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In the
United States Senate The United States Senate is the upper chamber of the United States Congress, with the House of Representatives being the lower chamber. Together they compose the national bicameral legislature of the United States. The composition and pow ...
election held in the
State of New York New York, officially the State of New York, is a state in the Northeastern United States. It is often called New York State to distinguish it from its largest city, New York City. With a total area of , New York is the 27th-largest U.S. state ...
on November 7, 2000,
Hillary Rodham Clinton Hillary Diane Rodham Clinton ( Rodham; born October 26, 1947) is an American politician, diplomat, and former lawyer who served as the 67th United States Secretary of State for President Barack Obama from 2009 to 2013, as a United States senat ...
, then First Lady of the United States and the first First Lady to run for political office, defeated
U.S. Representative The United States House of Representatives, often referred to as the House of Representatives, the U.S. House, or simply the House, is the lower chamber of the United States Congress, with the Senate being the upper chamber. Together they c ...
Rick Lazio Enrico Anthony Lazio (; born March 13, 1958) is an American attorney and former four-term U.S. Representative from the State of New York. A Long Island native, Lazio became well-known during his bid for U.S. Senate in New York's 2000 Senate e ...
. The general election coincided with the U.S. presidential election. This was both the first open Senate seat and in this seat since the 1958 Senate election. The race began in November 1998 when four-term incumbent Senator Daniel Patrick Moynihan announced his retirement. Both the
Democratic Party Democratic Party most often refers to: *Democratic Party (United States) Democratic Party and similar terms may also refer to: Active parties Africa *Botswana Democratic Party *Democratic Party of Equatorial Guinea *Gabonese Democratic Party *Demo ...
and Republican Party sought high-profile candidates to compete for the open seat. By early 1999 Clinton and Mayor of New York City Rudy Giuliani were the likely respective nominees. Clinton and her husband, President
Bill Clinton William Jefferson Clinton ( né Blythe III; born August 19, 1946) is an American politician who served as the 42nd president of the United States from 1993 to 2001. He previously served as governor of Arkansas from 1979 to 1981 and agai ...
, purchased a house in
Chappaqua, New York Chappaqua ( ) is a hamlet and census-designated place in the town of New Castle, in northern Westchester County, New York, United States. It is approximately north of New York City. The hamlet is served by the Chappaqua station of the Metro ...
, in September 1999; she thereby became eligible for the election, although she faced characterizations of
carpetbagging In the history of the United States, carpetbagger is a largely historical term used by Southerners to describe opportunistic Northerners who came to the Southern states after the American Civil War, who were perceived to be exploiting the lo ...
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 Mario Matthew Cuomo (, ; June 15, 1932 – January 1, 2015) was an American lawyer and politician who served as the 52nd governor of New York for three terms, from 1983 to 1994. A member of the Democratic Party, Cuomo previously served as ...
over Republican
George Pataki George Elmer Pataki (; born June 24, 1945) is an American lawyer and politician who served as the 53rd governor of New York from 1995 to 2006. An attorney by profession, Pataki was elected mayor of his hometown of Peekskill, New York, and went on ...
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 Enrico Anthony Lazio (; born March 13, 1958) is an American attorney and former four-term U.S. Representative from the State of New York. A Long Island native, Lazio became well-known during his bid for U.S. Senate in New York's 2000 Senate e ...
, a
U.S. Representative The United States House of Representatives, often referred to as the House of Representatives, the U.S. House, or simply the House, is the lower chamber of the United States Congress, with the Senate being the upper chamber. Together they c ...
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 Peter Thomas King (born April 5, 1944) is a former American politician who represented New York in the U.S. House of Representatives from 1993 to 2021. A member of the Republican Party, he represented a South Shore Long Island district that i ...
also considered running and had raised some funds. U.S. Representative
Nita Lowey Nita Sue Lowey ( ) ( Melnikoff; born July 5, 1937) is an American politician who formerly served as a U.S. Representative from New York from 1989 until 2021. She is a member of the Democratic Party. Lowey also served as co-Dean of the New York C ...
was the candidate first expected to be the Democratic nominee, while other mentioned possible candidates included
Secretary of Housing and Urban Development The United States secretary of housing and urban development (or HUD secretary) is the head of the United States Department of Housing and Urban Development, a member of the president's Cabinet, and thirteenth in the presidential line of succe ...
Andrew Cuomo Andrew Mark Cuomo ( ; ; born December 6, 1957) is an American lawyer and politician who served as the 56th governor of New York from 2011 to 2021. A member of the Democratic Party, he was elected to the same position that his father, Mario Cu ...
,
New York State Comptroller The New York State Comptroller is an elected constitutional officer of the U.S. state of New York and head of the New York state government's Department of Audit and Control. The New York State Comptroller is the highest-paid state auditor or ...
Carl McCall Herman Carl McCall (born October 17, 1935) is an American politician of the Democratic Party. A former New York State Comptroller and New York State Senator, McCall was the Democratic candidate for Governor of New York in 2002. McCall was the ...
, as well as U.S. Representative
Carolyn Maloney Carolyn Jane Maloney (née Bosher, February 19, 1946) is an American politician serving as the U.S. representative for since 2013, and for from 1993 to 2013. The district includes most of Manhattan's East Side, Astoria and Long Island City ...
. 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 Charles Bernard Rangel (, ; born June 11, 1930) is an American politician who was a U.S. representative for districts in New York from 1971 to 2017. A member of the Democratic Party, he was the second-longest serving incumbent member of the Ho ...
, urged First Lady
Hillary Rodham Clinton Hillary Diane Rodham Clinton ( Rodham; born October 26, 1947) is an American politician, diplomat, and former lawyer who served as the 67th United States Secretary of State for President Barack Obama from 2009 to 2013, as a United States senat ...
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.


