Caroline Kennedy's Next Move

Caroline Kennedy hasn’t lost her freshly acquired taste for life in the limelight. She may have taken some hard knocks—and absorbed no little embarrassment—during her disastrous campaign this year to be appointed to Hillary Clinton’s vacated Senate seat. But this once-publicity-shy East Side princess is still behaving like a candidate for something. The only question seems to be: What is Caroline running for?

An ambassadorship to the Vatican, as has been speculated in recent British press reports, seems very unlikely. But if Kennedy said the word, her close friend President Barack Obama would no doubt find her a plum assignment. Certainly a high-profile job during a third term of Mayor Mike Bloomberg, who actively touted her for the U.S. Senate, is hers for the asking. Elective office? Even that is a possibility. Despite speculation in the latest Vanity Fair, it’s improbable that Caroline, a lifelong New Yorker, would replace her uncle, Massachusetts Sen. Ted Kennedy, if his battle with brain cancer were to shorten his term. Yet, she’s giving every sign that she wants a starring role.

Even some of her blood relatives barely recognize her new incarnation and remain deeply mystified by her apparent fondness for the fray.

The last surviving member of JFK’s nuclear family—and, as such, the torch-bearer in chief for the Kennedy Mystique—has been very visibly making the rounds in recent weeks: First, there was a show-stealing cameo appearance during Bloomberg’s annual skit at New York’s Inner Circle Dinner for political and media heavyweights. Then she spoke at a widely covered city-government event promoting volunteerism, with the mayor at her side. And last Thursday she delivered the keynote address at a fundraising dinner for a senior center in Brooklyn. It was lost on nobody that Kennedy showed up for the dinner—hosted by Brooklyn Assemblyman Vito Lopez, the powerful chairman of the largest local Democratic Party organization in the United States—accompanied by her political consultant.

“She definitely has a future, if you’re judging by the support she gets,” says Lopez , who was among the first public officials to endorse Kennedy’s Senate quest after she told New York’s mercurial governor, David Paterson, that she was interested in the job. “When they introduced her last Thursday,” Lopez says, “everyone not only clapped but they stood up and clapped. Does that mean something to her? I don’t know. I can’t read her that well. But she’s very comfortable—she’s a very regular person. She was extremely impressive at the event. She talked to different types of people—she was tolerant and personable with people asking her to pose for photos—both politicians and just regular people. I was worried it might have been overbearing, but she must have posed for hundreds of photos.”

At least as telling was Kennedy’s surprising star turn last month at the Inner Circle Dinner, during a Little Mermaid parody in which she portrayed a possible candidate to succeed “Bloomfish,” played by Bloomberg, as mayor of an underwater city called NY Sea. Kennedy announced she’d run “only if I can give lots of interviews.” Bloomberg told her that the press “is looking forward to covering your administration”—as the theme from Jaws sounded. The black-tie crowd at the New York Hilton roared with delight. As an exercise in instant rehabilitation, Kennedy’s performance ranked with the one Nancy Reagan pulled off with her famously self-mocking rendition of Second Hand Rose at the 1982 Washington Gridiron Dinner, which effectively defused the first lady’s image as an out-of-touch Marie Antoinette.

This, of course, is a wildly different Caroline Kennedy than then spotlight-shunning, self-protective celebrity I used to encounter at various charity events when I was writing a gossip column in Washington and New York. Indeed, even some of her blood relatives barely recognize this new incarnation and remain deeply mystified by her apparent fondness for the fray.

Yet Caroline’s friends point out that at age 51, she is understandably blossoming as a public figure now that daughters Rose and Tatiana are off to college and son Jack is in high school, while her husband, Edwin Schlossberg, is pursuing his independent interests as an egg-headed exhibit designer. For Kennedy, working on yet another collection of favorite poems—which is due to be published a year from now—is not enough.

“She is clearly completely dedicated to some form of public service, but what exactly that will be is very hard to predict,” says one friend. “I know this sounds incredibly corny, but she grew up in a family where public service is a duty.” This friend says Kennedy had always preferred toiling quietly in the background—raising money for the New York City public schools, for instance—until she discovered, much to her surprise, that she actually enjoyed campaigning around the country for Barack Obama (for whom she ended up vetting vice-presidential picks). “She would have been a very different kind of senator than her uncle Ted—maybe not the most charismatic and back-slapping, but very effective.”

But what about the bitter aftertaste of the Senate debacle? “Honestly, it doesn’t faze her—she’s a tough nut,” says the friend.

Another friend, New York City School Chancellor Joel Klein, agrees. “I think she has enormous reservoirs of inner strength—this is a woman who has been through a tremendous amount… I wasn’t entirely surprised [by the abortive Senate episode]. I think the Obama campaign whetted her appetite.” During a recent weekend visit with Kennedy and her husband, Klein discussed Kennedy’s future with her. “She’s in very good shape. She’s obviously thinking about what she wants to do as she moves into the next phase of her life.”

Lloyd Grove is a frequent contributor to New York magazine and was a contributing editor for Condé Nast Portfolio.He wrote a gossip column for the New York Daily News from 2003 to 2006. Prior to that, he wrote the Reliable Source column for the Washington Post, where he spent 23 years covering politics, the media, and other subjects.