Jackie did send teenage John to boarding school at prestigious Phillips Academy in Andover, Massachusetts. The English instructor and dorm master Meredith Price remembers, “When he was in tenth grade, he was full of life and somewhat happy-go-lucky. There was absolutely nothing pretentious about him.”
“He had to deal with some incredible pressure,” John Jr.’s school friend Jim Bailinson remarks, but notes, “He turned out remarkably normal for someone who led such an abnormal existence. He did totally normal teen stuff, but his mother kept a pretty tight rein on him.”
The new student lives with a roommate, and, since he’s never taken public transportation, has to ask how the bus system works (though as an adult, he prides himself on navigating New York City’s public transit). Jackie “was a great boarding school mother,” sending cookies and care packages and coming for visits with Caroline. “Not all parents are attentive as she was,” Price says.
John Jr. uses his natural charm to “push the disciplinary envelope at Andover,” fellow alumnus and author William D. Cohan notes. “He didn’t intentionally flaunt the rules as much as sort of pretend they never really existed in the first place, since it was pretty clear from his own experiences in life that the rules of the road would never apply to him anyway.”
Admissions officers at Brown University see evidence of this when in 1979 Jackie completes John Jr.’s undergraduate application for him, since John is out of the country on an educational trip to Africa. She is careful to avoid trading on the famous Kennedy name. On the application, Jackie merely lists his late father’s occupation as being “in government” and that “mother, sister grew up in New York City.”
John Jr. may have opted out of traditional Kennedy alma mater Harvard, but not the academic struggles that his father and uncles variously encountered. When John fails to complete his freshman-year coursework, Jackie writes to a Brown official in July 1980. “I have never asked for special consideration for my children because I feel that is harmful to them,” she explains, “but there was an extra burden John carried this year that other students did not—and I would like to mention it. He was asked to campaign almost every weekend for his uncle.” She is referring to Ted Kennedy, then in the thick of his ultimately failed quest for the 1980 Democratic presidential nomination.
At school, John Jr. is naturally popular, even though he had the “bad habits of borrowing money and of losing his wallet, which occasionally had some borrowed money in it,” says Cohan. Newsweek’s Martha Brant writes of John’s need “to borrow a quarter every night for coffee,” contextualizing, “Like many rich people—including his own father—Kennedy often has to borrow cash, and he is sometimes forgetful about paying it back.”
John Jr. graduates in 1983 with a bachelor’s degree in American studies, and returns to New York. While at Brown, he had pursued a passion that sparked at Phillips Andover—acting—and on August 4, 1985, John makes his off-off-Broadway debut at the Irish Arts Center on Manhattan’s West Side, starring in Brian Friel’s Winners, set in Northern Ireland. On stage, he can be his character (a Catholic teenager with a pregnant fiancée), not a Kennedy. In the climactic scene, John plays a drowning victim (which many viewers consider loaded with symbolic reference to Chappaquiddick), though his mother and sister are out of town throughout the play’s six-show run and never see him perform.
“He’s one of the best young actors I’ve seen in years,” director Nye Heron recalls of John Jr., but feels he lacks the focus and determination needed to hone his natural talent to a professional-level skill. “John’s problem as an actor was that he didn’t take it seriously,” says Don Wilmeth, who directed John in Brown Theater Department productions. “He did it for fun and lacked discipline. He would work hard for short stints and then go off and lose it.”
“It’s only a hobby,” John tells reporters, mainly for Jackie’s benefit. When he talks of applying to Yale School of Drama, his mother steers him away from the stage and toward the courtroom. He lands at New York University Law School, earning his degree in 1989. In May 1990, the New York Post trumpets the humiliating news—“THE HUNK FLUNKS . . . AGAIN”—of John’s second failed attempt to pass the New York State Bar Exam. “I am very disappointed,” he tells the press. “God willing, I will be back [to take the test] in July. I am clearly not a legal genius.”
