Rudy Giuliani

When Giuliani was seven years old in 1951, his family moved from Brooklyn to Garden City South, where he attended the local Catholic school, St. Anne's. Later, he commuted back to Brooklyn to attend Bishop Loughlin Memorial High School, graduating in 1961.

Giuliani attended Manhattan College in Riverdale, Bronx, where he majored in political science with a minor in philosophy and considered becoming a priest. Giuliani 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. He graduated in 1965. Giuliani decided to forgo the priesthood and instead attended the New York University School of Law in Manhattan, where he made the NYU Law Review and graduated cum laude with a Juris Doctor degree in 1968.

Giuliani won by a margin of 53,367 votes. He became the first Republican elected Mayor of New York City since John Lindsay in 1965.

Giuliani started his political life as a Democrat. He 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. His conscription was deferred while he was enrolled at Manhattan College and NYU Law. Upon graduation from the latter in 1968, he was classified 1-A (available for military service), but in 1969 he was reclassified 2-A (essential civilian) as Judge MacMahon's law clerk. 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.

On October 26, 1968, Giuliani married Regina Peruggi, whom he had known since childhood. By the mid-1970s, the marriage was in trouble and they agreed to a trial separation in 1975. Peruggi did not accompany him to Washington when he accepted the job in the Attorney General's Office.

In 1975, Giuliani switched his party registration from Democratic to Independent. This occurred during a period of time in which he was recruited for a position in Washington, D.C. with the Ford administration: Giuliani served as the Associate Deputy Attorney General and chief of staff to Deputy Attorney General Harold "Ace" Tyler.

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 former boss, Ace Tyler. In later years, Tyler became "disillusioned" by what Tryler described as Giuliani's time as US Attorney, criticizing several of his prosecutions as "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:

Giuliani was born in the East Flatbush section, then an Italian-American enclave, in New York City's borough of Brooklyn, as the only child of working-class parents, Harold Angelo Giuliani (1908–1981) and Helen Giuliani (née D'Avanzo; 1909–2002), both children of Italian immigrants. Giuliani is of Tuscan origins from his father, as his paternal grandparents (Rodolfo and Evangelina Giuliani) were born in Montecatini Terme, Tuscany, Italy. He was raised a Roman Catholic. Harold Giuliani, a plumber and a bartender, had trouble holding a job, was convicted of felony assault and robbery, and served prison time in Sing Sing. Once released, he worked as an enforcer for his brother-in-law Leo D'Avanzo, who operated for organized crime a loan sharking and gambling ring at a restaurant in Brooklyn. The couple lived in East Flatbush until Harold died of prostate cancer in 1981, whereupon Helen moved to Manhattan's Upper East Side.

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 more than 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 testified that "political repression, at least in general, does not exist" under President of Haiti Jean-Claude Duvalier's regime.

In April 1981, Giuliani's father died at age 73 of prostate cancer at Memorial Sloan–Kettering Cancer Center. Nineteen years later in April 2000, Giuliani was 55 when diagnosed with prostate cancer on prostate biopsy after an elevated screening PSA. Giuliani chose a combination prostate cancer treatment consisting of four months of neoadjuvant Lupron hormonal therapy, then low dose-rate prostate brachytherapy with permanent implantation of ninety TheraSeed radioactive palladium-103 seeds in his prostate in September 2000, followed two months later by five weeks of fifteen-minute, five-days-a-week external beam radiotherapy at Mount Sinai Medical Center, with five months of adjuvant Lupron hormonal therapy.

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. The Giuliani-Peruggi marriage legally 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 reportedly because Giuliani had discovered that he and Peruggi were second cousins. Alan Placa, Giuliani's best man, later became a priest and helped get the annulment. Giuliani and Peruggi did not have any children.

In 1983, Giuliani was appointed to be U.S. Attorney for the Southern District of New York, which was technically a demotion but was sought by Giuliani because of his desire to personally litigate cases and because the SDNY is considered the highest profile United States Attorney's Office in the country, and as such, is often used by those who have held the position as a springboard for running for public office. 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. 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 and Hanover then married in a Catholic ceremony at St. Monica's Church in Manhattan on April 15, 1984. They had two children, son Andrew and daughter Caroline. Caroline Rose Giuliani is a filmmaker in the LGBTQ+ community, and described herself as "multiverses apart" from her father.

