The Kennedy Heirs: John, Caroline, and the New Generation - A Legacy of Tragedy and Triumph

By J. Randy Taraborrelli

From New York Times bestselling author J. Randy Taraborrelli comes The Kennedy Heirs, his most revealing Kennedy book yet.

A unique burden was inherited by the children of President John Fitzgerald Kennedy and his celebrated siblings, Senators Robert and Ted Kennedy. Raised in a world of enormous privilege against the backdrop of American history, this third generation of Kennedys often veered between towering accomplishment and devastating defeat. In his revelatory new book, acclaimed Kennedy historian J. Randy Taraborrelli draws back the curtain on the next generation of America’s most famous family.

John Kennedy, Jr.’s life in the public eye is explored, following the Kennedy scion as he faced the challenges posed by marrying his great love, Carolyn Bessette. Riveting new details are shared about the couple’s tragic demise—and why Ethel Kennedy advised Carolyn not to take the trip that would ultimately end her life. John’s sister, Caroline Kennedy, had her own complicated relationships, including a marriage to Ed Schlossberg that surprised her mother, Jacqueline Kennedy Onassis, and an unexpected bond with her mother-in-law, Mae Schlossberg.

Additional stories, many shared here for the first time, illuminate the rest of the Kennedy dynasty: Kara Kennedy, Ted’s daughter, and her valiant battle against lung cancer; how Ted’s wife, Vicki, introduced a new era of feminism to the Kennedy family; the lifelong struggles with addiction faced by Bobby Kennedy Jr. and Patrick Kennedy; the unexpected way pop star Taylor Swift helped Conor Kennedy heal after the death of his mother, Bobby’s wife Mary; and Congressman Joe Kennedy III’s rise to prominence. At the center of it all is the family’s indomitable matriarch, Ethel Kennedy—a formidable presence with her maddening eccentricities and inspiring courage.

Based on hundreds of exclusive first-hand interviews and cultivated over twenty years of research—including numerous Oral Histories from the JFK Library and the Edward M. Kennedy Institute—The Kennedy Heirs is an epic drama of ambition, scandal, pride and power.

• Language: English
• Publisher: Macmillan Publishers
• Release date: Jun 11, 2019
• ISBN: 9781250174086

J. Randy Taraborrelli

J. Randy Taraborrelli is a highly-acclaimed biographer, whose bestselling titles include Madonna: An Intimate Biography, Michael Jackson: The Magic and the Madness, Elizabeth, Once Upon a Time: The Story of Princess Grace, Prince Rainier and their Family, Call Her Miss Ross and Sinatra: The Man and the Myth. He is also a CBS-TV news analyst and lives in California.

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The Kennedy Heirs by J. Randy Taraborrelli

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For my sister, Roz,

a sister, a friend, a survivor

whose love for life, for family

inspires all who know her

to shine on

And even in our sleep, pain which cannot forget falls drop by drop upon the heart until in our own despair, against our will, comes wisdom through the awful grace of God.

—AESCHYLUS

Introduction

For our purposes with The Kennedy Heirs, I ask that you consider the first generation of Kennedys to be the one that includes those children born to Joseph Patrick Kennedy Sr. (born 1888) and his wife, Rose Elizabeth Fitzgerald Kennedy (born 1890). Their first child was Joseph Patrick Jr. (born 1915). The rest followed quickly: John Fitzgerald (born 1917), Rose Marie (born 1918), Kathleen Agnes (born 1920), Eunice Mary (born 1921), Patricia Helen (born 1924), Robert Francis (born 1925), Jean Ann (born 1928), and Edward Moore (born 1932).

The second generation are the surviving children of Joseph and Rose, and their spouses: John and Jacqueline Bouvier (born 1929), Eunice and Sargent Shriver (born 1915), Pat and Peter Lawford (born 1923), Bobby and Ethel Skakel (born 1928), Jean and Stephen Smith (born 1927), and Ted and Virginia Joan Bennett (born 1936) and, later, Victoria Reggie (born 1954).

The third generation—the primary subject of this work—comprises the progeny of the second, and there were many, twenty-nine in all.

John and Jackie were the parents of Caroline Bouvier (born 1957) and John Fitzgerald Jr. (born 1960).

Eunice and Sargent were the parents of Robert Sargent III (born 1954), Maria Owings (born 1955), Timothy Perry (born 1959), Mark Kennedy (born 1964), and Anthony Paul (born 1965).

Pat and Peter Lawford were the parents of Christopher Kennedy (born 1955), Sydney Maleia (born 1956), Victoria Francis (born 1958), and Robin Elizabeth (born 1961).

Bobby and Ethel were the parents of Kathleen Hartington (born 1951), Joseph Patrick II (born 1952), Robert Francis Jr. (born 1954), David Anthony (born 1955), Mary Courtney (born 1956), Michael LeMoyne (born 1958), Mary Kerry (born 1959), Christopher George (born 1963), Matthew Maxwell Taylor (born 1965), Douglas Harriman (born 1967), and Rory Elizabeth (born 1968).

Jean and Stephen were the parents of Stephen Edward Jr. (born 1957), William Kennedy (born 1960), Amanda Mary (born 1967), and Kym Maria (born 1972).

Edward (Ted) and Joan were the parents of Kara Anne (born 1960), Edward Moore Jr. (born 1961), and Patrick Joseph (born 1967).

The fourth generation, then, would be the many children of the third, some of whom are also considered for this work, such as Joseph Patrick III (son of Joseph II and Sheila Rauch, born 1980), John Conor (son of Robert II and Mary Richardson, born 1994), and John Jack Bouvier Kennedy (son of Caroline Kennedy and Edwin Arthur Schlossberg, born 1993).

