In the United States Senate election held in the State of New York on November 7, 2000, Hillary Rodham Clinton, then first lady of the United States and the first presidential spouse to run for political office, defeated U.S. representative Rick Lazio. The general election coincided with the U.S. presidential election.

The race began in November 1998 when four-term incumbent senator Daniel Patrick Moynihan announced his retirement, making this the first open Senate seat in New York since the 1958 Senate election. Both the Democratic Party and Republican Party sought high-profile candidates to compete for the open seat. By early 1999, Clinton and New York City mayor Rudy Giuliani were the frontrunners for their parties' respective nominations. Clinton and her husband, President Bill Clinton, purchased a house in Chappaqua, New York, in September 1999; she thereby became eligible for the election, although she faced accusations of carpetbagging since she had never resided in the state before. The lead in statewide polls swung from Clinton to Giuliani and back to Clinton as the campaigns featured both successful strategies and mistakes as well as dealing with current events.

In late April and May 2000, Giuliani's medical, romantic, marital, and political lives all collided in a tumultuous four-week period, culminating in his withdrawal from the race on May 19. The Republicans chose lesser-known U.S. representative Rick Lazio to replace him. The election included a record $90 million in campaign expenditures between Clinton, Lazio, and Giuliani and national visibility. Clinton showed strength in normally Republican upstate areas and a debate blunder by Lazio solidified Clinton's previously shaky support among women. Clinton won the election in November 2000 with 55 percent of the vote to Lazio's 43 percent, and became the first woman elected to the Senate from New York.

Background When four-term senator Daniel Patrick Moynihan announced his retirement in November 1998, his previously safe U.S. Senate seat became open in the 2000 U.S. Senate elections. Both parties tried to find high-profile candidates to run for it.

New York City mayor Rudy Giuliani, who was prevented by term limits from running for mayoral reelection in 2001, immediately indicated interest. Due to his high profile and visibility, Giuliani was supported by the New York State Republican Party, even though he had irritated many by endorsing incumbent Democratic governor Mario Cuomo over Republican George Pataki in 1994. Giuliani became the presumptive Republican nominee, and by April 1999 had formed a formal exploratory committee for a Senate run. There were still possible Republican primary opponents. Rick Lazio, a U.S. representative representing Suffolk County on Long Island, was raising money and had a candidacy announcement scheduled for August 16; he had openly discussed a primary against Giuliani, believing his more conservative record would be appealing to Republican primary voters. In early August, under pressure from state and national Republican figures, Pataki endorsed Giuliani. Pataki prevailed upon Lazio to forgo his candidacy, which Lazio agreed to despite frustration that Giuliani had still not officially announced that he was running; Lazio said, "If the mayor wants to be a candidate, I think he needs to get into this race. It is time to put the soap opera aside and step up to the plate." Nassau County U.S. representative Peter T. King also considered running and had raised some funds.

U.S. representative Nita Lowey was the candidate first expected to be the Democratic nominee, while other mentioned possible candidates included secretary of housing and urban development Andrew Cuomo, state comptroller Carl McCall, as well as U.S. representative Carolyn Maloney. State Democratic figures were concerned that neither Lowey nor the others had the star power to rival Giuliani, and that the seat would be lost. Late in 1998, prominent Democratic politicians and advisors, including U.S. representative Charles Rangel, urged First Lady Hillary Rodham Clinton to run for the U.S. Senate seat. An unprecedented action if she did it, Clinton spent considerable time mulling over the idea while Lowey waited in the wings. Her political advisors told her the race would be difficult and some of them told her she would lose. She waited for the impeachment proceedings of Bill Clinton to conclude,, pp. 203–204. which they did with his acquittal on February 12, 1999.

Initial campaigns Early Clinton campaign On February 16, 1999, the First Lady's office announced that she was considering running for the Senate seat. Once it was clear Clinton was going to run, Lowey stepped aside, although she would be disappointed at the lost opportunity. Clinton’s political adviser, Harold Ickes, lead the campaign during its early stages. Ickes assembled the initial campaign team, which included Terry McAuliffe and Laura Hartigan. Both had previously been the most senior members of Bill Clinton's finance team during his 1996 reelection campaign. In December 1999, after a series of campaign missteps, Bill de Blasio was brought on as the full-time campaign manager.

