Donald Trump's 14 Most Epic Business Failures

With so many business ventures, a few of Donald Trump's businesses were bound to go south. Sometimes, they went south only because of The Donald's decisions, and other times, ventures went belly up but Trump claimed he'd only licensed his name. Whether he was calling the shots or just investing, we've compiled a list of Donald Trump's failed businesses.

From an airline to two separate attempts at Trump board games, there are a number of epic business failures that Donald Trump has presided over or been involved in. Though he says he never once declared bankruptcy, the truth is that while he may not have personally done so, a number of his businesses have, and you'll find them here. There are a number of Donald Trump business ventures you could look at and wonder how he could have possibly ever thought they were anything but laughable.

Trump Steaks? Trump Vodka? How about Trump Mortgage, launched right before the global 21st century financial meltdown? The most Trumpian belly flops in business history are all accounted for on this list!

  • Also known as Trump Airlines. In 1989 Donald Trump decided that a bunch of airplanes would look better with his name on them. His airline had a few flight paths, mostly out of LaGuardia. He wanted to make it a luxury service and, as usual, a marketing platform for himself.

    At no point did Trump Shuttle turn a profit, and it was never considered successful - though that didn't stop the Donald from talking about his time in the airline business on The Apprentice

  • Trump: The Game

    In 2004, right as The Apprentice was heating up and starting Donald Trump's resurgence as a mogul, he decided to put out a board game, which was actually a reboot of a failed 1988 Trump game. The object of the 2004 game? "To make the most money." The game itself failed to accomplish this goal and joined its predecessor in the toy store bargain bin.

    Fun fact: the game had a six-sided dice, which is normal, except that the six is labeled "T" (for Trump). When you roll a T, you get to steal from another player.
  • Trump University

    Trump University was a school that started in 2005 as an outlet for Trump to educate people in real estate. It was not accredited, however, nor did it actually give degrees. In an add for the "schoo," Trump declared, "Just copy what I did and get rich." Well, no one got rich.

    To the point of the New York attorney general publicly called Trump University a scam. In 2010 Donald changed the name to avoid further lawsuits, but they keep on coming. 

  • Trump Steaks

    He called them "the world's greatest steaks," but something about mail order meat with this specific dude's name on it just seemed... unappealing. These were no ordinary steaks, but ultra-luxury steaks for high rollers. At one point, Trump Steaks sold for $999 a pack.

    While the steaks are still circulating through the Trump ecosystem, Sharper Image (which had exclusive rights) almost immediately stopped selling Trump's meat. 

  • Despite the fact that its name sounds like some sort of weird alcoholic beverage like Zima, Trump Ice is just bottled water. The labels (helpfully featuring a smiling Donald) claimed Trump Ice was "one of the highest quality spring waters in the world" and, of course, it was marketed as designer water.

    Trump Ice no longer exists, but the bottled water in his casinos and hotels has been rebranded Trump Natural Spring Water.

  • New Jersey Generals

    New Jersey Generals
    Photo: WI Connection / Wikimedia Commons / CC BY-SA 3.0

    The New Jersey Generals were a USFL team before the USFL merged with the NFL. Donald Trump owned them, then dropped out, then came back. The eventual collapse of the USFL has been blamed on Trump, who was trying to get the Generals to join the NFL under the other league's nose.

    Years later, Lisa Edelstein, who eventually played Dr. Cuddy on House, revealed that while she was a cheerleader for the Generals at 16 years old, the cheer squad was forced to hang out in bars in their skimpy clothing, regardless of the fact that many were minors.