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

by J. Randy Taraborrelli

  Ethel Kennedy’s present wealth is estimated at “just” $50 million, but a lot of that is old Skakel money she was finally able to access in the 2000s and not from the Chicago sale. Both she and Ted, whose estate was also estimated at $50 million, decided not to profit from the sale of the Merchandise Mart, trickling any of their parts down to their children.

  Ethel’s son Christopher Kennedy is quite wealthy after having run the Merchandise Mart as its president and later a top executive, even after the sale; he gave up the job in 2011. He remains one of the overseers of the family’s investments. Today, thanks in part to his twenty-five years with the Mart, he is worth at least $50 million. When Christopher ran unsuccessfully in the Illinois gubernatorial primary in 2018, he would not reveal his net worth.

  As for the fourth generation—the children of the third—most are also quite wealthy, again from the Merchandise Mart sale. For instance, Congressman Joe Kennedy III—son of Joe II—has an estate valued at at least $40 million; he’s by far one of the richest of all congressmen. Even Conor Kennedy—Bobby Kennedy Jr.’s son—is worth at least $10 million, and he hasn’t done a thing to earn it other than to just hire the best accountants to invest what has trickled down to him from the Chicago sale.

  Of course, John and Caroline did well when Jackie died and would never have to worry about money. Still, Caroline, like all her cousins, profited from the 1998 sale. Today her proceeds from the sale—including what was invested for her and not just what she received in liquidity—combined with what she already had and invested from her mom (and then, later, from her brother) makes her, by far, the wealthiest Kennedy of her third generation. In 2018, her wealth was estimated at about $250 million.

  Once, John Perry Barlow asked John about the big 1998 money deal, which John had begun to refer to as “the Big Chicago Fire Sale.” Barlow said, “That’s gotta be a lot of money for you, John.” John responded, “Well, you know, I don’t necessarily worry about money,” to which Barlow quipped, “Spoken like a man with a lot of money.” John smiled and said, “Yeah, well, you got me there.”

  Carolyn’s Emotional Affair

  “I love you,” John told Carolyn one day in front of friends. The two had just had a quick argument while having cocktails with friends at MercBar in Soho. No one seems to remember what was at issue; it was just a flash of anger between them, regrettable in that it had occurred in front of people. Embarrassed, John was now trying to make amends. “I said I love you,” he repeated to Carolyn. There was no response from her. Instead, she turned to someone else at the table and, picking up the menu, said, “Hmmm … I wonder what the specials are tonight.” John shook his head angrily.

  After Michael’s recent death and in light of Anthony’s ongoing battle for life, things had become a lot tenser between John and Carolyn. When the two showed up for the family’s 1998 Fourth of July celebration at the compound, they seemed to be barely speaking.

  Carolyn felt that John had changed. She said, “It’s as if the light in his eyes has dimmed.” Others in his life had to agree; he seemed edgy and irritable, and they attributed it to the ongoing anxiety over Anthony. “I felt John was becoming detached from his emotions,” said John Perry Barlow. “It was as if he was afraid to feel, or maybe he had forgotten how to feel after spending so many years suppressing emotions while trying to be strong in the face of Anthony’s cancer.”

  It could be said that Carolyn already had enough on her plate just getting through the day. When she thought about the future with John, she admitted to feeling trapped. Was divorce even an option? She’d never gotten over her parents’ divorce and had always said she’d never end a marriage of her own. As well as that conviction, she also couldn’t help but consider the public’s opinion of her. “People already hate me,” she lamented. “What will they think of me if I divorce John F. Kennedy Jr.? I won’t even be able to leave the house. I just want a normal life,” she complained. Some felt she should’ve thought about that before she married a Kennedy. “But I’m tired of being made to feel like I’m broken,” she also concluded—and that made her friends feel sorry for ever having had any judgment about her at all.

