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

by J. Randy Taraborrelli

  A few years earlier, Caroline had taken a position in the New York City Department of Education as executive director of the Office for Strategic Partnerships, dedicated to raising money for education from private sectors. She’d been given the job by Joel Klein, the head of the department. During her time there, she’d begun to see how capable she was in influencing people and in convincing them to be committed to matters she felt important to children as well as to teachers. After a couple of years of feeling successful in that venue, she left that position to become a board member of the Fund for Public Schools. Throughout this time, she enjoyed working within the educational system; it stimulated her curiosity. She wondered if it was possible for her to extend her reach.

  Of course, Caroline had always wanted to be of service. She’d been hearing her entire life that she had a responsibility to do so, and to a degree she felt she was satisfying the family mandate with her work in the education system and also by educating the public with her books. However, that wasn’t the same as being a public servant. The more she thought of it, the more she realized that yes, this was what she wanted—needed—to do. “I want something more from my life,” she told one trusted friend, “and I just can’t pretend anymore that this isn’t true.”

  It was shortly after these discussions with her cousins that Caroline began to campaign for Barack Obama. “She’d actually started watching his campaign in the fall of 2007, long before she threw her support behind him,” said her friend Gary Ginsberg, who was an executive vice president of News Corporation, “and I could sense even then that she’d started to think of it in more practical terms for herself.

  “She campaigned in places like Orlando and Indiana and Ohio, getting her hands dirty, doing real retail politics, and I think she was surprised by how much she enjoyed it. I think she found the whole political process more satisfying and engaging than she would have thought.”

  In stumping for Obama, Caroline came to a fuller realization that her opinions actually mattered. Her endorsement of the senator from Illinois had been vital to his campaign, and she knew it. Oprah Winfrey has this humorous story: “I was at Tina Turner’s house over Christmas [2007], talking to her about Barack Obama. She paid no attention to me. But when Caroline Kennedy came out for Barack Obama, I got a phone call from Tina. She said, ‘Oprah, I heard everything you said to me. But if Caroline says it—and because of what her whole family represents—then I’m for Barack, too.’ I thought, ‘I was sitting at your dinner table … and you don’t even know Caroline.’”

  David Axelrod, Obama’s political strategist at the time, recalls Caroline as being “the purest brand in American public life.” Of American royalty and untainted by scandal, she was greatly admired, and it felt good. A big problem for her, though, at least when it came to her public image, was that, despite everything she had going for her, Caroline could often appear somewhat cold and off-putting when being interviewed. For instance, after her speech at the Democratic National Convention, she seemed barely able to tolerate Katie Couric’s on-camera questioning, especially when she started referencing Caroline’s famous family. Treading cautiously, Katie asked Caroline if she felt “any pressure” given the prominence of the Kennedy dynasty. “I know you’re very shy…” Katie began.

  Oddly, Caroline took umbrage. “Are you going to ask me if I’m going to run for office, by any chance?” she asked, suddenly appearing combative. “Is that where you’re going with this question?”

  Katie was surprised at Caroline’s touchiness: “Well, what do you think?”

  Caroline shook her head in annoyance. “Well, you know, it’s incredible,” she said. “You’re just so … creative.”

  Undaunted, Katie pushed forward. “Maybe you have a renewed interest in going into political office,” she offered, “since, I mean, you are already in public service. Because of Teddy’s illness and because of the era sort of coming to a close, I’m just wondering if you feel any kind of responsibility.”

  One had to wonder why this line of questioning so bothered Caroline. Or, maybe more important, why wasn’t she able to camouflage her annoyance. Instead, Caroline just completely shut down. Staring straight ahead, she said she didn’t “make a lot of long-range plans” and left it there.

  It wasn’t a good moment. If anything, it showed that Hillary Clinton maybe wasn’t the only one who was “prickly.”

