A Democrat and Independent in the 1970s, and a Republican from the 1980s to the present, Giuliani served in the United States Attorney's Office for the Southern District of New York, eventually becoming U.S. Attorney. He prosecuted a number of high-profile cases, including ones against organized crime and Wall Street financiers.
Giuliani served two terms as Mayor of New York City, and was credited with initiating improvements in the city's quality of life and with a reduction in crime. He ran for the United States Senate in 2000 but withdrew due to being diagnosed with prostate cancer and to revelations about his personal life. Giuliani gained international attention during and after the September 11, 2001 attacks on the World Trade Center. In 2001, Time magazine named him "Person of the Year" and he received an honorary knighthood from Queen Elizabeth II in 2002.
After leaving office as mayor, Giuliani founded Giuliani Partners, a security consulting business; acquired Giuliani Capital Advisors (later sold), an investment banking firm; and joined the Bracewell & Giuliani law firm, which changed its name when he became a partner. Giuliani ran for the Republican Party nomination in the 2008 United States presidential election. After leading in national polls for much of 2007, his candidacy faltered late in that year and he did poorly in the early caucuses and primaries in 2008. After finishing in third place in the Florida primary, he withdrew from the race on January 30, 2008 and endorsed John McCain.
Early in life, Rudy Giuliani developed a lateral lisp which he still has to this day.
In 1951, when Giuliani was seven, his family moved from Brooklyn to Garden City South on Long Island. There he attended a local Catholic school, St. Anne's. Later, he commuted back to Brooklyn to attend Bishop Loughlin Memorial High School, graduating in 1961 with an 85 percent average.
Giuliani went on to Manhattan College in Riverdale, Bronx, where he majored in political science with a minor in philosophy. There he considered becoming a priest. Giuliani has stated that this was due in part to having studied theology for four years in college, though nine credits (three semesters) of religious studies courses is the minimum graduation requirement at Manhattan College, which is affiliated with the Roman Catholic Church.
He was elected president of his class in his sophomore year, but was not re-elected in his junior year. He joined the Phi Rho Pi fraternity, and was active in shaping its direction. He graduated in 1965.
Giuliani eventually decided to forego the priesthood, instead attending New York University School of Law in Manhattan, where he made law review and graduated cum laude with a Juris Doctor (J.D.) in 1968.
Giuliani started his political life as a Democrat. He has said that he admired the Kennedy family, and volunteered for Robert F. Kennedy's presidential campaign in 1968. He also worked as a Democratic party committeeman on Long Island in the mid-1960s, and voted for George McGovern for president in 1972.
Giuliani did not serve in the military during the Vietnam War. He received a student deferment while at Manhattan College and another while at NYU Law. Upon graduation from NYU Law in 1968, he was classified as 1-A, available for military service. He applied for a deferment but was rejected. In 1969, MacMahon wrote a letter to Giuliani's draft board, asking that he be reclassified as 2-A, civilian occupation deferment, because Giuliani, who was a law clerk for MacMahon, was an essential employee. The deferment was granted. In 1970, Giuliani received a high draft lottery number; he was not called up for service although by then he had been reclassified 1-A.
In 1970, Giuliani joined the United States Attorney's Office for the Southern District of New York.
In 1973, he was named Chief of the Narcotics Unit and was eventually appointed United States Attorney. In 1975, Giuliani switched his party registration from Democratic to Independent as he was recruited to Washington, D.C. during the Ford administration, where he was named Associate Deputy Attorney General and chief of staff to Deputy Attorney General Harold "Ace" Tyler. His first high-profile prosecution was of U.S. Representative Bertram L. Podell (NY-13), who was convicted of corruption.
From 1977 to 1981, during the Carter Administration, Giuliani practiced law at the Patterson, Belknap, Webb and Tyler law firm, as chief of staff to his previous DC boss, Ace Tyler. Tyler later became critical of Giuliani's turn as a prosecutor, calling his tactics "overkill".
