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=== 1997 === {{Main|1997 New York City mayoral election}} Giuliani's opponent in 1997 was Democratic Manhattan Borough president [[Ruth Messinger]], who had beaten [[Al Sharpton]] in the September 9, 1997, Democratic primary.<ref name="Oppmann-2007">{{cite web |url=http://www.cnn.com/ALLPOLITICS/1997/11/04/mayor/ |first=Justin |last=Oppmann |access-date=May 24, 2023 |title=Giuliani Wins With Ease |work=CNN |date=November 4, 2007 |archive-date=September 25, 2020 |archive-url=https://web.archive.org/web/20200925234015/http://www.cnn.com/ALLPOLITICS/1997/11/04/mayor/ |url-status=live }}</ref> In the general election, Giuliani once again had the Liberal Party and not the Conservative Party listing. Giuliani ran an aggressive campaign, parlaying his image as a tough leader who had cleaned up the city. Giuliani's popularity was at its highest point to date, with a late October 1997 [[Quinnipiac University Polling Institute]] poll showing him as having a 68 percent approval rating; 70 percent of New Yorkers were satisfied with life in the city and 64 percent said things were better in the city compared to four years previously.<ref>{{cite web |url=https://www.quinnipiac.edu/news-and-events/quinnipiac-university-poll/new-york-city/release-detail?ReleaseID=808 |title=Giuliani Approval, Satisfaction With City Hit New Highs, Quinnipiac College Poll Finds; Mayor's Lead Over Messinger Nears 2β1 |publisher=[[Quinnipiac University]] |date=October 29, 1997 |access-date=November 19, 2015 |archive-date=November 20, 2015 |archive-url=https://web.archive.org/web/20151120184337/https://www.quinnipiac.edu/news-and-events/quinnipiac-university-poll/new-york-city/release-detail?ReleaseID=808 |url-status=dead }}</ref> Throughout the campaign he was well ahead in the polls and had a strong fund-raising advantage over Messinger. On her part, Messinger lost the support of several usually Democratic constituencies, including gay organizations and large labor unions.<ref>{{cite news |url=http://www.time.com/time/magazine/article/0,9171,987322,00.html |archive-url=https://web.archive.org/web/20070930050256/http://www.time.com/time/magazine/article/0,9171,987322,00.html |url-status=dead |archive-date=September 30, 2007 |title=The Last of the Liberals |first=Peter |last=Beinart |author-link=Peter Beinart |date=November 10, 1997 |access-date=August 16, 2016 |magazine=Time}}</ref> The local daily newspapers{{snd}}''The New York Times'', ''[[Daily News (New York)|Daily News]]'', ''[[New York Post]]'' and ''[[Newsday]]''{{snd}}all endorsed Giuliani over Messinger.<ref>{{cite web |first=Norimitsu |last=Onishi |url=https://www.nytimes.com/1997/10/27/nyregion/1997-elections-campaigning-giuliani-goes-after-voters-messinger-s-stronghold.html |title=Giuliani Goes After Voters In Messinger's Stronghold |work=The New York Times |date=October 27, 1997 |access-date=June 24, 2007 |archive-date=November 2, 2012 |archive-url=https://web.archive.org/web/20121102100033/http://www.nytimes.com/1997/10/27/nyregion/1997-elections-campaigning-giuliani-goes-after-voters-messinger-s-stronghold.html |url-status=live }}</ref> In the end, Giuliani won 58% of the vote to Messinger's 41%, becoming the first registered Republican to win a second term as mayor while on the Republican line since [[Fiorello H. La Guardia]] in 1941.<ref name="Oppmann-2007" /> Voter turnout was the lowest in twelve years, with 38% of registered voters casting ballots.<ref>{{cite web |first=Adam |last=Nagourney |author-link=Adam Nagourney |url=https://www.nytimes.com/1997/11/05/nyregion/1997-elections-overview-giuliani-sweeps-second-term-mayor-whitman-holds-razor.html |title=The 1997 Elections: The Overview; Giuliani Sweeps To Second Term As Mayor; Whitman Holds On By A Razor-Thin Margin |work=The New York Times |date=November 5, 1997 |access-date=June 24, 2007 |archive-date=August 11, 2023 |archive-url=https://web.archive.org/web/20230811101438/https://www.nytimes.com/1997/11/05/nyregion/1997-elections-overview-giuliani-sweeps-second-term-mayor-whitman-holds-razor.html |url-status=live }}</ref> The margin of victory included gains<ref name="Firestone-1997">{{cite news |first=David |last=Firestone |url=https://www.nytimes.com/1997/11/06/nyregion/the-1997-elections-the-voters-big-victory-but-gains-for-mayor-are-modest.html |title=The 1997 Elections: The Voters; Big Victory, But Gains For Mayor Are Modest |work=The New York Times |date=November 6, 1997 |access-date=June 24, 2007 |archive-date=January 21, 2023 |archive-url=https://web.archive.org/web/20230121073125/https://www.nytimes.com/1997/11/06/nyregion/the-1997-elections-the-voters-big-victory-but-gains-for-mayor-are-modest.html |url-status=live }}</ref> in his share of the [[African American]] vote (20% compared to 1993's 5%) and the [[Hispanic]] vote (43% from 37%) while maintaining his base of white ethnic and Catholic and Jewish voters from 1993.<ref name="Firestone-1997" />
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