Donald Trump Trivia
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148 free Donald Trump trivia questions with answers — history quiz, new questions added Oct 2026.
40 free Donald Trump trivia questions with answers. Whatever you think of him, Donald Trump has lived one of the most documented lives in modern America, and this quiz sticks to the record. Forty questions cover the Queens childhood and the Wharton degree, the family real-estate business and Trump Tower, The Art of the Deal, the casinos, the airline, Miss Universe and Trump University, the WrestleMania hair match, The Apprentice and 'You're fired', the cameos, and the marriages and children. Then it moves to politics: the 2000 Reform Party run, the 2016 upset over Hillary Clinton, the two impeachments, the 2024 conviction, the Butler assassination attempt, the return to office as the 47th president and the records that came with it. Every stem is written neutrally; the point is whether you know the facts, not what you make of them. Every answer was checked against Wikipedia's articles on Trump, his businesses, his campaigns and the events involved, and each question carries its source.
30 of 148 questions with answers and explanations. Play the quiz
Q 01In which New York City borough was Donald Trump born?
Queens
Queens was where his father Fred built houses and apartment blocks; Donald joined the firm after college, then steered it towards Manhattan skyscrapers.
Q 02Trump graduated in 1968 from the Wharton School, which is part of which Ivy League institution?
Penn
Penn's Wharton School gave Trump his economics degree in 1968; press profiles long said he graduated first in his class, but the commencement program lists him among neither the honours graduates nor the prize winners.
Q 03Which boarding school did Trump's father send him to from eighth through twelfth grade?
New York Military Academy
New York Military Academy was his father's answer to schoolboy antics that had embarrassed the family: Fred sent him up the Hudson just before eighth grade, hoping its discipline would channel his energy.
Q 04What name did Donald Trump give the family real-estate business after his father made him its president?
The Trump Organization
The Trump Organization became his umbrella name for his father's string of companies in the 1970s, after Fred moved up to chairman and made Donald president.
Q 05Trump's first big Manhattan project, opened in 1980, was the renovation of which closed-down hotel by Grand Central?
The Commodore
The Commodore, shut since 1976 beside Grand Central, reopened in 1980 as the Grand Hyatt after Trump secured a 40-year tax abatement, the first New York City had granted on a commercial property.
Q 06On which Manhattan avenue does Trump Tower, his home and company headquarters, stand?
Fifth Avenue
Fifth Avenue is the address of the 58-storey tower, yet its top floor is numbered 68: Trump skipped ten floor numbers, arguing that the soaring atrium was as tall as ten ordinary storeys.
Q 07Which 1987 bestseller, ghostwritten by Tony Schwartz, made Trump a household name?
The Art of the Deal
The Art of the Deal sold Trump to the public as a master dealmaker, but Tony Schwartz, who wrote it, later called the book the greatest regret of his life and wished it were out of print.
Q 08Trump's hotel and casino companies filed for bankruptcy six times under which chapter of US law?
Chapter 11
Chapter 11 lets a business keep operating while it renegotiates its debts; Trump's companies used it six times between 1991 and 2009, though he never filed for personal bankruptcy.
Q 09Which Northeast shuttle airline did Trump buy and relaunch under his own name in 1989?
The Eastern Air Lines Shuttle
The Eastern Air Lines Shuttle became Trump Shuttle in June 1989; it never made a profit and passed to its bank lenders after he defaulted on the loans.
Q 10Which beauty pageant organisation did Trump buy in 1996?
Miss Universe
Trump bought the Miss Universe Organization, which then also ran Miss USA and Miss Teen USA, in 1996; NBC cut ties in 2015 over his campaign-launch remarks about Mexican immigrants, and he sold it within months.
Q 11In which Florida town is Mar-a-Lago, the estate Trump bought in 1985?
Palm Beach
Palm Beach's barrier island holds the estate, which runs from the Atlantic to Lake Worth Lagoon; Trump turned it into a private club in 1995 and switched his official residence there from New York in 2019.
Q 12Which gambling resort was home to Trump's casinos, including the Taj Mahal?
Atlantic City
Atlantic City housed Trump Plaza, Trump's Castle and the Taj Mahal, which opened in 1990 on a mountain of high-interest junk bonds and sought bankruptcy protection the very next year.
Q 13Which reality-TV producer created The Apprentice, which Trump hosted from 2004?
Mark Burnett
Q 21Which Trump venture was renamed after New York said it was not an academic institution?
Trump University
Trump University sold real-estate seminars for up to $35,000 and became the Trump Entrepreneur Initiative in 2010; days after his 2016 election win, Trump paid $25 million to settle fraud suits from former students.