On December 8, 1980, one month after the election of Ronald Reagan brought Republicans back to power in Washington, he switched his party affiliation from Independent to Republican. Giuliani later said the switches were because he found Democratic policies "naïve", and that "by the time I moved to Washington, the Republicans had come to make more sense to me." Others suggested that the switches were made in order to get positions in the Justice Department. Giuliani's mother maintained in 1988 that, "He only became a Republican after he began to get all these jobs from them. He's definitely not a conservative Republican. He thinks he is, but he isn't. He still feels very sorry for the poor."
In 1981, Giuliani was named Associate Attorney General in the Reagan administration, the third-highest position in the Department of Justice. As Associate Attorney General, Giuliani supervised the U.S. Attorney Offices' federal law enforcement agencies, the Department of Corrections, the Drug Enforcement Administration, and the United States Marshals Service.
In a well-publicized 1982 case, Giuliani testified in defense of the federal government's "detention posture" regarding the internment of over 2,000 Haitian asylum seekers who had entered the country illegally. The U.S. government disputed the assertion that most of the detainees had fled their country due to political persecution, alleging instead that they were "economic migrants." In defense of the government's position, Giuliani stated at one point that political repression under President Jean-Claude Duvalier no longer existed. After meeting personally with Duvalier, Giuliani testified that "political repression, at least in general, does not exist" in Haiti under Duvalier's regime.
In 1983, Giuliani was appointed U.S. Attorney for the Southern District of New York. It was in this position that he first gained national prominence by prosecuting numerous high-profile cases, resulting in the convictions of Wall Street figures Ivan Boesky and Michael Milken for insider trading. He also focused on prosecuting drug dealers, organized crime, and corruption in government. He amassed a record of 4,152 convictions and 25 reversals. As a federal prosecutor, Giuliani was credited with bringing the "perp walk," parading of suspects in front of the previously alerted media, into common use as a prosecutorial tool. After Giuliani "patented the perp walk", the tool was used by increasing numbers of prosecutors nationwide.
Giuliani's critics claim he arranged public arrests of people, then dropped charges for lack of evidence on high-profile cases rather than going to trial. In a few cases, his public arrests of alleged white-collar criminals at their workplaces, with charges later dropped or lessened, irreparably damaged their reputations. He claimed that veteran stock trader Richard Wigton, of Kidder, Peabody & Co. was guilty of insider trading; in February 1987 he had officers handcuff Wigton and march him through the company's trading floor, with Wigton in tears. Giuliani had his agents arrest Tim Tabor, a young arbitrageur and former colleague of Wigton, so late that he had to stay overnight in jail before posting bond. However, in three months, charges were dropped against both Wigton and Tabor; Giuliani said, "We're not going to go to trial. We're just the tip of the iceberg," but no further charges were forthcoming and the investigation did not end until Giuliani's successor was in place. Giuliani's high-profile raid of the Princeton/Newport firm ended with the defendants having their cases overturned on appeal on the grounds that what they had been convicted of were not crimes.
Although insider trading of this kind was illegal, laws prohibiting it were rarely enforced until Boesky was prosecuted. Boesky cooperated with the SEC and informed on several of his insiders, including junk bond trader Michael Milken:
"Boesky admitted to numerous offenses and then turned state's evidence, primarily against Milken. He received a 3 1/2 year prison sentence and $100 million fine after admitting to the charges and reached a plea bargain with Rudy Giuliani... [who would] draw criticism because Ivan was allowed to unload his holdings before his indictment was officially announced, realizing profits from it before being convicted. Others considered the sentence and fine as being too light. But Giuliani and company was [sic] after a much bigger fish, namely Milken.
In 1989, Giuliani charged Milken under the RICO Act with 98 counts of racketeering and fraud. In a highly-publicized case, Milken was indicted by a federal grand jury, and pleaded guilty to six lesser securities and reporting violations. He paid a total of $900 million in fines and settlements relating primarily to civil lawsuits and was banned for life from the securities industry.
In the general election, Giuliani ran as the fusion candidate of both the Republican and Liberal Parties. The Conservative Party, which had often co-lined the Republican party candidate, withheld support from Giuliani and ran Lauder instead. Conservative Party leaders were unhappy with Giuliani on ideological grounds. They cited the Liberal Party's endorsement statement that Giuliani "agreed with the Liberal Party's views on affirmative action, gay rights, gun control, school prayer and tuition tax credits.
