100 free Donald Trump trivia questions with answers — history quiz, new questions added Aug 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 100 questions with answers and explanations. Play the quiz
Q 01In which New York City borough was Donald Trump born?
Queens
He grew up in a 23-room house in Jamaica Estates, the fourth of Fred and Mary Anne Trump's five children.
Q 02Trump graduated in 1968 from the Wharton School, which is part of which Ivy League institution?
Penn
He spent his first two years at Fordham before transferring; he had considered film school in California.
Q 03Which boarding school did Trump's father send him to from eighth through twelfth grade?
New York Military Academy
He had attended the private Kew-Forest School through seventh grade before the move.
Q 04What new name did the family real-estate company get when Donald took over as its president in 1971?
The Trump Organization
Fred Trump's business managed middle-class apartments in Queens, Brooklyn and Staten Island; his son pushed it into Manhattan.
Q 05Trump's first big Manhattan project, opened in 1980, was the renovation of which derelict hotel by Grand Central?
The Commodore
It reopened as the Grand Hyatt with help from a $400 million city tax abatement arranged by his father.
Q 06How many storeys tall is Trump Tower on Fifth Avenue?
58
It opened in stages through 1983 next door to the Tiffany & Co. flagship, and its apartments sold out within months.
Q 07Who is credited as co-author of Trump's 1987 bestseller The Art of the Deal?
Tony Schwartz
The ghostwriter later publicly regretted the book; it made Trump a national celebrity as a dealmaker.
Q 08How many times did Trump's businesses file for Chapter 11 bankruptcy protection between 1991 and 2009?
Six
The filings covered the Plaza Hotel, the Atlantic City casinos and Trump Hotels & Casino Resorts; he never filed personally.
Q 09Which airline did Trump buy in 1988 and rename after himself?
The Eastern Air Lines Shuttle
Trump Shuttle was financed with $380 million in loans from 22 banks and passed to the lenders after he defaulted in 1991.
Q 10Which beauty pageant organisation did Trump buy in 1996?
Miss Universe
The deal included Miss USA and Miss Teen USA; NBC dropped the pageants in 2015 after his campaign-launch remarks about immigrants.
Q 11In which Florida town is Mar-a-Lago, the estate Trump bought in 1985?
Palm Beach
He turned it into 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
The Taj Mahal was his third venue there, bought in 1988 and financed largely with junk bonds.
Q 13Which reality-TV producer created The Apprentice, which Trump hosted from 2004?
Mark Burnett
The show ran on NBC, and its winners received a one-year $250,000 contract to promote a Trump property.
Q 21Which company, cofounded in 2005, was renamed because New York said it was not an academic institution?
Trump University
It sold real-estate seminars for up to $35,000, became the Trump Entrepreneur Initiative in 2010 and was sued by the state for $40 million in 2013.
Q 22In 2000, Trump briefly ran for the presidential nomination of which movement founded by Ross Perot?
The Reform Party
He withdrew after three months; he had registered as a Democrat in 2001, a Republican in 2009 and unaffiliated in 2011 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?
George H. W. Bush
Q 14What was Trump's catchphrase for eliminating contestants on The Apprentice?
'You're fired.'
The New York Times called the show's version of him 'a highly flattering, highly fictionalized version' of himself.
Q 15Which former governor replaced Trump as host of The Apprentice after NBC cut ties in 2015?
Arnold Schwarzenegger
NBC dropped Trump over remarks about Mexican immigrants in his June 2015 campaign announcement.
Q 16In which 1992 Christmas film does Trump appear as himself, giving directions in a hotel lobby?
Home Alone 2: Lost in New York
According to director Chris Columbus, the cameo was the price of filming inside the Plaza Hotel, which Trump owned at the time.
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
Each man picked a wrestler to fight for him; Trump's man Bobby Lashley won and McMahon was shaved bald in the ring.
Q 18Which wrestler represented Trump in that WrestleMania 23 match?
Bobby Lashley
Stone Cold Steve Austin was special guest referee, and the event set an all-time Ford Field attendance record of 74,287.
Q 19Trump's first wife Ivana was the mother of which three children?
Donald Jr., Ivanka and Eric
Tiffany is his daughter with Marla Maples and Barron his son with Melania.
Q 20Melania Trump was born in which country?
Slovenia
Born Melanija Knavs in what was then Yugoslavia, she began modelling at 16 and married Trump in 2005.
Bush called the request 'strange and unbelievable'; a year earlier Trump had taken out full-page ads on foreign policy.
Q 24How many electoral votes did Trump win in the 2016 election against Hillary Clinton?
304
He was the fifth president elected while losing the popular vote, trailing Clinton by about 2.87 million votes.
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
Every previous president had at least one of the two on his resume; Trump campaigned explicitly as an outsider.
Q 26Who served as Trump's vice president during his first term?
Mike Pence
The former Indiana governor later refused Trump's requests 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 whistleblower complaint said he had pressed Volodymyr Zelenskyy to investigate Joe and Hunter Biden; the Senate acquitted him.
Q 28How many Republican senators voted to convict Trump at his second impeachment trial in February 2021?
Seven
The House had charged him with incitement of insurrection after the January 6 Capitol attack; he had already left office when the vote came.
Q 29Roughly how many times did Trump post on Twitter between 2009 and his ban in January 2021?
57,000
Twitter began fact-check labels on some of his posts in May 2020; he launched his own platform in February 2022 after being banned.
Q 30Which platform, owned by Trump Media & Technology Group, launched in February 2022?
Truth Social
It has been described as a Twitter clone and was created in response to his bans after January 6.