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The Zany Adventures of (Senator) Caroline Kennedy

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Caroline Kennedy leaves Syracuse City Hall during her upstate swing on December 17.  

Isay quickly assembled a packed schedule of calls and meetings for Kennedy with the state’s power brokers—some of them obvious, many not. Kennedy’s team expected her to go through a rough baptism by press. But in any conventional campaign, the candidate can fight back with ads, speeches, listening tours. This time, her aides say, Kennedy was required to defer to Paterson’s shifting limits on what she and her competitors could do or say in pursuit of the Senate opening.

Kennedy’s camp debated how to maneuver. “Once Hillary Clinton says she’s gonna resign her seat, there’s a campaign for this job. There just is,” says one adviser who favored playing hardball from the beginning. “So as soon as Caroline expresses interest, she has ten people who are trying to kill her. Two of which are the Cuomos and the Clintons [still resentful of Kennedy’s endorsement of Obama], the two most vicious political organizations in the country in our lifetime. She can do one of two things: She can sit back and do nothing and just let people beat the shit out of her. Or get out there, in a subdued fashion. But you also play the game behind the scenes.”

Kevin Sheekey, Mayor Bloomberg’s political aide, was calling labor leaders, making the case for Kennedy as the front-runner and as the one choice with hooks to Obama. Conditioned by the cut-and-thrust of a standard campaign, though, Sheekey overdid the pitch, saying Paterson would be guilty of “political malpractice” if the governor chose anyone but Caroline Kennedy. Sheekey was thought to be Bloomberg’s elbows in this campaign, which didn’t help matters, given Bloomberg’s tense relationship with the governor. “Paterson told Kerry Kennedy that he would have appointed Caroline already, except that every time he gets ready to, Bloomberg or Sheekey makes one of these aggressive, nearly belligerent statements,” said a Kennedy intimate in early January.

Bloomberg and Sheekey turned down the volume, but the actions of Kennedy’s many surrogates had a more subtly corrosive effect: They fed into the image of Kennedy—recessive by nature and restrained by Paterson’s non-campaign rules—as a creature completely created by other actors. With all the clashing agendas, Kennedy was becoming a bystander in her own campaign.

With Kennedy out of sight after the brief and unhappy upstate tour, questions kept pouring in. Trying to fend off the calls for information yet play by Paterson’s rules, Kennedy’s campaign dug the hole even deeper, issuing vague written responses to policy questions. As her candidacy foundered heading into the holidays, some of Kennedy’s advisers raged privately at Paterson. With stories about Kennedy’s wealth and spotty voting record dropping daily, her team decided that the risk of angering Paterson paled compared with the continuing damage from staying silent. “You couldn’t put Paterson in a place where he couldn’t pick her,” one of her aides says, “and he couldn’t pick her if we had three weeks of, ‘She’s Sarah Palin, she’s hiding, what is she hiding?’ ”

Round one of Kennedy’s media blitz went well—a December 26 Associated Press interview followed by an appearance on NY1’s Inside City Hall. But the mood changed quickly the next morning. Kennedy walked into a reserved back room of the Lenox Hill Grill, on Lexington near 78th, and sat down with two reporters from the Times. She’d earnestly studied briefing papers on issues like immigration, the economy, education, and gay rights, and she’d been tutored by Ranny Cooper, a PR executive and former aide to Ted Kennedy. Instead, she was greeted with a series of questions on her motivations for wanting to be a senator—and soon became rattled and annoyed, her responses riddled with you knows and ums, which the Times, devastatingly, included in a transcript of the interview. Some of Kennedy’s relatives blamed Isay for not being tougher in readying Caroline for the interview.

Kennedy also smacked headlong into a newly emboldened Times city staff. “We’ve grown a pair of balls, and I’m amazingly proud of the paper,” says a Times reporter. “The turning point was the editorial page’s rolling over for Bloomberg on erasing term limits. The reaction from the reporters and editors is that we’re the last line of defense—we’ve got to hold the line.” Not for or against any particular politician, that is, but to stand up for small-d democracy. After inflating her candidacy by making her simple declaration of interest in the job the lead story of the day, they compensated by hitting her hard.

One larger problem, though, was Kennedy’s lifelong avoidance of anything resembling a personal question—and her delusion that politics is about issues. She had never come to terms with the fact that the reason she was in line for the job was that she was, well, a Kennedy, and that people loved Kennedys, what they ate, where they lived, what they felt about their triumphs and tragedies. Whereas she’d based her entire life on witholding such information. “There’s stuff that she needs to be able to deflect, stuff that no other candidate would get,” a friend says. “This is New York, and they’re gonna come after her. It’s not just going to be about abortion and Indian Point power plant. It’s gonna be all the things that nobody has dared to ask her when she was protected by the patina of being above all this.”

Though Kennedy made hundreds of calls to county leaders and willingly schlepped to outer-borough meetings, she was a novice in the networking aspect of politics. She’s long been a prolific e-mailer, sharing everything from YouTube clips to comments on world events with a circle of friends. Kennedy is less comfortable with the phone. “She’s never had to stay in touch with a lot of people,” says one relative. “She leaves her cell at home.”

Through the entire roller coaster, say her aides, Paterson encouraged Kennedy. He would have liked her rollout to go more smoothly, of course. The Reverend Al Sharpton, one of Paterson’s close friends, was seeing the same positive signs. “She’s got a tremendous amount of support and empathy in the black community,” Sharpton said in early January, “because she appeared to have stood up to the Clintons for Obama at a critical time.” Paterson certainly cared about Kennedy’s support in his home base. Right?


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