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The Zany Adventures of (Senator) Caroline Kennedy

In which the most private of persons decides to go public, only to learn that mother always knows best.


Caroline Kennedy was missing. For about five hours last Wednesday, as her wildly unlikely bid to become a U.S. senator was on the brink of collapse, one of the city’s most famous women disappeared. At 3 p.m., Kennedy had set off a political and media cataclysm with a single, out-of-the-blue phone call to Governor David Paterson from her Park Avenue apartment.

Seven weeks earlier, she’d upended a lifetime of privacy along with the race to replace Hillary Clinton by calling Paterson to declare her interest. Kennedy’s candidacy had been a weird ride ever since, but she’d bounced back from early mistakes. Now, the day after the inauguration of her friend President Barack Obama, her aides were discussing plans for the triumphal press conference.

Until Kennedy called Paterson to say she was pulling out. “Personal reasons” had emerged that made it impossible for her to accept the Senate seat. She was sorry, but she was done. Paterson told her to think it over and call him back. And then she vanished.

As the news erupted on the New York Post’s website; as Kennedy’s political aides frantically called and e-mailed her; as her stunned friends wondered whether this was some kind of dirty trick from one of her rivals to force Kennedy from the contest: Silence. Was Caroline Kennedy holed up at home wrestling with her options? Was she arguing with her husband, Ed Schlossberg? Was she having some kind of breakdown, caught between the warring voices of her parents—her father, the embodiment of the Kennedy political hunger, and her mother, who’d raised Caroline to fear the costs of that hunger? Had she realized senators can’t spend August on Martha’s Vineyard?

She resurfaced about 8 p.m. A conference call was arranged with close friends and political advisers. Kennedy wavered—she wasn’t sure what to do. And she wouldn’t specify what the “personal reasons” might be. Finally, just after midnight, the definitive word was sent to the media by e-mail.

And Governor Paterson? The man who had turned the search for a new New York senator into the defining circus of his rookie year in office and was now in danger of having it escalate into a bizarre embarrassment? His behavior was nearly as peculiar: At one of the most important moments of his political life, he decided to … go to bed. Paterson didn’t learn about Kennedy’s decision until the next morning.

The appointment was destined to be a mess—how could it not be? The cast of characters involved in choosing a new junior senator for New York included a lapsed priest, three of the country’s most bare-knuckled political dynasties, and an imperious mayor. Add to that a $15 billion budget deficit and a tainted plate of sushi. And start the whole crazy chain of dominoes with a hooker.

Yet in two months politics in New York devolved from dysfunctional to chaotic, tarnishing every major player involved. And sometimes it seemed that David Paterson wanted it exactly that way. His style of governance, a dizzy mix of ingratiation and trickeration, has turned what could have been a moment of triumph—a powerful new ally in the Senate, a relationship with President Obama—into a slapstick fiasco, a fitting sequel to the way Paterson got the job in the first place. Politics is often a contest of half-truths, where the winner is the best bullshitter. But thanks to Paterson and a cast of dozens, the fight to become the next senator became instead a world-class festival of lies.

For Caroline Kennedy, it was a bizarre rise and fall, an entire political career telescoped into seven weeks. Kennedy seemed to have an almost Victorian idea of rectitude and an extreme squeamishness about personal revelation, lessons about propriety drilled into her by her mother. But for all the care she’d devoted to maintaining a zone of privacy around herself, she ended up as sullied as any lifelong politician—with many of her wounds self-inflicted. From an elegant if slightly bloodless cipher, she’d become David Paterson’s comic foil.

It was the night before Super Duper Tuesday 2008, and Barack Obama’s campaign was surging—largely thanks to the stunning endorsements he’d received, one week earlier, from Ted Kennedy and, more surprisingly, from Ted’s niece Caroline. The crowd of 17,000 in the Hartford Civic Center stood and roared as they beheld a very rare sight: Caroline Kennedy, her generation’s closest thing to Greta Garbo, walking to the microphone.

Off to one side of the floor, in one of the arena’s tunnels, Obama’s political mastermind, David Axelrod, struggled to be heard over the ecstatic din. “Ted Kennedy is a link to a time when our politics had such meaning and possibility and people felt differently about it than they do today,” he said. “As for Caroline’s endorsement, someone said to me she’s the purest brand in American public life.”

That was because she’d nurtured her mystique by studiously avoiding the grubby side of politics. Kennedy had written or compiled seven books, and in 2002 she agreed to head fund-raising for the city’s public schools. After two years of part-time work, though, she retreated again to raise her three children and serve on the board of arts groups and charities, a kind of watered-down Mrs. Astor figure. Within her family, though, Kennedy could be just as competitive and politically savvy as the more outgoing members. “She’s always been very up on politics,” Kathleen Kennedy Townsend says. “There’s a difference between running for office and being knowledgeable about politics. Caroline is very smart and very interested and quite astute.”


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