In the Mafia Commission Trial, which ran from February 25, 1985, through November 19, 1986, Giuliani indicted 11 organized crime figures, including the heads of New York's so-called "Five Families", under the Racketeer Influenced and Corrupt Organizations Act (RICO) on charges including extortion, labor racketeering, and murder for hire. Time magazine called this "Case of Cases" possibly "the most significant assault on the infrastructure of organized crime since the high command of the Chicago Mafia was swept away in 1943", and quoted Giuliani's stated intention: "Our approach is to wipe out the five families." Gambino crime family boss Paul Castellano evaded conviction when he and his underboss, Thomas Bilotti, were murdered on the streets of Midtown Manhattan on December 16, 1985. However, three heads of the Five Families were sentenced to 100 years in prison on January 13, 1987. Genovese and Colombo leaders, Tony Salerno and Carmine Persico received additional sentences in separate trials, with 70-year and 39-year sentences to run consecutively. He was assisted by three Assistant United States Attorneys: Michael Chertoff, the eventual second United States Secretary of Homeland Security and co-author of the Patriot Act; John Savarese, now a partner at Wachtell Lipton Rosen & Katz; and Gil Childers, a later deputy chief of the criminal division for the Southern District of New York and now managing director in the legal department at Goldman Sachs.

Giuliani's critics claimed that he arranged for people to be arrested, then dropped charges for lack of evidence on high-profile cases rather than going to trial. In a few cases, his arrests of alleged white-collar criminals at their workplaces with charges later dropped or lessened, sparked controversy, and damaged the reputations of the alleged "perps". He claimed 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.

Ivan Boesky, a Wall Street arbitrageur who had amassed a fortune of about $200 million by betting on corporate takeovers, was originally investigated by the U.S. Securities and Exchange Commission (SEC) for making investments based on tips received from corporate insiders, leading the way for the US Attorney's Office of the Southern District of New York to investigate as well. These stock and options acquisitions were sometimes brazen, with massive purchases occurring only a few days before a corporation announced a takeover. 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 others, including junk bond trader Michael Milken. Per agreement with Giuliani, Boesky received a 3 ⁄2-year prison sentence along with a $100 million fine. 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 grand jury on these charges.

Giuliani first ran for New York City mayor in 1989, when he attempted to unseat three-term incumbent Ed Koch. He won the September 1989 Republican Party primary election against business magnate Ronald Lauder, in a campaign marked by claims that Giuliani was not a true Republican and after an acrimonious debate between the two men. In the Democratic primary, Koch was upset by Manhattan Borough president David Dinkins.

Four years after his defeat to Dinkins, Giuliani again ran for mayor. Once again, Giuliani also ran on the Liberal Party line but not the Conservative Party line, which ran activist George Marlin. The city was suffering from a spike in unemployment associated with the nationwide recession, with local unemployment rates going from 6.7% in 1989 to 11.1% in 1992, although crime rates had already begun to decline under Dinkins.

During Giuliani's administration, crime rates dropped in New York City. The extent to which Giuliani deserves the credit is disputed. Crime rates in New York City had started to drop in 1991 under previous mayor David Dinkins, three years before Giuliani took office. The rates of most crimes, including all categories of violent crime, made consecutive declines during the last 36 months of Dinkins's four-year term, ending a 30-year upward spiral. A small nationwide drop in crime preceded Giuliani's election, and some critics say he may have been the beneficiary of a trend already in progress. Additional contributing factors to the overall decline in New York City crime during the 1990s were the addition of 7,000 officers to the NYPD, lobbied for and hired by the Dinkins administration, 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 the FBI doesn't collect.

Giuliani spoke in support of the removal of the People's Mujahedin of Iran (MEK, also PMOI, MKO) from the United States State Department list of Foreign Terrorist Organizations. The group was on the State Department list from 1997 until September 2012. They were placed on the list for killing six Americans in Iran during the 1970s and attempting to attack the Iranian mission to the United Nations in 1992. Giuliani, along with other former government officials and politicians Ed Rendell, R. James Woolsey, Porter Goss, Louis Freeh, Michael Mukasey, James L. Jones, Tom Ridge, and Howard Dean, were criticized for their involvement with the group. Some were subpoenaed during an inquiry about who was paying the prominent individuals' speaking fees. Giuliani and others wrote an article for the conservative publication National Review stating their position that the group should not be classified as a terrorist organization. They supported their position by pointing out that the United Kingdom and the European Union had already removed the group from their terrorism lists. They further assert that only the United States and Iran still listed it as a terrorist group. However, Canada did not delist the group until December 2012.

