Donald Trump's 5 Biggest Business Failures

By Kyle James on 9 September 2015 5 comments

While Donald Trump is currently enjoying success on the campaign trail for the Republican nomination for president in 2016, the ride hasn't always been smooth for the controversial billionaire. Over the years, he's had many ventures simply fail to catch on for a variety of reasons. Here are five of his biggest business failures — some of which you've probably never heard of.

1. Trump: The Game

In 1989, Trump launched a board game from Milton Bradley similar to the iconic Monopoly. The game was initially met with excitement, but in the end, the market spoke and loudly said, "No thanks." The game was simply titled "Trump: The Game" and while it tried to be a shorter version of Monopoly, critics found it to lack strategy and it shortly went away.

Then in 2004, on the heels of The Apprentice, a different version of the game resurfaced with the catchphrase "I'm Back and You're Fired!" on the cover of the box. The game was based on the bidding and winning of properties but it also never gained traction (some considered it quite boring to play), and thus was discontinued, as well.

2. Trump Vodka

When Trump launched his own Vodka product in 2006, it was a bit of a head scratcher due to his adamancy that he has never had a drink (he actually had a brother who died from an addiction to alcohol). While Trump Vodka had the very appropriate slogan of "Success Distilled," sales were very meager and he was unable to take significant market share away from Grey Goose and Absolut. Production of Trump Vodka was finally halted in 2011 due to a lack of sales.

3. Trump Airlines

From 1989 to 1992, Donald Trump was heavily involved in the airline industry with Trump Shuttle, Inc., better known as Trump Airlines. In 1989, Trump purchased the landing rights and many of the assets from the defunct Eastern Airlines and began hourly flights between New York City, Boston, and Washington D.C. The downfall of the business venture began when Trump began upgrading his fleet in an effort to become a "luxury" carrier. The interior of his Boeing 727s boasted gold-colored lavatory fixtures, chrome seat belts, and maple wood veneer throughout.

Naturally, Trump's ticket prices began rising and so did his financial troubles. Unfortunately for Trump, most of his core travelers could care less about the fancy upgrades and wanted the convenience of a budget regional airline more than the luxury aspects Trump was trying to grow. In the end, Trump Shuttle was never able to make a profit and his high debt-load eventually led to defaulted loans. By April of 1992, Trump Shuttle failed to exist when his creditors sold all remaining assets to US Airways.

4. Trump Casinos

Trump Entertainment Resorts, the company behind three Atlantic City hotels and casinos, two of which no longer exist, has filed more than a couple of bankruptcies as of 2014. Trump appears to be losing interest in Atlantic City, as his only current tie to the city is the Trump Taj Majal casino resort, which bears his name and likeness in exchange for stock in the company.

5. Trump University

Back in 2005, Trump founded Trump University, a non-accredited school designed to teach his investing strategies and techniques along with his real estate prowess. Things went okay until 2010, when four students came forward with a lawsuit claiming the school was nothing more than an extended infomercial with a constant upsell trying to get students to purchase additional seminars.

Trump University was subsequently renamed the "Trump Entrepreneur Initiative," and after that failed to gain traction, the university went away altogether in 2011. Trump is expected to be questioned in court this month stemming from the class action lawsuit brought on by the former students.

To be fair to "The Donald," he's had many incredibly successful business ventures including Trump Tower, The Apprentice, 40 Wall Street, and the Grand Hyatt Hotel in Manhattan. Whenever you take the number of business risks that Trump has taken over the years, there are inevitably going to be failures along the way. As with any successful investors, a few failures along the way simply demonstrate their tenacity.

Should Donald Trump's business failures be used as a gauge for his possible effectiveness as President of the United States?

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Guest

Only 5 business mistakes.... Still better than Hilary Clinton entire career of failures. Just saying

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vasanta

Trump is a bombastic buffoon who only knows how to brag and insult people. What a disgrace if he becomes president. He has money but no class or breeding whatsoever.

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Guest

Trumps failures are nothing compared to Benghazi!

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Guest

If Trump wins the world will never forgive America.

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Guest

Only five failures listed? Trump Spring Water, GoTrump (travel), the USFL, Trump Magazine, Trump the Game, The Apprentice Board Game, Tour De Trump, Two failed marriages, Trump Ice, Trump Vodka, Trump Steaks, Trump Mortgage, Trump Airlines, Trump University. Speaking of Trump Casinos, it's more than "a couple of bankruptcies." 1991 Trump's Taj Mahal in Atlantic City, 1992 Trump Plaza Hotel in Atlantic City, 2004 Trump Hotels & Casinos Resorts, 2009 Trump Entertainment Resorts. Next?

One of his favorite vices he loves to brag about is filing for bankruptcy. I can see it now, Trump's plan for the US: Declare bankruptcy, shed half the deficit and give half controlling interest to Chinese creditors.