59 Fun Facts About Rudy Giuliani

As a prosecutor in the 1980s, Giuliani was credited with popularising which police ritual?

The perp walk. In 1987 he sent officers onto a Wall Street trading floor to handcuff a trader, who was photographed weeping; the charges were dropped months later.

Time made Giuliani its Person of the Year for 2001 after weeks of speculation it might pick which man?

Osama bin Laden. The title goes to whoever most changed the year, for better or worse, so many argued for the al-Qaeda leader; Time chose Giuliani as the symbol of the country's response.

Giuliani was widely nicknamed what after 9/11?

America's mayor. Oprah Winfrey introduced him by that name at a memorial service at Yankee Stadium twelve days after the attacks, and it stuck for years.

Giuliani opened which late-night show's first episode after 9/11, replying "Why start now" when asked if it could be funny?

Saturday Night Live. Flanked by firefighters and police officers, Giuliani said the show should go on, then gave producer Lorne Michaels the punchline.

Giuliani's father Harold served prison time in which New York prison?

Sing Sing. Harold Giuliani spent about a year and a half there for holding up a milkman in 1934, a story his son, the future prosecutor, said he only learned in full as an adult.

Giuliani graduated from which college that, despite its name, was in the Bronx?

Manhattan College. The Catholic school, now Manhattan University, is in the Bronx, and Giuliani spent his four years there still weighing the priesthood, an idea he dropped only once he reached law school.

Giuliani volunteered for whose 1968 presidential campaign, back when he was a Democrat?

Robert F. Kennedy. The self-described 'Robert Kennedy Democrat' voted for George McGovern in 1972 and registered as a Republican only a month after Reagan's 1980 victory.

Giuliani avoided the Vietnam draft partly through a 1969 essential-civilian reclassification while working as what?

A federal judge's law clerk. Judge Lloyd MacMahon wrote to the draft board to secure the deferment, and when it ran out Giuliani drew a high lottery number and was never called.

In 1981 Giuliani took the third-ranking job in which American government department?

Justice. As Reagan's Associate Attorney General he defended the detention of Haitian boat people, testifying after a two-day visit that political repression did not, in general, exist in Haiti.

From 1983 to 1989 Giuliani was U.S. Attorney for which jurisdiction?

Southern District of New York. It looked like a step down, since in Washington he already oversaw every U.S. attorney, but he wanted to try cases himself in the country's most visible office.

Giuliani's Mafia Commission trial used which law to indict the heads of the Five Families?

RICO. The racketeering law let prosecutors try the bosses together as a single criminal enterprise, and most of the eight men convicted were sentenced to 100 years.

An FBI memo says which boss urged the Five Families to kill Giuliani?

John Gotti. He and Colombo boss Carmine Persico pressed for a hit on the prosecutor who was trying their commission, but the Lucchese, Bonanno and Genovese bosses refused.

Which future Secretary of Homeland Security assisted Giuliani in the Mafia Commission prosecution?

Michael Chertoff. One of three young prosecutors on the case, he argued that the families' ruling commission ran the American Mafia, and its leaders drew sentences of up to 100 years.

Which Wall Street arbitrageur, prosecuted by Giuliani, had made a fortune betting on corporate takeovers?

Ivan Boesky. To win leniency he secretly taped junk-bond king Michael Milken, and his reported boast that 'greed is healthy' was echoed by Gordon Gekko in the film Wall Street.

Giuliani first ran for mayor in 1989 and lost narrowly to whom?

David Dinkins. He had upset three-term mayor Ed Koch in the Democratic primary, and his win in one of the closest races in the city's history made him its first Black mayor.

Which heir did Giuliani beat in the 1989 Republican mayoral primary?

Ronald Lauder. The Estée Lauder heir spent $14 million and lost two to one, then led the term-limits drive that would bar Giuliani from seeking a third term.

Shunned by the Conservative Party, Republican Giuliani also ran for mayor on which party's line?

Liberal. Giuliani ran as a fusion candidate in all three of his races, and the Liberals' chairman said on endorsing him that he shared the party's views on affirmative action and gun control.

Which borough's vote on leaving the city helped Giuliani's narrow 1993 win?

Staten Island. A referendum on seceding from the city was on the same ballot, and Giuliani's lead there alone was bigger than his citywide margin of about 53,000 votes.

Giuliani was the first Republican elected mayor of New York since which 1965 winner?

John Lindsay. He later quit the Republicans, became a Democrat and ran for president in 1972, the mirror image of Giuliani's own journey from Democrat to Republican.

In 1992 Giuliani addressed a rally of off-duty police officers that turned into a riot outside which building?

City Hall. The officers were protesting a plan for an all-civilian board to review complaints against them, and Giuliani took the microphone to blame the sitting mayor for their low morale.