---

MY MANDATE WITH this volume was not to write about every Kennedy of the third generation who ever drew breath. Admittedly, as I was doing my research, some held my fascination more than others. In the end, I sought to tell what I think are the stories that best explored the truth of who these people were in one another’s lives and that also revealed their true selves, warts and all, as well as their many contributions to our society. After all, this is a generation that was ubiquitous in our culture in the 1960s, ’70s, ’80s, into the ’90s, and beyond, and, as you will read on these pages, even today. Maybe Life once put it best when the magazine reported of them: They were America’s children. Born at a time when the nation itself seemed reborn, the grandchildren of Joseph and Rose Kennedy became a compelling symbol of the future for people hungry for change. And we couldn’t get enough of them. Americans probably saw more of the Kennedys on television and in photographs than they saw of their own families. At a time when the American family was said to be falling apart, the Kennedy family seemed of biblical strength.

A myth I think worth dispelling from the outset is that these particular Kennedys did little to nothing of any great significance in our culture. In fact, they were all raised to have a strong sense of noblesse oblige. Of course, when one considers the global ramifications of what President Kennedy did with his time in office, maybe not much can compare. The same holds true of the great work of Bobby and Ted, not to mention Sargent and Eunice. They’re all competing with icons and legends, political consultant David Axelrod, who has advised several of them, noted of the younger Kennedys. However, as you will read, so many of them have contributed a great deal to the world, if not in elected office, then as activists. Ethel’s daughters Rory and Kerry make films about poverty and travel the world as warriors for social justice, for instance; Eunice’s son Tim Shriver runs his mother’s Special Olympics; Jackie’s daughter, Caroline Kennedy, works tirelessly to raise funds for education. If such causes appear modest next to staring down the Russians, integrating the South or going to the moon, they are not, Time once observed. They are simply of their time. Some would change the world in small ways in the private sector, others in a much bigger manner while in public office. The number of legislation, for instance, either sponsored or cosponsored by Ted’s son Patrick Kennedy during his many years in government amounts to 3,156. Put it this way: There aren’t many who do nothing with their lives. Not in that family.

What I have also learned over the years as a Kennedy historian is that, despite the complexities of their lives, personal and political, it’s really not that difficult to understand them. Of course, some of their experiences have been amplified tenfold because of money, power, and prestige. Also, fame does tend to twist everything. However, at the heart of their stories are the kinds of choices and decisions similar, at least I think, to those we may have made in our own lives as we’ve attempted to navigate the sometimes rocky terrain of getting along with parents, siblings, and children. I believe we can relate to the Kennedys on a deep, visceral level that has to do with a thing so basic and so uncomplicated: our shared humanity. To my mind, this is why the Kennedys’ story continues to resonate. Plus, of course, the many tragedies of their lives have reached out to us over the years, causing our hearts to ache unbearably for them.

At a symposium on the legacy of the Kennedy women at the John Fitzgerald Kennedy Presidential Library and Museum, Kerry Kennedy told me, It’s difficult when your most private moments are also your most public moments, but it’s interesting, too, because we have never really felt alone in any of it. We have always felt at one with the American public, and I think they have felt the same dynamic with us. There’s this special, symbiotic relationship Americans have with my family going all the way back to my grandparents, to President Kennedy and my aunt Jackie, to my father, my mom … Uncle Teddy, Aunt Joan … my late brother David … and while I think a lot of it has to do with basic empathy, I also think it has to do with a collective human experience. All people have troubles in their lives. If understanding how we have dealt with our own problems can in some way help people cope with their own, well, then I think that’s good. In fact, I think that’s very good, and I know my family members would agree.

Senator Ted Kennedy put it this way in addressing the question of how the Kennedys dealt with tragedy. Yes, we have had some hard knocks, he told me. But we have survived because we have heart. And heart matters.

Here’s a hard truth, though: The name Kennedy can inflame as much as inspire; there are people for whom the very name stirs up anger and resentment. Their critics believe the Kennedys, especially those of the third and fourth generations, to be an entitled and spoiled lot used to getting away with bad behavior and never suffering true consequences because of it. Maybe Newsweek put it best in 1998 when describing what it called the duality of the Kennedy experience in the popular imagination—sin and service. There have certainly been times of great disgrace—many of which have to do with self-inflicted tragedies—that remain an integral part of family history and, as such, are closely examined in these pages. However, I hope you’ll agree that even those parents, sons, or daughters of this American dynasty who’ve at times been perhaps not so deserving of our admiration still have certain traits instantly recognizable not only in people we know and love, but maybe in ourselves, too.

Family is family, John Kennedy Jr. told me when I had a chance to interview him after the press conference for the unveiling of his George magazine in September 1995. You can pick the Kennedys apart, and I’m sure you will, he said with a nod at what he knew I did for a living, but at the end of the day, we’re just people trying to understand each other as we share this incredible life we’ve all been blessed with. It’s nothing more than just that, if you really want to know the truth.

I have come to believe it’s a lot more than just that, if you really want to know the truth. It is my hope that as you read The Kennedy Heirs you will agree.

BOOK I

PART I

Son of Camelot

Prologue

The Tide of Events

JULY 1999

John Kennedy didn’t want to have this fight again, but he also knew there was no way around it. He and his wife, Carolyn Bessette-Kennedy, had been invited to his cousin Rory’s wedding at the family’s private compound in Hyannis Port. And … here we go again, he told his personal assistant, RoseMarie Terenzio. He cursed under his breath, dreading the argument he knew was in the offing with his wife over it.

The problem John faced was that from the first time Carolyn ever set foot on the family’s property some four years earlier, she didn’t feel that she fit in with his family. While he and his relatives always felt insulated against the world at the compound, cocooned within its familiar, pleasant surroundings, she just felt exposed, as if her deepest insecurities were on display. On some level, he understood that only a person who’d actually been raised a Kennedy could truly fathom the complex machinations of the family’s culture—the competitive nature of their sportsmanship, the constant and not-so-gentle ribbing of one another, their unique camaraderie and secret language, not to mention their constant obsession over the family business: politics, of course. The Kennedys had always existed in an exclusive world, and even John had to admit that sometimes they weren’t welcoming to outsiders.

