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Donald Trump’s biggest business fails – from casinos to steaks, 6 times the future US president didn’t make anything ‘great again’

STORYLeah Simpson
The steak and meat brand Trump Steaks is just one of President Donald Trump’s many failed business ventures. Photo: @TrumpSteaks/Twitter
The steak and meat brand Trump Steaks is just one of President Donald Trump’s many failed business ventures. Photo: @TrumpSteaks/Twitter
Donald Trump

From Trump University, notorious for its fraud lawsuits, to Trump Taj Mahal and other New Jersey casinos that ended in bankruptcies, not all of Donald Trump’s business ideas were as ‘great’ as he hoped

Virgin Airlines boss Richard Branson once said, “Say yes, then learn how to do it later,” and it looks like his one-time airline rival Donald Trump lives by that motto.

If you thought the US president’s sudden interest in politics was random, his past pattern of business ventures shows that the saying “fake it ’til you make it” doesn’t exactly always work.

Here are six of Trump’s failed business ventures before he found fame on The Apprentice and nabbed the most important seat at the White House.

Casinos

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Trump had his name plastered on four properties in New Jersey’s casino resort area, in Atlantic City, between the 80s and 2010s: Trump Taj Mahal, Trump Marina (originally Trump’s Castle), Trump Plaza, and Trump’s World Fair at Trump Plaza. Trump didn’t generate enough money to repay the US$47.3 million interest on the US$675 million in financing for the Trump Taj Mahal. By 1991, he filed for bankruptcy for the property with US$3 billion debt, and by 1992 he filed bankruptcy a total of three times for his properties in the area. He stepped down from his role as CEO of Trump Entertainment Resorts in 2004.

Airlines

President Donald Trump flanked by his wife Melania arriving in France in 2019. Photo: Agence France-Presse
President Donald Trump flanked by his wife Melania arriving in France in 2019. Photo: Agence France-Presse

From 1989 to 1992, Donald Trump operated the Trump Shuttle commuter airline between New York City, Washington and Boston. For the US$365 million venture, he took over Eastern Air Lines’ hourly service to the US east coast cities, originally called Eastern Air Lines Shuttle, and rebranded 17 Boeing 727s by slapping his last name on the aircraft and decking them out with maple veneer, faux marble, leather seats and plush carpets.

However, Trump failed to earn enough from the luxury airline and defaulted on a US$1.1 million loan repayment. In the end he gave the company up in a Shuttle Inc merger deal.

Travel websites

Trump boards an Air Force One in Maryland in 2020. Photo: Agence France-Presse
Trump boards an Air Force One in Maryland in 2020. Photo: Agence France-Presse
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