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. 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 Madeleine Grunwald (born January 23, 1957) is an American professional political consultant and media advisor for the Democratic Party. Grunwald is one of the few women at the top of the field, having helped elect numerous senators and governors ...
. Hillary Clinton embarked upon a "listening tour" of all parts of New York after her entrance into the race.
Hillary Rodham Clinton Hillary Diane Rodham Clinton ( Rodham; born October 26, 1947) is an American politician, diplomat, and former lawyer who served as the 67th United States Secretary of State for President Barack Obama from 2009 to 2013, as a United States senat ...
, ''
Living History Living history is an activity that incorporates historical tools, activities and dress into an interactive presentation that seeks to give observers and participants a sense of stepping back in time. Although it does not necessarily seek to ree ...
'', 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 In the history of the United States, carpetbagger is a largely historical term used by Southerners to describe opportunistic Northerners who came to the Southern states after the American Civil War, who were perceived to be exploiting the lo ...
, 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 Dutch Colonial is a style of domestic architecture, primarily characterized by gambrel roofs having curved eaves along the length of the house. Modern versions built in the early 20th century are more accurately referred to as "Dutch Colonial Re ...
home in
Chappaqua, New York Chappaqua ( ) is a hamlet and census-designated place in the town of New Castle, in northern Westchester County, New York, United States. It is approximately north of New York City. The hamlet is served by the Chappaqua station of the Metro ...
, 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 Thomas Woodrow Wilson (December 28, 1856February 3, 1924) was an American politician and academic who served as the 28th president of the United States from 1913 to 1921. A member of the Democratic Party, Wilson served as the president of ...
'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 The New York Yankees are an American professional baseball team based in the New York City borough of the Bronx. The Yankees compete in Major League Baseball (MLB) as a member club of the American League (AL) East division. They are one of ...
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 The American League of Professional Baseball Clubs, known simply as the American League (AL), is one of two leagues that make up Major League Baseball (MLB) in the United States and Canada. It developed from the Western League, a minor league ...
rooting interest, since fans of the Cubs were not expected to root for the American League
Chicago White Sox The Chicago White Sox are an American professional baseball team based in Chicago. The White Sox compete in Major League Baseball (MLB) as a member club of the American League (AL) Central division. The team is owned by Jerry Reinsdorf, and ...
. 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 Mickey Charles Mantle (October 20, 1931 – August 13, 1995), nicknamed "the Commerce Comet" and "the Mick", was an American professional baseball player. Mantle played his entire Major League Baseball (MLB) career (1951–1968) with the New York ...
fan;" the book included a photograph of her with a Yankees cap on from 1992. More seriously, on November 11, 1999, at the dedication of a U.S.-funded health program in the
West Bank The West Bank ( ar, الضفة الغربية, translit=aḍ-Ḍiffah al-Ġarbiyyah; he, הגדה המערבית, translit=HaGadah HaMaʽaravit, also referred to by some Israelis as ) is a landlocked territory near the coast of the Mediter ...
, she exchanged kisses with Suha Arafat, wife of Palestinian President
Yasser Arafat Mohammed Abdel Rahman Abdel Raouf al-Qudwa al-Husseini (4 / 24 August 1929 – 11 November 2004), popularly known as Yasser Arafat ( , ; ar, محمد ياسر عبد الرحمن عبد الرؤوف عرفات القدوة الحسيني, Mu ...
, after Suha Arafat had delivered a speech claiming that
Israel Israel (; he, יִשְׂרָאֵל, ; ar, إِسْرَائِيل, ), officially the State of Israel ( he, מְדִינַת יִשְׂרָאֵל, label=none, translit=Medīnat Yīsrāʾēl; ), is a country in Western Asia. It is situated ...
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 Tear gas, also known as a lachrymator agent or lachrymator (), sometimes colloquially known as "mace" after the early commercial aerosol, is a chemical weapon that stimulates the nerves of the lacrimal gland in the eye to produce tears. In ...
' and not '
poison gas Many gases have toxic properties, which are often assessed using the LC50 (median lethal dose) measure. In the United States, many of these gases have been assigned an NFPA 704 health rating of 4 (may be fatal) or 3 (may cause serious or perman ...
'. 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 Arabic (, ' ; , ' or ) is a Semitic language spoken primarily across the Arab world.Semitic languages: an international handbook / edited by Stefan Weninger; in collaboration with Geoffrey Khan, Michael P. Streck, Janet C. E.Watson; Walter ...
-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." Somewhat surprisingly, 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 Ford commonly refers to: * Ford Motor Company, an automobile manufacturer founded by Henry Ford * Ford (crossing), a shallow crossing on a river Ford may also refer to: Ford Motor Company * Henry Ford, founder of the Ford Motor Company * Ford F ...
conversion van A conversion van is a full-sized cargo van that is sent to third-party companies to be outfitted with various luxuries for road trips and camping. It can also mean a full-size passenger van in which the rear seating have been rearranged for taxi ...
, 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 support In economics, a price support may be either a subsidy, a production quota, or a price control, each with the intended effect of keeping the market price of a good higher than the competitive equilibrium level. In the case of a price control, a p ...
s for the
dairy industry A dairy is a business enterprise established for the harvesting or processing (or both) of animal milk – mostly from cows or buffaloes, but also from goats, sheep, horses, or camels – for human consumption. A dairy is typically located on ...
, fares for air travel,
college tuition Tuition payments, usually known as tuition in American English and as tuition fees in Commonwealth English, are fees charged by education institutions for instruction or other services. Besides public spending (by governments and other public bo ...
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 The Associated Press (AP) is an American non-profit news agency headquartered in New York City. Founded in 1846, it operates as a cooperative, unincorporated association. It produces news reports that are distributed to its members, U.S. ne ...
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

