Barlow, best known as a lyricist for the Grateful Dead, recalled sitting at his desk one evening when the phone rang. Picking up the receiver, he heard that distinctive, breathy voice say, “Hi, this is Jacqueline Onassis.” Barlow, not sure if he was being pranked, responded, “In the highly unlikely event that this isn’t a joke, what can I do for you?” She assured him the call was not a joke and proceeded to ask if he could hire her son for the summer. A few days later, John showed up.
Barlow’s first impression of John was that he was “incredibly good-looking” and possessed “a kind of thoughtless grace.” He further described John as “permanently rambunctious but charming” and “physically powerful and fearless.” He also used a word commonly ascribed to John by adults: immature. Perhaps immaturity was one of the qualities that Mrs. Kennedy blamed in part on the Secret Service for not allowing him to experience the normal bumps and bruises of childhood. Now she was determined to create those challenging experiences, both mentally and physically, that would enhance John’s maturity before he went off to college. For his part, Barlow tried to toughen John by making him sleep in a partially flooded bunkhouse.
Barlow got an early sampling of John’s absentmindedness. As a child, John had once nearly suffocated his guinea pig by leaving it overnight in the back of a truck, and he was notorious for losing just about everything, from keys, to books, to articles of clothing. But Barlow experienced perhaps John’s most expensive act of inattentiveness. Once, he asked his new hire to drive his truck down a narrow path between two fences. They then hopped out and did some work before Barlow asked John to back the truck out on his own. John jumped into the driver’s seat and, now more confident in his navigating ability, gunned the engine. There was only one problem: he had forgotten to close the doors, which were immediately sheared off when they encountered the wooden fence posts. “Is that going to cost a lot to fix?” John asked.
If Mrs. Kennedy was looking for a responsible adult who would offer John guidance and adult supervision, Barlow may not have been the best choice. According to Barlow, John had experimented with acid in the past, but Barlow introduced him to a much larger dose: 300 micrograms. When they got high, the two men would hop in Barlow’s truck and go driving. They would also drop explosives down one of the uncapped gas wells surrounding the ranch. Such escapades were probably not the structured experiences that Jackie had planned for her son.
In November 1978 Mrs. Onassis threw a big party for John’s eighteenth birthday and Caroline’s twenty-first. The party took place on the Sunday after Thanksgiving and shortly after the fifteenth anniversary of President Kennedy’s assassination. It began with cocktails at her apartment. Afterward, about 150 guests attended a private disco party at New York’s chic Le Club. John spent most of his time on the dance floor. Later, partygoers enjoyed a cake with sparklers and a speech by John’s uncle Teddy. By midnight, the older crowd had left, while John and his friends stayed until four in the morning, when the owner kicked them out.
Outside of Le Club, photographers, including Ron Galella, jumped from their cars to get a glimpse of John. Galella was supposed to keep his distance, of course, but he likely believed he could blend into the pack. John peered through the peephole in the red leather–upholstered door and saw the photographers waiting for their prey. He then turned and asked the manager if there was a back door they could use. There was not. The photographers knew that John would have to come through the front, so they pulled back their hoodies on the cold night, extinguished their cigarettes, and readied their cameras.
Inside, John’s friends prepared for a confrontation. “Can we take them?” asked Noonan, a burly Irishman. After a night of drinking and drugs, John’s friends were not clear minded. Gustavo Paredes gathered everyone together by the front door and devised their exit strategy. “This is what we are going to do,” he announced. “We’re going to rush out and catch a cab. And we’re going to put on our sunglasses so that nobody will recognize who we are.” Everyone thought it was a brilliant plan, so they all donned their sunglasses and prepared to make their getaway. “I lined everybody up,” Paredes reflected in 2019. “I told Billy to take the lead.”
They formed a phalanx, with Billy in front and John and his girlfriend Jenny Christian in the middle. Since there was a car parked outside the club, they needed to move left down the street in search of a taxi. “There were photographers everywhere,” Gustavo recalled. According to Noonan, as he pushed forward, he warned a photographer to back away. “Fuck off, fat boy,” came the response. Billy recalled that he then charged at the photographer. John tried to hold him back but got pushed to the ground in the confusion.
Paredes has a very different recollection. He said that Billy kicked a photographer in the small of his back. “I saw the pain on the guy’s face,” he recalled. The paparazzo handed off his camera to someone and then charged at them. But instead of attacking Billy, who was clearly the guy who’d assaulted him, the guy headed straight for John. “He blindsides John, who flips over a car hood and lands on the pavement.” Paredes then grabbed the photographer by the collar of his shirt and took a swing. “I unleashed on him and lifted the guy a foot off the ground, pummeling him.” In the meantime, John jumped up and wanted to join the fight, but Gustavo yanked him by the front of his coat and threw him into a cab. Jenny jumped in with John, Gustavo hopped into the front, and they made their way home.
The whole incident lasted thirty seconds, but the photos screamed across the front pages of the New York tabloids the next day. When Billy called the next morning, John said he found the whole scene funny. The only problem was that “Mummy is not happy.” John tried to explain to her what happened—that he and his friends did nothing wrong—but she seemed unconvinced. “I think you should write a note,” he told Billy, letting her know what happened.
