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The Zany Adventures of (Senator) Caroline Kennedy

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But the overriding principle of Caroline Kennedy’s life had been one of sphinxlike silence. It could manifest as shyness, though at bottom it was a kind of policy toward her potential celebrity—private was private; in public, you wore a mask. “You can’t separate Caroline’s personality from her experiences,” says her longtime friend the novelist Alexandra Styron. “She’s very smart, very savvy; she’s learned to read a room quickly and tell when she’s safe and when she isn’t. Over time, she’s found more ways to operate out in the world in a more confident way—to be her best self out in public. But it’s taken a long time for her to grow into that.”

Styron’s mother and her father, the writer William Styron, were friends with JFK and Jackie beginning in the late fifties; Al Styron and Caroline Kennedy became close as adults. “When my father died, Caroline was the first, or one of the first, to call,” Styron says. “Often when you lose someone, people are not sure what to do—they don’t want to bother you, they don’t want to impose. Caroline didn’t wait. She comes from a place of deep experience with loss, and so she doesn’t waste a moment in being there for people when they’re in pain.”

Kennedy has been shaped by trauma. Her father’s murder and her brother’s death in a plane crash were wounds that were exponentially compounded by being so very public. Yet it was her mother, the most famous woman in the world, stalked by tragedy and by Ron Galella, who trained her to be always on her guard. Jackie’s fierce protection of her children produced two sane adults and provided something of a template for raising a family with good values in the public eye.

Caroline’s most rebellious act as an adult was marrying the older, Jewish artist Ed Schlossberg in 1986. But even their marriage has functioned as something of a cocoon. “Ed is her rock, and he always has been,” Styron says. “Ed is deeply cautious and very protective of her. He’s the organized, neat one, the one who makes sure the doors are locked and the seat belts are on. It gives her the opportunity to be lighthearted. He’s the sentry, in a way. He allows her a base from which to venture out into the world.” For the last year, various gossip outlets have speculated about the state of the marriage, but no one has ever substantiated the rumors.

Kennedy’s aloofness from conventional politics gave her endorsement of Obama as the second coming of her father in January 2008 great power. What wasn’t as clear at the time was just how meaningful the role was to Caroline. Now, at 51, with her youngest child 16, she had been thinking about what the next chapter in her life would be.

“Campaigning is heady if you haven’t ever really done it,” says her friend and agent Esther Newberg. “It gets you, and everything else seems less real. And I think Caroline realized that.”

She’d helped make a president, and she’d opened a door for herself. The question was what to do next with her newfound power. Just after Election Day, Obama provided her with an answer. And on December 3, she quietly declared her interest in replacing Hillary Clinton by calling New York’s governor.

David Paterson likes to open with a joke. It’s an ice-breaking tactic straight out of the hoary toastmaster’s bible, of course, but for Paterson, humor is a more complicated tool. He learned a long time ago the social awkwardness his blindness can create, especially when someone is meeting him for the first time. Yet Paterson wants to do more than cut the tension; he wants desperately, even more than most politicians, to be liked. Almost as much as he wants to be taken seriously.

The competing impulses have ruled Paterson’s life since he was a child. He was born into an elite New York family; his father, Basil, was a member of the “Gang of Four” that dominated Harlem politics. When Paterson was 3 months old, an infection destroyed the optic nerve in his left eye and severely limited the vision in his right eye. That he went on to graduate from Columbia and earn a law degree at Hofstra without ever learning Braille is testament to Paterson’s intelligence and determination. After college, he signed on with the 1985 Manhattan borough-presidential campaign of David Dinkins, one of his father’s closest friends. He’s depended on, and resented, the Gang’s help for most of his political career.

Last March, the world discovered Ashley Dupré and, shortly thereafter, made the acquaintance of David Paterson and his sense of humor, his remarkable working methods, and his dalliances with a co-worker at a Manhattan hotel. The circumstances of his own promotion from lieutenant governor only amplified his need to be his own man. The senatorial appointment became a kind of test case. “The last thing David Paterson wanted was this process to make it look like he was being rolled,” says a state Democrat who knows Paterson well. “He’s African-American, and he’s blind, so he’s been underestimated his entire life, so he wants to show he’s in charge. Look at how he travels: At the Democratic convention in Denver, you’d see Jon Corzine and he’d have two people with him. You’d see David Paterson and he’d have 60 people with him.”


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