In truth, Carolyn wasn’t really that close to Rory, the late Senator Robert F. Kennedy’s daughter. Was she really expected to be friends with every one of John’s twenty-seven cousins and their spouses and other partners, as well as all his aunts and uncles? That wasn’t the primary reason for Carolyn’s trepidation, however. Nor did it have to do with the feelings of inadequacy that somehow always washed over her whenever she was around the Kennedys. She’d dealt with it all in the past and had managed to get through many uncomfortable visits. The truth about this upcoming wedding was that she had a sinking intuition, maybe even a premonition about it. Whatever it was, it was telling her not to go.

To John, Carolyn’s reasoning seemed pretty weak. "You just don’t want to?" After four years of tolerating his relatives, he didn’t understand why she couldn’t just endure one more party. So John went ahead and sent back the RSVP for two. It was a family obligation, he decided, and Carolyn would just have to sort through her emotions about it and attend. She was a Kennedy by marriage, and sometimes Kennedys had to do what they didn’t want to do for the sake of the greater good. The storm would pass.

John was wrong; Carolyn wouldn’t let the storm blow over. In fact, it just grew in intensity. They had a pretty big argument about it, said a very good friend of Carolyn’s. "What was at stake for her was more than just getting her way. It had to do with respect, with being visible in her marriage, with being recognized … acknowledged. In a family full of loud voices, one thing Carolyn had learned about being around the Kennedys was that she had to speak up if she ever wanted to be heard."

The irony of this marital dispute would not have eluded anyone aware of John’s personal history. He and Carolyn were actually of the same mind, at least in some important respects. Especially in recent years, John had been battling preconceived notions of how he was supposed to act as the namesake and only son of America’s thirty-fifth President, John Fitzgerald Kennedy, and First Lady Jacqueline Bouvier Kennedy Onassis. Like Carolyn, he didn’t like being told what to do either, and he roundly rejected the cookie-cutter version of how a Kennedy of his generation was supposed to act. If he squinted at the equation hard enough, he probably would have been able to identify with Carolyn’s side of it. However, as often happens when a person is in the middle of a big fight, he could only see his side. Carolyn’s not going, he glumly told RoseMarie Terenzio a few days before the Saturday wedding. I just have to accept that I’m going alone.

But John, that’s only asking for trouble, RoseMarie said.

Well, I’m not going to fight her on it anymore, John said, seeming fed up with it all.

It’s just not good, John, she said. Not only did RoseMarie feel Carolyn should be present as John’s spouse, she worried that her absence would send a message to the world about the state of their union. It would definitely spark a firestorm of rumors, she felt, which, as usual, she would then be responsible for containing. After all, John was a special case in the Kennedy family. Any of them could show up without their partners and it wouldn’t have mattered much to the press. It’s not as if Ethel’s son Bobby Jr. or Ted’s son Teddy Jr. would have caused a media sensation by going stag to a cousin’s wedding. However, as the most popular member of the new generation, all eyes were always on John—and even more so in recent years since taking Carolyn as his wife. His being alone would be noticed, and the following week would find RoseMarie inundated with queries—all of which could be avoided if Carolyn just went to the doggone wedding. Therefore, without being asked to do so by John, she slipped into his office and called Carolyn herself.

RoseMarie, a New York Italian American, was known to be a straight shooter, forthright and blunt. Carolyn, are you fucking kidding me? she asked, getting right to the point. What are you doing? You’re smarter than this. You don’t want to put John in a position where he has to explain where you are, and you don’t want to put yourself in a position of being judged. You get enough of that. Somehow RoseMarie was able to convince Carolyn that her judgment was being crippled by emotion. Eventually, Carolyn agreed to accompany John to the wedding.

Of course, when Carolyn told John she’d changed her mind, he was elated. He promised that this would be the last time he’d ever insist that she go with him to this kind of family event at the Kennedy compound. I’ll owe you one is how he put it. He would fly them both up to Hyannis Port in his Piper Saratoga, he said. They’d attend the wedding, spend the night, and leave the very next day. She wouldn’t regret it. Just wait and see, he assured her. Things are going to be great. Then he flashed his dazzling smile, usually her cue to melt into his arms. What she didn’t do, though, was tell him how she really felt. That deep sadness she’d been trying to shake for longer than she cared to admit somehow now felt even more acute.

She told me she felt manipulated and compromised, said Carolyn’s trusted friend, as if she had no authority over her own life. She said she was putting John on probation. ‘I’m going to give it three more months and see how I feel,’ she said. ‘Are you sure you’re not just pissed off because you don’t like being told what to do?’ I asked her. She admitted that this might be the case. She felt she needed a cooling-off period and that in a few months she’d have more clarity. They’d been having a lot of marital problems lately, she said, and she was worn down by them.

Was she thinking divorce? "Who divorces John Kennedy Jr.? she asked. You’d have to be insane, or at least that’s what people will think. However, she said that if she decided on it she would steel herself for a serious fight and get through it as best she could. Even though she was thrown by events from time to time, Carolyn had demonstrated a new kind of focus and determination ever since she married John. Maybe in that respect she was becoming a little more Kennedy" than even she knew. Whatever the case, Carolyn said she actually felt better about things because at least now she had a plan. She just needed more time.

As for John, there wasn’t as much joy in his victory as Carolyn believed. He knew she felt bullied. This same fight you keep having with her about being with your relatives, it has to stop, his good friend John Perry Barlow told him. It’s not good, John. Not for you. Not for her. Definitely not for your marriage.

John had to agree. He’d set it all straight after Rory’s wedding, he decided. Like Carolyn, he, too, just needed a little more time, not to figure out how he felt, but instead how to fix things with the woman he truly loved. Who knows? Perhaps John, a real student of history when it came to his father’s administration, could hear the words of President Kennedy echoing in his head: The hour of decision has arrived. We cannot afford to wait and see what happens, while the tide of events sweeps over and beyond us. We must use time as a tool … We must carve out our own destiny.

John knew what his destiny held, and it was to be with Carolyn. He wanted to make it right with her.

He was thirty-eight. She was only thirty-three. They had all the time in the world.