Even though John’s been working under the watchful eye of Manhattan district attorney Robert M. Morgenthau (who was with Bobby at Hickory Hill when J. Edgar Hoover called to break the news of JFK’s death), should he fail the test a third time, he’ll be forced to leave his position. In July 1990, he passes, is appointed assistant district attorney, and in August 1991, wins his first victory at trial. “This case would have posed serious difficulties for any defense,” says veteran lawyer William Kunstler of the robbery defendant known as the “Sleeping Burglar” (apprehended while napping in his victim’s apartment, pockets filled with her stolen jewelry), but John Jr. takes the high road, declaring, “Winning is better than losing.”
Chapter 56
Despite Jackie’s repeated warnings of the dangers of paparazzi (“Don’t let them steal your soul,” she tells him), John Jr. continues to live his life fully in the public eye. Photographers swarm to document his string of celebrity girlfriends—including Cindy Crawford, Daryl Hannah, and Sarah Jessica Parker—and his frequent, bare-chested outings in Central Park, where he Rollerblades and plays Frisbee with his dog, Friday. Photographer Victor Malafronte recalls “trying to get this gorgeous image of the man skating down West Broadway,” when John stepped in for a handshake. “Hi, I’m John” (his preferred form of address—no middle initial or suffix; the “John-John” nickname was used purely in the press). “I was blown away,” Malafronte says, and so are the editors at the New York Post and People, who deem his close-up pictures cover-worthy.
In the summer of 1988, twenty-seven-year-old John Jr. starts dating thirty-year-old pop star Madonna (still technically married to, but estranged from, actor Sean Penn). John and Madonna quarrel over how to handle fame—she seeks it; he shuns it. According to J. Randy Taraborrelli, they’re running through the park, arguing. “I’m just a guy,” John says. An eyewitness takes in Madonna’s response. “You’re not ‘just a guy,’ you’re a Kennedy.”
That September, People magazine names John F. Kennedy Jr. 1988’s “Sexiest Man Alive.” But according to his personal assistant RoseMarie Terenzio, John has a major hang-up about one aspect of his appearance. “He hated his hair,” Terenzio says. “He was constantly putting stuff in it to hold it down. That’s why he always wore a hat, ’cause he hated his hair.”
“Whenever he would get on one of those best-dressed lists,” recalls Richard Wiese, a college friend, “we would just howl.” Just as Rose always criticized Jack for sloppiness, John Jr. “would always be walking around with some stain on his shirt. He was a mess.”
Of the magic of Camelot, Richard Goodwin, a former aide to JFK and RFK, observes that Jackie’s creation is in little peril—if only its caretakers remember that “magicians are only as good as their last illusions.”
* * *
In 1993, John Jr. finally chooses to seek out light from the Kennedy flame. While still employed by the city of New York, he and his friend Michael Berman approach potential investors with a concept for a political magazine. John is less than receptive to concerns over limited interest in the topic. “It was the worst presentation I have ever seen in my life,” says one publisher who took the pitch. “He was like, ‘I’m JFK, so there you go.’”
In an interview with JFK Jr. biographer Steven M. Dillon, Berman reveals a unique duality in his business partner. “It must be interesting to be you,” he says to John in a crowded restaurant dining room, watching heads whirl in recognition of the son of the late president. “You don’t know a soul here, but they all know who you are.”
“That’s not the weird part,” John answers. “The weird part is they all remember [JFK], and I don’t.”
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John was only two years old when his father was killed, after all—he spent his third birthday famously saluting his father’s casket. But he’s reluctant to delve deeper into the meaning his name carries, or the accompanying responsibility. “It’s hard for me to talk about a legacy or a mystique,” Kennedy states in 1993. “It’s my family. The fact that there have been difficulties and hardships, or obstacles, makes us closer.”
Of his sister Caroline, John Jr. tells Oprah, “We’re obviously very close. As a younger brother, you look up to your sister. I was the ‘man’ of the family, as it were. I feel so lucky to have such a close relationship with her.”
He’s especially close with his cousins on his mother’s side, his aunt Lee Bouvier Radziwill’s children, particularly his cousin Anthony. “Anthony was more of a brother than a friend to John. He was the closest family member to John and they really did grow up together. They remained close throughout their lives and they spoke nearly every single day,” RoseMarie Terenzio recalls.
Anthony’s wife, Carole Radziwill, agrees, saying, “Given the life that John led so publicly, I think he really felt completely himself around Anthony. He knew Anthony had his back, and Anthony felt the same way about him. That was a nice thing to see, and it was nice to be around—that feeling of complete trust.”