Giuliani has been widely criticized for his decision to locate the Office of Emergency Management headquarters on the 23rd floor inside the 7 World Trade Center building. Those opposing the decision perceived the office as a target for a terrorist attack in light of the previous terrorist attack against the World Trade Center in 1993. The office was unable to coordinate efforts between police and firefighters properly while evacuating its headquarters. Large tanks of diesel fuel were placed in 7 World Trade to power the command center. In May 1997, Giuliani put responsibility for selecting the location on Jerome M. Hauer, who had served under Giuliani from 1996 to 2000 before being appointed by him as New York City's first Director of Emergency Management. Hauer has taken exception to that account in interviews and provided Fox News and New York Magazine with a memo demonstrating that he recommended a location in Brooklyn but was overruled by Giuliani. Television journalist Chris Wallace interviewed Giuliani on May 13, 2007, about his 1997 decision to locate the command center at the World Trade Center. Giuliani laughed during Wallace's questions and said that Hauer recommended the World Trade Center site and claimed that Hauer said the WTC site was the best location. Wallace presented Giuliani a photocopy of Hauer's directive letter. The letter urged Giuliani to locate the command center in Brooklyn, instead of lower Manhattan. The February 1996 memo read, "The [Brooklyn] building is secure and not as visible a target as buildings in Lower Manhattan."

Since leaving office as mayor, Giuliani has remained politically active by campaigning for Republican candidates for political offices at all levels. When George Pataki became Governor in 1995, this represented the first time the positions of both Mayor and Governor were held simultaneously by Republicans since John Lindsay and Nelson Rockefeller. Giuliani and Pataki were instrumental in bringing the 2004 Republican National Convention to New York City. He was a speaker at the convention, and endorsed President George W. Bush for re-election by recalling that immediately after the World Trade Center towers fell,

Bratton was featured on the cover of Time Magazine in 1996. Giuliani reportedly forced Bratton out after two years, in what was seen as a battle of two large egos in which Giuliani was not tolerant of Bratton's celebrity. Bratton went on to become chief of the Los Angeles Police Department. Giuliani's term also saw allegations of civil rights abuses and other police misconduct under other commissioners after Bratton's departure. There were police shootings of unarmed suspects, and the scandals surrounding the torture of Abner Louima and the killings of Amadou Diallo, Gidone Busch and Patrick Dorismond. Giuliani supported the New York City Police Department, for example by releasing what he called Dorismond's "extensive criminal record" to the public, including a sealed juvenile file.

Giuliani's opponent in 1997 was Democratic Manhattan Borough president Ruth Messinger, who had beaten Al Sharpton in the September 9, 1997 Democratic primary. 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.

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.

An early 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, polling for the race dramatically reversed, with Giuliani now pulling nine points ahead of Clinton, in part because his campaign was able to take 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 normally 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 said his duties as mayor prevented him from campaigning more. Clinton was now eight to ten points ahead of Giuliani in the polls.

Giuliani was still married to Hanover in May 1999 when he met Judith Nathan—a sales manager for a pharmaceutical company—at Club Macanudo, an Upper East Side cigar bar. In 1996, Donna Hanover had reverted to her professional name and virtually stopped appearing in public with her husband amid rumors of marital problems. Nathan and Giuliani formed an ongoing relationship. In summer 1999, Giuliani charged the costs for his NYPD security detail to obscure city agencies in order to keep his relationship with Nathan from public scrutiny. In early 2000, the police department began providing Nathan with city-provided chauffeur services.

By March 2000, Giuliani had stopped wearing his wedding ring. The appearances that he and Nathan made at functions and events became publicly visible, although the appearances were not mentioned in the press. In early May 2000, the Daily News and the New York Post both broke news of Giuliani's relationship with Nathan. Giuliani first publicly acknowledged her on May 3, 2000, when he said Judith was his "very good friend".

On May 10, 2000, Giuliani called a press conference to announce that he intended to separate from Hanover. Giuliani had not informed Hanover about his plans before his press conference. This was an omission for which Giuliani was widely criticized. Giuliani then went on to praise Nathan as a "very, very fine woman" and said about 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."

Giuliani moved out of Gracie Mansion by August 2001 and into an apartment with a couple he was friends with. 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 or meeting his children before the divorce was final.

Due to term limits, Giuliani was ineligible to run in 2001 for a third term as mayor. In November 1998, four-term incumbent Democratic 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. Due to 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-U.S. First Lady Hillary Clinton to run for Moynihan's seat, hoping she might combat his star power.

The 9/11 Commission Report noted 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 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 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 H. 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 cleanup workers lacked adequate protective gear.

