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

Mike Rothschild
1.8k votes 436 voters 15.5k views 28 items

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.
1 160 VOTES

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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2 105 VOTES

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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3 106 VOTES

Trump Steaks


Trump Steaks is listed (or ranked) 3 on the list All of Donald Trump's Businesses, Ranked by Dubiousness
Photo: The Sharper Image
While only a minor part of the Trump empire, Trump's failure in the meat business gained an outsized reputation. He had trademarked the name in the '90s, but didn't start selling his steaks until 2007, when he made a deal with The Sharper Image. Priced way above the market norm ($200 for four steaks and 12 burgers, just to start), the catalog struggled to sell them, moving virtually none. After two months, the steaks were pulled from The Sharper Image stores, and the brand ceased to exist.
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4 65 VOTES

The USFL


The USFL is listed (or ranked) 4 on the list All of Donald Trump's Businesses, Ranked by Dubiousness
Photo: USFL

Trump made a big splash in the nascent United States Football League, purchasing the New Jersey Generals and spending major money. Trump had even bigger plans for the spring football league, hoping to move its games to the fall and merge it with the NFL. But Trump bought his team a year into the USFL's existence, and while the league was doing well, it was nowhere near fiscally solvent enough to challenge the NFL.

Sure enough, Trump persuaded most of the other owners in the league to go along with him, and moved the league to fall games in 1986. ABC withdrew its TV deal, and Trump sued the NFL for anti-trust violations. He "won" the suit - and the USFL was awarded damages of $1. The league collapsed, and Trump walked away from the whole thing, calling the USFL "small potatoes."
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