During two televised debates, Giuliani framed himself as an agent of change, saying that "I'm the reformer," that "If we keep going merrily along, this city's going down," and that electing Dinkins would represent "more of the same, more of the rotten politics that have been dragging us down." Giuliani also accused Dinkins of not having paid his taxes for many years and of several other ethical missteps, in particular a stock transfer to his son. Dinkins said the tax matter had been fully paid off, denied other wrongdoing, and said that "what we need is a mayor, not a prosecutor," and that Giuliani refused to say "the R-word - he doesn't like to admit he's a Republican." Dinkins won the endorsements of three of the four daily New York newspapers, while Giuliani won approval from the New York Post.
In the end, Giuliani lost to Dinkins by 47,080 votes out of 1,899,845 votes cast, in the closest election in city history.
In addition, the city was suffering from a spike in unemployment associated with the nationwide recession, with local unemployment rates going from 6.7 percent in 1989 to 11.1 percent in 1992. There was also a public perception that crime was increasing, although in fact the crime rate in most categories had decreased during the Dinkins administration; for example, the per capita murder rate had peaked and then begun to decline under Dinkins, and rapes decreased in each year of his term.
Giuliani promised to focus the police department on shutting down petty crimes and nuisances as a way of restoring the quality of life: "It's the street tax paid to drunk and drug-ridden panhandlers. It's the squeegee men shaking down the motorist waiting at a light. It's the trash storms, the swirling mass of garbage left by peddlers and panhandlers, and open-air drug bazaars on unclean streets.
Dinkins and Giuliani never debated during the campaign, because they were never able to agree on how to approach a debate. Dinkins was endorsed by The New York Times and Newsday, while Giuliani was endorsed by the New York Post and, in a key switch from 1989, the New York Daily News.
In the end Giuliani won by a margin of 53,367 votes, with 49.25 percent of the electorate to the incumbent's 46.42 percent. He became the first Republican elected Mayor of New York City since John Lindsay in 1965.
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. All four daily New York newspapers—The New York Times, New York Daily News, New York Post, and Newsday—endorsed Giuliani over Messinger.
In the end, Giuliani won 59 percent of the vote to Messinger's 41 percent, and became the first Republican to win a second term as mayor since Fiorello H. La Guardia in 1941. Voter turnout was the lowest in 12 years, with 38 percent of registered voters casting ballots. The margin of victory included gains in his share of the African American vote (20 percent compared to five percent in 1993) and the Hispanic vote (43 percent from 37 percent) while maintaining his base of white and Jewish voters from 1993.
During Giuliani's administration, crime rates dropped in New York City, which Giuliani's presidential campaign website has credited to his leadership. The extent to which his policies deserve the credit is disputed, however. A small nationwide drop in crime preceded Giuliani's election, and critics say that he may have been the beneficiary of a trend already in progress. Additional contributing factors to the overall decline in crime during the 1990s were federal funding of an additional 7,000 police officers and an overall improvement in the national economy. Changing demographics were a key factor contributing to crime rate reductions, which were similar across the country during this time. Because the crime index is based on that of the FBI, which is self-reported by police departments, some have alleged that crimes were shifted into categories that the FBI doesn't collect.
Giuliani's supporters cite studies concluding that New York's drop in crime rate in the '90s and '00s exceeds all national figures and therefore should be linked with a local dynamic that was not present as such anywhere else in the country: what University of California sociologist Frank Zimring calls "the most focused form of policing in history". In his book The Great American Crime Decline, Zimring claims that "up to half of New York’s crime drop in the 1990s, and virtually 100 percent of its continuing crime decline since 2000, has resulted from policing.
Bratton was featured on the cover of Time in 1996. Giuliani forced Bratton out of his position after two years, in what was generally seen as a battle of two large egos in which Giuliani was not tolerant of Bratton's celebrity.
Giuliani's term also saw allegations of civil rights abuses and other police misconduct. There were police shootings of unarmed suspects, and the scandals surrounding the sexual torture of Abner Louima and the killings of Amadou Diallo and Patrick Dorismond. Giuliani supported the New York Police Department, for example by releasing what he called Dorismond's "extensive criminal record" to the public, including a sealed juvenile file.