Giuliani gained international attention in the wake of the attacks and was widely hailed for his leadership role during the crisis. Polls taken just six weeks after the attack showed a 79 percent approval rating among New York City voters. This was a dramatic increase over the 36 percent rating he had received a year earlier, which was an average at the end of a two-term mayorship. Oprah Winfrey called him "America's Mayor" at a 9/11 memorial service held at Yankee Stadium on September 23, 2001. Other voices denied it was the mayor who had pulled the city together. "You didn't bring us together, our pain brought us together and our decency brought us together. We would have come together if Bozo was the mayor," said civil rights activist Al Sharpton, in a statement largely supported by Fernando Ferrer, one of three main candidates for the mayoralty at the end of 2001. "He was a power-hungry person," Sharpton also said.

On December 24, 2001, Time magazine named Giuliani its Person of the Year for 2001. Time observed that, before 9/11, Giuliani's public image 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 became that of a man who could be counted on to unite a city in the midst of its greatest crisis. Historian Vincent J. Cannato concluded in September 2006:

In May 2001, Giuliani's attorney revealed that Giuliani was impotent due to 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." In a court case, Giuliani argued that he planned to introduce Nathan to his children on Father's Day 2001 and that Hanover had prevented this visit. Giuliani and Hanover finally settled their 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. Giuliani married Nathan on May 24, 2003, and gained a stepdaughter, Whitney. It was also Nathan's third marriage after two divorces.

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). He threatened to challenge the law imposing term limits on elected city officials and run for another full four-year term, if the primary candidates did not consent to the extension of his mayoralty. In the end leaders in the State Assembly and Senate indicated that they did not believe the extension was necessary. The election proceeded as scheduled, and the winning candidate, the Giuliani-endorsed Republican convert Michael Bloomberg, took office on January 1, 2002 per normal custom.

For his leadership on and after September 11, Giuliani was given an honorary knighthood (KBE) by Queen Elizabeth II on February 13, 2002.

After leaving the New York City mayor's office, Giuliani founded a security consulting business, Giuliani Partners LLC, in 2002, a firm that has been categorized by various media outlets as a lobbying entity capitalizing on Giuliani's name recognition, and which has been the subject of allegations surrounding staff hired by Giuliani and due to the firm's chosen client base. Over five years, Giuliani Partners earned more than $100 million. In June 2007 he stepped down as CEO and Chairman of Giuliani Partners, although this action was not made public until December 4, 2007; he maintained his equity interest in the firm. Giuliani subsequently returned to active participation in the firm following the election. In late 2009, Giuliani announced that they had a security consulting contract with Rio de Janeiro, Brazil regarding the 2016 Summer Olympics. He faced criticism in 2012 for advising people once allied with Slobodan Milošević who had lauded Serbian war criminals.

In 2005, Giuliani joined the law firm of Bracewell & Patterson LLP (renamed Bracewell & Giuliani LLP) as a name partner and basis for the expanding firm's new New York office. When he joined the Texas-based firm he brought Marc Mukasey, the son of Attorney General Michael Mukasey, into the firm.

Similarly, in June 2006, Giuliani started a website called Solutions America to help elect Republican candidates across the nation.

On March 15, 2006, Congress formed the Iraq Study Group (ISG). This bipartisan ten-person panel, of which Giuliani was one of the members, was charged with assessing the Iraq War and making recommendations. They would eventually unanimously conclude that contrary to Bush administration assertions, "The situation in Iraq is grave and deteriorating" and called for "changes in the primary mission" that would allow "the United States to begin to move its forces out of Iraq".

On May 24, 2006, after missing all 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 "previous time commitments". 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 he had started thinking about running for president, and being on the panel might give it a political spin.

In November 2006 Giuliani announced the formation of an exploratory committee toward a run for the presidency in 2008. In February 2007 he filed a "statement of candidacy" and confirmed on the television program Larry King Live that he was indeed running.

Despite a busy schedule, Giuliani was highly active in the day-to-day business of the law firm, which was a high-profile supplier of legal and lobbying services to the oil, gas, and energy industries. Its aggressive defense of pollution-causing coal-fired power plants threatened to cause political risk for Giuliani, but association with the firm helped Giuliani achieve fund-raising success in Texas. 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.

According to an FBI memo revealed in 2007, leaders of the Five Families voted in late 1986 on whether to issue a contract for Giuliani's death. Heads of the Lucchese, Bonanno, and Genovese families rejected the idea, though Colombo and Gambino leaders, Carmine Persico and John Gotti, encouraged assassination. In 2014, it was revealed by a former Sicilian Mafia member and informant, Rosario Naimo, that Salvatore Riina, a notorious Sicilian Mafia leader, had ordered a murder contract on Giuliani during the mid-1980s. Riina allegedly was suspicious of Giuliani's efforts prosecuting the American Mafia and was worried that he might have spoken with Italian anti-mafia prosecutors and politicians, including Giovanni Falcone and Paolo Borsellino, who were both murdered in 1992 in separate car bombings. According to Giuliani, the Sicilian Mafia offered $800,000 for his death during his first year as mayor of New York in 1994.