  A big mistake Carolyn made, her friends felt, was in quitting her job when she started dating John. She had loved her work at Calvin Klein and had been there for a number of years. She abandoned it in order to see what else might be out there for her. However, once she became consumed by her relationship with John, she never pursued other opportunities. There’s no doubt, looking back, that a woman as ambitious as Carolyn would have benefited from having something else in her life other than her husband. Though she tried to stay busy with charity work, it wasn’t enough to give her a sense of fulfillment. “I know now that I need a purpose,” she told one friend. “I don’t know what that is, though. I feel lost.”

  Unfortunately, John’s own work wasn’t going well. Advertising was down at George because sales had plummeted. There seemed no way to save it. He was at the office late almost every night trying to come up with a plan. Carolyn had supported his venture, wanting this success for him. Lately, though, she seemed to have lost all interest. “I certainly didn’t think it was going to become his whole world,” she explained to Carole Radziwill. “It’s like the clock is ticking and we’re running out of time to be happy.”

  One George executive recalls Carolyn calling John at the office and trying to get into a fight with him about his long hours there. John had just about had it with her. “I don’t want to hear anything else from you unless it’s ‘I love you and I understand,’” he said, shutting her down and then hanging up on her.

  Considering that John seemed so emotionally unavailable to her at this time, maybe it wasn’t that surprising that Carolyn felt the need to connect with someone else, a person who might hear her problems and offer empathy and advice. In a best-case scenario, she would have continued to turn to her husband and hope to find a better way for them to communicate. Or she could have gone into therapy and utilized a psychiatrist to try to work through her marital issues. Instead, she turned to a male friend, someone she’d known from her days at Calvin Klein. The two had reconnected in the spring of 1998 after running into each other at a benefit dinner. Since he had known her before John, she felt he could better understand the changes she’d undergone in her life since becoming a Kennedy.

  The two began to meet regularly for coffee. Years later, he would remember, “We ended up on this complicated journey having to do with her confiding in me because she felt I was a safe place for her. I wanted to be there for her. She was a wonderful person. Something about it felt wrong, though. We both knew it.”

  One night, when John was out of town, Carolyn and her friend had dinner together, which he would later say “felt a little bit like a date.” Afterward, she went up to his apartment and they continued a conversation having to do with John not wanting her to go on his trip with him. She was crying, he was consoling her, and somehow they ended up kissing. It was brief, he remembered, but consensual. Then she pulled away and said, “No. What am I doing? I can’t be here right now,” and quickly gathered her things and left.

  The next day, Carolyn called and said the kiss could never happen again. She was extremely regretful. She wanted to continue the friendship but said that it could be nothing more. She also said she felt she had to tell John about the kiss. “I told her it was a big mistake,” recalled her friend. “However, she said she couldn’t lie to her husband. ‘That’s just not who I want to be in this marriage,’ she said. But it was nothing, I told her. Why cause trouble? She was adamant about it, though. It started to feel to me like she really wanted to blow things up between them and that she was maybe using me to do that.”

  Two days later, Carolyn’s friend was jolted out of a sound sleep at about two in the morning by the sound of his intercom buzzer. When he went to the speaker and asked who it was, the voice on the other end said it was a police officer who needed emergency access to the building. Against hi
s better judgment, he let the person in. Minutes later there was a pounding on his door. He opened the door to find John Kennedy on the other side, his face twisted in anger. Before he had a chance to say a single word, John swung a haymaker at him, clocking him on the side of his head and causing him to crumple into a heap on the floor. According to him, John then looked down and hollered at him, “Stay away from my wife! Do you hear me? Stay away from my goddamn wife.” And then he left. The entire incident—from the time the door was opened to the time John ducked out—took maybe thirty seconds.

  “The next day, Carolyn called, full of apologies,” he recalled. “I told her we were finished, that I didn’t want our friendship to continue. She agreed, said she was sorry, and hung up. I didn’t feel like it was over, though. I was right. A couple weeks later, she called me and we started up again with the sharing of her life. We were close to having sex and we both knew it. There was something wrong about it, yet there was also something exciting about it. It was hard to know what to make of it, actually.”