An early January 1999 Marist Institute of Public Opinion poll showed Giuliani trailing Clinton by 10 points. By January 2000, the Marist poll showed Giuliani up by 9 points. Giuliani's tactics involved intentionally baiting the Clinton campaign with deliberate overstatements, keeping them off balance and behind in the response cycle. Giuliani emphasized his depiction of Clinton as a carpetbagger. He made a one-day visit to
Little Rock, Arkansas ( The "Little Rock") , government_type = Council-manager , leader_title = Mayor , leader_name = Frank Scott Jr. , leader_party = D , leader_title2 = Council , leader_name2 ...
, where he announced he would fly the Arkansas state flag over New York's City Hall. When Hillary Clinton visited New York from Washington, he said, "I hope she knows the way. I hope she doesn't get lost on one of the side streets." Giuliani's campaign prepared a 315-page
opposition research In politics, opposition research (also called oppo research) is the practice of collecting information on a political opponent or other adversary that can be used to discredit or otherwise weaken them. The information can include biographical, le ...
dossier that went back to her time at Wellesley College; it included eleven pages of what they termed "Stupid Actions and Remarks". The Giuliani campaign had no problems raising money, getting over 40 percent of its funds from out-of-state and outraising Clinton overall two-to-one. The Giuliani campaign showed some structural weaknesses. So closely identified with New York City, he had somewhat limited appeal to naturally Republican voters in
Upstate New York Upstate New York is a geographic region consisting of the area of New York State that lies north and northwest of the New York City metropolitan area. Although the precise boundary is debated, Upstate New York excludes New York City and Long Is ...
. The Farmersville Garbage Scandal was indicative of his lower levels of support upstate. By late December 1999, Clinton adapted to Giuliani's
psychological warfare Psychological warfare (PSYWAR), or the basic aspects of modern psychological operations (PsyOp), have been known by many other names or terms, including Military Information Support Operations (MISO), Psy Ops, political warfare, "Hearts and M ...
, saying in response to one such gambit, "I can't be responding every time the mayor gets angry. Because that's all I would do." A February 2000 attempt by Giuliani to capitalize on a Clinton campaign event's accidental playing of Billy Joel's suburban drug tale "
Captain Jack Captain Jack may refer to: People * Calico Jack (1683–1720), a pirate in the 18th century * Captain Jack (Hawaiian) (died 1831), Naihekukui, commander of Kamehameha's fleet and father of Kalama * Captain Jack (fl. 1830s on), Kaurna man in c ...
" led to more ridicule for him than for her. On March 11, 2000, Giuliani and Clinton met face-to-face for the first time since the campaigning began, at the New York Inner Circle press dinner, an annual event in which New York politicians and the press corps stage skits,
roast Roasting is a cooking method that uses dry heat where hot air covers the food, cooking it evenly on all sides with temperatures of at least from an open flame, oven, or other heat source. Roasting can enhance the flavor through caramelizatio ...
each other and make fun of themselves, with proceeds going to charity. Giuliani was on stage in male disco garb spoofing John Travolta in '' Saturday Night Fever'', but also appeared in drag in taped video clips that reworked the "Rudy/Rudia" theme of a past Inner Circle dinner, as well as in an exchange with
Joan Rivers Joan Alexandra Molinsky (June 8, 1933 – September 4, 2014), known professionally as Joan Rivers, was an American comedian, actress, producer, writer and television host. She was noted for her blunt, often controversial comedic persona—heavi ...
that sought to make fun of Clinton. Other performers' skits made fun of Clinton's Yankees claim and the infidelity of her husband. The New York Police Department's fatal shooting of
Patrick Dorismond Patrick Moses Dorismond (February 28, 1974 – March 16, 2000) was an American security guard and father of two children who was killed by undercover New York City Police Department officers during the early morning of March 16, 2000. He was ...
on March 15, 2000, inflamed Giuliani's already strained relations with the city's minority communities, and Clinton seized on it as a major campaign issue. By April, reports showed Clinton gaining upstate and generally outworking Giuliani, who stated that his duties as mayor prevented him from campaigning more. He gave priority to city duties over campaign activities. Some Giuliani aides and national Republican figures concluded that his interest in the campaign was flagging, as although he was desirous of winning in political combat against a Clinton, he was by nature an executive personality and the prospect of serving as one of a hundred legislators was unappealing to him. By this time, Clinton was 8 to 10 points ahead of Giuliani in the polls. In retrospect, ''
The New York Times ''The New York Times'' (''the Times'', ''NYT'', or the Gray Lady) is a daily newspaper based in New York City with a worldwide readership reported in 2020 to comprise a declining 840,000 paid print subscribers, and a growing 6 million paid d ...
'' would write that the battle so far between the two had comprised "a blistering year of mental gamesmanship, piercing attacks, contrasts in personalities and positions, and blunders played out by two outsize political figures in a super-heated atmosphere."


