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
Donald Trump was born in Queens on June 14, 1946, the fourth of Fred and Mary Anne Trump's five children, and grew up in a 23-room house there.
Q 02Trump graduated in 1968 from the Wharton School, which is part of which Ivy League institution?
Penn
Wharton is the business school of the University of Pennsylvania (Penn); Trump transferred there and earned a bachelor's degree in economics in 1968.
Q 03Which boarding school did Trump's father send him to from eighth through twelfth grade?
New York Military Academy
Trump entered New York Military Academy in Cornwall-on-Hudson at 13 and graduated from it in 1964, after attending the private Kew-Forest School through seventh grade.
Q 04What new name did the family real-estate company get when Donald took over as its president in 1971?
The Trump Organization
Trump took over Elizabeth Trump & Son in 1971 and renamed it The Trump Organization, pushing his father's outer-borough apartment business into Manhattan.
Q 05Trump's first big Manhattan project, opened in 1980, was the renovation of which derelict hotel by Grand Central?
The Commodore
The Commodore, a rundown hotel beside Grand Central Terminal, reopened in 1980 as the Grand Hyatt after Trump's renovation with Hyatt, helped by a 40-year city tax abatement.
Q 06How many storeys tall is Trump Tower on Fifth Avenue?
58
Trump Tower has 58 storeys, though its floor numbers run up to 68; it opened in 1983 beside the Tiffany & Co. flagship on Fifth Avenue.
Q 07Who is credited as co-author of Trump's 1987 bestseller The Art of the Deal?
Tony Schwartz
Tony Schwartz ghostwrote The Art of the Deal and later said he regretted it; the 1987 book spent 48 weeks on the New York Times bestseller list.
Q 08How many separate Chapter 11 bankruptcy filings did Trump's businesses make between 1991 and 2009?
Six
Six separate Chapter 11 filings, from the Taj Mahal casino in 1991 to Trump Entertainment Resorts in 2009, involved Trump's businesses; he never filed for personal bankruptcy.
Q 09Which airline did Trump buy in 1988 and rename after himself?
The Eastern Air Lines Shuttle
Trump bought the Eastern Air Lines Shuttle's Boston–New York–Washington service and relaunched it as 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 in 1996, which also runs Miss USA and Miss Teen USA; NBC cut ties in 2015 over his campaign-launch remarks about Mexican immigrants, and he sold it that year.
Q 11In which Florida town is Mar-a-Lago, the estate Trump bought in 1985?
Palm Beach
Mar-a-Lago sits on the barrier island of Palm Beach, between the Atlantic and Lake Worth Lagoon; Trump bought it in 1985, made it a private club in 1995 and declared it his primary residence in 2019.
Q 12Which New Jersey resort town 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 financed with about $675 million in junk bonds and went bankrupt the 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, launched in 2005, sold real-estate seminars costing up to $35,000; New York regulators objected to the 'university' label and it became the Trump Entrepreneur Initiative in 2010.
Q 22In 2000, Trump briefly ran for the presidential nomination of which movement founded by Ross Perot?
The Reform Party
The Reform Party, founded by Ross Perot in 1995, was Trump's vehicle for a short 2000 exploratory run; he quit in February 2000 and later bounced between Democratic, Republican and no registration before settling as a Republican in 2012.
Q 23Which Republican nominee did Trump ask, via Lee Atwater in 1988, to make him his running mate?
Mark Burnett, who also produced Survivor, created The Apprentice for NBC in 2004; its winners received a one-year $250,000 contract with a Trump company.
Q 14What was Trump's catchphrase for eliminating contestants on The Apprentice?
'You're fired.'
'You're fired.' closed each boardroom segment of The Apprentice; Trump even filed to trademark the phrase in 2004.
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 one season in 2017 after NBC dropped Trump over his June 2015 campaign-launch remarks about Mexican immigrants.
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 17At WrestleMania 23, what was at stake in the '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, fought for Trump and beat Vince McMahon's pick Umaga, with Stone Cold Steve Austin as special guest referee.
Q 19Trump's first wife Ivana was the mother of which three children?
Donald Jr., Ivanka and Eric
Donald Jr. (1977), Ivanka (1981) and Eric (1984) are Ivana's children; Tiffany is Trump's daughter with Marla Maples and Barron his son with Melania.
Q 20Melania Trump was born in which country?
Slovenia
Melania Trump was born Melanija Knavs in Novo Mesto, Slovenia, then part of Yugoslavia, in 1970; she began modelling at 16 and married Trump in January 2005.
George H. W. Bush
George H. W. Bush, the 1988 nominee, wrote in his diary that Trump's request to be considered for running mate was 'strange and unbelievable'; Bush chose Dan Quayle instead.
Q 24How many electoral votes did Trump win in the 2016 election against Hillary Clinton?
304
Trump received 304 electoral votes to Clinton's 227 once faithless electors were counted; he was the fifth president elected while losing the popular vote, trailing Clinton by about 2.87 million.
Q 25Trump was the first president to have done neither of which two things before he was inaugurated?
Served in the military or held public office
Trump was the first president who had neither served in the military nor held public office; every predecessor had at least one, and he campaigned explicitly as an 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 28How many Republican senators voted to convict Trump at his second impeachment trial in February 2021?
Seven
Seven Republicans — Burr, Cassidy, Collins, Murkowski, Romney, Sasse and Toomey — joined every Democrat and independent for a 57–43 vote, short of the 67 needed to convict on incitement of insurrection.
Q 29Roughly how many times did Trump post on Twitter between 2009 and his ban in January 2021?
57,000
Trump posted about 57,000 tweets from 2009 until Twitter permanently suspended him on January 8, 2021, two days after the Capitol attack; Twitter had begun fact-check labels on his posts in May 2020.
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.