  What Kennedys Do

  Everyone knew that Caroline was very different from her late brother, John. In many ways, she was just the opposite. She was an introvert who kept her own counsel, whereas John was always gregarious and outgoing. Because of these maybe superficial differences in their personalities, everyone believed John to be the sibling destined for public office, especially after he began publishing George. Now that he was gone, things were different, or at least they were for Caroline. She’d never been sure of her suitability as a politician—she once asked her grandmother Rose, “That’s not really me? Is it?” To which Rose responded, “You bet it is.” Caroline began to believe that she should be the one to throw her hat into the ring. She set her sights high, too: She wanted Hillary Clinton’s seat in the Senate representing New York, a position that would be open for two years before the next election. New York’s governor, David Paterson, would have to appoint Clinton’s successor in the interim, and his decision would be influenced by not only whoever was the most qualified for the job but also by who Paterson’s constituency felt was the best fit. Caroline wanted it to be her.

  Caroline had only a few vague ideas about policy having to do with education. She knew she would have her work cut out for her. After all, she had no experience in the political arena. However, what she did have going for her was her natural curiosity about things, her eagerness to learn, her desire to serve, and, of course, her name. She was a woman who could get anyone on the phone, anytime; she had Obama on speed dial. Certainly, she could use her influence to do a lot for New York. Even if she was rusty on the specifics of New York government, she was smart and well-read and could learn. She’d also become a pretty good speaker in front of an audience; she could definitely command a crowd.

  Of course, if she was going to go for Clinton’s seat, Caroline would need Ted’s support. She feared that he would discourage her from pursuing it. If so, she knew she would be deflated; she had so much respect for him. Still, she needed to know. Therefore, she and Ed arranged to meet with him and Vicki at their home on the Cape, where he was staying while undergoing treatment. She was surprised at his reaction. Yes, he said, it was a good idea. She should do it. “I think you have what it takes,” he told her.

  Ed was surprised. He had fully expected Ted to veto Caroline’s idea, and maybe he’d even hoped Ted’s disapproval would be the end of it. He was actually perplexed by Caroline’s sudden interest in politics. He wasn’t sure she was made for it. He attempted to reason it out with her, warning her about the invasive nature of the game. After all, she was someone who could barely sit through an interview with Ladies’ Home Journal without feeling attacked. Had she considered the kinds of probing questions she’d be asked by reporters if she was a candidate? They would certainly be a lot more difficult to address than whether she let her kids eat sugar. While Caroline listened to his concerns, she disagreed. That was fine with Ed; once he was sure that this was what she wanted, he would join Ted in supporting her.

  The truth is that Caroline had caught Ted at his most vulnerable. After all, he was dying. He was also taking stock.

  “The way Ted had been raised by his parents was to always consider the future of the Kennedy dynasty and to seek out the answer to the question: Who’s next in line?” observed Dun Gifford, who had been his legislative assistant. “After all, there had been a Kennedy in the Senate for half a century. Ted thought it important that a Kennedy keep his seat after he was gone. He’d thought Patrick could go all the way to the Senate just by virtue of the fact that he’d been such a credible Congressman. Though he could sometimes
be critical of Pat, he had to admit that his boy was tenacious and a good fighter.”

  Lately, though, Patrick had been hinting about possibly quitting politics altogether. It had been tough on him, all those years in Congress. Also, despite his time in rehab, he was still misusing many drugs, mostly Adderall, which he called his “primary drug of abuse.” He was now looking for a real solution to his life, a way to wrestle his bipolar disorder into submission. Recently, Vicki had even been working behind the scenes to keep Patrick away from his father because she feared if Ted knew how bad off he was, it would be too debilitating to him during an already difficult time. This strategy drove a wedge between son and stepmother. “You don’t get to tell me when and if I can see my own father,” Patrick told her in front of family members. He raised his voice at her, which she clearly didn’t appreciate. She looked at him with hard eyes. “Oh really?’ she said. “I beg to differ, Pat,” she continued. “I think I do get to do that, and I think I will do that.” She further said that her primary concern was for her husband, and that until she knew for sure that Patrick had his problems under control, she would closely monitor Ted’s exposure to him, “for both your sakes.”