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 (EPA), reportedly said the EPA had pushed for workers at the WTC site to wear respirators but she had been blocked by Giuliani. She said she believed the subsequent lung disease and deaths suffered by WTC responders were a result of these actions. However, former deputy mayor Joe Lhota, then with the Giuliani campaign, replied, "All workers at Ground Zero were instructed repeatedly to wear their respirators."

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.

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, he remained one of the few candidates for president to unequivocally support both the basis for the invasion and the execution of the war.

Early polls showed Giuliani with one of the highest levels of name recognition ever recorded along with high levels of support among the Republican candidates. Throughout most of 2007 he was the leader in most nationwide opinion polling among Republicans. Senator John McCain, who ranked a close second behind the New York Mayor, had faded, and most polls showed Giuliani to have more support than any of the other declared Republican candidates, with only former Senator Fred Thompson and former Governor Mitt Romney showing greater support in some per-state Republican 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.

By March 2007, The New York Times and the Daily News reported that Giuliani had become estranged from both his son Andrew and his daughter Caroline. In 2014, he said his relationship with his children was better than ever, and was spotted eating and playing golf with Andrew.

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.

Despite his strategy, Giuliani competed 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, when 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 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. During the 2008 Republican National Convention, Giuliani gave a prime-time speech that praised McCain and his running mate, Sarah Palin, while criticizing Democratic nominee Barack Obama. He cited Palin's executive experience as a mayor and governor and belittled Obama's lack of same, and his remarks were met with wild applause from the delegates. Giuliani continued to be one of McCain's most active surrogates during the remainder of McCain's eventually unsuccessful campaign.

Giuliani said his political career was not necessarily over, and did not rule out a 2010 New York gubernatorial or 2012 presidential bid. A November 2008 Siena College poll indicated that although Governor David Paterson—promoted to the office via the Eliot Spitzer prostitution scandal a year before—was popular among New Yorkers, he would have just a slight lead over Giuliani in a hypothetical matchup. By February 2009, after the prolonged Senate appointment process, a Siena College poll indicated that Paterson was losing popularity among New Yorkers, and showed Giuliani with a fifteen-point lead in the hypothetical contest. In January 2009, Giuliani said he would not decide on a gubernatorial run for another six to eight months, adding that he thought it would not be fair to the governor to start campaigning early while the governor tries to focus on his job. Giuliani worked to retire his presidential campaign debt, but by the end of March 2009 it was still $2.4 million in arrears, the largest such remaining amount for any of the 2008 contenders. In April 2009, Giuliani strongly opposed Paterson's announced push for same-sex marriage in New York and said it would likely cause a backlash that could put Republicans in statewide office in 2010. By late August 2009, there were still conflicting reports about whether Giuliani was likely to run.

On December 23, 2009, Giuliani announced that he would not seek any office in 2010, saying "The main reason has to do with my two enterprises: Bracewell & Giuliani and Giuliani Partners. I'm very busy in both." The decisions signaled a possible end to Giuliani's political career. During the 2010 midterm elections, Giuliani endorsed and campaigned for Bob Ehrlich and Marco Rubio.

On October 11, 2011, Giuliani announced that he was not running for president. According to Kevin Law, the Director of the Long Island Association, Giuliani believed that "As a moderate, he thought it was a pretty significant challenge. He said it's tough to be a moderate and succeed in GOP primaries," Giuliani said "If it's too late for (New Jersey Governor) Chris Christie, it's too late for me."

At a Republican fund-raising event in February 2015, Giuliani said, "I do not believe, and I know this is a horrible thing to say, but I do not believe that the president Obama loves America," and "He doesn't love you. And he doesn't love me. He wasn't brought up the way you were brought up and I was brought up, through love of this country." In response to criticism of the remarks, Giuliani said, "Some people thought it was racist—I thought that was a joke, since he was brought up by a white mother ... This isn't racism. This is socialism or possibly anti-colonialism." White House deputy press secretary Eric Schultz said he agreed with Giuliani "that it was a horrible thing to say", but he would leave it up to the people who heard Giuliani directly to assess whether the remarks were appropriate for the event. Although he received some support for his controversial comments, Giuliani said he also received several death threats within 48 hours.