Giuliani's tumultuous four weeks

Giuliani's marriage to his wife, broadcast journalist and actress
Donna Hanover Donna Hanover (born Donna Ann Kofnovec; February 15, 1950) is an American journalist, radio and television personality, television producer, and actress, who appears on CUNY TV in New York City. From 1994 through 2001 she was First Lady of New Yo ...
, had been distant since 1996, and the two were rarely seen in public together. There had been no formal announcement of any change in their relationship, although Hanover had indicated that she and their children would not move to Washington if Giuliani won the race. Beginning in October 1999, a new woman was being spotted at mayoral functions. p. 434. By March 2000, Giuliani had stopped wearing his wedding ring and was being seen more in the company of this other woman, including at the Inner Circle press dinner, the St. Patrick's Day parade, and town hall meetings, but it was not yet fully clear whether the relationship was personal or professional.Harpaz, ''The Girls in the Van'', p. 113. While this woman had become a frequent subject of insider talk among the New York political circle, she had not been mentioned in the press. On April 20 Hanover announced that she would soon be taking over the lead role in Eve Ensler's controversial play ''
The Vagina Monologues ''The Vagina Monologues'' is an episodic play written in 1996 by Eve Ensler which developed and premiered at HERE Arts Center, Off-Off-Broadway in New York and was followed by an Off-Broadway run in at Westside Theatre. The play explores c ...
''. Political observers speculated that Hanover was partly engaging in a political act against her husband, as Ensler was a friend and supporter of Hillary Clinton and the role would not go over well with
social conservative Social conservatism is a political philosophy and variety of conservatism which places emphasis on traditional power structures over social pluralism. Social conservatives organize in favor of duty, traditional values and social instituti ...
s within the Republican Party. Giuliani declined to say whether he would attend one of her performances. On April 22, the ''
New York Post The ''New York Post'' (''NY Post'') is a conservative daily tabloid newspaper published in New York City. The ''Post'' also operates NYPost.com, the celebrity gossip site PageSix.com, and the entertainment site Decider.com. It was established ...
'' obtained photographs of Giuliani openly strolling on a Manhattan street with the other woman after they left a restaurant, but did not have more than a first name for her;Barrett, ''Rudy!'', p. 437. the ''Post'' sat on the story, but it was clear the relationship was a personal one. On April 26, television channel
NY1 NY1 (also officially known as Spectrum News NY1 and spoken as New York One) is an American cable news television channel founded by Time Warner Cable, which itself is owned by Charter Communications through its acquisition in May 2016. The channe ...
reported that Giuliani had undergone a second round of tests for prostate cancer at
Mount Sinai Medical Center Mount Sinai Hospital, formerly at times known as Mount Sinai Medical Center, is a 319-bed major urban hospital in Chicago, Illinois, with its main campus located adjacent to Douglass Park at 15th Street and California Avenue on the city's West Sid ...
; the same disease had led to the death of his father. On April 28, Giuliani held a news conference to announce that he did in fact have prostate cancer, but it was in an early stage. He was unsure of which of several types of treatment he might undergo, and that decision would impact whether he could stay in the Senate race or not. Hanover was not present at the conference, but issued a note saying she would support him in his decision process. As Giuliani mulled over his medical options, on May 1 Hanover announced that she was postponing her appearance in ''The Vagina Monologues'' due to "personal family circumstances." On May 2 the '' New York Daily News'' published a brief item about Giuliani's other woman, without name or description.Barrett, ''Rudy!'', p. 436. On May 3 the ''New York Post'' finally published its photographs of Giuliani and the woman, now identified as
Judith Nathan Judi Ann Stish Ross Nathan GiulianiJudy Bachrach"Giuliani's Princess Bride" '' Vanity Fair'', September 2007. Accessed August 15, 2007. (born December 16, 1954)Jodi Kantor, "Judi, Jeri and the Rest", in "Hurtling Toward a Nomination, 2008", ''The ...
, leaving a restaurant together, under the front-page headline "Rudy's Mystery Brunch Pal is Upper East Side Divorcée". (Some observers felt that Giuliani, known for his ability to manipulate the New York media, had been eager for news of the relationship to come out.) Later that day, Giuliani responded to a barrage of questions on the subject at a news conference by acknowledging Judith Nathan publicly for the first time, calling her "a very good friend" and expressing his annoyance that her privacy was being invaded. The next days were filled with New York media coverage on Nathan's background and on the relationship. On May 6 Hanover held an unusually-located news conference at the back of St. Patrick's Cathedral before the funeral of Cardinal John O'Connor; visibly trembling, she said, "I will be supportive of Rudy in his fight against his illness, as this marriage and this man have been very precious to me." The following day half the press tried to stake out Nathan's known locations while the rest pestered Nathan's hometown relatives in
Hazleton, Pennsylvania Hazleton is a city in Luzerne County, Pennsylvania, United States. The population was 29,963 at the 2020 census. Hazleton is the second largest city in Luzerne County. It was incorporated as a borough on January 5, 1857, and as a city on Decembe ...
;Barrett, ''Rudy!'', p. 438. Giuliani looked weak in a public appearance. On May 10, Giuliani held what ''The New York Times'' described as an "extraordinary, emotional news conference" in
Bryant Park Bryant Park is a public park located in the New York City borough of Manhattan. Privately managed, it is located between Fifth Avenue and Avenue of the Americas ( Sixth Avenue) and between 40th and 42nd Streets in Midtown Manhattan. The e ...
to announce that he was seeking a separation from Hanover, saying, "This is very, very painful. For quite some time it's probably been apparent that Donna and I lead in many ways independent and separate lives." Regarding Nathan, Giuliani said "I'm going to need her now more than maybe I did before", making reference to his battle with cancer and her background in nursing. Regarding the Senate race, he again did not commit to a decision, saying, "I don't really care about politics right now. I'm thinking about my family, the people that I love and what can be done that's honest and truthful and that protects them the best. I'm not thinking about politics. Politics comes at least second, maybe third, maybe fourth, somewhere else. It'll all work itself out some way politically." Giuliani had, however, neglected to inform Hanover in advance of his announcement; her reaction was described as distraught. Three hours later, she held her own news conference at
Gracie Mansion Archibald Gracie Mansion (commonly called Gracie Mansion) is the official residence of the Mayor of New York City. Built in 1799, it is located in Carl Schurz Park, at East End Avenue and 88th Street in the Yorkville neighborhood of Manhattan. ...
, where she said, "Today's turn of events brings me great sadness. I had hoped to keep this marriage together. For several years, it was difficult to participate in Rudy's public life because of his relationship with one staff member." In this, she was making reference to Cristyne Lategano, the former communications director for Giuliani; '' Vanity Fair'' had reported in 1997 that Lategano and Giuliani were having an affair, which both of them had denied. Hanover continued, "Beginning last May, I made a major effort to bring us back together. Rudy and I re-established some of our personal intimacy through the fall. At that point, he chose another path." State Republican leaders, who until now had avoided talk of replacements for Giuliani should he not run, now gave more attention to the matter, with the state party convention coming up on May 30. Former possible contenders Rick Lazio and Pete King immediately indicated they were available; other names mentioned included Wall Street financier Theodore J. Forstmann and Governor Pataki, although the latter indicated no interest. Giuliani continued to ponder his Senate race decision; when he had dinner with Nathan on May 12, they were trailed by a flock of photographers. Giuliani canceled campaigning and fundraising trips to upstate New York and California on May 13, suggesting he would not run, but then resumed fundraising and suggested he was inclined towards running on May 15. Two Republican county chairmen became upset at the indecision, saying, "Like ''Waiting for Godot'', we have ''Waiting for Rudy''", and, "We need a decision. Like tomorrow would be nice. Because this is getting ridiculous." A top state Republican said, "He seem to like the attention. He seems to be going through some sort of catharsis in public. And we're like psychiatrists watching it. I can't quite figure it out. I don't think anybody can." Clinton, meanwhile, said as little as possible about the situation, preferring to let Giuliani's drama play out on its own; on May 17, as he huddled with his doctors over whether to choose surgery or radiation as his treatment while facing conflicting political advice from his aides, she won the unanimous approval of delegates to the Democratic Party state convention at the Pepsi Arena in Albany, giving a constrained acceptance speech because she did not know her general election opponent. Finally, on May 19, Giuliani held what ''The New York Times'' again described as "an emotional, riveting news conference" that "reached a new level of introspection" to announce that he was dropping out of the Senate race: "This is not the right time for me to run for office. If it were six months ago or it were a year from now or the timing were a little different, maybe it would be different. But it isn't different and that's the way life is." He added that, "I used to think the core of me was in politics, probably. It isn't. When you feel your mortality and your humanity you realize that, that the core of you is first of all being able to take care of your health." He said that he would instead devote the remainder of his mayoralty trying to overcome the hostile relations he had with many of the city's minority groups.