  John’s Political Musings

  Because she already wanted more of his time, no doubt Carolyn would have also been concerned about John’s latest curiosity: he was contemplating running for the United States Senate in 2000, for Daniel Patrick Moynihan’s seat.

  “I think I’m ready to make the leap,” John told his close friend Gary Ginsberg. To test the waters, Ginsberg met with Republican strategist Roger Ailes, who at the time was building Fox News, in order to evaluate John’s viability as a candidate. Though decidedly on the other side of the aisle, Ailes was someone who always had his finger on the pulse of current-day politics and, Ginsberg felt, could be trusted to venture an informed opinion—and then to keep that opinion to himself and not go to the press with it. The two had lunch to discuss John’s possible candidacy, which in the end Ailes felt was feasible. When Gary reported this good news back to John, he was heartened by Roger’s enthusiasm. It was in line with what other political strategists and reporters on the beat had told him.

  “Most people felt sure that John could win that Senate seat should he go for it, and that there was no reason he shouldn’t at least try,” said family attorney Benedict F. Fitzgerald Jr. “I think a concern of John’s, though, was that Hillary Clinton was making overtures for that seat after she and her husband were out of office. John didn’t want to run against her.”

  Besides the fact that the Clintons and the Kennedys were close, John was sure he wouldn’t win against Hillary. Not only that, he felt bad for her considering what was going on at the time with the Monica Lewinsky scandal. However, John’s cousin Kathleen urged him to not allow too many side issues to influence his decisions going forward in politics. “There will always be one thing or another,” she told him, according to one account, “and you have to take some things into consideration, but not everything.” In November 1998, Kathleen would win another term as lieutenant governor of Maryland, so John had a lot of respect and appreciation for her point of view. “I’m wishy-washy, I know,” he told her. “I need to be more like you.” She countered with “No. Be more like you, John.”

  Key in the equation as to whether John should run for office would be, of course, his wife’s attitude about it. How would Carolyn ever be able to adjust to life as a politician’s wife? She was still having trouble reconciling things as just the wife of someone famous. Add politics to John’s celebrity and there was no telling how it might impact her life.

  Still, there was a lot of optimism about John’s future. “There was never any doubt in my mind that John planned to run for the U.S. Senate in the next decade,” said his friend the noted historian Douglas Brinkley. Or … maybe something else? “John had talked a lot about possibly running for governor in 2002,” confirmed RoseMarie Terenzio, “and I think he would have ended up doing that. It came up a lot between us and between him and others. Something was going to happen for John in government. We just didn’t know yet what that would be.”

  Could Therapy Be the Answer?

  By March 1999, Carolyn’s emotional infidelity with her male friend had been going on for about ten months. While John thought it had ended with his visit to the man’s apartment, it hadn’t; Caroline had continued with it and kept it from John. He wasn’t so checked out that he didn’t have his suspicions, though. One night, Carolyn ducked out, saying she had something to do. When John followed her to her confidant’s apartment, he was crushed and felt betrayed. He was also furious. He sat outside the building for two hours, fuming. He later told one friend that when Carolyn emerged, he grabbed her hard by the arm, threw her into a cab, and got her home, where they really had it out. He then spent the next couple of nights at the Stanhope Hotel.

  On some level, John actually felt it would have been better if Carolyn had been physically intimate with the trespasser in their marriage. At least then maybe he wouldn’t have felt the relationship was so important to her. Under those circumstances, he might have considered it an insignificant one- or two-night stand. It would have hurt, but perhaps it could have been worked out. This kind of infidelity, though—which he called “emotional foreplay”—was worse in John’s mind in that he felt his wife was breaking a marital trust and sharing with someone else that which she should have been sharing with him. He was crushed by it, especially when Carolyn became defensive and said she felt she deserved the relationship. If she couldn’t have candor with John about her feelings, she felt she had a right to seek it out elsewhere. Since she had continued the friendship after saying it had ended, now John wasn’t so sure Carolyn hadn’t also crossed the line sexually. If she had lied to him once, why not twice? “Of course, his pride kicked in, too,” recalled one of John’s former coworkers at George. “After all, he was freakin’ JFK Jr. He could have the pick of the litter if he needed ‘companionship,’ and he’d managed to resist it. So who was she to cheat on him?