Chosen One

FIVE YEARS EARLIER: MAY 19, 1994

Thirty-three-year-old John Kennedy Jr. stood next to the telescope he had so loved as a child, still in the exact same place it had been when he was growing up—in the corner of a large square drawing room with high ceilings, wide windows, and French doors facing an exquisite view of the city, north, south, and west all the way to the reservoir. On either side of the telescope, falling with grace onto polished hardwood floors, were red-and-gold silk drapes. Around it were multiple stacks of books and magazines on shelves, on tables, on the floor. Orderly chaos, is how John’s mother, Jacqueline Kennedy Onassis, once put it, having lived among it for almost thirty years.

Always loved this thing, John told his uncle Yusha Auchincloss as he slid his fingers across the telescope. Mummy bought this for me when I was a kid, he added as he bent down and peered into the tube at the iridescent New York vista.

It’s a beaut, all right, said Yusha. Yusha, the stepbrother of John’s mother, then recalled to John the day Jackie first showed him the telescope in a Manhattan store window. She said she wanted to buy it for her boy on the occasion of his seventh birthday. He remembered it as being typical of his stepsister to purchase a present she felt could be used as a learning tool.

Just an hour earlier, John and Yusha had wept while their beloved Jackie took her last breath. As the two men spoke, John’s aunt Ethel Kennedy puttered around in the kitchen, preparing tea for those who’d stayed behind after saying their final goodbyes, including John’s uncle Ted Kennedy and his wife, Vicki.

It had all happened so quickly. Jackie had just been diagnosed with non-Hodgkin’s lymphoma a few months earlier, in January. After the diagnosis, a priority for her was the spending of quality time with her longtime companion, the financier Maurice Tempelsman; her children, John and Caroline; and her grandchildren by Caroline—Rose, Tatiana, and John, better known as Jack.

Taking a step back from the telescope, John rose to his full six-foot-one height. Somehow he always seemed taller, though. Maybe it was his self-confidence that gave him the appearance of greater stature; his body was lean and trimly built like that of a dedicated athlete. He was arguably the best-looking of the Kennedys of his generation, with his square-jawed, lean, and angular features, his shock of thick black hair, the deep brown eyes and gleaming smile. The moment a person shook his hand, John made a deep impression. It wasn’t just the firm grip, it was also the laser-focused eye contact—friendly, curious, intense, all at the same time.

Like his mother, John had mastered the art of making anyone with whom he was engaged feel as if he were the only person of relevance in that moment. His sister, Caroline, didn’t possess quite the same gift. Not always comfortable with direct eye contact from people, especially reporters, she’d make it clear that she didn’t welcome intrusion. Caroline was like Jackie; both could shut a person down if he had the temerity to ask an intrusive question. John was more like his father; he didn’t avoid invasive inquiries, he addressed them eagerly, almost like a politician, but without the slickness that comes with a hidden agenda.

Again, much like a person in politics, John could also command a room. He had an innate ability to communicate ideas with eloquence and passion, qualities a lot of people felt were genetic. However, not every Kennedy was blessed with them. For instance, John’s cousin Patrick—Ted’s son—was less authoritative. Even though he’d been in government since he was just twenty-one—elected to the Rhode Island House of Representatives in 1988 as the youngest member of the family to ever hold office—Patrick had to work hard at, as he once put it, "being that guy, when, actually, I’m this guy." Time noted, Speechmaking so terrified Patrick that colleagues recalled seeing his hands shake from across the chamber. Patrick, of course, proved himself over time because he put in the work to do so. However, it definitely wasn’t a fait accompli that just because a person was born Kennedy he or she would be a natural communicator; Patrick’s uncle Bobby Kennedy Sr. was also a clumsy speaker at first; he, too, had to really work at it. However, when John Kennedy Jr. addressed the Democratic National Convention in July 1988 to introduce his uncle Teddy, he somehow seemed to have it naturally, whatever it is:

Over a quarter century ago my father stood before you to accept the nomination for the presidency of the United States. So many of you came into public service because of him. In a very real sense because of you he is with us still, and for that I’m grateful to all of you. I owe a special debt to the man his nephews and nieces call Teddy, not just because of what he means to me personally but because of the causes he’s carried on. He has shown that an unwavering commitment to the poor, to the elderly, to those without hope, regardless of fashion or convention, is the greatest reward of public service. I’m not a political leader, but I can speak for those of my age who have been inspired by Teddy to give their energy and their ideas to their community … He has shown that our hope is not lost idealism but a realistic possibility.

It wasn’t much, but it was enough to convince a lot of people that John could very well be the heir apparent to the Kennedy throne. A two-minute standing ovation for the twenty-seven-year-old Kennedy scion said it all.

When People magazine named him Sexiest Man Alive that same year, John took it in stride and accepted as par for the course the gentle ribbing from friends and relatives that went along with such silliness. He didn’t surround himself with sycophants. It didn’t matter who a person was, John showed that person respect if he was engaged by him. One observer of his life aptly noted, he had the ability to spend twenty seconds with you and leave you feeling as if the sun had just shone on you and you alone. For example, once at Hickory Hill—the home owned by Ethel Kennedy, where his cousins had been raised—John was having a conversation with Fina Harvin about politics. She was smart and engaging, even if she was only the daughter of Ethel’s governess. As they spoke, a beautiful and sophisticated young woman approached and began hitting on John, completely ignoring Fina. Maybe the interloper even wondered what such a plain-clothed, ordinary girl could possibly mean to him. John looked at the gorgeous stranger and said, "Excuse me, but I’m talking to this young lady right now." Then he turned his back on the other person and continued his conversation with Fina.

Another interesting component to his personality was his temper. John had a short fuse. He could take a lot, but there would come a point when he would just explode. When that happened he could unleash a fury that was surprising considering his generally amiable personality. Madonna, when she dated him back in 1985, used to complain about it to her friends. At the time, she was separated from her husband, Sean Penn, also known for his volatile temper. She told one person that John was slightly more frightening. Whereas Sean would act out, perhaps give a photographer a body shot just to vent, somehow John’s way seemed more personal. Madonna said he would get up in her face, maybe an inch away, and scream at her at the top of his lungs when they were in a fight. That romance lasted just six months. All the women with whom John would become romantically involved would eventually feel the brunt of his fury, and none would ever forget it.