Giuliani supported protection for illegal immigrants. He continued a policy of preventing city employees from contacting the Immigration and Naturalization Service about immigration violations, on the grounds that illegal aliens should be able to take actions such as sending their children to school or reporting crimes to the police without fear of deportation.
During his mayoralty, gay and lesbian New Yorkers received domestic partnership rights. Giuliani induced the city's Democratic-controlled New York City Council, which had avoided the issue for years, to pass legislation providing broad protection for same-sex partners. In 1998, he codified local law by granting all city employees equal benefits for their domestic partners.
In 2000, Giuliani appointed 34-year-old Russell Harding, the son of Liberal Party of New York leader and longtime Giuliani mentor Raymond Harding, to head the New York City Housing Development Corporation, although Harding had neither a college degree nor relevant experience. In 2005, Harding pleaded guilty to defrauding the Housing Development Corporation and to possession of child pornography. He was sentenced to five years in prison. In a related matter, Richard Roberts, appointed by Giuliani as Housing Commissioner and as chairman of the Health and Hospitals Corporation, pleaded guilty to perjury after lying to a grand jury about a car that Harding bought for him with City funds.
Giuliani was a longtime backer of Bernard Kerik, who started out as a NYPD detective driving for Giuliani's campaign. Giuliani appointed him as the Commissioner of the Department of Correction and then as the Police Commissioner. After Giuliani left office, Kerik pleaded guilty to state corruption charges dating from his Corrections days. Kerik is currently awaiting trial on related federal charges of conspiracy, tax fraud and obstruction of justice. Giuliani has not been implicated in any of the Kerik scandals.
A January 1999 poll showed Giuliani trailing Clinton by 10 points. In April 1999, Giuliani formed an exploratory committee in connection with the Senate run. By January 2000, Giuliani had reversed the polls situation, pulling nine points ahead after taking advantage of several campaign stumbles by Clinton. Nevertheless, the Giuliani campaign was showing some structural weaknesses; so closely identified with New York City, he had somewhat limited appeal to Republican voters in Upstate New York. The New York Police Department's fatal shooting of Patrick Dorismond in March 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 2000, reports showed Clinton gaining upstate and generally outworking Giuliani, who stated that his duties as mayor prevented him from campaigning more. Clinton was now 8 to 10 points ahead of Giuliani in the polls.
Then followed four tumultuous weeks, in which Giuliani's medical life, romantic life, marital life, and political life all collided at once in a most visible fashion. Giuliani discovered that he had prostate cancer and needed treatment; his extramarital relationship with Judith Nathan became public and the subject of a media frenzy; he announced a separation from his wife Donna Hanover; and, on May 19, 2000 he announced his withdrawal from the Senate race.
The 9/11 attacks occurred on the scheduled date of the mayoral primary to select the Democratic and Republican candidates to succeed Giuliani. The primary was immediately delayed two weeks to September 25. During this period, Giuliani sought an unprecedented three-month emergency extension of his term from January 1 to April 1 under the New York State Constitution (Article 3 Section 25), but the State Assembly and Senate did not approve it. The request was backed by the threat of a run for a third mayoral term as a Conservative Party candidate, requiring a legal challenge to the law imposing term limits on elected New York City officials.
Giuliani claimed to have been at the Ground Zero site "as often, if not more, than most workers.... I was there working with them. I was exposed to exactly the same things they were exposed to. So in that sense, I'm one of them." Some 9/11 workers have objected to those claims. While his appointment logs were unavailable for the six days immediately following the attacks, after that Giuliani spent a total of 29 hours over three months at the site. This contrasted with recovery workers at the site who spent this much time at the site in two to three days.
When Saudi Prince Alwaleed bin Talal suggested that the attacks were an indication that the United States "should re-examine its policies in the Middle East and adopt a more balanced stand toward the Palestinian cause", Giuliani asserted, "There is no moral equivalent for this act. There is no justification for it... And one of the reasons I think this happened is because people were engaged in moral equivalency in not understanding the difference between liberal democracies like the United States, like Israel, and terrorist states and those who condone terrorism. So I think not only are those statements wrong, they're part of the problem." Giuliani subsequently rejected the prince's $10 million donation to disaster relief in the aftermath of the attack.