Giuliani supported Donald Trump in the 2016 U.S. presidential election. He gave a prime time speech during the first night of the 2016 Republican National Convention. Earlier in the day, Giuliani and former 2016 presidential candidate Ben Carson appeared at an event for the pro-Trump Great America PAC. Giuliani also appeared in a Great America PAC ad entitled "Leadership". Giuliani's and Jeff Sessions's appearances were staples at Trump campaign rallies.

In August 2016, Giuliani, while campaigning for Trump, claimed that in the "eight years before Obama" became president, "we didn't have any successful radical Islamic terrorist attack in the United States." On the contrary, 9/11 happened during George W. Bush's first term. Politifact brought up four more counter-examples (the 2002 Los Angeles International Airport shooting, the 2002 D.C. sniper attacks, the 2006 Seattle Jewish Federation shooting and the 2006 UNC SUV attack) to Giuliani's claim. Giuliani later said he was using "abbreviated language".

Giuliani was believed to be a likely pick for Secretary of State in the Trump administration. However, on December 9, 2016, Trump announced that Giuliani had removed his name from consideration for any Cabinet post.

In mid April 2018, Giuliani joined Trump's legal team, which dealt with the special counsel investigation by Robert Mueller into Russian interference in the 2016 U.S. elections. Giuliani said his goal was to negotiate a swift end to the investigation.

Tom Bossert, a former Homeland Security Advisor in the Trump administration, described Giuliani's theory that Ukraine was involved in 2016 U.S. election interference as "debunked"; Giuliani responded that Bossert "doesn't know what the hell he's talking about".

Giuliani left the firm in January 2016, by "amicable agreement", and the firm was rebranded as Bracewell LLP.

In January 2016, Giuliani moved to the law firm Greenberg Traurig, where he served as the global chairman for Greenberg's cybersecurity and crisis management group, as well as a senior advisor to the firm's executive chairman. In April 2018, he took an unpaid leave of absence when he joined Trump's legal defense team. He resigned from the firm on May 9, 2018.

On January 12, 2017, the president-elect named Giuliani his informal cybersecurity adviser. The status of this informal role for Giuliani is unclear because, in November 2018, Trump created the Cybersecurity and Infrastructure Security Agency (CISA), headed by Christopher Krebs as director and Matthew Travis as deputy. In the weeks following his appointment, Giuliani was forced to consult an Apple Store Genius Bar when he "was locked out of his iPhone because he had forgotten the passcode and entered the wrong one at least 10 times," belying his putative expertise in the field.

In January 2017, Giuliani said he advised President Trump in matters relating to Executive Order 13769, which barred citizens of seven Muslim-majority countries from entering the United States for 90 days. The order also suspended the admission of all refugees for 120 days.

Giuliani privately urged Trump in 2017 to extradite Fethullah Gülen.

Dmytry Firtash is a Ukrainian oligarch who is prominent in the natural gas sector. In 2017, the Justice Department characterized him as being an "upper echelon (associate) of Russian organized crime". Living in Vienna, Austria, for five years he has been fighting extradition to the United States on bribery and racketeering charges, and has been seeking to have the charges dropped. Firtash's attorneys obtained a September 2019 statement from Viktor Shokin, the former Ukrainian prosecutor general who was forced out under pressure from multiple countries and non-governmental organizations, as conveyed to Ukraine by Joe Biden. Shokin asserted in the statement that Biden actually had him fired because he refused to stop his investigation into Burisma. Giuliani, who asserts he has "nothing to do with" and has "never met or talked to" Firtash, has promoted the statement in television appearances as purported evidence of wrongdoing by the Bidens. Giuliani told CNN he met with a Firtash attorney for two hours in New York City at the time he was seeking information about the Bidens.

Later in May 2018, Giuliani, who was asked on whether the promotion of the Spygate conspiracy theory is meant to discredit the special counsel investigation, said the investigators "are giving us the material to do it. Of course, we have to do it in defending the president ... it is for public opinion" on whether to "impeach or not impeach" Trump. In June 2018, Giuliani claimed that a sitting president cannot be indicted: "I don't know how you can indict while he's in office. No matter what it is. ... If President Trump shot then-FBI director James Comey, he'd be impeached the next day. ... Impeach him, and then you can do whatever you want to do to him."

In June 2018, Giuliani also said Trump should not testify to the special counsel investigation because "our recollection keeps changing." In early July, Giuliani characterized that Trump had previously asked Comey to "give then-national security adviser Michael Flynn a break". In mid-August, Giuliani denied making this comment: "What I said was, that is what Comey is saying Trump said." On August 19 on Meet the Press, Giuliani argued that Trump should not testify to the special counsel investigation because Trump could be "trapped into perjury" just by telling "somebody's version of the truth. Not the truth." Giuliani's argument continued: "Truth isn't truth." Giuliani later clarified that he was "referring to the situation where two people make precisely contradictory statements".