Giuliani's first police commissioner, who championed "broken windows" policing, was who?

Bill Bratton. Falling crime made him a celebrity and put him on the cover of Time, and after a battle of egos Giuliani reportedly forced him out just 27 months into the job.

The "broken windows" theory adopted under Giuliani was set out in 1982 by George Kelling and which co-author?

James Q. Wilson. The pair argued that one unrepaired window signals that no one cares and invites worse, an idea they drew from an experiment with abandoned cars.

What is the name of the crime-mapping system the NYPD introduced under Giuliani in 1994?

CompStat. It plots crimes on a daily-updated map so commanders answer for their own precincts; critics say that pressure led some to manipulate the figures.

Which Democrat did Giuliani face in the 1997 mayoral election?

Ruth Messinger. She cleared the 40 percent needed to avoid a primary runoff against Al Sharpton by just 658 votes, then lost to Giuliani by 58 percent to 41.

Giuliani quit the 2000 Senate race against Hillary Clinton after being diagnosed with what?

Prostate cancer. The same disease had killed his father, and the diagnosis came in the very weeks his marriage fell apart in public, so he withdrew and left the field to Clinton.

Which retiring senator's seat were Giuliani and Hillary Clinton competing for in 2000?

Daniel Patrick Moynihan. Term limits barred Giuliani from seeking a third term as mayor, and when the four-term Democrat announced his retirement Giuliani turned to the Senate.

Giuliani was criticised for putting the city's emergency command centre in which building?

The tower had been a terrorist target in 1993 and collapsed on 9/11, hampering coordination.

After 9/11, Giuliani declared what in New York "safe and acceptable"?

Air quality. Crews at Ground Zero dug through the smouldering debris, most of them without respirators, and thousands of recovery workers went on to suffer long-term illness.

What did Queen Elizabeth II give Giuliani in February 2002?

An honorary knighthood (KBE). As a foreign citizen he was not dubbed with a sword and may not call himself Sir Rudolph, though he can put the letters after his name.

Whom did Giuliani endorse to succeed him as mayor in 2001?

Michael Bloomberg. The billionaire, a recent convert to the Republicans, was lifted by a Giuliani television ad weeks after Giuliani's own push for three extra months in office went nowhere.

Which former police commissioner did Giuliani recommend for Homeland Security in 2004?

Bernard Kerik. Giuliani was reportedly the first choice but put forward his friend, who withdrew within days over an undocumented nanny and later went to prison for tax fraud.

Giuliani's 2008 presidential campaign staked almost everything on which state's late-January primary?

Florida. Betting on big later states over the small early ones, he had staff go without pay to fund the push, finished a distant third and quit the race the next day.

Which televangelist endorsed Giuliani's 2008 campaign in November 2007?

Pat Robertson. The Christian Coalition founder backed him even though Giuliani supported abortion rights and gay rights, a sign that evangelicals might overlook those differences.

Giuliani joined Trump's legal team hoping to end whose investigation quickly?

Robert Mueller. Giuliani signed on in 2018 hoping to negotiate a swift end to the special counsel's Russia inquiry, but it ran for nearly another year before Mueller reported.

Giuliani's November 7, 2020 election press conference was famously held at what kind of Philadelphia business?

A landscaping company. Trump's tweet said 'Four Seasons', which many took for the luxury hotel; Giuliani spoke in the car park of Four Seasons Total Landscaping just as the networks called the election against Trump.

What did Giuliani call for in his speech at the January 6, 2021 rally?

"Trial by combat". He told the crowd that if the fraud claims were wrong 'we will be made fools of', and later said the line was a nod to Tyrion Lannister, not a call to violence.

In December 2023 a jury ordered Giuliani to pay how much to election workers Ruby Freeman and Shaye Moss?

$148 million. Giuliani had falsely accused the mother and daughter of rigging the vote count; he filed for bankruptcy within a week of the verdict and later reached a settlement.

Giuliani was indicted in August 2023 alongside Trump and 17 others by a grand jury in which state?

Georgia. Prosecutors said the 19 defendants conspired to overturn the state's result, citing Giuliani's false claims of fraud to Georgia lawmakers; he surrendered at an Atlanta jail nine days later.

Which penalty did a New York court impose on Giuliani in 2024?

Disbarment. The court had suspended his licence in 2021 over false and misleading statements about the 2020 election, and Washington, D.C. struck him off too in September 2024.

Giuliani's first wife proved to be his second cousin, so the Church granted him what?

An annulment. The couple had never obtained the dispensation cousins then needed to marry, so the Church erased the 14-year marriage and he could wed his second wife in church.

Donna Hanover learned that Giuliani meant to leave her in May 2000 when he announced it where?