  “What is wrong with you?” he demanded to know.

  “Funny,” she answered, “I was just going to ask you that same question.”

  Patrick got it, though. He recognized that his problems were serious and he understood that Vicki was right to try to protect his father from them. Though his relationship with her would always be complex, deep down—as he would admit years later—he knew that she was almost always right in the tough decisions he’d all but forced her to make because of his illness.

  Though Vicki tried to protect him, Ted knew what was going on; he knew his son well and could intuit that he was still in trouble. No, he finally decided. Even if Patrick didn’t quit politics, he was clearly not cut out for it anymore. He needed a break—and Ted even told Patrick as much. He didn’t want to die and have his son think he didn’t care about his well-being. While the two were boating on Nantucket Sound, Ted leaned in so Patrick could hear him over the din and said, “You know, you don’t have to do this if you don’t want to. I don’t want you to feel forced to continue in public office. You should do what makes you happy.”

  Patrick would recall being so stunned by Ted’s advice, he didn’t even know how to respond. He had spent his entire life trying to get his father’s approval, which was why he’d gone into government in the first place. It had been hard. He barely got through some days, and lately, his addictions seemed more out of control than ever. Ted’s words came as a great relief to Patrick; he really did want out. Now it would just be a matter of time.

  With Patrick out of the running, who was left? Teddy Jr. wasn’t a politician at the time, and neither was Kara. There were a couple of Shrivers who maybe could go far, but as much as he loved them, Ted never felt that the Shrivers were taken seriously when it came to running for office. Ted had more faith in Bobby’s kids. Bobby Jr., though, was an environmentalist, so he was out of the political game. Joe was always a good bet, and probably he would have been able to reenter politics. After all, who even remembered who Sheila Rauch was after all these years? However, Joe was completely content at Citizens Energy, far from the scrutiny of public life. Kathleen? She didn’t want anything to do with it anymore, either. She was happy with her own lot just as it was, working in tandem with several charities. There were a few others in the family who sometimes spoke of running, but none seriously. Some of the younger fourth generation, the grandkids of the old guard, like Joe’s son Joe III, had lately been expressing interest; maybe one day he would be a contender for some office. However, for now, it looked like Patrick’s quitting would mean there would be no Kennedy in office for the first time in fifty years. That proposition was something Ted simply couldn’t accept.

  Another persistent narrative about the Kennedys of the younger generation was that they had done little to nothing to change the world. It was always about Jack and Bobby whenever historians examined the storied history of the family and its impact on the world, and to a lesser extent, Ted. “But how could any person compare with JFK’s achievements of dealing with the Cuban Missile Crisis or even his stunning failure of the Bay of Pigs?” asked Dun Gifford. “What could ever be compared to the way Bobby took on the underworld as attorney general? The history-making achievements of him and Jack and even Ted could never be matched by their kids unless they found themselves in similar positions of government…”

  Ted, especially since 1980, had achieved even more than his brothers in terms of governmental accomplishments—of course, he had had more time to do so—but even he remained in their shadow. It certainly wasn’t true, though, that the next generation had done nothing. It was just a way for critics to be reductive of them. “Think of Patrick’s many years in Congress alone and of all the legislation for which he was responsible,” pointed out Dun Gifford. “Outside of government, look at what Bobby Jr. had done for the environment, and consider everything Joe had done for the underprivileged with Citizens Energy. Most of the generation, in fact, was made up of political activists of one sort or another. I mean, look at what the Shrivers had all achieved. Still, the perception that the next generation lacked accomplishment was persistent, and I know for a fact that Ted absolutely hated it.”