In January 2008, an eight-page memo was revealed which detailed the New York City Police Department's opposition in 1998 to location of the city's emergency command center at the Trade Center site. The Giuliani administration overrode these concerns.
The 9/11 Commission noted in its report that lack of preparedness could have led to the deaths of first responders at the scene of the attacks. The Commission noted that the radios in use by the fire department were the same radios which had been criticized for their ineffectiveness following the 1993 World Trade Center bombings. Family members of 9/11 victims have said that these radios were a complaint of emergency services responders for years. The radios were not working when Fire Department chiefs ordered the 343 firefighters inside the towers to evacuate, and they remained in the towers as the towers collapsed. However, when Giuliani testified before the 9/11 Commission he said that the firefighters ignored the evacuation order out of an effort to save lives. Giuliani testified to the Commission, where some family members of responders who had died in the attacks appeared to protest his statements. A 1994 mayoral office study of the radios indicated that they were faulty. Replacement radios were purchased in a $33 million no-bid contract with Motorola, and implemented in early 2001. However, the radios were recalled in March 2001 after a Probationary Firefighter's calls for help at a house fire could not be picked up by others at the scene, leaving firemen with the old analog radios from 1993. A book later published by Commission members Thomas Kean and Lee Hamilton, Without Precedent: The Inside Story of the 9/11 Commission, argued that the Commission had not pursued a tough enough line of questioning with Giuliani.
An October 2001 study by the National Institute of Environmental Safety and Health said that cleanup workers lacked adequate protective gear.
On December 24, 2001, Time magazine named Giuliani its Person of the Year for 2001. Time observed that, prior to 9/11, the public image of Giuliani had been that of a rigid, self-righteous, ambitious politician. After 9/11, and perhaps owing also to his bout with prostate cancer, his public image had been reformed to that of a man who could be counted on to unite a city in the midst of its greatest crisis. Thus historian Vincent J. Cannato concluded in September 2006, "With time, Giuliani's legacy will be based on more than just 9/11. He left a city immeasurably better off — safer, more prosperous, more confident — than the one he had inherited eight years earlier, even with the smoldering ruins of the World Trade Center at its heart. Debates about his accomplishments will continue, but the significance of his mayoralty is hard to deny.
Giuliani was praised by some for his close involvement with the rescue and recovery efforts, but others, including some firefighters, police, rescue workers, and families of WTC victims argue that "Giuliani has exaggerated the role he played after the terrorist attacks, casting himself as a hero for political gain. Giuliani has collected $11.4 million from speaking fees in a single year (his demand increasing after the attacks). Before September 11, Giuliani's assets were estimated to be somewhat less than $2 million, but his net worth could now be as high as 30 times that amount.
Giuliani took control away from agencies such as the Federal Emergency Management Agency, the Army Corps of Engineers and the Occupational Safety and Health Administration, leaving the "largely unknown" city Department of Design and Construction in charge of recovery and cleanup. Documents indicate that the Giuliani administration never enforced federal requirements requiring the wearing of respirators. Concurrently, the administration threatened companies with dismissal if cleanup work slowed. In June 2007, Christie Todd Whitman, former Republican Governor of New Jersey and director of the Environmental Protection Agency, reportedly stated that the EPA had pushed for workers at the WTC site to wear respirators but that she had been blocked by Giuliani. She stated that she believed that the subsequent lung disease and deaths suffered by WTC responders were a result of these actions. However, former deputy mayor Joe Lhota, now with the Giuliani campaign, replied, "All workers at Ground Zero were instructed repeatedly to wear their respirators." A safety professional who worked at Ground Zero added, "I was absolutely aghast at the refusal of the workers at ground zero to wear the personal protective equipment. All of my efforts to convince these guys to wear the masks was for naught.
Giuliani asked the city's Congressional delegation to limit the city's liability for Ground Zero illnesses be limited to a total of $350 million. Two years after Giuliani finished his term, FEMA appropriated $1 billion to a special insurance fund to protect the city against 9/11 lawsuits.