Q 22In 2000, Trump briefly ran for the presidential nomination of which movement founded by Ross Perot?
The Reform Party
The Reform Party was tearing itself apart by 2000: Trump's ally Jesse Ventura walked out, and days later Trump quit too, saying its infighting left any nominee no chance of winning.
Q 23Whom did George H. W. Bush pick in 1988 after noting in his diary that Trump wanted the vice-presidential slot?
Mark Burnett, the producer of Survivor, struck an unusual deal with his star: half the show's profits, which paid Trump nearly $200 million over 16 years.
Q 14What was Trump's catchphrase for eliminating contestants on The Apprentice?
'You're fired.'
'You're fired.' ended every boardroom showdown, and Trump kept using it off screen: when his successor as host quit in 2017, Trump insisted the man had been fired instead.
Q 15Which former governor replaced Trump as host of The Apprentice after NBC cut ties in 2015?
Arnold Schwarzenegger
Arnold Schwarzenegger hosted The New Celebrity Apprentice for a single season in 2017, then quit after its ratings sagged and Trump, still an executive producer, mocked him for them in public.
Q 16In which 1992 Christmas film does Trump appear as himself, giving directions in a hotel lobby?
Home Alone 2: Lost in New York
Home Alone 2: Lost in New York shot in the Plaza Hotel, which Trump then owned; director Chris Columbus said the cameo was Trump's condition for filming there.
Q 17What was at stake in WrestleMania 23's 'Battle of the Billionaires' between Trump and Vince McMahon?
The loser's head would be shaved
The loser's head would be shaved: each billionaire backed a wrestler, and when Trump's man won, Trump and Stone Cold Steve Austin shaved Vince McMahon bald in the ring.
Q 18Which wrestler fought for Trump in the 'Battle of the Billionaires' at WrestleMania 23?
Bobby Lashley
Bobby Lashley, then ECW champion, beat Vince McMahon's pick Umaga before a record pay-per-view audience, and WWE went on to induct Trump into its Hall of Fame in 2013.
Q 19Trump's first wife Ivana was the mother of which three children?
Donald Jr., Ivanka and Eric
Donald Jr., Ivanka and Eric are Ivana's children, and all three later sat beside their father as boardroom advisers on The Apprentice; Tiffany's mother is Marla Maples and Barron's is Melania.
Q 20Melania Trump was born in which country?
Slovenia
Slovenia, then part of Yugoslavia, is where Melania was born Melanija Knavs in 1970; a wooden statue of her near her hometown of Sevnica was torched on July 4, 2020 and replaced with a bronze one.
Dan Quayle
Dan Quayle, a young Indiana senator, got the job; Bush's diary called Trump's overture, relayed by strategist Lee Atwater, 'strange and unbelievable'.
Q 24What are electors called who break their pledge, as two Texans did to cut Trump's 2016 total to 304?
Faithless electors
Faithless electors cost Trump two votes and Hillary Clinton five, leaving him ahead by 304 to 227; he was the fifth president elected while losing the popular vote.
Q 25Before Trump, every US president had brought which experience to the job?
Military or government service
Military or government service had been on the record of every earlier president; Trump, elected from real estate and television, had neither, which let him run as the outsider.
Q 26Who served as Trump's vice president during his first term?
Mike Pence
Mike Pence, a former Indiana governor, was vice president from 2017 to 2021 and refused Trump's demand to reject electoral votes on January 6, 2021.
Q 27Trump's first impeachment in December 2019 arose from a phone call with the president of which country?
Ukraine
A July 2019 call with Ukraine's president Volodymyr Zelenskyy, in which Trump pressed for investigations of Joe and Hunter Biden, led to the impeachment; the Senate acquitted him in February 2020.
Q 28Which Republican senator voted to convict Trump at both of his impeachment trials?
Mitt Romney
Mitt Romney was the only Republican to vote guilty in 2020; six more joined him in 2021's 57–43 vote, the most bipartisan conviction vote in any presidential impeachment trial yet ten short of the 67 needed to convict.
Q 29What was the handle of Trump's personal Twitter account, banned in January 2021?
@realDonaldTrump
@realDonaldTrump had some 88 million followers when Twitter suspended it for good two days after the Capitol attack, citing the risk of further incitement; the account was restored in November 2022.
Q 30Which platform, owned by Trump Media & Technology Group, launched in February 2022?
Truth Social
Truth Social launched on February 21, 2022, under Trump Media & Technology Group as Trump's own outlet after Twitter and Facebook banned him following January 6, 2021.