companies All of Donald Trump's Businesses, Ranked by Dubiousness  

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List Rules Vote up the businesses started by Trump that you think sound the most dubious and suspect.

Since announcing his run for president in 2015, a spotlight has been shining bright on Donald Trump's most dubious business ventures. Some of them were total disasters, while others were successful companies that ran into legal or political trouble. Even with the many failures, Trump has run a successful and profitable company here and there.

The worst Donald Trump companies are the ones that involve a business he doesn't understand (airlines, alcohol, radio), or ones that were never anything but cheap scams in the first place (Trump University, mortgages, vitamins). Some of these are so dubious that they've led to lawsuits, settlements, even corporate bankruptcy.

Here are the most dubious Trump businesses, ranked from the worst to the most honest.
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Trump University


Trump University is listed (or ranked) 1 on the list All of Donald Trump's Businesses, Ranked by Dubiousness
Photo: Trump Entrepreneur Initiative
Most of Trump's dubious businesses were vanity cash grabs that didn't hurt anyone. But Trump University was different. Launched in 2005, it purported to teach would-be real estate investors the tricks of the trade that Trump himself used to become a billionaire. Pitching itself as an actual accredited college (which it was not), Trump University bragged about the resumes of its "teachers" and offered classes in asset management, real estate, and wealth creation. The costs ranged from thousands to tens of thousands of dollars - and the classes proffered no information that couldn't be gotten much cheaper elsewhere.

The "school" was the subject of a number of fraud allegations and lawsuits, with former students and employees claiming it was a pyramid scheme that preyed on elderly and desperate people, making them think their "classes" would lead to unimaginable wealth. It was legally forced to change its name in 2010, and folded a year later. It still has a number of legal actions pending against it.
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Trump Mortgage


Trump Mortgage is listed (or ranked) 2 on the list All of Donald Trump's Businesses, Ranked by Dubiousness
Photo: Internet Wayback Machine
Getting into the mortgage business just as the mortgage business was collapsing is either brilliant or insane. To Trump, it was brilliant. He announced his mortgage lending firm in late 2006, just as the real estate bubble was bursting - an economic calamity that Trump claimed to have heard about but "hadn't seen." His prospective customers had, and Trump Mortgage failed to reach any of its financial goals. Trump pulled the plug after 18 months. He later claimed his only attachment to the business was slapping his name on it, and that he still made money.
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Trump Shuttle


Trump Shuttle is listed (or ranked) 3 on the list All of Donald Trump's Businesses, Ranked by Dubiousness
Photo: Freebase/CC-BY-SA
Trump's mini-airline opened in 1989, making flights from New York to Boston and Washington with 20 decades-old jets. Despite its luxury flourishes (Trump called his shuttle service "an absolute diamond"), the airline never made money. Trump financed the airline's purchase through massive loans that defaulted in less than a year, leaving him in massive debt.

A mechanic's strike, Trump's total lack of knowledge about the airline industry, and soaring fuel costs thanks to the Gulf War finished off the airline, and by 1992, it was sold off. Trump's crushing debt load from the purchase of the jets was a major factor in the first of his bankruptcies.
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Trump Taj Mahal


Trump Taj Mahal is listed (or ranked) 4 on the list All of Donald Trump's Businesses, Ranked by Dubiousness
Photo:  BruceEmmerling/Pixabay/CC0 1.0
The grand Trump Taj Mahal Casino began construction in Atlantic City in 1984, but the builder died, putting the site up for auction. Trump purchased it in 1987, and spent the next three years pouring money into the complex. He also got into a much publicized lawsuit battle with TV magnate Merv Griffin, who also wanted the site. The casino finally opened in 1990 - and declared bankruptcy a year later, $3 billion in the red - almost all on junk bonds.

The filing let Trump reorganize the casino's debt, in exchange for lower interest rates. The Taj went bankrupt again, along with most other Trump casinos, in 2004 - and again in 2014, with the casino set to close in December of that year. At the last second, Trump sold the complex and stepped down as Chair of Trump Entertainment Resorts. The Taj was also beset by legal problems, labor issues, shootings, and violations of federal currency laws.