The Cinderella Kennedy

Illustration by André Carrilho

Caroline Kennedy said a perky hello to Kevin Sheekey, Mayor Bloomberg’s political strategist, who was standing next to me. She nodded, silently, in my direction, and kept moving, while her husband smiled, extended his hand, and offered a jovial “Ed Schlossberg!”

We were all in a Queens park on a freezing, crystalline November morning for the renaming of the Triborough Bridge in honor of Caroline’s uncle Bobby. Maybe she remembered me—I’d interviewed her five years ago for a story about her work raising money for the city’s public schools—but that’s doubtful, and totally unnecessary, given Kennedy’s radar for reporters, finely tuned by a lifetime of being hounded by and avoiding them. Her taste for the spotlight in general was demonstrated by her choice of seats for the ceremony: She and Ed climbed to the next-to-last row of the far-right corner of the bleachers, about as far as they could get from the podium and still be on the same stage with Kennedy’s 100 cousins, nieces, nephews, and in-laws.

Kennedy applauded the speeches enthusiastically, but she didn’t speak; even though she was the second biggest star onstage, after Bill Clinton, this was a day for the RFK wing of the family. So Kennedy’s modesty was both characteristic and honorable. Still, she stood out: In the sea of dark business suits and proper, somber overcoats, she wore a bright-maroon knit ski hat, pulled low over her ears. She looked endearingly dorky. And she looked to be just about the last person in the State of New York who would volunteer to be a United States senator.

Exactly two weeks later, Bobby Kennedy Jr. got a big surprise. On December 3, the day after he had removed his own name from the Senate sweepstakes and floated Caroline’s to a Times reporter, Bobby went over to his cousin’s apartment on Park Avenue to nudge her a bit more. His mission appeared to be a long shot, but it turned out Caroline was already seriously interested. So serious that that night she called Governor David Paterson to tell him so.

The leaking of the Caroline-Paterson conversation two days later seemed a highly calculated trial balloon and set off a media frenzy, to the annoyance of some in the governor’s camp. Paterson has been beset by an escalating series of crises—the $15 billion state-budget chasm, the bizarre power struggle in the State Senate—that he sometimes appears helpless to resolve. The growing circus surrounding Hillary Clinton’s soon-to-be-vacant seat was beginning to look like one more process the governor couldn’t control, so Paterson has routinely refused to publicly discuss which possible contenders he’s spoken with. He felt he had no choice, however, when it came to the Kennedy chatter. “When Bobby Kennedy is calling reporters and going on the record, David would have seemed really defensive to just say, ‘I’m not talking about it at all,’ ” a Paterson associate says. (Bobby Kennedy denies initiating any calls to the media and says that he only answered reporters’ questions.)

Paterson isn’t likely to hold the very public lobbying effort against Caroline—that is, when he finally does begin calculating his Senate selection. “When he says he hasn’t focused on the Senate seat yet, that’s the truth,” an associate says. But that day is coming, soon. What, ultimately, will the governor care about most when it comes to picking Hillary’s replacement? Publicly, Paterson has emphasized a high-minded approach. Those who know him bluntly acknowledge that Paterson will of course think about the seat pragmatically—even though he will come nowhere near Blagojevich-level venality. “What will be important to him are the history of the seat, the woman thing, the opportunity for upstate, and the importance of somebody who can deliver for New York,” a Democratic operative says. “But also somebody who can actually run a campaign for themselves in 2010 and again in 2012. You can’t ignore that David Paterson is an inherently political guy. He’s not going to ignore the fact that this is a mountainous task you’re asking someone to take on, in terms of the amount of money you have to raise.”

Andrew Cuomo fits, but not because there’s any realistic chance of him challenging Paterson one-on-one in a 2010 Democratic gubernatorial primary. Cuomo’s credentials are that he’s run statewide before; has enviable name recognition and fund-raising experience; and, as attorney general, has retooled his pugnacious image: Now he’s a fighter-for-the-common-man. Kirsten Gillibrand checks several of the boxes, too, including good relations with Chuck Schumer. But the second-term congresswoman from upstate Hudson is untested in the big arena. Kennedy, of course, has the star power to attract sizable contributions, and she’s schmoozed donors before. But her two-year fund-raising effort for the city’s public schools, while producing a welcome $65 million, was part-time and small beer compared with what it takes to run statewide. And she hasn’t demonstrated any talent for the extroverted glad-handing requisite for a political campaign. New York’s career pols, who have their own well-honed sense of entitlement, are already taking angry potshots, led by Queens congressman Gary Ackerman, who ridiculed Kennedy as being just as qualified for the Senate as J.Lo.

Why, after a lifetime of privacy and relative normalcy, would Caroline Kennedy want to jump with both feet into the family business? In one respect, Kennedy’s flirtation with the Senate isn’t totally out of character: Relatives say she’s always been politically astute and competitive, just quietly, and that she greatly enjoyed her campaign trips for Barack Obama. It’s also true that Caroline’s curiosity has been piqued by the decline of her Uncle Teddy, but not in the way conventional wisdom has rendered it. Yes, the man who became the closest thing to a father figure after JFK’s death is nearing the end of his days in office, but Caroline isn’t interested in a Senate seat because she thinks it is a family heirloom. She genuinely, cornily, wants to advance the ideas the family cares about, and she knows better than most that only so much can be accomplished through symbolism. An actual seat at the bargaining table is still more valuable. This is also the way in which her choice makes the most sense for New York, and elevates her candidacy beyond her thin résumé and mere sentiment: Kennedy’s Democratic patrician values and her power-elite connections are not negligible assets. And of course, there are all the sword-in-the-stone connotations, the political magic (fantasy?) that a new Kennedy in the Senate conjures.

But the plot has some weaknesses. Perhaps it’s still possible to be a different kind of senator, in the Paul Simon–Pat Moynihan mold: a legislator-intellectual, above and in the fray at the same time, who leaves office with his good name intact. Caroline Kennedy’s desire to deploy her brains and her celebrity on a grander stage, primarily in service of public education, is admirable. But even if her motives are pure, and even if she’s able to navigate the swamp of modern politics, there’d be something sad about seeing her subjected to all the grubby gossiping and money-hustling that the job inevitably entails. We’d be gaining a senator, possibly even a good one. But we’d be losing an icon.


The Cinderella Kennedy