On February 4, 2000, Bill Clinton and a small group of aides gathered in the White House movie theater to help Hillary rehearse her formal-announcement speech. Standing at the lectern, shifting uncomfortably from foot to foot, Hillary began reading haltingly from her draft speech.

All of a sudden the president jumped up from his seat. “You need to say why you're running here and now!” he shouted.

“Because I'm a masochist,” Hillary shot back, half in jest.

The president looked down at the copy of the draft in his hand and began re-arranging the order of the paragraphs.

“She'll announce,” he said. “They'll cheer and dance around. That's fine. Why is she doing it? Why not Illinois, Arkansas, Alaska? Why not rake in some dough? Why ask to be trashed right now? What I wish you could do, Hillary, is a sentence here: 'The overwhelming reason is that I don't want to give up my life in public service.' ” [Vanity Fair, July 2005, page 125]

She had another adviser: the President. He had been enthusiastic about her running. On February 4, 2000, he joined a small group of us to help prepare the candidate for her formal announcement speech, to be delivered on February 6. We rehearsed in the White House movie theater, just as we did for the President's State of the Union addresses. But it was Hillary, not Bill, at the podium, and he sat with the rest of us, offering pointers and word changes. Clinton had a hard time staying seated.

He'd leap up excitedly, advising, “You need to say why you're running here and now.”

“Because I'm a masochist,” Hillary said. We all burst out laughing.

He began rearranging the sequence at the beginning of the speech. “She'll announce. They'll cheer and dance around. That's fine. Why is she doing it? Why not Illinois, Arkansas, Alaska? Why not rake in some dough? Why ask to be trashed right now? What I wish you could do, Hillary, is a sentence here: The overwhelming reason is that I don't want to give up my life in public service.” That was, after all, her motive. [Blumenthal, The Clinton Wars, pages 686-687 (paperback)]

In fact, Hillary made so many gaffes during her first few months on the campaign trail that people began to wonder if she was cut out for the rough-and-tumble of electoral politics.

When the Yankees won the World Series and went to the White House, Manager Joe Torre presented Hillary with a team cap. She promptly put it on and declared that she had “always been a big Yankees fan.” After the laughter died down in the saloons and taverns throughout New York City, Hillary looked more like an out-of-touch carpetbagger than ever.

When president Clinton granted pardons to 16 imprisoned Puerto Rican terrorists in an obvious bid to help his wife win New York's two million Hispanic votes, Hillary said she had not been involved in the decision - a claim that almost no one believed. In fact, Hillary's bother Hugh Rodham and campaign treasurer, William Cunningham III, had both lobbied to win other pardons from the president.

When Pardongate became yet another Clinton scandal, Hillary spoke out against the clemency decision. But her failure to alert Latino officials in advance of her about-face prompted howls of protest from Fernando Ferrer, the Bronx borough president and the highest-ranking Puerto Rican official in the city.

When Hillary made the obligatory trip to Israel to win Jewish votes back home, she went to the Palestinian-controlled city of Ramallah. There she appeared onstage with Yasser Arafat's wife, Suha, who made the outrageous charge that Israel was poisoning Palestinian women and children with toxic gas. At the end of Mrs. Arafat's speech, Hillary marched to the podium and gave Suha Arafat a big hug and kiss. The photo of the two women kissing, which was played around the world, sowed serious doubts about Hillary in the minds of many Jewish voters.

[...]

When a reporter asked Hillary if she planned to march in the Saint Patrick's Day Parade, she promptly responded, “I sure hope to!” Those four words, perhaps more than any others, revealed Hillary's ignorance of New York's convoluted politics. For years Democrats had avoided the parade because the Ancient Order of Hibernians refused to allow gays and lesbians to march under their own banner. By saying she would march, Hillary offended one of her core constituencies -- homosexuals. [Vanity Fair, July 2005, pages 124-125]

[E]very trap was baited for her. Throughout 1999, she walked straight into some of them. Almost all these rites of passage had to do with the snares of local politics. The first mistake was minor but telling, and it riveted attention on her status as an interloper.

On June 10, the President received the World Champion New York Yankees at the White House, and both he and Hillary were presented with Yankee caps. She put hers on and it became an early symbol of her lack of authenticity. ... She was showing a tin ear for New York politics. She hadn't yet grasped that New Yorkers are at once sophisticated and parochial, that aspiring to be a New Yorker was acceptable, but pretending to be one too soon excited local prejudices and latent hostilities.

In August, the President announced that he was granting clemency to sixteen Puerto Rican nationalists, members of a group that had committed acts of violence, though these particular people had not. His act was the result of painstaking work by the White House counsel Charles Ruff, and Hillary had had nothing to do with it. But, instantly, she and the President were accused of abusing presidential powers on behalf of her political ambition. A week after the President's statement, she declared her disagreement with it, which only made her seem more opportunistic and drew the fire of Puerto Rican leaders, who claimed they hadn't been consulted about the decision to begin with.

These were teacup wars compared to the explosion that occurred following Hillary Clinton's trip to Israel. On November 11, she appeared at a day care center in Ramallah with Yasser Arafat's wife, Suha, who gave a speech denouncing what she called the 'daily and intensive use of poison gas' by the Israeli Defense Forces against the Palestinians, and claiming that Israel was poisoning the water supply in Palestinian areas. Hillary listened politely to the speech, given in Arabic, and, following protocol, kissed Mrs. Arafat on both cheeks when she finished. The cameras snapped.

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A Democratic candidate requires about two-thirds of New York City's Jewish vote to win in New York state, and she had aroused the furies in what should have been one of her most secure bases. The kiss seemed to be an error of biblical scope.

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Hillary did not end the year without making another mistake. On December 8, at an Irish breakfast, where leaders of the Irish community in New York lauded her contributions to peace in Northern Ireland, a reporter asked a trick question that seemed on the surface to be a simple one. Would she march in the St. Patrick's Day parade? “I sure hope to,” she replied. For almost a decade, the official parade, conducted by the Ancient Order of Hibernians, had been a matter of great controversy because it had refused to allow the Irish Lesbian and Gay Organization to join the march. Every year, the event had been marked by noisy demonstrations and arrests. Hillary's innocent eagerness led her to become caught between two contentious constituencies. [Blumenthal, The Clinton Wars, pages 681-683 (paperback)]