In August 2018, Giuliani was retained by Freeh Group International Solutions, a global consulting firm run by former FBI Director Louis Freeh, which paid him a fee to lobby Romanian president Klaus Iohannis to change Romania's anti-corruption policy and reduce the role of the National Anticorruption Directorate. Giuliani argued that the anti-corruption efforts had gone too far.

On April 4, 2018, Nathan filed for divorce from Giuliani after 15 years of marriage. According to an interview with New York magazine, "For a variety of reasons that I know as a spouse and a nurse ... he has become a different man." The divorce was settled on December 10, 2019.

Since at least May 2019, Giuliani has been urging Ukraine's newly elected president, Volodymyr Zelensky, to investigate the oil company Burisma, whose board of directors once included Joe Biden's son Hunter Biden, and to check for irregularities in Ukraine's investigation of Paul Manafort. He said such investigations would benefit his client's defense, and that his efforts had Trump's full support. Toward this end, Giuliani met with Ukrainian officials in June 2019 and August 2019. In July 2019, Buzzfeed News reported that two Soviet-born Americans, Lev Parnas and Igor Fruman, were liaisons between Giuliani and Ukrainian government officials in this effort. Parnas and Fruman, prolific Republican donors, have neither registered as foreign agents in the United States, nor been evaluated and approved by the State Department. Giuliani responded, "This (report) is a pathetic effort to cover up what are enormous allegations of criminality by the Biden family." Yet as of September 2019, there has been no clear evidence of wrongdoing by the Bidens.

As of October 1, 2019, Giuliani hired former Watergate prosecutor Jon Sale to represent him in the House Intelligence Committee's impeachment investigation. The committee also issued a subpoena to Giuliani asking him to release documents related to the Ukraine scandal. The New York Times reported on October 11, 2019, that the United States Attorney for the Southern District of New York, which Giuliani had once led, was investigating him for violating lobbying laws related to his activities in Ukraine. The following month, Bloomberg News reported that the investigation could extend to bribery of foreign officials or conspiracy, and The Wall Street Journal reported Giuliani was being investigated for a possible profit motive in a Ukrainian natural gas venture. Giuliani has denied having any interest in a Ukrainian natural gas venture. In late November, the Wall Street Journal reported that federal prosecutors had just issued subpoenas to multiple associates of Giuliani to potentially investigate certain individuals, apparently including Giuliani, on numerous potential charges, including money laundering, obstruction of justice, conspiracy to defraud the United States, making false statements to the federal government, and mail/wire fraud.

On October 9, 2019, Parnas and Fruman were arrested for campaign finance violations while attempting to board a one-way flight to Frankfurt from Washington Dulles International Airport. Giuliani was paid $500,000 to consult for Lev Parnas' company named "Fraud Guarantee". Republican donor and Trump supporter Long Island attorney Charles Gucciardo paid Giuliani on behalf of Fraud Guarantee in two $250,000 payments, in September and October 2018.

In May 2019, Giuliani described Ukraine's chief prosecutor Yuriy Lutsenko as a "much more honest guy" than his predecessor, Viktor Shokin. After Lutsenko was removed from office, he said in September 2019 that he found no evidence of wrongdoing by the Bidens, and that he had met Giuliani about 10 times. Giuliani then reversed his stance, saying that Shokin is the one people "should have spoken to", while Lutsenko acted "corruptly" and "is exactly the prosecutor that Joe Biden put in in order to tank the case".

In September 2019, as reports surfaced that a whistleblower was alleging high-level misconduct related to Ukraine, Giuliani went on CNN to discuss the story. When he was asked if he had tried to get Ukrainian officials to investigate Biden, he initially replied "No, actually I didn't," but thirty seconds later, "Of course I did." In a later tweet he seemed to confirm reports that Trump had withheld military assistance funds scheduled for Ukraine unless they carried out the investigation. He said, "The reality is that the president of the United States, whoever he is, has every right to tell the president of another country you better straighten out the corruption in your country if you want me to give you a lot of money. If you're so damn corrupt that you can't investigate allegations—our money is going to get squandered."

