All of Donald Trump's Businesses, Ranked by Dubiousness

Voting 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.

  • 1
    361 VOTES

    Trump University

    Trump University
    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.
    361 votes
  • 2
    269 VOTES
    Trump Mortgage
    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.

    269 votes
  • 3
    274 VOTES

    Trump Taj Mahal

    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.
    274 votes
  • 4
    261 VOTES

    The Trump Network

    The Trump Network
    Photo: CBS News

    The Trump Network was not a TV network, but a vitamin-shilling pyramid scheme. In 2009, Trump purchased a dodgy supplements company called Ideal Health (which had dozens of complaints pending against it when Trump bought it), slapped his name on it, and started marketing it as a post-recession get-rich-now opportunity. Essentially, one was to take a $100 test that would determine what supplements you needed, and then you'd be sold those vitamins at an outrageous markup.

    The company was a scam on a number of levels, taking customers' money and giving nothing back. Even if it had given customers anything, it would have merely been a meaningless test and the same vitamins you can buy in any CVS. The Trump Network sold a bunch of other woo crap as well, including energy drinks, kid snacks, and skin-care products.

    All the while, Trump told the press his Network would become bigger than Amway. It did not, and Trump sold the company after two years, beset by complaints that vendors weren't getting paid. As many as 21,000 people lost at least some amount of money.
    261 votes
  • 5
    207 VOTES

    Trump Model Management

    Trump Model Management
    Photo: ABC News
    Trump launched his model talent agency in 1999, signing a host of foreign and domestic models. While the business has been successful, it's also been hit with multiple lawsuits and accusations that it broke federal visa laws.
    207 votes
  • Trump opened the Plaza Hotel and Casino in Atlantic City in 1984, and it immediately ran into branding issues, with dozens of unsold luxury suites. It finally began turning a profit until 1990, when it began losing money - to Trump's own Taj Mahal. Trump had to take out a mortgage on the property's parking garage to keep it afloat, and after a bankruptcy and several renovations, planned to dump it for $20 million. Even that deal fell through, and it closed in 2014. Over a thousand employees were put out of work.

    Naturally, Trump claimed he'd cashed out years earlier, and only kept his name on the casino out of charity.

    183 votes