Donald Trump’s 4 Biggest Failures By Daniel B. Kline, The Motley Fool October 11, 2015 at 10:00 am If you listen to Donald Trump, you’d think the man-who-would-be-president has never failed at anything. The business titan with the peculiar hair has enormous self confidence, but in reality, while Trump has made lots of money and been very successful, he has also had his share of missteps. There are a few cases where the former host of The Apprentice did not do such a great job and perhaps deserved to hear his own signature line: “You’re fired.” And, of course, like he does with his successes, Trump’s failures are liberally splashed with his own name. This is a man who, in success and the occasional failure, never keeps anyone guessing as to who’s calling the shots behind the scenes. All of these failures proudly bore the Trump name, and most used more than just a little of his signature gold color. Trump Casinos Donald Trump has never personally declared bankruptcy. The same cannot be said of the casinos that carry his name. Various parts of these enterprises — which Trump no longer has any day-to-day involvement with — have declared bankruptcy multiple times. The various filings were catalogued in a recent Vanity Fair article, which explained them as follows: 1991, Trump’s Taj Mahal in Atlantic City: This was the rare case where Trump himself was on the hook for as much as $900 million. To get out of trouble, the company filed for Chapter 11 bankruptcy, which allowed him to reorganize the debt while the casino remained open. The debacle cost the now-billionaire half his stake in the casino. 1992, Trump Plaza Hotel in Atlantic City: This time Trump was not personally on the hook, but he had to give up his 49% stake in the hotel as part of its bankruptcy deal. He did stay CEO, but that was in name only as he relinquished his salary and day-to-day operational role. 2004, Trump Hotels and Casinos Resorts: With his company nearly $2 billion in debt, Trump again used Chapter 11 to reorganize. This time he reduced his stake to around 25% and again gave up control. 2009, Trump Entertainment Resorts: In his most-recent filing, the latest iteration of the Trump casino business filed for Chapter 11, leading to him resigning from the board and reducing his stake even further. Stop saying I went bankrupt. I never went bankrupt but like many great business people have used the laws to corporate advantage—smart! — Donald J. Trump (@realDonaldTrump) June 19, 2015 Source: Donald Trump’s Twitter feed Trump University While it wasn’t actually an accredited, degree-granting university, that did not stop Trump University from selling various “educational” programs to students during its 2005-2010 run. The school taught everything from real estate classes to what were essentially self-help seminars using Trump’s own philosophy, CNN reported. “At Trump University, we teach success,” Trump said in a 2005 infomercial when the program was launched. “That’s what it’s all about. Success. It’s going to happen to you.” That sounds nice, but the school was dogged by rumors of fraud, and the mogul now faces three separate lawsuits — two class action suits filed in California, and one filed by New York’s attorney general — claiming fraud and general deception. “We started looking at Trump University and discovered that it was a classic bait-and-switch scheme. It was a scam, starting with the fact that it was not a university,” New York Attorney General Eric Schneiderman told CNN’s New Day after filing suit in 2013. Trump denies the allegations and is fighting the lawsuits. Trump Shuttle If you lived in New York in 1998, you might remember the billionaire’s attempt to get into the airline industry — Trump Shuttle. The entrepreneur purchased the assets of Eastern Airline’s Shuttle service for $365 million, TIME reported. For his money, Trump got 17 airplanes (which he slapped his name on and upgraded with gold-colored accessories) and landing rights in Boston, New York City, and Washington, D.C. “His gamble was a bust,” according to the news magazine. “A lack of increased interest from customers (who favored the airline for its convenience, not its fancy new look) combined with high pre-Gulf War fuel prices meant the shuttle never turned a profit.” High debt forced Trump to default on his loans, and creditors ended up seizing the assets of the airline, which stopped operations in 1992. Tour de Trump Originally conceived as a bike race from Manhattan to Atlantic City, New Jersey, Tour de Trump was an attempt to mimic the success of Europe’s Tour de France in the United States. The initial race in 1998 was actually somewhat of a success, being televised on NBC and attracting Greg LeMond, who at the time was the only American to ever win the Tour de France. When the concept was pitched to him, even Trump knew to be at least a little incredulous about the name. ”When it was initially stated, I practically fell out of my seat,” Trump told The New York Times in 1989. ”I said, ‘Are you kidding? I will get killed in the media if I use that name. You absolutely have to be kidding.”’ Of course, when it comes to using his name on a product, Trump doesn’t require much arm twisting. The race was indeed named after him and had a somewhat successful first year. Tour de Trump even returned in 1990, but the second run did not garner the same interest as the first, and the billionaire quietly left the racing world. Tour de Trump remerged in 1991 as the Tour Du Pont, which limped along as a professional bike racing event until 1996. The next billion-dollar iSecret The world’s biggest tech company forgot to show you something at its recent event, but a few Wall Street analysts and the Fool didn’t miss a beat: There’s a small company that’s powering their brand-new gadgets and the coming revolution in technology. And we think its stock price has nearly unlimited room to run for early, in-the-know investors! To be one of them, just click here. The article Donald Trump’s 4 Biggest Failures originally appeared on Fool.com. Daniel Kline owned at least one Trump-themed board game. Try any of our Foolish newsletter services free for 30 days. 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