One of the problems John Kennedy faced was that most of his relatives viewed him as a sort of chosen one since he was the son and namesake of the family’s only President. His father had gotten an early start in politics. At twenty-nine, John Fitzgerald Kennedy was elected to Congress. At thirty-four, his son told a reporter, I’ve never really been a long horizon type person.

These days, most of John’s cousins were invested in political and philanthropic activities, while he toiled away at a boring nine-to-five in the Manhattan district attorney’s office. When, at twenty-six, Representative Patrick Kennedy was asked if he wanted to one day be President, he didn’t even hesitate. Yes. Absolutely, he said. Another cousin, Joe—Ethel’s eldest son—had started a company, Citizens Energy, to provide oil to the underprivileged. He abandoned that enterprise in 1986 to become a Massachusetts congressman (in the same seat John’s father had held from 1947 to 1953). At that time, Joe turned Citizens over to his brother Michael, who was now doing an admirable job with it. Yet another cousin, Kathleen—Ethel’s oldest—also had her eye on politics; she would become lieutenant governor of Maryland in just a year’s time. Her brother Bobby was an environmental activist and an attorney for Hudson Riverkeeper, dedicated to keeping the Hudson River and its shores clean. Many of John’s other relatives of his generation were charting similar paths.

It wasn’t as if John had never fulfilled the family’s long-standing mandate to be of service, noted Senator George Smathers in a 1999 interview; he was one of JFK’s best friends in the Senate and had been an usher at his wedding to Jackie. I remember that when he was fifteen, he and his cousin Tim [Shriver] went to Guatemala to assist earthquake survivors. When he was in his twenties, he worked on a program to help the disabled in New York City. I know he dabbled in an organization to assist in youth drug prevention. Nothing really stuck, though.

More recently, John had founded Reaching Up, a foundation he designed specifically to care for the mentally ill. He was also on the board of the Robin Hood Foundation, a retinue founded by Wall Street millionaires devoted to programs benefiting New York’s poor children. Though he was obviously trying—and a lot of people thought he was doing well with philanthropy—John still couldn’t shake the feeling that he wasn’t making much of an impression, at least not like many of his Kennedy cousins. You are what you do, his aunt Ethel had told him. "But how do you compete with those people? John later asked, speaking of Ethel’s children, as well as Ted’s and Eunice’s, in particular. It didn’t help that some of his cousins rubbed his nose in their overachieving ways. During a particularly virulent argument, one cousin who had always been competitive with John said, When I stack my value to society against yours, I win. I win by a lot, and you know it." John never got over the criticism.

John’s sister, Caroline, had a more clear-eyed vision of how she wanted things to unfold in her life. She sailed through school with mostly good grades, traveled a great deal, and had a lot of friends. Though she became a lawyer, she wasn’t practicing because she’d decided to focus on her husband and children. Like her mother, she was devoted to family. She also had a wide range of charities in which she was passionately involved. Whereas John felt he was just killing time in the DA’s office, his sister’s days were full of scheduled activity. John would sometimes complain to her that he’d been at a crossroads for most of his life, trying to determine the best way forward in terms of keeping up with the other Kennedys. This would always cause Caroline to lose patience with him. She couldn’t have cared less about keeping up with the other Kennedys.

The Kennedy siblings were different in other ways, too, such as in the way they handled the burden of their family responsibility to legacy, as evidenced by a wide-ranging discussion between brother and sister about funeral preparation the night their mother died.

Caroline said she didn’t want any mention of Aristotle Onassis during the service, Yusha Auchincloss would recall in a 1999 interview. "But John didn’t want to ignore Onassis’s place in their mother’s life. ‘After all, she’s Jacqueline Kennedy Onassis,’ he said. ‘How can we not mention that she was married to Ari?’ After Ari’s death back in 1975, Jackie could have dropped the ‘Onassis’ surname and reverted to ‘Kennedy’ or even ‘Bouvier.’ She didn’t. Caroline’s mind was made up about it, though. In terms of Jackie’s place in American history, she reasoned, she should only be remembered as a former First Lady who’d been married to an assassinated President. The Onassis years were a private matter for family, Caroline said, not something my stepsister ever meant to be played out in public. It was only the press who had made it such a spectacle."

John didn’t agree. He reasoned that even though Jackie knew full well when she married Ari that the world would not approve, she’d had the courage of her convictions to do so anyway. In his mind, marrying Ari had been a brave move, one that should be lauded during the funeral service, not ignored. He felt that Caroline’s targeting of the press in the Onassis matter was disingenuous; the real truth was that she simply didn’t want the man’s name mentioned because she just hadn’t liked him.

While John had gotten along with the Greek tycoon, Caroline never warmed to him. He could never replace her father, not that he ever tried. However, John took Ari at his word when he said he wasn’t trying to be his father; he just wanted to take him to baseball games or out on his yacht where he would teach him how to fish. John didn’t have high expectations of Ari. He could see, even as a kid, that what mattered most was that Ari made his mother happy, or as Jackie once put it, Aristotle Onassis rescued me at a time when my life was engulfed in shadows.

What should I call your mom when I meet her? John’s friends would often ask him. Call her ‘Mrs. Onassis,’ unless she tells you otherwise would be his quick answer. In the matter of Onassis’s placement at Jackie’s service, though, Caroline would prevail. The Greek tycoon’s name would not be mentioned, nor would any of his relatives or friends who knew Jackie be invited to the funeral.

Then there was a debate about Jackie’s sister, Lee. Should she be allowed to speak? The two hadn’t been close in recent years; it was only in the final months of Jackie’s life that Lee emerged as a supportive presence. Caroline was angry at her aunt and didn’t want her to have a significant place in the service. John was torn; Lee’s son, Anthony, was not only his cousin but his best friend. He pled his case but, in the end, Caroline again had her way.