At a press conference. He had not told his wife first, and it was he who later moved out of Gracie Mansion to a friends' apartment while she stayed on with their children.

Giuliani played himself in a 1993 Seinfeld episode about a mayoral race and which dessert?

Non-fat yogurt. The writers prepared a version for each possible winner, and Giuliani filmed his cameo, vowing to crack down on the fattening treat, the morning after he won the real election.

Which actor portrayed Giuliani in the 2003 TV film Rudy: The Rudy Giuliani Story?

James Woods. The cable biopic found a second life in 2020, when a clip of his Giuliani wooing his wife on a moonlit beach went viral and viewers mocked the dialogue.

On The Masked Singer, Giuliani was unmasked as which character?

Jack in the Box. He said he did the show for his granddaughter; when the mask came off, judge Ken Jeong folded his arms and walked off as Giuliani sang 'Bad to the Bone'.

Giuliani guest-starred as himself in a 2007 episode of which animated series?

The Simpsons. He recorded a cameo sending the family's dog off from a police-dog academy, but it was reportedly cut from the first broadcast because he had become a presidential candidate.

Giuliani's podcast, launched in January 2020, was titled Rudy Giuliani's what?

Common Sense. He launched it during Trump's first Senate impeachment trial and used the opening episode to make the defence case he had not been chosen to argue in person.

Trump's November 2025 pardon of Giuliani was called largely symbolic because he faced no charges of which kind?

Federal. A president can pardon only federal offences, and the criminal cases against Giuliani over the 2020 result were brought by state prosecutors, beyond the reach of the proclamation for 77 allies.

At Brooklyn's Bishop Loughlin High School, the teenage Giuliani developed a passion for which art form?

Opera. A teacher encouraged an interest Giuliani said he hid from friends who would have mocked it, and he went on to start an opera club with his closest classmates.

Giuliani's first police commissioner, who left after 27 months, went on to lead which city's police department?

Los Angeles. He took over the LAPD in 2002 and ran it for seven years, then returned to New York in 2014 for a second spell in the job he had left after clashing with Giuliani.

Giuliani rejected a $10 million 9/11 relief cheque from a prince of which country, who had blamed American Middle East policy?

Saudi Arabia. Prince Alwaleed bin Talal handed over the cheque at Ground Zero, then urged America to rethink its stance on the Palestinians; Giuliani called such talk 'part of the problem'.

Giuliani resigned from which 2006 panel after missing all its meetings, including a Petraeus briefing?

The Iraq Study Group. The sessions he skipped clashed with highly paid speeches, and once co-chairman James Baker pressed members to turn up or make way, Giuliani quit, citing time commitments.

After abandoning his 2008 presidential bid, Giuliani immediately endorsed which Republican rival?

John McCain. Giuliani flew to the Reagan Library in California to back his longtime friend, who predicted Giuliani would be his 'strong right arm' for the rest of the campaign.

Which Peruvian presidential candidate did Giuliani advise during the 2011 election?

Keiko Fujimori. Hiring a famous American crime-fighter was meant to offset the shadow of her jailed father, former president Alberto Fujimori, but she lost the runoff to Ollanta Humala.

After leaving office, Giuliani founded Giuliani Partners in 2002 to sell what kind of service?

Security consulting. Clients such as Qatar's interior ministry paid for the reputation he had won on 9/11, and the firm grew into a multimillion-dollar business.

Which drugmaker hired Giuliani to negotiate with federal prosecutors over misleading claims about its painkiller?

Purdue Pharma. The company and three executives pleaded guilty in 2007 over OxyContin and paid $634.5 million, but under the plea deal Giuliani helped negotiate none of the three executives went to jail.

Giuliani was paid $500,000 to consult for which company run by Lev Parnas?

Fraud Guarantee. Parnas promoted it as a way to protect investors from fraud, then pleaded guilty in 2022 to conspiring to defraud the people who had put money into it; Giuliani was never charged over it.

Soon after Dominion sued Giuliani for $1.3 billion, which rival voting-technology firm sued him and Fox News for $2.7 billion?

Smartmatic. Giuliani had said on Fox News that it was founded by Hugo Chavez and wrote Dominion's software, but Chavez was not among its founders and the two rivals have no ownership ties.

Which comedian's 2020 film showed Giuliani in a hotel bedroom with an actress posing as a journalist?

Sacha Baron Cohen. In his Borat sequel, Maria Bakalova played a reporter who led Giuliani to a bedroom rigged with hidden cameras; he said afterwards that he had only been tucking in his shirt.

Giuliani's 2019 push for Ukraine to investigate which Democrat was at the heart of Trump's first impeachment?

Joe Biden. Giuliani was central in pushing corruption claims against Biden and his son Hunter, and House investigators subpoenaed his Ukraine records during the impeachment inquiry.