A year earlier, in 2007, Caroline Kennedy turned fifty. Throughout the next year, she often confided to friends and family members that she felt a little lost. Of course, a sense of not being fulfilled, of worrying that one is missing out on a true calling, is not unusual for a person of her age; a midlife crisis is how it might best be described. Caroline’s children were now teenagers; she didn’t feel they needed her as much. Her marriage to Ed was solid; they were happy together, and she would never complain about him. They had a shared history, which they cherished; they’d been through some sad times together and had survived them. She wondered, though, according to what she said in rare moments of openness, what would happen when the kids all went to college and just she and Ed remained at home? Would they be able to connect? He had his work and was invigorated by it, whereas Caroline just had what she called “the blahs” and felt that she needed … something. She kept telling her kids to hold fast to their dreams, but the question remained: What were hers?
This isn’t to say that Caroline wasn’t busy; she was still involved in a number of fulfilling charities. She was also still writing books; she’d written about the Bill of Rights and the right to privacy and had also compiled a series of anthologies, such as The Best Loved Poems of Jacqueline Kennedy Onassis as well as A Family of Poems: My Favorite Poetry for Children and A Patriot’s Handbook, which included patriotic poems and speeches. She’d also edited Profiles in Courage of Our Time, a collection of essays about those who’d won the JFK Library’s Profiles in Courage award. The books were bestsellers—but still, she had to admit she was bored. She had a yearning for something new.
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.”