Donald Trump’s 10 Worst Business Failures



Real estate mogul. Billionaire. Reality TV star. President of the United States. Donald Trump goes by a lot of titles, and whichever side of the political arena you’re on, I’m sure there’s a lot more you can say about this man. Currently, Mr. Trump is America’s most polarizing character and no one knows what he’ll say or do next.

But, if it’s one thing Trump seems good at doing, it’s slapping the TRUMP name on things to sell his brand. If you were to visit Trump Tower in New York City, you’ll see gift shops stuffed full of items and souvenirs with his name stamped on there somewhere. While Trump loves to promote his brand, he’s not always successful at doing so.

Here are 10 of Donald Trump’s worst business failures:

1) Trump University

Let’s get the most well-known failure out of the way. Trump, a knowledgeable businessman, thought he could add to his fortune by teaching others the art of the deal. In 2005, Trump University was born. Because the college was never accredited, many students (who, in some cases, paid as much as $35,000 to take the course), felt the whole thing was a fraud.

Eric Schneiderman, New York Attorney General, sued Trump in 2013 on the basis of fraud. The case was eventually settled in 2016 after then President-Elect Donald Trump agreed to pay $25 million in settlement fees.

2) Trump Vodka

So, what happens when a man, who claims he doesn’t drink, tries to get into the alcohol business? Well, it goes belly up. Trump vodka, released in 2007, was supposed to become “the most popular drink in America”, but didn’t even survive two years on the market. It disappeared, never to be heard from again.

3) Trump Airlines

Everyone has seen Trump’s famous plane on TV with his name covering the fuselage, but his plane wasn’t intended to be the only one. After Eastern Air Lines went belly-up, Trump bought the airline for $365 million to provide first class accommodations to businessmen and women traveling between New York, Boston, and Washington D.C.

The idea didn’t get too far. Trump ended up selling the company to USAir after it defaulted on its debts.

4) Trump Steaks

Another popular talking point during the 2016 election was Trump Steaks. In 2007, Trump decided to hop into the beef game with business partners QVC and Sharper Image. They claimed to sell “a taste of Donald Trump’s luxurious lifestyle”. The partnership lasted a while until 2014 before dying out completely.

5) Trump Mortgage

What does a real estate mogul know about real estate? Well, you’d think a lot, but Mr. Trump made a bad mistake. One year, the future president decided to start his own mortgage company, claiming that the real estate market would be strong for a ‘very, very long time’. The problem? It was 2006. Two years later, the housing market collapsed, killing Trump Mortgage.

6) Trump Magazine

Do the super-rich and famous have time to sit down and read magazines? That’s the audience Trump was going for when he launched Trump Magazine back in 2007. What many people considered “wealth porn”, the magazine was full of things the average reader wouldn’t associate with, such as reviews for mega yachts, expensive watches covered in jewels, how to make over your private jet, and so much more.

The magazine’s number one model? Donald Trump himself. He featured in a lot of the images and ads himself, making it an Ode to Trump. The magazine was done just two years later in 2009.

7) Trump: The Game

If you were tired of just being moderately rich playing Monopoly, you could try your hand at Trump: The Game. This was a game just like Monopoly where the various players attempt to one-up each other by buying/selling real estate and becoming the Trump of the game. Partnering with Milton Bradley, the game didn’t meet expectations and later disappeared.

8) Trump Casinos

Everyone knows that Donald Trump owns casinos all over the country, except when they start to go downhill. After Trump Casinos filed for its 3rd Chapter 11 bankruptcy, Trump claimed that he has nothing to do with that business, and that all he’s done is slap his name on the building. He later resigned as head of the Trump Entertainment wing of his empire.


Not even online booking giant Travelocity could keep from going under. This site was meant to serve as a search engine for luxury flights, but it didn’t even last a year.

10) Trump Beverages

Trump has made a few attempts at selling beverages. We talked about Trump vodka earlier, but he also tried his hand at Trump Ice (bottled water) and other types of beverages. He filed for a trademark of the name “Trump Fire”, but never did anything with it. Same with Trump Power. They were non-alcoholic drinks, but the whole plan was later scrapped.

Love him or hate him, Donald Trump has had his share of both success and failure. Most entrepreneurs fail many times over before finally making it to the big time. Either way, we can’t blame the man for trying!

Last modified: February 27, 2018