually ran their course.
Jackie curated another series of special experiences for her son, this time out west. She was very focused on him having a male influence aside from Secret Service agents. After a stint at the Youth Conservation Corps program at Yellowstone National Park went awry due to too much press attention, Jackie hatched another plan. She contacted Teno Roncalio, a longtime US congressman from Wyoming. Roncalio told Jackie about John Perry Barlow, a Grateful Dead lyricist who had inherited his father’s cattle ranch near Pinedale, Wyoming. Jackie decided that John should spend the rest of the summer working for Barlow.
Jackie called Barlow on the phone. Barlow remembered: “It was fairly late in the evening. I was sitting at the galactic headquarters of the Bar Cross Land and Livestock Company in Cora, Wyoming. I get this breathy voice on the phone that says, ‘Hi, this is Jacqueline Onassis.’ And I said, ‘Well, in the highly unlikely event that this isn’t some kind of a joke, what can I do for you?’ Two days later, [John] was on the ranch.… My job was to transform him into a ranch hand for about a month. He dug holes for fence posts and looked after some of the animals.… He was rambunctious and at that point a bit directionless,” he said. “But he was full of good juice and amiability and that wonderful alert curiosity he had about everything all of the time. Everything was interesting to him. He wasn’t afraid to ask questions.”
Barlow used to fly his plane around his ranch, and John took a keen interest in it. “He always wanted to go along on that,” Barlow remembered, “and I eventually said, ‘Obviously, you want to know how to drive one of these things. It’s not that hard. Let me teach you.’” They just clicked. “It was one of those moments you have in your life every now and again when you meet someone and you know you’re going to be friends for life,” he said. And they were.
John returned to Andover for his unwanted third year without the group of friends he had surrounded hims
elf with during his first two years. Even his mother abandoned her usual practice of staying a day or two at the Andover Inn when she dropped John off. He returned determined to settle down for the rest of the school year, and to make it to graduation. He made the varsity soccer team—even though he wasn’t much of a team sports athlete—and scored a goal in the game against rival Exeter. He got more involved in the drama department at Andover, acting in Shakespeare’s The Comedy of Errors; he also played the lead in Ken Kesey’s One Flew Over the Cuckoo’s Nest and Neil Simon’s Come Blow Your Horn, and directed Edward Albee’s The Zoo Story. John’s interest in acting was genuine and passionate. But while his mother encouraged him in it for a while by attending his performances, she was dead set against John getting too caught up in the pursuit of it. She thought it was too trivial for him.
There was no doubt John was still struggling academically at Andover. To try to help him, his mother enlisted Ted Becker, a noted New York City child psychiatrist who specialized in helping troubled teens. For several months during his senior year at Andover, John went to New York once a week to see Becker. Jackie was upset about his poor grades, his interest in acting, and his pot habit; she feared the negative influence of other members of the Kennedy clan. By all accounts, it was a bit of a peripatetic extra year for John. He was at Andover during the week and then would head to Boston on the weekends. He would stay at Harvard with Jenny Christian or with Pucillo, who recalled how when John attended the dedication ceremony for the Kennedy School of Government, in October 1978, with his mother and his sister, he didn’t have a suit to wear. So he borrowed from Pucillo a rather unstylish and pedestrian tan three-piece suit and an ugly tie. “His mother was horrified because it didn’t quite fit,” Pucillo said.
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