That conversation was followed by another having to do with the scope of the funeral. Ted Kennedy wanted it to be big and ceremonial for public consumption, with cameras in the church. John agreed. However, Caroline was against it. She wanted the service to be more private, no cameras. Again, she would have her way; Jackie’s service would end up being a private one at St. Ignatius Loyola Church, where she had been baptized and confirmed, and with no cameras, just a public address system to the crowds gathered on the streets in front of the church.

In the end, Caroline had won all three debates. This dynamic had always prevailed in the siblings’ relationship, though. One of the problems John faced was that as forthcoming as he was with others, he was reticent about expressing himself to his own sister. He never wanted to argue with her. Jackie had raised them to be there for each other, always. John loved his older sibling, trusted her implicitly, and simply didn’t want to fight with her. Of course, this sometimes meant that he would bottle up his feelings, which would sometimes result in those infamous flashes of anger toward others.

At the end of the day, as always, Caroline had her way with the arrangements, John later complained to his friend John Perry Barlow. Barlow was a former Grateful Dead lyricist who went on to become an internet rights pioneer and human rights activist. He and John had been close friends for years, ever since Jackie made arrangements for her son to be a wrangler on Bar Cross Ranch near Pinedale, Wyoming (where Barlow grew up), for a couple of months back when John was seventeen.

Why don’t you, for once in your life, stand up to your sister? Barlow asked. No, that’s not how we are, John said. She’s usually right, anyway, he added.

But it’s not good, John, Barlow told him. She walks all over you. Sounding defeated, John said he understood that but it’s just the way it had always been with them. Well, change it, Barlow exclaimed. John said he would, one day soon.

A few days later, following the funeral Mass, members of the family and a few close friends boarded a chartered plane at LaGuardia that would also take Jackie’s body to Washington, D.C. She was then to be laid to rest next to John Fitzgerald Kennedy, the thirty-fifth President of the United States, at Arlington National Cemetery. Fewer than a hundred people would then gather on a hillside before the same eternal flame that was first lit years earlier by Jackie in honor of her martyred husband.

Guess we’re orphans now, me and Caroline, John told Gustavo Paredes after Jackie was buried. Gustavo, who was five years older than John, had spent most of his youth and then early adult life in the company of the Kennedys. He was the son of Providencia Paredes—Provi—from the Dominican Republic, Jackie’s assistant at the White House who then transitioned into a new role as a close friend of the former First Lady’s. When he was about seven, Gustavo used to have such admiration for President Kennedy’s well-tailored suits. "Sure wish I could have a suit like that, he would tell him. Jack would promise that once he was out of office, he would give him a couple suits as souvenirs by which to remember his administration. Shortly after he made that vow, second grader Gustavo was being picked up by Secret Service men at his Catholic school for his own protection because the President had been shot. He then attended JFK’s funeral. Now, all these years later, he was at John’s side as Jack’s widow was also being laid to rest. You get to this place in life, and you think, now what? John told him. Who are you? Are you a grown-up now? At some point, all of us face this existential crisis, don’t we?"

Gustavo wasn’t sure how to respond. He said that the John Kennedy he knew just lived his life in the moment and avoids questions to which there are no easy answers.

John nodded. But maybe it’s time I challenged myself, he said, all this according to Gustavo’s memory as the two men walked back to their car after the service. Gustavo agreed with John, but also reminded him that he had his whole life ahead of him. Just don’t forget what your mother used to say, he cautioned him: ‘Whatever you do, don’t end up being some old Kennedy living on a hill with lots of money and lots of people kissing your ass, none of whom expect much from you because…’

‘… they know you don’t expect much of yourself,’ John said, finishing the thought with a smile.

---

BY JUNE 1994, a month had passed since the the death of John’s mother. Sorry, man, he apologized as he slid his lanky frame into a restaurant booth at one of his favorite Italian restaurants, Ecco in Tribeca. He was meeting his childhood friend Stephen Styles-Cooper, with whom he had gone to school.

John was exactly fifteen minutes late, just as he was for almost every appointment, which, for him, happened to be right on time. It was his employment of what he called the system. He’d learned a long time ago that he could never arrive in a restaurant before a friend because, if so, he would have to sit alone and field questions from strangers, sign autographs, and be for them who they so desperately wanted him to be. If he showed up late, at least there would probably be someone at the table waiting for him who could then run interference. If his dinner companion was later than he was, he’d just have to circle the block until that person showed up. Then he’d give that friend hell. You can’t be late, he’d insist. Because if you are, it totally screws with the system.

After John settled in, the two friends quickly ordered their food. It was difficult for Stephen to ignore the stares of other diners as the room began to buzz. During a wide-ranging conversation typical of friends catching up, the subject turned to John’s love life.

For almost six years, John had been dating the actress Daryl Hannah. Something about it never seemed right, though. Was it because Jackie never approved of her? She tried, and at some points along the way actually got along with her, but John knew that his mother always had reservations. John had measured most of the women in his life by Jackie’s opinion of them. If his mother approved, as she did of a girlfriend named Christina Haag, John would decide he wasn’t sure how he felt about her. He usually ended up pulling away from her. However, if Jackie disapproved, as she did of Daryl Hannah, John became even more attached. Was it because he didn’t want to give his mother the satisfaction of being right?

Daryl should have been over long ago, John admitted. He said she was still attached to her previous boyfriend, the musician Jackson Browne, and that he was tired of trying to figure out why. Besides, a new woman had just entered the picture, someone his mother had not had the chance to meet. John probably would have introduced them had Jackie not suddenly become so ill. Maybe it was a blessing in disguise, though. Without his mother’s view, any relationship that unfolded with this newcomer would have to either succeed or fail strictly on its own merits, and perhaps that was a good thing.

Her name is Carolyn, John told Stephen Styles-Cooper as they got ready to leave the restaurant. And what about Daryl? Stephen wondered. John shook his head. To every thing there is a season, I guess, he said as he threw twenty bucks onto the table. "Ahhh, yes, Ecclesiastes, Stephen concluded with a nod. Um … no, John said, grinning. The Byrds."

