Rudy Giuliani Trivia
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59 free Rudy Giuliani trivia questions with answers — history quiz, new questions added Oct 2026.
Few American careers have swung as far as Rudy Giuliani's. The prosecutor who indicted the heads of New York's Five Families became the mayor who presided over a historic crime drop, then "America's mayor" and Time's Person of the Year after September 11, an honorary knight, and the early front-runner for the 2008 Republican nomination. Two decades later he was disbarred in New York and Washington, bankrupt after a $148 million defamation verdict, and pardoned by Donald Trump. This Rudy Giuliani trivia quiz runs 59 questions across that whole arc: East Flatbush and Bishop Loughlin, Manhattan College and NYU Law, the Podell and Boesky cases, the Mafia Commission trial, the 1989 loss to David Dinkins and the 1993 win, Bill Bratton, CompStat and squeegee men, the aborted 2000 Senate race against Hillary Clinton, 7 World Trade Center, the knighthood, Bernard Kerik, the Florida strategy of 2008, Four Seasons Total Landscaping, "trial by combat", the Georgia election workers, and the cameos on Seinfeld, The Simpsons and The Masked Singer. Easy questions come first; the last third is for people who remember Ronald Lauder. Every answer is verified against Wikipedia's biography of Giuliani, with the supporting sentence quoted under each question. Fans of this quiz should also try our New York City and US politics quizzes.
30 of 59 questions with answers and explanations. Play the quiz
Q 01As a prosecutor in the 1980s, Giuliani was credited with popularising which police ritual?
The perp walk
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.
Q 02Time made Giuliani its Person of the Year for 2001 after weeks of speculation it might pick which man?
Osama bin Laden
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.
Q 03Giuliani was widely nicknamed what after 9/11?
America's mayor
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.
Q 04Giuliani 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
Saturday Night Live. Flanked by firefighters and police officers, Giuliani said the show should go on, then gave producer Lorne Michaels the punchline.
Q 05Giuliani's father Harold served prison time in which New York prison?
Sing Sing
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.
Q 06Giuliani graduated from which college that, despite its name, was in the Bronx?
Manhattan College
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.
Q 07Giuliani volunteered for whose 1968 presidential campaign, back when he was a Democrat?
Robert F. Kennedy
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.
Q 08Giuliani avoided the Vietnam draft partly through a 1969 essential-civilian reclassification while working as what?
A federal judge's law clerk
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.
Q 09In 1981 Giuliani took the third-ranking job in which American government department?
Justice
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.
Q 10From 1983 to 1989 Giuliani was U.S. Attorney for which jurisdiction?
Southern District of New York
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.
Q 11Giuliani's Mafia Commission trial used which law to indict the heads of the Five Families?
RICO
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.
Q 12An FBI memo says which boss urged the Five Families to kill Giuliani?
John Gotti
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.
Q 13Which future Secretary of Homeland Security assisted Giuliani in the Mafia Commission prosecution?
Michael Chertoff
Q 21Giuliani's first police commissioner, who championed "broken windows" policing, was who?
Bill Bratton
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.
Q 22The "broken windows" theory adopted under Giuliani was set out in 1982 by George Kelling and which co-author?
James Q. Wilson
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.
Q 23What is the name of the crime-mapping system the NYPD introduced under Giuliani in 1994?
CompStat
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.
Q 14Which Wall Street arbitrageur, prosecuted by Giuliani, had made a fortune betting on corporate takeovers?
Ivan Boesky
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.
Q 15Giuliani first ran for mayor in 1989 and lost narrowly to whom?
David Dinkins
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.
Q 16Which heir did Giuliani beat in the 1989 Republican mayoral primary?
Ronald Lauder
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.
Q 17Shunned by the Conservative Party, Republican Giuliani also ran for mayor on which party's line?
Liberal
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.
Q 18Which borough's vote on leaving the city helped Giuliani's narrow 1993 win?
Staten Island
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.
Q 19Giuliani was the first Republican elected mayor of New York since which 1965 winner?
John Lindsay
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.
Q 20In 1992 Giuliani addressed a rally of off-duty police officers that turned into a riot outside which building?
City Hall
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.
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.
Q 24Which Democrat did Giuliani face in the 1997 mayoral election?
Ruth Messinger
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.
Q 25Giuliani quit the 2000 Senate race against Hillary Clinton after being diagnosed with what?
Prostate cancer
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.
Q 26Which retiring senator's seat were Giuliani and Hillary Clinton competing for in 2000?
Daniel Patrick Moynihan
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.
Q 27Giuliani was criticised for putting the city's emergency command centre in which building?
7 World Trade Center
The tower had been a terrorist target in 1993 and collapsed on 9/11, hampering coordination.
Q 28After 9/11, Giuliani declared what in New York "safe and acceptable"?
Air quality
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.
Q 29What did Queen Elizabeth II give Giuliani in February 2002?
An honorary knighthood (KBE)
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.
Q 30Whom did Giuliani endorse to succeed him as mayor in 2001?
Michael Bloomberg
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.