  “He told me he was going to go to the guy’s place and this time really pulverize him. I begged him not to, telling him that he was lucky the man hadn’t gone to the press with that first punch. I told him I felt he and Carolyn needed to go into couple’s counseling and work this thing out, that Carolyn’s affair of the heart wasn’t the real issue, that it was a symptom of a bigger problem. I know others had been telling John the same thing.”

  After he cooled off, John realized his friends were probably right; there was a reason Carolyn had turned to someone else, and he had to own it; it was as much his fault as it was hers. His mandate had always been that he wouldn’t have the same kind of marriage as many of his cousins, and now it would appear that he was headed down that exact same road. He felt he needed to stop and reevaluate things before they got out of hand.

  By the middle of April, John and Carolyn were in couple’s counseling.

  On May 1, the Kennedys attended the White House Correspondents’ Dinner; certainly one photograph of the couple taken that night with Carolyn—sporting a long Gaultier clamshell necklace—happily nestled on John’s lap is, today, an enduring image of this time in their lives. “They never looked more content and in love than they did that evening,” recalled White House reporter Helen Thomas. “I thought, My God, this is Jack and Jackie all over again, isn’t it? They were so compelling; you actually couldn’t take your eyes off them. The way photographers swarmed them, it really reminded me of the old days, the so-called Camelot days.”

  It was definitely true that when the couple was in public, they seemed to be incredibly content with each other. Looking back on photographs like the ones taken at the Correspondents’ Dinner begs the question of how Carolyn was able to pull it off. Was it all an act? While it’s easy to paint complex relationships with a wide brushstroke, it’s usually not wise. The Kennedys certainly had their personal problems, but that didn’t preclude them from also having moments of great happiness, especially after they started marriage counseling. Based on what we now know about her, Carolyn wasn’t a good actress. She wore her heart on her sleeve. It’s
a safe bet that when we saw her looking pleased with John, in that moment she’d found a measure of contentment. Conversely, when we saw her looking sad or discontented, those emotions were authentic as well.

  A Woman’s Intuition

  “You are enough.” Those had been Ethel Kennedy’s words to Carolyn Bessette-Kennedy more than three years earlier in March 1996 after the infamous argument in Central Park. Since that time, Carolyn and Ethel had gotten closer; Carolyn would often call the Kennedy matriarch for words of encouragement. However, an interesting twist had recently occurred in the way Carolyn interpreted Ethel’s advice. Rather than imbue her with courage to socialize with the other Kennedys at the compound, it gave her the resolve she needed to decline invitations there. It emboldened her, in other words, to make her own decisions relating to whether she wanted to attend family gatherings. Sometimes, she would be up for them and she would go. John would be happy. Other times, she would decline. John would then be unhappy. That was fine with Carolyn as long as she wasn’t being forced to do something she didn’t want to do. Ethel actually approved. It wasn’t exactly the takeaway she had expected from her advice, but it was still good, she said, that Carolyn wasn’t being cowed by anyone and that she was living her life her own way.

  In the summer of 1999, John and Carolyn were invited to the wedding of Ethel’s daughter Rory. By this time, Rory—the daughter Ethel gave birth to in 1968 after Bobby was killed—was a Brown University graduate who was beginning a career as a documentarian; in a few years’ time she would direct and coproduce the Emmy-nominated series Pandemic: Facing AIDS. She was marrying a guy named Mark Bailey. The wedding was to take place at the compound, of course.