John’s relationships with his Kennedy cousins are mainly warm if somewhat distant, and occasionally competitive. Chris Lawford describes the relationship between John Jr. and Joe, Bobby’s oldest son, as the most fraught. “I think he [Joe] loved John, hated John, and wanted to be John all at the same time,” Chris says, pointing out that rivalry among the cousins is to be expected, after all: “We were all, every one of us, raised to be President.”
As authors Collier and Horowitz remark of the Kennedy cousins in their 1981 book, The Kennedys, “Together in one place, they looked like a remarkable experiment in eugenics—several strains of one particularly attractive species.” Eunice’s children are “darkly handsome…with their father’s sensitive eyes and their mother’s aggressive jaw”; Teddy’s kids are “blond and surprisingly frail”; Jean’s children have a “round-face impassivity”; while Pat’s have her ex-husband’s “good looks—and a hint of his troubled vulnerability”; and Bobby’s kids have the “big bones and imposing size of Ethel’s family.” Unsurprisingly, Caroline and John Jr., “posing for nonstop photography since infancy…had acquired a poise all the others lacked.”
But the authors also note that Bobby and Ethel’s children (who tend to see themselves as “the most Kennedy”) “would sometimes tell their cousins, ‘You’re not Kennedys, you’re only Shrivers [or Smiths or Lawfords].’” They taunted John Jr. as a “‘Mama’s boy’ and said he wasn’t a ‘real Kennedy.’”
To the rest of the world, though, no one embodies the Kennedys more than John Jr. “I understand the pressure you’ll forever have to endure as a Kennedy, even though we brought you into this world as an innocent,” his mother writes him. “You, especially, have a place in history. No matter what course in life you choose, all I can ask is that you and Caroline continue to make me, the Kennedy family, and yourself proud.”
John Jr. is thirty-three when Jackie dies at age sixty-four on May 19, 1994, not long after receiving a diagnosis of non-Hodgkins lymphoma. In her eulogy, Ted names Caroline and John as “her two miracles.” At Arlington National Cemetery, under a headstone reading “Jacqueline Kennedy Onassis,” she is buried alongside JFK, only the second First Lady, after Mrs. William Howard Taft, to be so honored.
So it falls to Ethel, the new Kennedy matriarch, to assess the latest woman to appear in John’s life: twenty-eight-year-old Carolyn Bessette, who was voted “Ultimate Beautiful Person” at Catholic St. Mary’s High School in her hometown of Greenwich, Connecticut, and is now head of public relations at the fashion label Calvin Klein. “She’s an ordinary person,” John tells his friend John Perry Barlow, but “he couldn’t get his mind off her.”
Barlow, best known as a former lyricist for the Grateful Dead, finds Carolyn charismatic, quirky, and a little reminiscent of Jackie herself, but after a Labor Day weekend introduction to the Kennedy clan at the Hyannis Port compound, where Carolyn fails miserably at Kennedy political and athletic gamesmanship, Ethel is less impressed. “I’m afraid Carolyn isn’t everything she portrays herself as being,” she tells her son Joe. Citing the knowledge that comes with raising four Kennedy daughters, Ethel adds, “If there’s one thing I know, it’s girls. Trust me, that one is all smoke and mirrors.”
“Oh, he definitely chased her,” says Brian Steel, who works alongside John as a Manhattan assistant district attorney, in an interview for the ABC documentary The Last Days of JFK Jr. “Early on he would be frustrated. He would say, ‘I called her and she hasn’t called me back.’”
Carole Radziwill recalls John, her husband’s cousin, being “really besotted” with Carolyn. “He was so enthralled with her, and she with him, but she was kind of fierce. She was very confident. He liked that. She was very much her own person. She was this great combination of kind of seriousness and wild child,” she says.
Carolyn’s elusive behavior is reminiscent of Jackie’s resistance to Charles and Martha Bartlett’s “shameless” matchmaking between her and Jack. And like then, it works—by the spring of 1995, Carolyn and John Jr. are living together, and over the Fourth of July 1995, during a fishing trip on Martha’s Vineyard, John proposes. Carolyn “held the proposal off for about three weeks”—just as Jackie had done when she traveled to London to cover Queen Elizabeth II’s coronation—“which I think just made him all the more intent on marrying her,” a friend of the couple tells People.
