May 11, 2011 3:05PM ET

The Many Business Failures of Donald Trump

He’s running for president (maybe) on his business record. One problem: that record sucks

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Rolling Stone's Eric Hedegaard sat down recently with real-estate mogul, Reality TV star and – who can tell? – presidential candidate Donald Trump for a profile that appears in the magazine's May 26, 2011 issue. When they get around to talking about Trump's presidential aspirations, the Donald barks, 'We need a businessman, and I've been successful.' But, as Hedegaard points out, Trump's business career is at least as remarkable for its colossal screwups – including multiple bankruptcies – as for its lucrative successes. Here, an incomplete roundup of Donald Trump's business failures.

Launched in 2006 under the slogan "success distilled," Trump Super Premium Vodka was destined to make the T&T (Trump & Tonic) the most-ordered drink in the country. At least that was the idea. Sadly, the brand went kaput in 2010, having "failed to meet the threshold requirements."

Related: One Top-Notch Novelty Act: A Conversation with Donald Trump by Eric Hedegaard

Shawn Ehlers/WireImage

GoTrump, a Travelocity-powered search engine billed as customers' ticket to "travel Trump style," debuted amid plenty of fanfare in 2006. It featured private jets, tickets to exclusive events, and (supposedly) personal recommendations and travel tips from Trump himself, as well as a 120 percent price guarantee on certain hotel deals. A financial analyst quoted in the Washington Post when the site
launched called gotrump a "vanity site" that wouldn't make much money; and he turned out to be correct — GoTrump shut down in 2007.

Related: One Top-Notch Novelty Act: A Conversation with Donald Trump by Eric Hedegaard

Sylvain Gaboury/FilmMagic

Trump's third shot at a luxury magazine (after two failed attempts), this luxury quarterly launched in late 2007 and got off to a good start, leading the Luxist, a luxury lifestyle website to wonder, "could this, once again, be the year of Trump?" Well, no. Trump Magazine went down in 2009.

Related: One Top-Notch Novelty Act: A Conversation with Donald Trump by Eric Hedegaard

J. Kempin/FilmMagic

Launching his new mortgage brokering business in April 2006, the Donald said, "Trump Mortgage is going to take better care of people than anyone in the mortgage industry ever has." But, as CNN Money put it, "if Trump is trying to build a mortgage brand on honesty, he seems to have said 'You're hired' to the wrong executive.' It turned out the guy he tapped to head the company, who'd claimed to be "a top
executive at one of Wall Street's most prestigious investment banks" had only meager banking credentials (albeit solid experience in nutritional supplement business). Trump Mortgage didn't make it
through 2007.

Related: One Top-Notch Novelty Act: A Conversation with Donald Trump by Eric Hedegaard

AP Photo/David A. Cantor

In October 1988, Trump bought a fleet of 17 no-frills Boeing 727s and gussied them up with "maple-wood veneer to the floors, chrome seat-belt latches and gold-colored bathroom fixtures." But the new airline never (ahem) took off with customers. Trump ended up defaulting on his loans, and the company was turned over to creditors. In 1992, it ceased to exist under the Trump Shuttle name.

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Trump was on hand 2006 for the ground breaking of a 52-story luxury apartment building that was going to redefine Tampa's skyline. The project went bust in fairly short order. It later emerged that Trump wasn't even a the developer of the tower. He recently told MSNBC: It was just a licensing deal. … I licensed the name 'Trump' to those buildings. Investors are suing Trump to recoup some of the money they lost in the doomed project.

Related: One Top-Notch Novelty Act: A Conversation with Donald Trump by Eric Hedegaard

mattypantaloons via flickr

In 1989, Trump went in with Milton Bradley on Trump: The Game, a real estate-themed board game a la Monopoly. It sold about 800,000 copies, well short of the 2 million Trump had forecast, and was discontinued. (In 2004, figuring to capitalize on the success of The Apprentice, Hasbro released a reboot of the game, complete with the slogan "You're Fired!" on the cover.)

Related: One Top-Notch Novelty Act: A Conversation with Donald Trump by Eric Hedegaard

Mario Tama/Getty

Not so much a university as a series of seminars, Trump University charges students $35,000 for a 'gold seminar' imparting the secrets of Donald Trump's success. Students nationwide have complained about TU's misleading marketing claims. Former students in California have filed a class-action lawsuit, and the Texas Attorney General's Office had opened up an investigation into possible deceptive trade practices against Trump University, dropping it only after Trump University told the AG they would stop doing business in Texas.

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William Thomas Cain/Getty Images, Ron Galella/WireImage

Trump Entertainment Resorts runs Trump Plaza, Trump Marina, and Trump Taj Mahal hotels and casinos in Atlantic City, N.J. But though his name is plastered all over the town, Trump himself exited the company in 2009, shortly before it declared bankruptcy for the third time. By that time, the Donald had gained a rep for honoring his debts late, when he honored them at all. "There are plenty of bankers you could find that would not do business with Donald Trump again," says Roger Gros, publisher of Global Gaming Business Magazine."

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