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=== 2000 U.S. Senate campaign === {{Main|2000 United States Senate election in New York}} [[File:Rudy Giuliani speaking.jpg|thumb|left|Giuliani campaigned for Senate in 2000 before withdrawing after being diagnosed with cancer]] With [[term limits]], Giuliani was ineligible to run in 2001 for a third term as mayor. In November 1998, four-term incumbent Democratic [[United States Senator|U.S. Senator]] [[Daniel Patrick Moynihan]] announced his retirement and Giuliani immediately indicated an interest in running in the 2000 election for the now-open seat. Because of his high profile and visibility, Giuliani was supported by the state Republican Party. Giuliani's entrance led Democratic Congressman [[Charles Rangel]] and others to recruit then-[[First Lady of the United States|First Lady]] [[Hillary Clinton]] to run for Moynihan's seat, hoping she might combat his star power. In April 1999, Giuliani formed an exploratory committee in connection with the Senate run. By January 2000, polling for the race showed Giuliani nine points ahead of Clinton, in part because his campaign was able to take advantage of several campaign stumbles by Clinton.<ref>{{cite news |url=https://www.nytimes.com/2000/01/31/opinion/losing-the-women.html |title=Losing the Women |first=Lee M. |last=Miringoff |work=[[The New York Times]] |date=January 31, 2000 |access-date=September 27, 2007 |archive-date=November 2, 2012 |archive-url=https://web.archive.org/web/20121102082349/http://www.nytimes.com/2000/01/31/opinion/losing-the-women.html |url-status=live }}</ref> In March 2000, however, the [[New York Police Department]]'s fatal shooting of [[Patrick Dorismond]] inflamed Giuliani's strained relations with the city's minority communities,<ref name="Gerth-2007">{{cite book |last1=Gerth |first1=Jeff |author-link=Jeff Gerth |first2=Don Jr. |last2=Van Natta |author2-link=Don Van Natta Jr. |title=Her Way: The Hopes and Ambitions of Hillary Rodham Clinton |year=2007 |publisher=[[Little, Brown and Company]] |location=New York |isbn=978-0-316-01742-8 |url=https://archive.org/details/herwayhopesambit00gert |page=211 |access-date=21 December 2023 }}</ref> and Clinton seized on it as a major campaign issue.<ref name="Gerth-2007" /> By April 2000, reports showed Clinton gaining upstate and generally outworking Giuliani, who said his duties as mayor prevented him from campaigning more.<ref>{{cite news |url=https://www.nytimes.com/2000/04/08/nyregion/despite-polls-giuliani-says-that-he-won-t-alter-his-campaign-style.html |title=Despite Polls, Giuliani Says That He Won't Alter His Campaign Style |last=Nagourney |first=Adam |work=[[The New York Times]] |date=April 8, 2000 |access-date=September 27, 2007 |author-link=Adam Nagourney |archive-date=November 2, 2012 |archive-url=https://web.archive.org/web/20121102082413/http://www.nytimes.com/2000/04/08/nyregion/despite-polls-giuliani-says-that-he-won-t-alter-his-campaign-style.html |url-status=live }}</ref> Clinton was now eight to ten points ahead of Giuliani in the polls.<ref name="Gerth-2007" /> Then followed [[2000 United States Senate election in New York#Giuliani's tumultuous four weeks|four tumultuous weeks]] in which Giuliani learned he had [[prostate cancer]] and needed treatment; his extramarital relationship with [[Judith Nathan]] became public and the subject of a media frenzy; and he announced a separation from his wife [[Donna Hanover]]. After much indecision, on May 19, Giuliani announced his withdrawal from the Senate race.<ref>{{cite news |last=Bumiller |first=Elisabeth |author-link=Elisabeth Bumiller |url=http://partners.nytimes.com/library/politics/camp/052000sen-ny-gop.html |title=Giuliani Quits Race for Senate, and G.O.P. Rallies Around Lazio |newspaper=The New York Times |date=May 20, 2000 |access-date=August 3, 2015 |archive-date=March 5, 2016 |archive-url=https://web.archive.org/web/20160305202329/http://partners.nytimes.com/library/politics/camp/052000sen-ny-gop.html |url-status=live }}</ref>
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