Caroline Kennedy's Shaky Quest for Camelot II

In the annals of political cluelessness, it would be hard to top the moment on Dec. 26 when NY1 television anchor Dominic Carter asked Caroline Kennedy whether "there is a sense of entitlement" that makes her think she should be picked to fill Hillary Clinton's soon-to-be-vacant Senate seat. "In my family in particular, I think," she replied, "there was a sense we have to work twice as hard."

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For most people, the salient biographical fact about Caroline Kennedy — let alone the reason to seriously consider her candidacy for the Senate — is her last name. Being a Kennedy has not exactly proved to be an obstacle to success over the past century of American life. You would think that someone with the Kennedy political DNA would have a better understanding of her relative head start in life, but thus far, the only thing Caroline Kennedy has established is that she hasn't inherited the Kennedy charisma gene. (See pictures of J.F.K.'s presidential campaign.)

Her high-powered team of handlers is making sure she goes through the rituals, lunching with Al Sharpton in Harlem and calling on officials upstate. Behind the scenes, her Uncle Ted is making no secret of his desire to see his niece join him in the Senate and carry on the Camelot legacy. But Caroline's naturally reserved and cautious personality ("bookish," said one who has worked with her) is not an easy fit in a place where politics is a blood sport. Though her uncle Robert once held the very Senate seat that Kennedy now eyes, her own campaign experience has consisted primarily of giving speeches before adulatory audiences, most recently on behalf of Barack Obama. Acquaintances say they find it hard to picture Kennedy putting up with constant badgering by the Manhattan tabs and TV outlets, or immersing herself in the intricacies of the Northeast Interstate Dairy Compact.

On policy questions, her answers have run from cautious to vague, except for her declared support for gay marriage. She does not appear to have given much thought to the specifics of what she would try to accomplish once in office — even on education, which presumably is her area of expertise, given the six years she spent as a volunteer raising money for the New York City public school system. In a contentious interview with the New York Times, she refused to engage in one of the hottest education debates of the day, declining to say whether she supported abolishing tenure for teachers and giving them merit pay instead.

Initial reports of Kennedy's interest in elective office — albeit through the route of being appointed to it — focused on her star power and drew comparisons with Hillary Clinton. But the reviews of her unsteady performance since then have critics likening her more to Sarah Palin. Kennedy, 51, never fails to mention her family's history of public service, but she has also had to explain why she failed to even vote in a number of contested elections in recent years, including one for the Senate seat that she now wants. And she is hardly a compelling speaker: according to a count by the British Daily Telegraph, she used the phrase "you know" 142 times in that interview with the New York Times. In a column headlined "Say Goodnight, Caroline," Michael Goodwin of the New York Daily News wrote that her audition thus far is becoming "a cringe-inducing experience, as painful to watch as it must be to endure." (Kennedy, who is a contributor to TIME, declined through a spokesman to be interviewed for this article.)

And yet, thanks to the unique circumstances that surround the vacant Senate seat, Kennedy still looks to be the leading contender for the job. Governor David Paterson has said he will not announce his pick until after Clinton has been confirmed as Obama's Secretary of State, likely in the next few weeks. Whoever gets the nod will have to start campaigning and raising money right away for two elections over the next four years: a special contest to fill the seat in 2010, followed by another in 2012, when the term expires. By some projections, it may take as much as $100 million to win those back-to-back statewide races — an amount that would be a big challenge for a lesser-known name to raise. It also helps that Kennedy was one of the few political figures in the state to support Obama against Clinton in the Democratic presidential primary, which she could argue would give her an edge in getting things done (and raising money) in Washington. Obama says Kennedy "has become one of my dearest friends."

What the entire exercise is testing is how well the old magic can still work for a new generation of Kennedys, who have had mixed success in venturing into politics. Some years back, I asked Rhode Island Congressman Patrick Kennedy, who is Ted's son, how things have changed. The invincibility simply is no longer there, he told me. "Disabuse yourself of the notion that there's this machine out there that just kind of materializes when you say, 'Yes — go!' Growing up watching politics as my cousins and I did, you had this warped sense that that's all you needed to do. That was the way it was for my father's generation." The Kennedy name was Caroline's birthright, but it may be that a seat in the U.S. Senate is something she has to earn on her own.

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