* * *
—
John had transferred from Collegiate to the exclusive Phillips Academy Andover in Massachusetts in the fall of 1976. It would be his first experience living away from his family. The Secret Service stayed with him through most of the fall semester and then left after his sixteenth birthday. John lived in a two-story dormitory that housed twenty-seven students on Chapel Avenue, immediately north of the administration buildings. John stayed in Alfred E. Stearns House in rear room 29, located on the second floor, overlooking Rabbit Pond.
With both John and Caroline living away from home for the first time, Jackie settled into a new routine. In 1975 she had started a career as an editor at Viking Press, but she quit two years later when the company published a fictionalized account of a future assassination plot against President Ted Kennedy. She moved to rival Doubleday, where she settled into a long career as a respected editor.
Her private life had also stabilized. She dated after Ari’s death, but eventually she settled down with Maurice Tempelsman, a portly, balding diamond merchant whom she had known for decades. Born in Belgium, Tempelsman fled the Nazis with his family in 1940 and moved to New York, where his father established a successful diamond brokerage. Maurice joined the family business, cultivating an extensive political network that allowed him to broker diamond deals between the United States and Africa. As a major contributor to the Democratic Party, he first met Jackie in the late 1950s and had set up a meeting between President-elect Kennedy and African mining officials.
During his first semester at Andover, John met Sasha Chermayeff, who would become one of his closest friends. He would later refer to her as the “platonic love of my life” and “coolest, least fucked-up girl I know.” Both were city kids. She had attended the prestigious Dalton School while John was at Collegiate, and they had both made the unusual decision to transfer to Andover in the eleventh grade. “It was unusual,” she reflected, “because most people did not go to Andover for only two years.” They either went for the entire four years or, if they transferred, did so in the sophomore year. Since both of them were new to campu
s and did not know many people, John and Sasha naturally bonded. They ended up being enrolled in many of the same classes and could often be seen walking together from one classroom to another. “Two weeks into that first semester, we were already quite friendly,” Sasha recalled. She described him as “this funny, sweet, loving guy.” John, she reflected in 2018, “became like a brother to me.”
It was Mrs. Onassis’s decision to transfer John from Collegiate, where he was well liked and performing well, to a new school in rural Massachusetts. Partly it was to get him away from the emerging drug scene in New York. These were critical years in John’s development, and his mom did not want him around the temptations of the city. John had a short attention span and was easily distracted by New York City’s endless social possibilities. She likely believed that Andover’s rural environment would help John remain focused on his studies. No nightclubs or other social diversions existed. But the main reason was safety. “His mother was very anxious about safety in Manhattan,” recalled Collegiate history teacher Bruce Breimer. “She was afraid he was going to get hurt, that some nut was going to find him.” John was about to be without Secret Service protection for the first time in his life, and everyone knew it. He would be an obvious target, and his mom felt that the remoteness of a rural boarding school offered more protection than the bustling streets of Manhattan.
On the surface, John seemed casual, easygoing, and unpretentious. Sasha described his fashion style as “schleppy,” joking with him that none of his clothes ever seemed to fit. “Everything was falling off,” she recalled. “He would never even dream of having a pair of matching socks.” But Sasha and John engaged in long conversations, and she quickly realized that he was more complicated than he appeared. “John didn’t have a carefree background,” she reflected, “yet he came off like this carefree guy.” She learned from their conversations “that there were difficulties in his life,” and his problems became “more complex” as he got older. “That was a beautiful thing,” she said. “It wasn’t easy being John, but he carried his burden with such enormous grace.”
In many of their evening conversations, John confided to Sasha about his identity crisis. Due to his name and family background, people imposed their own expectations on him. Even walking around the Andover campus, John noticed many students, faculty, and administrators with “Kennedy fixations.” Though he understood why people treated him a particular way, he also knew that to have a fulfilling life he needed to break out of these boundaries. His family was a source of great pride, but it could also create crushing burdens. Wherever he went, the ghost of his father haunted him. Sasha noticed that John was frequently torn between doing what he wanted—camping or skiing with friends—and attending family events. His uncle Ted Kennedy was running for reelection to the Senate in November 1976, and Jackie permitted John and Caroline to make a limited number of appearances for him. John reluctantly agreed. He did not enjoy being on display, but he adored his uncle and would do anything Teddy asked of him. “He had more obligations than we did,” Sasha recalled. “We could be tired and hung over, and we could do whatever we wanted, but John always had obligations.”
At Andover, John’s favorite distraction from such family obligations was acting. He had appeared in Oliver!, the musical version of Charles Dickens’s Oliver Twist, while at Collegiate. He appeared in three more plays while at Andover: William Shakespeare’s The Comedy of Errors; One Flew over the Cuckoo’s Nest, based on a novel by Ken Kesey; and a production of Megan Terry’s Comings and Goings. “He really got into theater,” recalled Andover friend Wilson McCray. “John loved acting, and if he hadn’t been born a prince, I think he’d love to have gone further with it.” However, Holly Owen, head of Andover’s acting department, admitted that although he noticed John’s obvious passion for acting, he questioned how committed he was to being onstage. “He had a facility for acting, a knack, a great deal of personal charisma,” he said, “but he didn’t have the inner drive for it.”