In February 2007, the International Association of Fire Fighters issued a letter asserting that Giuliani rushed to conclude the recovery effort once gold and silver had been recovered from World Trade Center vaults and thereby prevented the remains of many victims from being recovered: "Mayor Giuliani's actions meant that fire fighters and citizens who perished would either remain buried at Ground Zero forever, with no closure for families, or be removed like garbage and deposited at the Fresh Kills Landfill," it said, adding: "Hundreds remained entombed in Ground Zero when Giuliani gave up on them. Lawyers for the International Association of Fire Fighters seek to interview Giuliani under oath as part of a federal legal action alleging that New York City negligently dumped body parts and other human remains in the Fresh Kills Landfill.
Similarly, in June 2006, Giuliani started a website called Solutions America to help elect Republicans candidates across the nation.
After campaigning on Bush's behalf in the 2004 election, he was reportedly the top choice for Secretary of Homeland Security after Tom Ridge's resignation. When suggestions were made that Giuliani's confirmation hearings would be marred by details of his past affairs and scandals, he turned down the offer and instead recommended his friend and former New York Police Commissioner Bernard Kerik. After the formal announcement of Kerik's nomination, information about Kerik's past — most notably, that he had ties to organized crime, had been sued for sexual harassment and had employed an undocumented alien as a domestic servant — became known. The political fallout damaged the perception of competence in the White House vetting process and doubts as to Giuliani's ethics and political judgment in recommending Kerik in the first place.
A May 14, 2007 New York Daily News poll indicates that 56 percent of polled New Yorkers believe that Michael Bloomberg has done a better job as mayor, and that 29 percent believed that Giuliani had been a better mayor. 46 percent of those polled also indicated they would choose Bloomberg over Giuliani as President; Giuliani received the support of only 29 percent of New Yorkers.
On May 24, 2006, after missing all of the group's meetings, including a briefing from General David Petraeus, former Secretary of State Colin Powell and former Army Chief of Staff Eric Shinseki, Giuliani resigned from the panel, citing his "previous time commitments". It later was discovered that Giuliani's fundraising schedule had kept him from participating in the panel, a schedule which raised $11.4 million in speaking fees over 14 months, and that Giuliani had been forced to resign after being given "an ultimatum to either show up for meetings or leave the group" by group leader James Baker. Giuliani subsequently said that he had started thinking about running for President, and being on the panel might give it a political spin. But Slate noted that Giuliani had "been set to run for months, if not years" before he accepted appointment to the study group.
Giuliani was described by Newsweek in January 2007 as "one of the most consistent cheerleaders for the president’s handling of the war in Iraq and as of June 2007 remained one of the few candidates for president to unequivocally support both the basis for the invasion and the execution of the war.
While there was early speculation that the firm would merge with Giuliani Partners, this is a legal impossibility because as a matter of ethics, lawyers cannot share legal fees with non-lawyers. However, while the firm is completely independent of the consulting business, the two entities maintain a close strategic partnership.
On May 15, 2007 the Associated Press reported that Giuliani "has profited from his firm's work representing corporate clients before nearly every Cabinet department, exposing himself to a wide range of potential ethical entanglements." It was further reported that Giuliani's efforts on behalf of clients such as the Kingdom of Saudi Arabia and the chewing tobacco manufacturer UST Inc. [née United States Tobacco] had "contributed toward his personal net worth of millions of dollars.
Bracewell & Giuliani has also been tied to the Trans-Texas Corridor, as the firm represents Cintra Concesiones de Infraestructuras de Transporte, S.A, one of the investment firms involved in the financing of the project.
In 2006, Giuliani acted as the "lead counsel and lead spokesmen" for Bracewell & Giuliani client Purdue Pharma, the makers of Oxycontin, during their negotiations with federal prosecutors over charges that the pharmaceutical company misled the public about Oxycontin's addictive properties; the agreement reached resulted in Purdue Pharma and some of its executives paying $634.5 million in fines.
A draft movement began in late 2005 to get Giuliani to run for President of the United States in 2008. Throughout 2006, rumors circulated regarding a possible Giuliani campaign, abetted by hints from the former Mayor himself. In November 2006 Giuliani announced the formation of an exploratory committee. In February 2007 he filed a "statement of candidacy" and confirmed on the television program Larry King Live that he was indeed running.
