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60 free Rudy Giuliani trivia questions with answers — history quiz, new questions added Aug 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 60 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 60 questions with answers and explanations. Play the quiz
Q 01Rudy Giuliani was mayor of which city from 1994 to 2001?
New York
He was the city's 108th mayor and its first Republican mayor in nearly three decades.
Q 02For his leadership after the September 11 attacks, Giuliani was named Time magazine's Person of the Year for which year?
2001
Time noted his image had shifted from rigid and self-righteous to a man who could unite a city in crisis.
Q 03Giuliani was widely nicknamed what after 9/11?
America's mayor
Queen Elizabeth II honoured him in February 2002 for the same leadership.
Q 04Giuliani was born in 1944 in which Brooklyn neighbourhood?
East Flatbush
It was then a largely Italian American enclave; his parents were both children of Italian immigrants.
Q 05Giuliani's father Harold served prison time in which New York prison?
Sing Sing
He was convicted of felony assault and robbery and later worked as an enforcer for a loan-sharking ring.
Q 06Giuliani majored in political science at which institution in Riverdale, Bronx?
Manhattan College
He considered becoming a priest before choosing NYU Law, where he graduated cum laude in 1968.
Q 07Giuliani volunteered for whose 1968 presidential campaign, back when he was a Democrat?
Robert F. Kennedy
He voted for George McGovern in 1972, went independent in 1975 and became a Republican in December 1980.
Q 08Giuliani avoided the Vietnam draft partly through a 1969 essential-civilian reclassification while working as what?
A federal judge's law clerk
When reclassified 1-A in 1970 he drew a high lottery number, 308, and was never called.
Q 09In 1981 Giuliani became U.S. Associate Attorney General, the third-highest post in which department?
Justice
He supervised the U.S. attorneys, the DEA and the U.S. Marshals under President Reagan.
Q 10From 1983 to 1989 Giuliani was U.S. Attorney for which jurisdiction?
Southern District of New York
Technically a demotion, but the highest-profile prosecutor's office in the country and a classic springboard to politics.
Q 11Giuliani's Mafia Commission trial used which federal law to indict the heads of the Five Families?
RICO
The Racketeer Influenced and Corrupt Organizations Act let him charge extortion, labour racketeering and murder for hire together.
Q 12How many organised crime figures did Giuliani indict in the Mafia Commission trial?
Eleven
Time later called it possibly the most significant assault on organised crime since the Chicago Mafia was swept up in 1943.
Q 13Which future Secretary of Homeland Security assisted Giuliani in the Mafia Commission prosecution?
Michael Chertoff
Chertoff, later a co-author of the Patriot Act, was one of three assistant U.S. attorneys on the case.
Q 21Giuliani's first police commissioner, who championed "broken windows" policing, was who?
Bill Bratton
Bratton made the cover of Time in 1996 and was reportedly forced out after two years in a clash of egos.
Q 22The "broken windows" policing theory adopted under Giuliani is associated with which scholar?
James Q. Wilson
It targeted graffiti, turnstile jumping and the "squeegee men" to signal that order would be maintained.
Q 23What was the name of the computer-driven crime-mapping system introduced by Bratton and Jack Maple?
CompStat
Critics say it tempts commanders to underreport crime; it has since spread to departments worldwide.
Q 14Which Wall Street arbitrageur, prosecuted by Giuliani, had made a fortune betting on corporate takeovers?
Ivan Boesky
Boesky cooperated with the SEC and helped bring down junk-bond king Michael Milken.
Q 15Giuliani first ran for mayor in 1989 and lost narrowly to whom?
David Dinkins
Dinkins had upset three-term incumbent Ed Koch in the Democratic primary.
Q 16Whom did Giuliani beat in the 1989 Republican mayoral primary?
Ronald Lauder
The cosmetics heir then ran on the Conservative line against him in the general election.
Q 17Besides the Republican line, Giuliani ran his mayoral campaigns on which other ballot line?
Liberal
The Conservative Party refused to endorse him and ran its own candidates in 1989, 1993 and 1997.
Q 18Giuliani won the 1993 mayoral election by roughly how many votes?
53,000
He became the first Republican elected mayor in 28 years.
Q 19Giuliani was the first Republican elected mayor of New York since which 1965 winner?
John Lindsay
His 1997 re-election made him the first Republican to win a second term on that line since La Guardia in 1941.
Q 20Whose blessing did Giuliani seek in 1993 by visiting the Lubavitcher Rebbe?
Rabbi Menachem Mendel Schneerson
The visit came in a campaign shaped by the Crown Heights riot.
Q 24Which Democrat did Giuliani face in the 1997 mayoral election?
Ruth Messinger
She had beaten Al Sharpton in the primary; Giuliani won 58 percent to 41.
Q 25Giuliani quit the 2000 Senate race against Hillary Clinton after being diagnosed with what?
Prostate cancer
His father had died of the same disease in 1981; the same weeks saw his separation from Donna Hanover become public.
Q 26Which retiring senator's seat were Giuliani and Hillary Clinton competing for in 2000?
Daniel Patrick Moynihan
Charles Rangel recruited the First Lady to counter Giuliani's star power.
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 28How many days after the 9/11 attacks did Wall Street reopen, under Giuliani's push?
Six
He told the public that first month that "the air quality is safe and acceptable," a claim later heavily criticised.
Q 29Which honour did Queen Elizabeth II give Giuliani in February 2002?
An honorary knighthood (KBE)
As an American he cannot use the title "Sir," but may add KBE after his name.
Q 30Whom did Giuliani endorse to succeed him as mayor in 2001?
Michael Bloomberg
Bloomberg, a recent Republican convert, took office on January 1, 2002, after Giuliani's bid to extend his own term fizzled.