The Girl for John

Carolyn Jean Bessette-Kennedy was born on January 7, 1966, in White Plains, New York, the youngest child of William and Ann Bessette. She had two siblings, twins Lauren and Lisa, born in 1964. William, an architectural engineer, and Ann, who was a schoolteacher and later an administrator in the Chappaqua public school system, divorced around 1970. After Ann married Richard Freeman, an orthopedic surgeon with three children of his own, the blended family relocated to Old Greenwich, Connecticut. Carolyn never really reconciled her parents’ divorce and, some of her relatives have said, on a deep level felt abandoned by her natural father even though they did have a relationship. He wasn’t there for her in the way she would have liked, and she often questioned her mother as to why the couple made the decision to divorce, said her good friend from Old Greenwich Stewart Price. It troubled her. She was raised Roman Catholic and used to say she would never divorce. ‘It just will never happen,’ she told me. ‘I have these weird daddy issues,’ she said, ‘and I would never want to do that to a child of my own.’

Carolyn attended Juniper Hill Elementary School and then St. Mary’s High School before going off to Boston University School of Education, from which she graduated in 1988. Sometimes she seemed a little standoffish, that is until you got to know her, said Stewart Price. Then, when you were someone she trusted, she was affectionate, the kind of woman who would touch you when she talked to you, connected to you. She was a real hugger, and not just quick hugs but the best, warmest kind.

Carolyn was tall, about five foot ten, thin, and held herself like a high-fashion model, with golden-blond hair—her stylist once described her natural color as pale brown—an aquiline nose, and wide-set, cornflower-blue eyes under artfully designed brows. She was stunning. While she considered becoming a model, she ultimately found herself working as a saleswoman at the Calvin Klein store in Boston’s Chestnut Hill Mall and then as a rep handling Klein’s celebrity clientele.

During her seven years at Calvin Klein, Carolyn would rise up the ranks from celebrity sales to director of PR at the flagship store in Manhattan and the head of show production, putting in long hours casting models for shows and scouting nightclubs for new faces. That’s when she met John, at a function hosted by Calvin Klein.

She was exactly the kind of girl I imagined would date someone like John Kennedy Jr.—and she intimidated the hell out of me, recalled his personal assistant, RoseMarie Terenzio, of Carolyn in her book, Fairy Tale Interrupted. Wearing a Calvin Klein pencil skirt, a white T-shirt, stiletto heels, and blue nail polish, she looked like a model, effortlessly perfect in an unstudied yet elegant outfit. When John introduced us, I felt like I’d gained ten pounds and shrunk three inches. But after he left her with me in the reception area, I could tell Carolyn was different from the typical gorgeous girls you see around Manhattan. She wasn’t trying too hard. She wasn’t trying at all.

The downloading of John-John history, as one of Carolyn’s friends put it (though he would never refer to himself that way) happened quickly and effortlessly. Over a series of what he later described as intense dates, John opened up to Carolyn about a wide range of personal subjects. For instance, he talked about starting his private schooling at St. David’s on Manhattan’s East Side before being transferred to Collegiate for third grade. He explained that his mother thought the second school was more understanding of youngsters who couldn’t catch on. He confided that he had trouble because of his ADD, which, combined with dyslexia, compromised his learning ability to the point where Jackie often found herself pleading with his instructors for leniency. He also opened up about the trauma of dealing with the assassination of a father he barely remembered.

It was only because of his loving and understanding mother, he said, that his youth hadn’t just spun completely out of control, especially after his uncle was also murdered. For instance, she did everything possible to make sure an overprotective Secret Service didn’t interfere with his being able to have as normal a childhood as possible. It was amazing, John noted, that Jackie had been able to devote herself to him and his sister, considering her own personal problems. He talked about the PTSD—post-traumatic stress disorder—she experienced after having witnessed the killing of her husband and the courage she then displayed in finding ways to live life on her own terms. He said he felt the least he could do in return was to be, as he put it, a good son and try to live up to her expectations even if he didn’t always agree with them. In particular, he hated letting her down with his continuing bad grades. As a young man, he would fail the bar exam twice, which would be especially difficult on his mother given the attention these failures generated in the media.

Carolyn had a mixed reaction to John. First of all, her heart went out to him. He’d obviously not had an easy life, and the way he opened up to her about it endeared him to her. Having her feel sorry for him wasn’t his intention, though, and she sensed as much. She realized that his only goal was to have her know him as something more than President Kennedy’s son, arguably the most famous Kennedy of his generation. His life was what it was, the good and the bad. It was an extraordinary story, epic really, with iconic characters as diverse as Bobby Kennedy and Aristotle Onassis in major roles. She knew he hoped that in explaining some of it to her she might understand him on a level deeper than what she’d maybe heard or read about in the past. Carolyn was also impressed by John’s love for his mother. To have such respect for the woman who raised him spoke well of him; Carolyn felt the same way about her own mother, who’d always been there for her without fail.

Also adding to Carolyn’s overall impression of John was—as much as she tried to hide it—her complete disbelief that the John F. Kennedy Jr. was not only sitting across from her, but that he was being so vulnerable with her. She was quite conscious of the fact that this person had been a pop culture icon since the age of three when he stood next to his grieving mother and sister and stole America’s heart by saluting his father’s coffin. She’d been hearing about him most of her life, and especially after she got to New York, where he was a constant fixture, a local as well as national celebrity. Many women had been swept away by this gorgeous man, and, though she wouldn’t have wanted him to know it during their first dates, certainly Carolyn was now one of them. She later said, "He’s staggeringly handsome. I don’t know how else to put it. Who looks like that? She once described getting to know John as an out of body experience. In other words, she could barely believe he was even in her presence. I kept having to say, ‘Snap out of it, he’s just a guy,’ is how she put it to her friend Carole DiFalco (who would soon marry John’s cousin Anthony Radziwill in August 1994). The first time he kissed her, she would later recall, was a real revelation. He leaned in and caressed her lips with his own. When he finally pulled away, she stared at him with wonderment. She was only able to manage two words: Holy shit."