Early polls showed him with one of the highest levels of name recognition and support and the front-runner in the opinion polls for the Republican nomination. As of September 2007, most polls showed Giuliani to have more support than any of the other declared Republican candidates, with only Senator Fred Thompson and Governor Mitt Romney showing greater support in some state polls. On November 7, 2007, Giuliani's campaign received an endorsement from evangelist, Christian Broadcasting Network founder, and past presidential candidate Pat Robertson. This was viewed by political observers as a possibly key development in the race, as it gave credence that evangelicals and other social conservatives could support Giuliani despite some of his positions on social issues such as abortion and gay rights.
Giuliani's campaign hit a difficult stretch during November and December 2007, in which Bernard Kerik, whom Giuliani had appointed to or recommended for several top positions, was indicted on 16 counts of tax fraud and other federal charges; the media reported that while Mayor of New York, Giuliani had billed to obscure city agencies several tens of thousands of dollars of mayoral security expenses incurred while visiting Judith Nathan, with whom he was having an extramarital affair (later analysis showed the billing to likely be unrelated to hiding Nathan); and several stories were published in the press regarding clients of Giuliani Partners and Bracewell & Giuliani being in opposition to goals of American foreign policy. Giuliani's national poll numbers began steadily slipping and his unusual strategy of focusing more on later, multi-primary big states rather than the smaller, first-voting states was seen at risk.
Despite his strategy, Giuliani did compete to a substantial extent in the January 8, 2008 New Hampshire primary, but finished a distant fourth with 9 percent of the vote. Similar poor results continued in other early contests, as Giuliani's staff went without pay in order to focus all efforts on the crucial late January Florida Republican primary. The shift of the electorate's focus from national security to the state of the economy also hurt Giuliani, as did the resurgence of Senator John McCain's similarly-themed campaign. On January 29, 2008, Giuliani finished a distant third in the Florida result with 15 percent of the vote, trailing McCain and Romney. Facing declining polls and lost leads in the upcoming large Super Tuesday states, including that of his home New York, Giuliani withdrew from the race on January 30, endorsing McCain.
Giuliani's campaign ended up $3.6 million in arrears, and in June 2008 Giuliani sought to retire the debt by proposing to appear at Republican fundraisers during the 2008 general election, and have part of the proceeds go towards his campaign. After Giuliani's campaign ended he supported the candidacy of John McCain.
On September 3, 2008, the third night of the Republican National Convention in St. Paul, Minnesota, Giuliani addressed the assembled delegates in a speech praising McCain and his running-mate, Sarah Palin, while criticizing Democratic nominee Barack Obama. He cited Palin's executive experience, saying of her, "She's vetoed legislation, she's taken on corruption, and in her party, and won. She took on the oil companies and won. She administered a budget successfully." Of Obama, he said "He's never run a city, he's never run a state, he's never run a business, he's never administered a payroll, he's never led people in crisis". Rudy's remarks were met with wild applause from the delegates.
Giuliani has been married three times. On October 26, 1968, soon after he graduated from law school, he married his second cousin, educator Regina Peruggi, whom Giuliani had known since childhood. In the mid-70s the marriage was in trouble and in 1975 they agreed to a trial separation. Peruggi did not accompany him to Washington when he accepted the job in the Attorney General's Office. Giuliani met local television personality Donna Hanover sometime in 1982, and they began dating when she was working in Miami. Giuliani filed for legal separation from Peruggi on August 12, 1982. Giuliani and Hanover started living together later that year in Washington, D.C. The Giuliani-Peruggi marriage was ended in two ways: a civil divorce was issued by the end of 1982, while a Roman Catholic Church annulment of the Giuliani-Peruggi marriage was granted at the end of 1983, according to Giuliani, because he discovered after 14 years of marriage that he and his wife were second cousins once removed, rather than third cousins, and they did not have the Church dispensation thus needed. Giuliani and Peruggi did not have any children.