  Ted wanted to prove the skeptics wrong. Caroline joining him in the Senate? That just might do it. Therefore, when she came to him with her proposition, he was intrigued. If anything, this was a bit of a Hail Mary strategy on the Senator’s part, though, and he had to have known it. After all, this was the same man who felt that Hillary wasn’t cut out for President because of her personality. He had to have known his niece’s chances were slim, if just based on how she acted in the public eye alone. It was rather like expecting the ever-so-private Jackie to wake up one day and suddenly decide she was going to be a politician.

  One of Ted’s aides has this story to tell:

  Ted, Vicki, Ethel, and a few other Kennedys, including Kathleen, along with some of their acolytes, were at the Cape together after Caroline’s visit. They were talking about her news. Bobby thought yes, Caroline should go for it, as did Patrick and Teddy. Joe wasn’t so sure; he’d been burned by politics in the past and wondered if his cousin could handle it.

  Ethel thought it was a terrible idea. Caroline was not a politician—“not yet, anyway,” Ethel said. The fact that Ethel would challenge Ted at this time when she was so worried about his health and scared to lose him said a lot about how strongly she felt about the matter at hand. She said she felt it was his responsibility to talk some sense into Caroline, that he owed it to her late father to protect her. Invoking the name of the slain President was a dramatic move for Ethel; she never did so lightly. However, she seemed truly worried that Caroline would take Ted’s encouragement too far and would actually run for office. “You know, that was once Bobby’s seat,” Ethel added. It was a sacred trust, she reminded everyone; Caroline was not ready for it.

  Kathleen was perplexed. “You were so encouraging of me when I wanted to run for office back in ’86,” she noted. “Why are you not of Caroline?” Ethel answered, “Isn’t it obvious?” Of course, Ethel was referencing the stark difference in the cousins’ personalities. Maybe she was the more outgoing, Kathleen agreed, but she also warned her mother not to underestimate Caroline. She noted her recent electrifying performance at the Obama rally. Not only that, Caroline was a constitutional scholar and had authored some good books. She’d also raised millions for the New York City school system. Kathleen had long been involved in the scholastic system; after becoming the first Kennedy to ever lose an election when she lost that Congressional seat back in 1986, she took a post in the state’s department of education. She knew it was hard work. “She definitely knows how to reach people,” Kathleen said of Caroline. “Besides, Mummy, she’s very smart and very curious about things.”

  Ethel wasn’t convinced.
“I’m very smart and I’m very curious about things,” she countered. “You think I should run for the Senate, too? Fine, then,” she said. “Sign me up. Let’s see how far I get.” Her sarcasm belied her cold, calculating objectivity. After all, Ethel had been immersed in politics as long as Ted. She felt that the position of senator held immense power and that Caroline simply wasn’t ready for it. Of course Ethel wanted her niece to serve. However, she felt Caroline would be better off serving in the state legislature first, and then thinking about the Senate. Starting out slow, she said, made a lot more sense. “Don’t forget about what happened to Max,” she said. There was silence for a moment; no one could ever forget what had happened to Max.

  Matthew Maxwell Taylor Kennedy—Max—is the ninth of Ethel’s children and a graduate of Harvard and of the University of Virginia Law School; he was named after Maxwell Taylor, chairman of the Joint Chiefs under JFK. Back in 2001, he had his own foray into politics when he decided to run for a Massachusetts Congressional seat. A former assistant district attorney of Philadelphia, he’d long been a human rights and environmental activist, making many philanthropic missions through Central and Latin America. As well as writing the bestselling book Make Gentle the Life of This World: The Vision of Robert F. Kennedy, Max also worked on the campaigns of his uncle Teddy, Michael Dukakis, Al Gore, and John Kerry. He would travel a rough road, though, once he began campaigning for himself. He seemed ill-prepared to give speeches, his demeanor reminding some of his cousin Patrick before he put the work into becoming a good orator. Poor responses to Max’s public persona chipped away at his self-confidence until, finally, he just dropped out of the race. Though she was proud of him for at least trying, Ethel felt her son hadn’t really thought his candidacy through all the way. Now Ethel felt that Caroline was doing the same thing.