A change of Republicans: Lazio

While previous Republican candidates and fellow Long Island Congressmen Rick Lazio and Pete King had both indicated an interest in replacing Giuliani, upon Giuliani's withdrawal the state party quickly rallied around Lazio, who had more campaign funds and who was viewed as a potentially strong candidate. In particular, Governor Pataki — who never cared much for Giuliani to begin with — was strongly in favor of Lazio, and praised him as a "fresh, unencumbered challenger" to Clinton. This also caused a shuffle in New York's unique third-party ballot-line alignments: the Liberal Party of New York, which was previously set to run Giuliani (whom they had supported in all three of his mayoral races), now switched to Clinton, while the Conservative Party of New York, which had previously been loath to endorse the socially liberal Giuliani (and was set to nominate former Westchester Congressman
Joe DioGuardi Joseph John DioGuardi (; born September 20, 1940) is an American certified public accountant and a Republican politician. DioGuardi served in the House of Representatives representing the 20th Congressional district of New York from 1985 to 19 ...
) lined up behind Lazio. Lazio accepted the unanimous approval of delegates to the Republican Party state convention at a hotel ballroom in Buffalo on May 30. Clinton now faced a lesser-known candidate in Lazio. While a relative moderate among House Republicans, Lazio had frequently supported former House Speaker Newt Gingrich, a largely despised figure among many New Yorkers. Lazio did bring to the table an ethnic suburban background familiar to many New Yorkers, and had a reputation as an energetic campaigner. One formality left were New York's late-in-the-season primary elections on September 12, which in this case merely served to ratify the state party conventions' choices. Lazio won unopposed, while Clinton won 82 percent of the vote in easily defeating unknown Manhattan doctor Mark McMahon, who ran on the grounds that "the Clintons have tried to hijack the Democratic Party." For her part, Clinton said that she was "surprised, in a way o see her name in the voting booth I stood there for a minute, staring at my name." In any case, the general election was already well underway.


Democratic primary


Results


Republican primary


Polling


General election


Polling

;Clinton v. Giuliani ;Clinton v. D'Amato ;Clinton v. Pataki ;Clinton v. King ;Lowey v. Giuliani ;Lowey v. D'Amato ;Lowey v. Lazio


Campaign

The contest drew considerable national attention and both candidates were well-funded. By the end of the race, Democrat Clinton and Republicans Lazio and Giuliani had spent a combined $90 million, the most of any U.S. Senate race in history. Lazio outspent Clinton $40 million to $29 million, with Clinton also getting several million dollars in
soft money The financing of electoral campaigns in the United States happens at the federal, state, and local levels by contributions from individuals, corporations, political action committees, and sometimes the government. Campaign spending has risen ...
from Democratic organizations. Among Clinton antagonists circles, direct mail-based fundraising groups such as the Emergency Committee to Stop Hillary Rodham Clinton sprung up, sending out solicitations regarding the "carpetbagging" issue. Clinton secured a broad base of support, including endorsements from conservation groups and organized labor, but notably not the New York City police union which endorsed Lazio while firefighters supported Hillary. While Clinton had a solid base of support in New York City, candidates and observers expected the race to be decided in upstate New York where 45 percent of the state's voters lived. During the campaign, Clinton vowed to improve the economic picture in upstate New York, promising that her plan would deliver 200,000 New York jobs over six years. Her plan included specific tax credits with the purpose of rewarding job creation and encouraging business investment, especially in the high-tech sector. She called for targeted personal tax cuts for college tuition and long-term care. Lazio faced a unique tactical problem campaigning upstate. The major issue there was the persistently weak local economy, which Lazio hoped to link to his opponent's husband's tenure in office. Attacks on the state of the upstate economy were frequently interpreted as criticism of incumbent Republican governor
George Pataki George Elmer Pataki (; born June 24, 1945) is an American lawyer and politician who served as the 53rd governor of New York from 1995 to 2006. An attorney by profession, Pataki was elected mayor of his hometown of Peekskill, New York, and went on ...
, however, limiting the effect of this line of attack. In July 2000, the release of ''State of a Union: Inside the Complex Marriage of Bill and Hillary Clinton'' by author
Jerry Oppenheimer Jerry Oppenheimer is an American author who has written several unauthorized biographies of public figures including Hillary and Bill Clinton, Anna Wintour, Rock Hudson, Martha Stewart, Barbara Walters, Ethel Kennedy, Jerry Seinfeld and the Hil ...
led to reports that Clinton had called someone a "fucking Jew bastard" in 1974. The report, which received international media coverage, "rocked" Clinton's campaign, with ''
The Daily Telegraph ''The Daily Telegraph'', known online and elsewhere as ''The Telegraph'', is a national British daily broadsheet newspaper published in London by Telegraph Media Group and distributed across the United Kingdom and internationally. It was f ...
'' describing the campaign as having "mounted a frantic damage limitation exercise after details of the alleged incident were leaked". Clinton had reportedly screamed the insult at Paul Fray, who managed Bill Clinton's unsuccessful 1974 congressional campaign. Fray, his wife, and another campaign staffer stated that they had heard Clinton's outburst, while both Clintons adamantly denied that she had referenced Fray's heritage (while Oppenheimer wrote that Fray's father was Jewish, in reality Fray was a Southern Baptist whose closest Jewish ancestor was a paternal great-grandmother). Bill Clinton did allow that Hillary might have simply called Fray a "bastard". In media interviews, Fray and his wife acknowledged several factors that tended to undermine his credibility: he had lost his license to practice law for altering court records; he had made false accusations against the Clintons in the past; and he had suffered a brain hemorrhage with some resultant losses of memory. Opponents continued to make the carpetbagging issue a focal point throughout the race and during debates.
Talk radio Talk radio is a radio format containing discussion about topical issues and consisting entirely or almost entirely of original spoken word content rather than outside music. Most shows are regularly hosted by a single individual, and often featu ...
hammered on this, with New York-based
Sean Hannity Sean Patrick Hannity (born December 30, 1961) is an American talk show host, conservative political commentator, and author. He is the host of '' The Sean Hannity Show'', a nationally syndicated talk radio show, and has also hosted a commen ...
issuing a daily mantra, "Name me three things Hillary Clinton has ever done for the people of New York!" Clinton's supporters pointed out that the state was receptive to national leaders, such as
Robert F. Kennedy Robert Francis Kennedy (November 20, 1925June 6, 1968), also known by his initials RFK and by the nickname Bobby, was an American lawyer and politician who served as the 64th United States Attorney General from January 1961 to September 1964, ...
who was elected to the Senate in 1964 despite similar accusations. In the end, according to exit polls conducted in the race, a majority of the voters dismissed the carpetbagging issue as unimportant. During the campaign,
Independent Counsel The Office of Special Counsel was an office of the United States Department of Justice established by provisions in the Ethics in Government Act that expired in 1999. The provisions were replaced by Department of Justice regulation 28 CFR Part ...
Robert Ray filed his final reports regarding the long-running
Whitewater Whitewater forms in a rapid context, in particular, when a river's gradient changes enough to generate so much turbulence that air is trapped within the water. This forms an unstable current that froths, making the water appear opaque and ...
,"Ray: Insufficient evidence to prosecute Clintons in Whitewater probe"
,
CNN.com CNN (Cable News Network) is a multinational cable news channel headquartered in Atlanta, Georgia, U.S. Founded in 1980 by American media proprietor Ted Turner and Reese Schonfeld as a 24-hour cable news channel, and presently owned by ...
, September 20, 2000. Retrieved April 30, 2007.
"
Travelgate The White House travel office controversy, sometimes referred to as Travelgate,
''
","Ray: First lady's answers false in travel office probe, but no prosecution"
,
CNN.com CNN (Cable News Network) is a multinational cable news channel headquartered in Atlanta, Georgia, U.S. Founded in 1980 by American media proprietor Ted Turner and Reese Schonfeld as a 24-hour cable news channel, and presently owned by ...
, October 18, 2000. Retrieved June 16, 2007.
and "
Filegate The White House FBI files controversy of the Clinton Administration, often referred to as Filegate,
"Neil A. Lewis
"Report Clears White House In Inquiry Over F.B.I. Files"
''The New York Times'', March 17, 2000. Retrieved June 9, 2007.
investigations of the White House, each of which included specific investigations of Hillary Clinton actions. The reports exonerated her on the files matter, said there was insufficient evidence regarding her role in Whitewater, and said that she had made factually false statements regarding the Travel Office firings but there was insufficient evidence to prosecute her. Although ''The New York Times'' editorialized that the release of the reports seemed possibly timed to coincide with the Senate election, in practice the findings were not seen as likely to sway many voters' opinions. A September 13, 2000 debate between Lazio and Clinton proved important. Lazio was on the warpath against
soft money The financing of electoral campaigns in the United States happens at the federal, state, and local levels by contributions from individuals, corporations, political action committees, and sometimes the government. Campaign spending has risen ...
and the amounts of it coming from the Democratic National Committee into Clinton's campaign, and challenged Clinton to agree to ban soft money from both campaigns. He left his podium and waved his proposed paper agreement in Clinton's face;Gerth, Van Natta Jr., ''Her Way'', pp. 212–213. many debate viewers thought he had invaded her
personal space Proxemics is the study of human use of space and the effects that population density has on behaviour, communication, and social interaction. Proxemics is one among several subcategories in the study of nonverbal communication, including haptics ...
and as a result Clinton's support among women voters solidified. Late in the campaign Lazio criticised Clinton for accepting campaign donations from various Arab groups in the wake of the USS ''Cole'' bombing. The Lazio campaign orchestrated a wave of telephone calls to voters using this attack. This issue caused former New York Mayor
Ed Koch Edward Irving Koch ( ; December 12, 1924February 1, 2013) was an American politician, lawyer, political commentator, film critic, and television personality. He served in the United States House of Representatives from 1969 to 1977 and was ma ...
to take out ads telling Lazio to "stop with the sleaze already," and did not change the dynamic of the race. Some of Lazio's campaign strategists would later say that the ''Cole''-based attack had backfired and became the campaign's biggest blunder.