The engagement story, broken by the New York Post just before Labor Day, nearly overshadows John’s other surprise announcement, scheduled for September 7, 1995: that he’s launching a new magazine. “For almost two and a half years,” he tells USA Today, “it was like I didn’t have a job. I was sort of [developing this magazine] in secret and everyone was like, ‘What’s John been doing with his time?’”
The answer is George, a celebrity-tinged political magazine backed by publisher Hachette Filipacchi which debuts with a double issue in October/November 1995. The inaugural issue features a cover portrait by celebrity photographer Herb Ritts of supermodel (and former JFK Jr. flame) Cindy Crawford, dressed as a midriff-baring George Washington.
“He called my hotel,” Cindy Crawford recalls of John’s request she be his first cover model. “He reached out directly. And who’s going to say no?”
The first two issues sell out and break magazine-industry financial records, and the unusual office atmosphere quickly becomes the stuff of publishing legend. Two associate editors recall going “rollerblading with John in Central Park at midnight. And it was just the fucking coolest.”
But not even the novelty of JFK Jr. as publisher can easily overcome the substantial challenges of publishing expensive-to-produce glossy magazines profitably. Even in the early glow of success, investors are on watch.
John and Carolyn live together in John’s TriBeCa loft at 20 North Moore Street, and at times publicly reveal that each of them possesses a tempestuous temper. On February 25, 1996, during a heated argument in Central Park, Carolyn removes her engagement ring and throws it at John. The entire exchange is photographed, and worth a quarter of a million dollars to the National Enquirer.
“That video was terrible for her, because it framed her as this sort of mean harpy,” says George Rush, one half (with his wife, Joanna) of the New York Daily News gossip column Rush & Malloy. “She never recovered from that branding, really.”
Six months later, however, on September 21, 1996, when the George magazine staff believes John and Carolyn are traveling in Ireland, the couple is actually exchanging wedding vows. The ultraprivate ceremony takes place on remote Cumberland Island off the coast of Georgia, once a retreat for Carnegies and Rockefellers, in a hand-built, wood-frame First African Baptist Church. The church,
lit only by natural light and candlelight, has personal and historic significance. On November 22, 1963, islanders gathered there to mourn John’s father, President John F. Kennedy.
But today, thirty-three years later, it’s a celebration—and hardly anyone knows it’s happening. “If Mr. Kennedy wanted privacy, this was a good place to find it,” says a Cumberland Island official from the National Park Service. “We were so excited to have fooled everybody,” says one of only a few dozen guests, who include Oprah Winfrey, multiple Kennedys, and John’s cousin and best man, Anthony Radziwill. His sister, Caroline, is the matron of honor, and her three children are the flower girls and ring bearer.
Staffers at the local Greyfield Inn sign confidentiality agreements about the wedding and reception details, and a fifty-person security team is brought in to cover the island—“In other words,” one outlet later notes, “there was more security than wedding guests.”
Carolyn wears a bespoke Narciso Rodriguez white silk crepe bias-cut gown that to this day inspires the flattery of imitation. “There is something mysterious and female in the world, and she has a good connection to it,” says John’s friend John Perry Barlow of the bride. “It’s deep and primordial and lovely.”
But the feeling of privacy is fleeting. The couple is recognized three days into their Turkish honeymoon. Two weeks later, at home in New York, John begs the relentless paparazzi for “any privacy or room you could give” his new bride. The New York Daily News translates John’s polite plea into tabloid language: “JUST LEAVE HER ALONE.”
For John, the paparazzi are a part of life. The demands of fame he feuded over with Madonna back in the late 1980s have only intensified. “We’re used to a certain degree of being watched,” he tells Oprah in a September 1996 interview not long before the wedding. He’s only half joking when he says that if he weren’t a Kennedy, “you wouldn’t have invited me on your show.” As RoseMarie Terenzio observes, “John was never not famous. He was born famous. So for John, it was a part of his life.”
The House of Kennedy Page 26