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The Zany Adventures of (Senator) Caroline Kennedy

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Caroline Kennedy with her very private mother, left, and very public father in 1960.  

But the pol, with a laugh, added a note of warning. “I’ve known David for twenty years, and he takes great pleasure in twisting people up and confusing them. He’s made many, many decisions in his life where people afterward said, ‘What the fuck?’ ”

Kennedy’s big black borrowed GMC Denali was racing west down the Thruway from Syracuse to Rochester. It was December 17, and she was in the front passenger seat, glancing out the window at the featureless gray sky and lumps of dirty snow. Kennedy had just made her first official visit as a candidate to replace Hillary Clinton. Her short chat with the mayor of Syracuse had been pleasant enough. Suddenly, though, there was a commotion in the back seat.

Her political consultant, Josh Isay, was squinting at his BlackBerry in alarm. Ten minutes after they’d left Syracuse, the New York Times’ website posted a story. “In a carefully controlled strategy reminiscent of the vice-presidential hopeful Sarah Palin,” read the first sentence, “aides to Caroline Kennedy interrupted her on Wednesday and whisked her away when she was asked what her qualifications are to be a United States senator.”

Kennedy had emerged from her meeting with Syracuse mayor Matt Driscoll to find a scrum of twenty reporters and cameramen elbowing for position between the office Christmas tree and a secretary’s cubicle. She’d stopped and improvised a bland 30-second statement, her eyes darting all over the room. Dashing for the door, Kennedy looked more like a perp than a potential U.S. senator.

From the moment she had called him, she was the front-runner for the job. Her choice would have solved many of Paterson’s problems, allowing him to avoid choosing among warring small-fry congressional contenders; unlike Andrew Cuomo, she’d be his candidate, his senator; and her appointment would make the kind of dramatic splash he sought. The media mob that followed her everywhere was evidence of that. But she was a risk—and he wanted her out proving herself, floating like a human trial balloon. Paterson had told her to go upstate and introduce herself to some elected officials, even dictating the order of the cities Kennedy should visit. Crazily, he’d also told her not to take questions from the media. (Paterson now denies having instructed her.)

As the SUV cruised, a call was placed to Albany. Paterson couldn’t be reached. Kennedy and her team decided that stiff-arming the press was untenable and took a few questions in Rochester and Buffalo. A peculiar dynamic had been set in motion: missed communications and mixed signals between two protagonists who had spent their starkly different lives being obscure.

Just as the uproar from the upstate trip was settling down, Kennedy’s bid was hit with a new barrage of criticism, and this one showed how much anger she’d stirred among the state’s Democratic Establishment. Gary Ackerman, a Queens congressman, told a radio interviewer that Kennedy was as qualified as J.Lo—a celebrity and nothing more. Other Democrats were attacking with more sophisticated subterfuges, using surrogates, covering their tracks. This was partly because at least ten other New York politicians—including Andrew Cuomo, Carolyn Maloney, Tom Suozzi, and Steve Israel—thought they should be first in line for the job. But Paterson said he wouldn’t name HRC’s successor till she was officially gone. So he didn’t do what a normal politician might have: make the decision and be done with it.

“If he would have named someone early on, people would have gotten behind it,” one New York political strategist said midway through the saga. “Instead, not only didn’t he pick someone, he went in reverse—he told Randi Weingarten maybe she should be senator. He meets with Liz Holtzman, who actually thinks she can be a senator now. So now people have to rip the front-runner. Because in this campaign, you can’t be seen as openly promoting yourself, so all you can do is the negative part, making sure your surrogates, or unnamed sources, are ripping the shit out of the other people.”

It was partly to combat forces like these that Kennedy hired Josh Isay. Isay, 39, had risen through the ranks of Chuck Schumer’s Senate aides, eventually becoming chief of staff. In 2002, Isay left government to co-found Knickerbocker SKD, a powerhouse consulting and lobbying firm whose clients included Bloomberg’s 2005 reelection campaign. Kennedy had met Isay when he did some work for the public-school fund-raising drive. Isay’s connection with Schumer helped fuel the belief that Kennedy was Schumer’s candidate, too—and that Schumer particularly wanted to make sure Andrew Cuomo didn’t become yet another junior senator with a higher political Q rating than he had.

A more shadowy player in the drama was Charles O’Byrne. As a Roman Catholic priest, O’Byrne had officiated at the wedding and funeral of Caroline’s brother. O’Byrne quit the priesthood, however, and came out as a gay man. In 2004, he went to work on the State Senate staff of David Paterson and rose to become Paterson’s most trusted consigliere and his hot-tempered enforcer. O’Byrne was chief of staff to the accidental governor until the fall of 2008, when his failure to pay taxes for five years became a scandal. His resignation was an enormous destabilizing blow to Paterson’s operation in Albany. But O’Byrne remained in contact with Paterson and became an emissary between the governor and Caroline Kennedy.


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