On July 7, 1999, Clinton formally announced an exploratory committee for the Senate run;Gerth, Van Natta Jr., Her Way, pp. 208–209. the setting was Moynihan's farm in Pindars Corners, in rural Delaware County., p. 540. Bill Clinton was less than enthusiastic about her candidacy. The staging of the event was brokered by the Clintons' political consultant Mandy Grunwald. Hillary Clinton embarked upon a "listening tour" of all parts of New York after her entrance into the race.Hillary Rodham Clinton, Living History, Simon & Schuster, 2003, , pp. 508. She planned to visit all 62 counties in New York, talking to New Yorkers in small-group settings according to the principles of retail politics.Gerth, Van Natta Jr., Her Way, p. 210. During the race, she spent considerable time campaigning in traditionally Republican upstate regions. Clinton faced charges of carpetbagging, since she had never resided in the State of New York nor directly participated in state politics prior to her Senate race.

Meanwhile, in September 1999, the Clintons purchased a $1.7 million, 11-room, Dutch Colonial style home in Chappaqua, New York, north of New York City. Even the commonplace activity of house hunting leading up to this was the subject of considerable media attention; coverage of personal lives would be the norm in this contest of two "electrifying and polarizing figures" (as one reporter put it). In November 1999, Hillary Clinton announced that she would set aside most of her official duties as First Lady in order to take up residency in New York and pursue her campaign. Her move-in took place in January 2000, with the house furnished with many of the couple's possessions from their Arkansas days. It became the first time since Woodrow Wilson's first wife died in 1914 that a president lived in the White House without a spouse.

The early stages of her campaign were not without mistakes, and as she later wrote, "Mistakes in New York politics aren't easily brushed aside."Living History, p. 509. In a much-publicized move, Clinton donned a New York Yankees baseball cap at a June 1999 event when she had been a lifelong fan of the Chicago Cubs. This brought her much criticism, and Thomas Kuiper would later write an anti-Clinton book titled: I've Always Been a Yankees Fan: Hillary Clinton in Her Own Words. Clinton said she had to develop an American League rooting interest, since fans of the Cubs were not expected to root for the American League Chicago White Sox. In her 2003 autobiography, she said that putting on the hat had been a "bad move", but reiterated what had been reported in the press prior to the incident, that she had been "a die-hard Mickey Mantle fan;"Living History, p 509. the book included a photograph of her with a Yankees cap on from 1992.Living History, plate 40, first photo section.

More seriously, on November 11, 1999, at the dedication of a U.S.-funded health program in the West Bank, she exchanged kisses with Suha Arafat, wife of Palestinian president Yasser Arafat, after Suha Arafat had delivered a speech claiming that Israel had deliberately poisoned Palestinians through environmental degradation and the use of "poisonous gas". Some Israeli supporters said that Clinton never should have kissed the wife of the Palestinian leader, especially after such inflammatory remarks. The following day, Clinton denounced Suha Arafat's allegations, and said that Palestinian negotiator Saeb Erekat had told her Suha Arafat had been referring to 'tear gas' and not 'poison gas'. The kiss became a campaign issue, especially with Jewish voters. Clinton said it was a formality akin to a handshake, saying that to not have done so would have caused a diplomatic incident. Clinton later wrote that the live Arabic-to-English translation had failed to convey the accurate nature of her remarks: "Had I been aware of her hateful words, I would have denounced them on the spot."Living History, pp. 509–510.

Clinton faced an erosion of support from women voters during her campaign, with her numbers declining throughout 1999. This was partly a typical pattern seen with women candidates where they have an early surge of female support, which then wears off, and it was partly due to her early campaign stumbles. But it also reflected the particular set of mixed feelings that women had towards Clinton's marriage and the ambition and the power she derived from it. The problem was especially acute among some female demographics; one of her longtime advisers later said, "Women in the educated professional class? They fucking couldn't stand her. We could never figure out why. We had psychologists come in."

Clinton's campaign to all counties, carried by a Ford conversion van, helped to defuse the carpetbagger issue,Bernstein, A Woman in Charge, p. 542 with many New York residents saying that Clinton "seems like one of us." She discussed local issues such as price supports for the dairy industry, fares for air travel, college tuition levels, and the brain drain in parts of the state. Her political positions were well matched to the different constituencies in the state that she targeted. In a January 2000 appearance on the Late Show with David Letterman, she established a rapport with the host that would continue throughout her Senate years and into her 2008 presidential campaign.Gerth, Van Natta Jr., Her Way, p. 211. Clinton formally announced her official candidacy in Purchase, New York in February 2000, adopting the simple name "Hillary" for her campaign literature.

Distrustful of the press since her husband's 1992 presidential campaign and her early days as First Lady, she imposed limits on her availability to the press van following her. Associated Press reporter Beth Harpaz later recounted a typical day from this time: "But we'd been told there'd be no 'avail' today, and we'd accepted it. That didn't prevent me from feeling slightly humiliated. I was so worn down and so exasperated by the lack of access and the lack of news in this campaign that I'd given up fighting." p. 86.

Early Giuliani campaign