On September 30, 2019, the House Intelligence Committee issued a subpoena to Giuliani asking him to release documents concerning the Ukraine scandal to Committee members by October 15, 2019. On October 2, 2019 Steve Linick, the State Department's inspector general, delivered a 40-page packet of apparent disinformation regarding former vice president Joe Biden and former Ambassador to the Ukraine, Marie Yovanovitch, to Capitol Hill. Linick told congressional aides his office questioned Ulrich Brechbuhl, Pompeo's advisor about the origins of the packet. Brechbuhl noted the packet came to him from Pompeo, who said it "came over", and Brechbuhl reportedly presumed it was from the White House. Later that day, Giuliani acknowledged he passed the packet to Pompeo regarding the Ukraine and attacks on Yovanovich. In a November 2019 interview he confirmed that he had "needed Yovanovitch out of the way" because she was going to make his investigations difficult. "They (the State Department) told me they would investigate it," Giuliani added.

On November 22, 2019, Giuliani sent a letter to Senator Lindsey Graham, Chairman of the Committee on the Judiciary, informing him of at least three witnesses from Ukraine who Giuliani claimed had direct oral, documentary, and recorded evidence of Democratic criminal conspiracy with Ukrainians to prevent Trump's election and, after his election, to remove him from office via contrived charges. Giuliani's letter also claims that the witnesses had evidence of the Biden family's involvement in bribery, money laundering, Hobbs Act extortion, and other possible crimes. The letter sought Graham's help obtaining U.S. visas for the witnesses to testify. The next month, Graham invited Giuliani to share his findings with the Judiciary Committee, and soon advised him "to share what he got from Ukraine with the [intelligence community] to make sure it's not Russia propaganda".

Firtash is represented by Trump and Giuliani associates Joseph diGenova and his wife Victoria Toensing, having hired them on Parnas's recommendation. The New York Times reported in November 2019 that Giuliani had directed Parnas to approach Firtash with the recommendation, with the proposition that Firtash could help provide compromising information on Biden, which Parna's attorney described was "part of any potential resolution to [Firtash's] extradition matter". Shokin's statement notes that it was prepared "at the request of lawyers acting for Dmitry Firtash". Bloomberg News reported on October 18 that during the summer of 2019 Firtash associates began attempting to dig up dirt on the Bidens in an effort to solicit Giuliani's assistance with Firtash's legal matters, as well as hiring diGenova and Toensing in July. Bloomberg News also reported that its sources told them Giuliani's high-profile publicity of the Shokin statement had greatly reduced the chances of the Justice Department dropping the charges against Firtash, as it would appear to be a political quid pro quo.

On December 3, 2019, the House Intelligence Committee's report included phone records, acquired via subpoenas to AT&T and/or Verizon Wireless, including numerous phone calls made by Giuliani between April and August 2019. Calls involved Giuliani in contact with Kurt Volker, Republican Representative and House Intelligence Committee Ranking Member Devin Nunes, Lev Parnas, numbers associated with the Office of Management and Budget and the White House switchboard, and an unidentified White House official whose phone number is referenced as "-1". Chairman Adam Schiff of the House Intelligence Committee announced after the report's release that his committee was investigating whether "-1" referred to President Trump, citing grand jury evidence from the trial of convicted Trump-associate Roger Stone in which the phone number "-1" was shown to have referred to Trump. Writing for The Washington Post, analyst Phillip Bump reasoned that Giuliani's calls with "-1" are 'likely' calls with Trump citing that Giuliani speaks longer with "-1" than any other person, "-1" always calls Giuliani, and generally after Giuliani calls the White House switchboard, and timing of some of President Trump's actions shortly after Giuliani's calls with "-1" ended.

On November 9, 2019, during the Ukraine scandal, Giuliani retained two attorneys with the Los Angeles law firm Pierce Bainbridge Beck Price & Hecht which has also represented George Papadopoulos and Tulsi Gabbard and one attorney with the New York law firm Davidoff Hutcher & Citron who previously represented Michael Cohen.

In November 2020, Trump placed Giuliani in charge of lawsuits related to alleged voter fraud in the 2020 United States presidential election, attempting to delegitimize the succession of Joe Biden as president. Giuliani claims to have over 200 signed affidavits attesting to voter fraud and election official misconduct in Michigan and Pennsylvania but is yet to win a case proving the validity of any of the allegations of fraud.

In October 2020, following myriad joint public appearances, Giuliani confirmed that he is in a relationship with Maria Ryan, a nurse practitioner and hospital administrator whom his ex-wife Nathan has alleged to have been his mistress for an indeterminate period during their marriage. As of 2018, Ryan was married to United States Marine Corps veteran Robert Ryan, with Giuliani characterizing the couple as platonic friends in response to contemporaneous press inquiries.