Results

:''Per New York State law, Clinton and Lazio totals include their minor party-line votes: Liberal Party of New York and
Working Families Party The Working Families Party (WFP) is a minor political party in the United States, founded in New York in 1998. There are active chapters in California, Colorado, Connecticut, Delaware, the District of Columbia, Georgia, Illinois, Maryland, Ne ...
for Clinton, Conservative Party for Lazio.''


Analysis

Clinton won the election on November 7 with 55 percent of the vote to Lazio's 43 percent, a difference larger than most observers had expected. Clinton won the traditionally Democratic base of New York City by large margins, and carried suburban
Westchester County Westchester County is located in the U.S. state of New York. It is the seventh most populous county in the State of New York and the most populous north of New York City. According to the 2020 United States Census, the county had a population ...
, but lost heavily populated Long Island, part of which Lazio represented in Congress. She won 13 of 61 counties, with surprising victories in Upstate counties, such as Cayuga, Rensselaer, and Niagara. Overall, she lost Upstate to Lazio by only 3 percentage points, to which her win has been attributed. In comparison with other results, Clinton's 12-point margin was smaller than Gore's 25-point margin over Bush in the concurrent presidential contest, but was slightly larger than the 10-point margin by which fellow New York senator
Charles Schumer Charles Ellis Schumer ( ; born November 23, 1950) is an American politician serving as Senate Majority Leader since January 20, 2021. A member of the Democratic Party, Schumer is in his fourth Senate term, having held his seat since 1999, and ...
defeated incumbent Republican
Al D'Amato Alfonse Marcello D'Amato (born August 1, 1937) is an American politician born in Brooklyn, Kings County, New York. He served as United States Senator for New York between 1981 and 1999. He subsequently founded a lobbying firm, Park Strategies. ...
in the hotly contested 1998 race, but was considerably smaller than the 47-point margin by which Senator Schumer won reelection in 2004 race against little-known Republican challenger
Howard Mills Howard D. Mills III (born May 29, 1964) is an American insurance consultant and former politician from Goshen, New York. He served as New York's Superintendent of Insurance from 2005 to 2006, and previously held elective office in both the New ...
. The victory of a Democrat in the Senate election was not assured, because in recent decades the Republicans had won about half the elections for governor and senator. Lazio's bid was handicapped by the weak performance of
George W. Bush George Walker Bush (born July 6, 1946) is an American politician who served as the 43rd president of the United States from 2001 to 2009. A member of the Republican Party, Bush family, and son of the 41st president George H. W. Bush, he ...
in New York in the 2000 election, but it was also clear Hillary Clinton had made substantial inroads in upstate New York prior to Lazio's entry into the race. Exit polls also showed a large gender gap with Clinton running stronger than expected among moderate women and unaffiliated women.