While at Andover, John started dating Jenny Christian, who was regarded as one of the most glamorous women on campus. Jenny soon became part of the family and, in 1978, joined Jackie, Lee, Tina, and Anthony on a vacation to the Caribbean island of Saint Martin, where they stayed at the same luxury resort as a young, blonde actress, Daryl Hannah. John found it odd that Daryl seemed to carry a teddy bear with her wherever she went, but he also found her fascinating.
Although secluded, Andover offered no refuge from the emerging drug craze in America. In the 1960s, radical youth culture remained confined to a small number of hippies, but it became commonplace in the 1970s. “In the seventies, hardly anybody was a hippie, because everybody was,” declared one observer. Emblems of sixties protest, such as long hair and casual dress, gained mainstream appeal during the 1970s. So did experimenting with drugs. Smoking marijuana became a rite of passage for young people. Meanwhile, their parents managed to get their drugs legally. The most popular drug of the decade was the tranquilizer Valium. The Rolling Stones, John’s favorite rock band, poked fun at the older generation’s dependency on tranquilizers in their 1966 song “Mother’s Little Helper.”
While at Andover, John and some friends were caught smoking pot by a campus police officer. John had to meet with a school administrator, and his mother was notified of the infraction. While some schools had a zero-tolerance policy for drugs, Andover was more lenient. John, like everyone else found with drugs or alcohol, received a warning.
Though John dabbled in the drug culture and had a serious girlfriend, his top priority remained schoolwork. History and literature were his best subjects, but he struggled with math and science. While he earned an occasional A in history, he gravitated toward Bs and more than a few Cs. Holly Owen described John as “a modest student” who had trouble keeping up with the intense academic atmosphere at Andover, which attracted many overachievers. John also had a short attention span and did not help himself by missing classes often. “He certainly wasn’t at the top of his class,” a faculty member told the journalist Michael Gross.
John ended up staying for a third year and graduating as part of the class of ’79, because he needed another year to finish the math requirement. Andover required students to pass general exams in five subjects, including math. Normally, if a student failed any of the tests, he or she would be asked to leave. John’s mother, however, worked out an arrangement with administrators that would allow John to spend an extra year at the school. “I think his mom felt that he was still a little immature,” Sasha recalled. “She was a little wary of sending him off to college right away.” His graduation may have been delayed a year, but that setback did not diminish Jackie’s enthusiasm when he finally donned a cap and gown and received his diploma on June 7, 1979. As expected, dozens of photographers and reporters showed up to document John’s every move.
Shortly after graduation, Mrs. Onassis reached out to Bruce Breimer in his capacity as the director of college guidance at Collegiate. “Is it okay if John does not go to the family school?” she asked in her breathless voice. “He doesn’t want to go to Harvard.” When she told him that John was planning to attend Brown University, Breimer replied, “Why not? It’s not like he’s going to some third-rate institution. Let him go.”
Little did I know that our lives were about to intersect.
CHAPTER 5
“THE QUESTION IS, WHERE IS THIS ALL TAKING ME?”
Founded in 1764, Brown University was the seventh college established in the North American colonies. Its charter called upon the university to produce graduates who would lead “lives of usefulness and reputation.” As the first Ivy League school to accept students from all religious affiliations, Brown has long prided itself on its openness. Located on College Hill, the picturesque campus of historic homes and modern buildings now overlooks the gritty working-class downtown of Providence, Rhode Island.
Considering its quirky reputation, Brown seemed like an unu
sual choice for John, especially given his family’s close ties to Harvard. His grandfather, the late ambassador Joseph P. Kennedy, along with his father and his uncles—Joseph Jr., Bobby, and Edward—all graduated from Harvard. But John’s decision to enroll at Brown highlighted his lifelong quest to establish an independent identity and to challenge expectations. Brown was also better suited to his interests and style: it was more casual than the other Ivies, its twenty-eight-credit requirement was the lowest among elite schools in the United States, and it boasted a strong theater arts department. Admitting John also served Brown’s needs, as the institution sought high-profile students who could elevate its stature and help raise money. When John entered in the fall of 1979, Brown was a sleepy, second-tier Ivy League university. It was no coincidence that by the time he left, Brown had become the hottest college in America. During his four years on campus, John changed Brown as much as the institution changed him.
His time at Brown was among the happiest and most fulfilling of John’s life. The press left him alone, and students grew accustomed to seeing him around campus. He formed a close group of trusted friends who stayed by his side for the rest of his life. Although he struggled academically, he immersed himself in college activities, playing rugby, joining a fraternity, and even appearing in several plays. Brown, however, failed to provide him with a clear sense of direction. After earning his diploma in June 1983, John traveled to India, which had been one of his mother’s favorite travel destinations, in search of further inspiration.
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