The Kennedy Heirs: John, Caroline, and the New Generation

by J. Randy Taraborrelli

  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 he
r 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 y
oungest, 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 weren’t exactly peaceful. The boys, especially, would feel the brunt of her frustration and, at times, rage, at the way things had turned out for her. She would often become physically abusive, slapping or hitting them.

  Sometimes she would walk up to one of her offspring and, standing within just inches of the child, raise her hands and clap loudly three times in order to get their attention, chastise them, or demand silence. “She’s like some kind of crazy person,” is how one of her sons once put it. “Who does that?” It was one thing to do it to a child, but Ethel would sometimes do the same thing to the adults in her life! Ethel’s brother Jim Skakel once explained that she got the habit from their mother, Ann. “She did the same thing,” he said, “but it was usually three claps followed by two pretty good slaps right across the face.”