Post-election charges


Hasidic pardons

In January 2001, two months after Hillary Rodham Clinton's election to the Senate, President Clinton pardoned four residents of the
New Square New Square ( yi, שיכון סקווירא, Shikun Skvir) is an all-Hasidic village in the town of Ramapo, Rockland County, New York, United States. It is located north of Hillcrest, east of Viola, south of New Hempstead, and west of New Cit ...
Hasidic enclave in
Rockland County Rockland County is the southernmost county on the west side of the Hudson River in the U.S. state of New York. It is part of the New York metropolitan area. It is about from the Bronx at their closest points. The county's population, as of t ...
, New York, who had been convicted of defrauding the federal government of $30 million by establishing a fictitious religious school. New Square had voted almost unanimously for Hillary Rodham Clinton in the New York Senate race. A lawyer following the matter stated that even if Clinton had promised to lobby her husband for clemency in exchange for the town's votes — a claim for which there was no proof — it would be difficult to establish a crime had taken place: "Politicians make promises all the time. That's nothing new — or illegal." Clinton acknowledged sitting in on a post-election meeting discussing possible clemency for the four, but said she had played no part in her husband's decision. A federal investigation launched to investigate various Clinton pardons, closed its investigation of the New Square matter in June 2002 by taking no action against Bill Clinton, Hillary Rodham Clinton, or any residents of New Square.


Hollywood fundraiser

146px, Hillary Clinton with her largest 2000 contributor, Peter Paul, at the Gala Hollywood Farewell Salute to President Clinton. Hillary Clinton's former finance director, David Rosen, was indicted on January 7, 2005 on campaign finance charges related to a fund-raising event produced by Peter F. Paul. Paul, a convicted drug dealer who would soon after be convicted on stock fraud charges after being extradited from Brazil, stated that he spent $1.2 million to produce the August 12, 2000 Hollywood Gala Salute to President William Jefferson Clinton event, which was both a tribute to honor President Clinton and a fundraiser for the First Lady's 2000 Senate campaign. The Justice Department indictment charged Rosen with filing false reports with the
Federal Election Commission The Federal Election Commission (FEC) is an independent regulatory agency of the United States whose purpose is to enforce campaign finance law in United States federal elections. Created in 1974 through amendments to the Federal Election Cam ...
by reporting only $400,000 in contributions. On May 27, 2005, the jury acquitted Rosen on all counts. On January 5, 2006 it was reported that Clinton's campaign group agreed to pay a $35,000 fine related to the underreporting of the fundraiser's expenses. Peter Paul also filed a civil suit in this matter, '' Paul v. Clinton''. On April 10, 2006, the judge in charge of the case removed Hillary Clinton as a defendant, citing a lack of evidence, but leaving open the possibility that she might still be called to testify as a witness in the case. The removal was upheld by the California Second District Court of Appeal on October 16, 2007. Meanwhile, by the time of Hillary Clinton's 2008 presidential campaign, a 13-minute video produced by Paul and describing his various allegations against Hillary Clinton had become quite popular on the Internet, gaining 1.4 million hits on
Google Video Google Video was a free video hosting service launched by the multinational technology company Google on January 25, 2005. Similar to YouTube, this platform allowed video clips to be hosted on Google servers and embedded on to other website ...
and about 350,000 on
YouTube YouTube is a global online video sharing and social media platform headquartered in San Bruno, California. It was launched on February 14, 2005, by Steve Chen, Chad Hurley, and Jawed Karim. It is owned by Google, and is the second mo ...
in a single week in October 2007.