Giuliani and Hanover then married in a Catholic ceremony at St. Monica's Church in New York on April 15, 1984. They had two children, son Andrew Harold (born January 30, 1986 in New York) and daughter Caroline (born 1989). Andrew first became a familiar sight by misbehaving at Giuliani's first mayoral inauguration, then with his father at New York Yankees games, of which Rudy Giuliani is an enthusiastic fan; Andrew also was an accomplished junior golfer.
Beginning in 1996, Giuliani and Hanover's public relationship became distant, with Hanover appearing at few public events. In 1997, a Vanity Fair article reported that Giuliani had a romantic relationship with Cristyne Lategano, the mayor's communications director. The mayor and Lategano denied the allegations. On Father's Day, 1995 Giuliani had told reporters that he was returning to Gracie Mansion to play ball with Andrew. However, he instead went to City Hall, to a basement suite with his press secretary. Three hours later, Hanover, angered, appeared at City Hall; A mayoral aide prevented her from entering the suite.
Giuliani met Judith Nathan, a sales manager for a pharmaceutical company, in May 1999 at Club Macanudo, an Upper East Side cigar bar; he took the initiative in forming an ongoing relationship that was kept secret for almost a year. Beginning in summer 1999, costs for his New York Police Department security detail during weekend visits to her in Southhampton, New York were charged to obscure city agencies. In early 2000, Nathan began getting city-provided chauffeur services from the police department. By March 2000, Giuliani had stopped wearing his wedding ring, and his and Nathan's appearances together at functions and events became publicly visible but not mentioned in the press. In early May 2000, the New York Daily News and then the New York Post broke news of Giuliani's relationship with Nathan. Giuliani first publicly acknowledged her on May 3, 2000, stating that Nathan was his "very good friend."
On May 10, 2000, Giuliani called a press conference to announce that he intended to separate from Hanover. Hanover, however, had not been told about his plans before his press conference, an omission for which Giuliani was widely criticized. Giuliani now went on to praise Nathan as a "very, very fine woman", and said about his marriage with Hanover, that "over the course of some period of time in many ways, we've grown to live independent and separate lives." Hours later Hanover said, "I had hoped that we could 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," a reference to Lategano. Giuliani, Hanover and Nathan appeared on the cover of People in the aftermath.
Giuliani then moved out of Gracie Mansion and into an apartment belonging to two gay friends. Giuliani filed for divorce from Hanover in October 2000, and a public battle broke out between their representatives. Nathan was barred by court order from entering Gracie Mansion (where Hanover still lived) or meeting his children before the divorce was final. In May 2001, in an effort to mitigate the bad publicity from the proceedings, Giuliani's attorney revealed (with the mayor's approval) that Giuliani was impotent due to his prostate cancer treatments and had not had sex with Nathan for the preceding year. "You don't get through treatment for cancer and radiation all by yourself," Giuliani said. "You need people to help you and care for you and support you. And I'm very fortunate I had a lot of people who did that, but nobody did more to help me than Judith Nathan." Giuliani argued in a court case that he aimed to introduce Nathan to his children on Father's Day, 2001, and that Hanover had prevented this visit. Giuliani and Hanover finally settled their acrimonious divorce case in July 2002, after his mayoralty had ended, with Giuliani paying Hanover a $6.8 million settlement and granting her custody of their children.
By March 2007, The New York Times and the New York Daily News reported that Giuliani had become estranged from both his son Andrew and his daughter Caroline, missing major events in their lives, such as graduations, and sometimes going long stretches without talking to them, and that neither of them was taking part in his presidential campaign. Caroline uses her mother's surname, Hanover, rather than Giuliani's, and according to reports, she did not inform Giuliani when she was accepted to Harvard. Caroline apparently linked her personal Facebook page to a page related to the campaign of Democratic presidential candidate Senator Barack Obama. After a slate.com contributor reported this link, Caroline removed it from her Facebook page.
Giuliani is the godfather to former New York City police commissioner Bernard Kerik's two youngest children.
Giuliani has declined to comment publicly on his religious practice and beliefs, although he identifies religion as an important part of his life. When asked if he is a practicing Catholic, Giuliani answered, "My religious affiliation, my religious practices and the degree to which I am a good or not-so-good Catholic, I prefer to leave to the priests.