The fascination was reciprocal. John found it easy to be candid with Carolyn for one reason: he sensed from the outset that she was someone who’d be special to him for many years to come. Maybe it was love at first sight, or at least it felt that way to John. It was as if he’d known her all his life, as if they already had a history together. You know how you always hear about meeting a girl and knowing instantly that she’s the one, and you think, nah … that kind of instant connection doesn’t happen in real life, he told Gustavo Paredes after meeting Carolyn. Well, that happened to me. Another of his friends, Rob Littell, noted, She had an aura that pulled him in. So taken was he by her, he couldn’t wait for the Kennedys to meet her. This was unusual. ‘We’re sort of a tribe,’ he would say. ‘I don’t want to scare a woman off.’

John knew, though, the greatest challenge for Carolyn would probably be as it had been for many others he’d dated: meeting the senior women of the family. It had always been tough for his girlfriends to meet Jackie for the first time, of course. Now that she was gone, meeting Ethel Kennedy was the loaded proposition.

John told Carolyn that Ethel was the family’s matriarch now that his grandmother Rose was so infirm. It wasn’t Eunice, Jean, or Pat—the other senior women in the immediate family—or Joan, who had married into it by taking Ted as her husband. Because of the power of her personality and her utter devotion to all the Kennedys, if someone wanted to fit in with the family these days, that person would have to work hard to please one woman and one woman alone: Bobby’s widow, Ethel.

The Matriarch

Ethel Skakel Kennedy was born on April 11, 1928, to Ann Brannack and George Skakel in Chicago, Illinois, the sixth child of seven: three sons and four daughters. The entrepreneurial George was a self-made man. Though he didn’t finish grade school, he became wealthy thanks to his business, Great Lakes Carbon. His company eventually became a multibillion-dollar, high-tech manufacturer of graphite and carbon used as substitutes for coal in domestic heating. The family lived in an enormous mansion, waited on hand and foot by a legion of dutiful maids, butlers, and other household functionaries. The Skakels always treated their household employees with old-world formality, a manner Ethel would one day adopt with her own staff at her homes in Virginia and Massachusetts.

Ethel’s mother, Ann, was a real character. Called Big Ann because she weighed more than 250 pounds, she was deeply religious and strict but also had a wild sense of humor. She was notoriously cheap, and clever about it, too. For instance, she had business cards printed up that identified her in different ways—Ann B. Skakel’s Hardware & Tools or Ann B. Skakel’s Garage Parts and Accessories—and would extract from her purse the one that might get a shopkeeper to believe she had her own business and deserved some sort of discount on whatever goods she desired. Saving a buck really made her day.

The Skakels moved to New York when Ethel was about about four. An avid sports enthusiast, she was always adventurous and fun-loving. She attended the all-girls Greenwich Academy in Connecticut as well as the Convent of the Sacred Heart and then the parochial Manhattanville College in New York. She wasn’t a good student and, always one to flaunt the rules, was often in trouble. Or as she jokingly once told her daughter Rory, I wasn’t a deep thinker, like I am now. Her son Christopher put it this way: Mummy is a Skakel, and as a Skakel she inherited a healthy disregard for authority in all its forms.

When her friend from Manhattanville College Jean Kennedy introduced Ethel to her older brother Robert Kennedy—Bobby—in the winter of their freshman year of 1945, the two seemed perfect for each other: he appreciated her sense of humor; she was attracted to his intelligence and his desire to be of service to others, which, as she would learn, was how he’d been raised. Somehow, though, Bobby ended up dating Ethel’s older sister Pat—and he did so for two years. With a smile, Ethel now refers to this period in her life as a dark time. Finally, Bobby saw the light, and he and Ethel had a three-year courtship and then married on June 17, 1950, at St. Mary’s Roman Catholic Church in Greenwich. She and Bobby went on to have eleven children: Kathleen, Joseph, Robert Jr., David, Courtney, Michael, Kerry, Christopher, Max, Douglas, and, after Bobby’s death, Rory, whom she was expecting when he was assassinated. She was pregnant an astonishing ninety-nine months over roughly a seventeen-year period.

In the spring of 1957, Ethel purchased a new family home, the sprawling estate known as Hickory Hill at 1147 Chain Bridge Road in McLean, Virginia. Bobby Kennedy Jr. recalled, The antebellum estate was formerly home to Robert E. Lee’s father, ‘Light Horse Harry’ Lee, a Revolutionary War hero, and later to General George McClellan, the Union Army’s supreme commander during the early years of the Civil War. Supreme Court Justice Robert H. Jackson, who presided over the trials of the Nazis at Nuremberg, later acquired the house and sold it to Uncle Jack and Jackie. When they opted for a smaller Georgetown residence, my mother bought Hickory Hill. Note that Bobby is clear that Ethel purchased the property, not she and Bobby. In fact, she bought the estate with her own money from her family’s great wealth.

In years to come, Ethel would remain focused on raising her family and on Bobby’s ascension to political power, while clinging to devout Roman Catholic values. Meanwhile, she had big dreams of her own, especially after her brother-in-law Jack was elected President and Bobby became his attorney general (the youngest, at thirty-five, since 1814). When Bobby decided to run for President in 1968, Ethel felt sure she was destined for the White House, following Jackie Kennedy as First Lady. Most people agreed she would be a different kind of First Lady than her sister-in-law but also a very good one. Those dreams were dashed when Bobby was assassinated by Sirhan Sirhan in June 1968.

At the time of Bobby’s death, Ethel was just forty and pregnant with Rory. The country was touched by her tremendous courage as she tried to put her life back together and raise her children as the single mother of a very private public family. The only way to deal with eleven children, with their friends, and with their first cousins is with structure, discipline, routine, and organization, said her son Christopher. And Mummy brought structure, discipline, routine, and organization to every aspect of our lives.

She sent the older kids to places and countries around the world so we could understand and live with different cultures, added Kerry. So Kathleen went and lived on an Indian reservation. Joe lived with a family in Spain. Bobby lived with a group of people in Africa. Courtney and I worked on a farm in Utah. David worked with Cesar Chavez. Some people took a somewhat dimmer view of Ethel’s sending the children away, though. They felt Ethel really just wanted distance from them. After all, when they were around, things