Legacy

Clinton's victory would establish her as an effective campaigner and an electoral force on her own, able to capture Republican and independent votes and overcome her polarizing image. She would easily win re-election in 2006, and in 2007 began her presidential campaign for 2008. Lazio gave up his House seat to run for Senate. Following his defeat, which set a record for the most money spent in a losing Senate effort, he took positions in the corporate world and avoided electoral politics until becoming a candidate in New York's 2010 gubernatorial election. However, he was defeated by a wide margin in the Republican primary. Giuliani would undergo treatment for his cancer and eventually recover; he would also divorce Donna Hanover and eventually marry Judith Nathan. After his campaign withdrawal, his political future looked uncertain at best. But less than a year after the senate general election, the
September 11, 2001 terrorist attacks The September 11 attacks, commonly known as 9/11, were four coordinated suicide terrorist attacks carried out by al-Qaeda against the United States on Tuesday, September 11, 2001. That morning, nineteen terrorists hijacked four commer ...
took place, with Giuliani still mayor. Giuliani's performance in the aftermath of September 11 earned him many accolades and resurrected his political prospects. After a successful stint in the private sector, in 2007 he also began his presidential campaign for 2008. Throughout much of 2007, Clinton and Giuliani led in national polls for their parties' respective nominations, and media reports often looked back to the 2000 "race that wasn't" as a preview of what might lie in wait for the entire nation in 2008. Such extrapolating ended with the Giuliani campaign's precipitous decline and January 2008 withdrawal. Clinton as well failed to gain the 2008 nomination and, in June 2008, she finished in a close second place to Illinois Senator
Barack Obama Barack Hussein Obama II ( ; born August 4, 1961) is an American politician who served as the 44th president of the United States from 2009 to 2017. A member of the Democratic Party, Obama was the first African-American president of the ...
. In December 2008, Lowey would have another chance at the Senate seat, when Clinton was nominated for
U.S. Secretary of State The United States secretary of state is a member of the executive branch of the federal government of the United States and the head of the U.S. Department of State. The office holder is one of the highest ranking members of the president's Ca ...
by President-elect Obama and Lowey was considered a front-runner to be named as her appointed replacement. But Lowey withdrew from consideration, as in the intervening years she had gained enough seniority to become one of the powerful "cardinals" on the
House Appropriations Committee The United States House Committee on Appropriations is a committee of the United States House of Representatives that is responsible for passing appropriation bills along with its Senate counterpart. The bills passed by the Appropriations Commi ...
and did not want to relinquish that position. When
Caroline Kennedy Caroline Bouvier Kennedy (born November 27, 1957) is an American author, attorney, and diplomat serving in the Biden administration as the United States Ambassador to Australia since 2022. She previously served in the Obama administration as th ...
announced her interest in the vacancy, comparisons were drawn to Clinton in 2000, with both being famous people seeking to hold elective office for the first time. Others pointed out that Clinton had won election to the office while Kennedy would first be appointed. In any case, Kennedy's effort soon faltered, in part due to not having the same desire or willingness to work for the seat as Clinton had had, and she soon withdrew as abruptly as she had entered.
Kirsten Gillibrand Kirsten Elizabeth Gillibrand (; ; born December 9, 1966) is an American lawyer and politician serving as the junior United States senator from New York since 2009. A member of the Democratic Party, she served as member of the U.S. House of ...
received the appointment, and attention then turned to who would run against her in the 2010 Senate special election. By November 2009, Giuliani was seriously considering a run for his old would-have-been Senate seat, but the following month he announced he was not running for it or anything else in 2010, signalling an end to his political career. Giuliani and Clinton got another chance to battle each other during the
2016 U.S. presidential election The 2016 United States presidential election was the 58th quadrennial presidential election, held on Tuesday, November 8, 2016. The Republican ticket of businessman Donald Trump and Indiana governor Mike Pence defeated the Democratic ticket ...
, when she was the Democratic nominee and he was one of the few high-profile Republicans to enthusiastically campaign for that party's nominee,
Donald Trump Donald John Trump (born June 14, 1946) is an American politician, media personality, and businessman who served as the 45th president of the United States from 2017 to 2021. Trump graduated from the Wharton School of the University of P ...
. As ''
The Washington Post ''The Washington Post'' (also known as the ''Post'' and, informally, ''WaPo'') is an American daily newspaper published in Washington, D.C. It is the most widely circulated newspaper within the Washington metropolitan area and has a large nati ...
'' wrote, "Rudy Giuliani is finally running the race against Hillary Clinton that he first contemplated some 17 years ago: a brutish bout under a white-hot spotlight." His actions on behalf of Trump included not only fiery attacks on Clinton's record as Secretary of State but also charges that she was experiencing significant problems with her health. A Clinton spokesperson responded by pointing out that it was Giuliani who had left the 2000 senatorial race in part for health reasons, not Clinton. Giuliani said Clinton was "too stupid to be president" for having stayed married to her husband following the
Lewinsky scandal Monica Samille Lewinsky (born July 23, 1973) is an American activist and writer. President Bill Clinton admitted to having an affair with Lewinsky while she worked at the White House as an intern in 1995 and 1996. The affair, and its repercus ...
. Clinton sent some mild barbs Giuliani's way during the
Alfred E. Smith Memorial Foundation Dinner The Alfred E. Smith Memorial Foundation Dinner, commonly known as the Al Smith Dinner, is an annual white tie dinner in New York City, United States, to raise funds for Catholic charities supporting children of various needs in the Archdioce ...
in October 2016, to which Giuliani responded to with stone-faced silence rather than the usual playing-along mirth. The former mayor also issued a false charge against Clinton's statements regarding her role following the September 11 attacks that he had to apologize for. And in the days leading up to the election, Giuliani implied, and then denied, that he had had inside knowledge of the
FBI The Federal Bureau of Investigation (FBI) is the domestic intelligence and security service of the United States and its principal federal law enforcement agency. Operating under the jurisdiction of the United States Department of Justice, t ...
's late-in-the-campaign reopening of its investigation into the Clinton emails matter. Following Clinton's loss, Giuliani was considered to be on Trump's short list for both Attorney General – if picked, he said he would be open to prosecuting Clinton – and Clinton's past job of Secretary of State – where his potential conflicts from his post-mayoral consulting work, advisor roles, and paid speeches for foreign clients and corporations could have exposed him to some of the same charges that he had made against Clinton when she had held that position. In the event, he was not selected for either position. The attacks continued; in March 2018 Giuliani made a joke at a fundraiser at Trump's
Mar-a-Lago Mar-a-Lago ( from the Spanish for ''sea to lake'') is a resort and national historic landmark in Palm Beach, Florida, owned by former U.S. president Donald Trump. Trump acquired Mar-a-Lago in 1985 and referred to it as his "Winter White House ...
resort, the premise of which was that Clinton was almost too fat to fit through doorways. Judith Giuliani was reported to have given her husband a "most foul look" following the remark; the Giulianis announced they were getting divorced a few weeks later. News of the breakup caused media outlets to recall how the Rudy-Judith relationship had all first come to light during the hectic weeks of the 2000 senatorial campaign. Giuliani became even more in the public spotlight as a central figure in the
Trump–Ukraine scandal The "Trump–Ukraine scandal" refers to efforts by U.S. President Donald Trump to coerce Ukraine and other countries into providing damaging narratives about 2020 Democratic Party presidential candidate Joe Biden, and giving misinformatio ...
and the
attempts to overturn the 2020 United States presidential election After Joe Biden won the 2020 United States presidential election, then-incumbent Donald Trump pursued an unprecedented effort to overturn the election, with support and assistance from his campaign, proxies, political allies, and many of ...
, and then as the subject of a federal investigation about possible wrongdoing regarding his actions in the Ukraine. Asked about her onetime campaign opponent in April 2021, Clinton said that Giuliani has "been behaving so erratically and seemingly illegally for so long" that "I don't recognize him now. I don't know what's gotten into him, and we'll see what the investigation concludes."


See also

*
2000 United States Senate elections The 2000 United States Senate elections were held on November 7, 2000. The elections coincided with other federal and state elections, including the presidential election which was won by Republican George W. Bush. It featured a number of fierce ...


References


External links

;Official campaign websites (archived)
Hillary Clinton

Rick Lazio
{{good article New York
2000 File:2000 Events Collage.png, From left, clockwise: Protests against Bush v. Gore after the 2000 United States presidential election; Heads of state meet for the Millennium Summit; The International Space Station in its infant form as seen from S ...
United States Senate The United States Senate is the upper chamber of the United States Congress, with the House of Representatives being the lower chamber. Together they compose the national bicameral legislature of the United States. The composition and pow ...
Hillary Clinton Rudy Giuliani