As privacy ends for Kennedy, rough path awaits

By Adam Nagourney and Nicholas Confessore

updated 10:56 p.m. ET Dec. 16, 2008

WASHINGTON - On the day Caroline Kennedy declared she wanted to succeed Senator Hillary Rodham Clinton , one of the first people she called was the mayor of Buffalo.

She told him she wanted to visit western New York. She told him she wanted to learn more about regional issues.

The mayor, Byron W. Brown , said he would welcome her. But he had a message for Ms. Kennedy, too, offering her a preview of what her life is about to become: “I think upstaters are going to want an upstater on the ticket,” he said.

The decision by Ms. Kennedy to end a highly private existence and enter politics — New York politics, no less — presents what even her supporters acknowledge is a gamble on a carefully cultivated reputation for quiet competence and dignity established over the 45 years since her father was assassinated.

She must overcome skepticism about her experience and credentials, and deflate what some Democrats view as a sense of entitlement by a member of a storied American political family trying to begin her political career near the top of the ladder.

These concerns are coming into sharp relief as Ms. Kennedy begins an understated if carefully orchestrated rollout, with calls to political leaders early this week, and a trip upstate, including a private meeting with the mayor of Syracuse, on Wednesday.

Video   Caroline Kennedy makes her case Dec. 17: Hoping to smooth over concerns about her Senate candidacy, Caroline Kennedy met with officials in upstate New York Wednesday. NBC's Andrea Mitchell reports. Nightly News

“Obviously she is a celebrity,” said H. Carl McCall , the former state comptroller and the Democratic candidate for governor in 2002.

“But I think the real issue here is, do you want someone who is a celebrity and comes from the right family and gives the sense that this is something for a person of privilege? Or do you go with someone who has paid some political dues, for whom you have a sense of how they might perform.”

He added: “She’s never been tested, and there are a lot of people out here who have been.”

For Ms. Kennedy, it’s not only the inevitable (and history suggests surmountable) resistance from upstaters to a Manhattan lawyer who makes her home on Park Avenue, or the wariness of New York political leaders who expect a certain amount of deference and dues-paying.

After years of being largely given a pass by New York’s notoriously rambunctious tabloid press, which have yielded to her desire for privacy, Ms. Kennedy is almost certainly about to get a working over by reporters who may not be as enchanted with, or intimidated by, the Kennedy presence as reporters of an earlier generation were.

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“The tabloid culture is going to relentlessly follow her across the state,” said Robert Hardt, the political director for NY1, the 24-hour New York City news station, and a former political reporter for The New York Post. “If she doesn’t dot every I and cross every T, the New York tabloids are going to be, ‘Gotcha!’ ”

“New York political reporters just don’t know Caroline Kennedy,” Mr. Hardt continued. “We just can’t wait to talk to her.”

The extent to which her late brother John Kennedy Jr. became a fixture in the tabloids after he raised his profile by co-founding George Magazine is instructive, Democrats said. And Ms. Kennedy’s arrival on the public stage is taking place while bad feelings still linger between the Kennedy family and Andrew M. Cuomo , the state’s attorney general, who engaged in a bitter divorce battle with Kerry Kennedy, one of Caroline’s cousins.

Ms. Kennedy’s supporters acknowledge that she has her work cut out for her; if Gov. David A. Paterson appointed her, she would have to run for office in 2010, and potentially again in 2012. Still, they said that New York, for all its challenges — turf-minded political leaders, intensely ambitious rivals, bomb-throwing reporters and a minefield of tough issues — might prove a good training ground.

“New York likes candidates like Pat Moynihan and Robert Kennedy and Hillary Clinton and I would put Caroline in that category,” said Robert Shrum, a Democratic consultant with strong ties to the Kennedy family. “We always assume that they are going to have more trouble than they do.”

“It’s a state that likes people of stature. It’s a state that elected Robert Kennedy, Andrew Cuomo, Hillary Clinton,” he said.

And there is clearly enthusiasm for her among some powerful people; Senator Harry Reid of Nevada, said on Tuesday that he had called Mr. Paterson last week and urged him to choose Ms. Kennedy. “We have a lot of stars from New York: Bobby Kennedy. Hillary Clinton,” he told Las Vegas 1, an all-news station in Nevada. “I think Caroline Kennedy would be perfect.”

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