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Republican presidential candidate Donald Trump waits to speak as he is introduced at the New York Veterans Police Association during a campaign event in the New York City borough of Staten Island, NY, on April 17, 2016. New York State Primaries will held on April 19, 2016. (Photo by Anthony Behar) *** Please Use Credit from Credit Field ***
Anthony Behar—Sipa USA/AP

10 Donald Trump Business Failures

Updated: Oct 11, 2016 11:14 AM ET | Originally published: Apr 29, 2011

Donald Trump talks a lot about his business successes, but he’s had more than a few failures over the years as well. Here’s a look at some of the missteps he’s made in his long career.

NWA Inc., parent company of Northwest Airlines, is negotiating to operate and eventually to own the Trump Shuttle at New York’s LaGuardia Airport on Friday, March 8, 1991, according to a published report on Friday. The move would cost developer Donald Trump a major asset, but would help him reduce his debt, the Wall Street Journal said. (AP Photo/David A. Cantor)
David A. Cantor—AP

Trump Airlines

In October 1988, Donald Trump threw his wallet into the airline business by purchasing Eastern Air Shuttle, a service that for 27 years had run hourly flights between Boston, New York City and Washington, D.C. For roughly $365 million, Trump got a fleet of 17 Boeing 727s, landing facilities in each of the three cities and the right to paint his name on an airplane. Trump pushed to give the airline the Trump touch, making the previously no-muss, no-fuss shuttle service into a luxury experience. To this end, he added maple-wood veneer to the floors, chrome seat-belt latches and gold-colored bathroom fixtures. But his gamble was a bust. 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. The high debt forced Trump to default on his loans, and ownership of the company was turned over to creditors. The Trump Shuttle ceased to exist in 1992 when it was merged into a new corporation, Shuttle Inc.

SCOTTSDALE, AZ - FEBRUARY 02: Atmosphere at Trump Vodka VIP Lounge at 944 Super Village on February 2, 2008 in Scottsdale, Arizona. (Photo by Michael Bezjian/WireImage) *** Local Caption ***
Michael Bezjian—WireImage/Getty Images

Trump Vodka

In April 2006, Trump announced that, after years in the real estate business, he was launching a mortgage company. He held a glitzy press conference at which his son Donald Jr. predicted that Trump Mortgage would soon be the nation’s No. 1 home-loan lender. Trump told CNBC, “Who knows more about financing than me?” Apparently, plenty. Within a year and a half, Trump Mortgage had closed shop. The would-be lending powerhouse was done in by timing (the housing market cratered in 2007) and ironically enough, given Trump’s Apprentice TV show, poor hiring. The executive Trump selected to run his loan company, E.J. Ridings, claimed to have been a top executive at a prestigious investment bank. In reality, Ridings’ highest role on Wall Street was as a registered broker, a position he held for a mere six days.

Donald Trump during Donald Trump New York City Press Launch For Latest Venture Trump Mortgage LLC at Trump Tower in New York City, New York, United States. (Photo by J. Kempin/FilmMagic)
J. Kempin—FilmMagic/Getty Images

Trump Mortgage

In April 2006, Trump announced that, after years in the real estate business, he was launching a mortgage company. He held a glitzy press conference at which his son Donald Jr. predicted that Trump Mortgage would soon be the nation's No. 1 home-loan lender. Trump told CNBC, "Who knows more about financing than me?" Apparently, plenty. Within a year and a half, Trump Mortgage had closed shop. The would-be lending powerhouse was done in by timing (the housing market cratered in 2007) and ironically enough, given Trump's Apprentice TV show, poor hiring. The executive Trump selected to run his loan company, E.J. Ridings, claimed to have been a top executive at a prestigious investment bank. In reality, Ridings' highest role on Wall Street was as a registered broker, a position he held for a mere six days.

This is a Hasbro Inc., undated handout photo showing the new board game Trump. Donald Trump is lending his name to a new board game marketed by Pawtucket-based Hasbro Inc., the nation's second largest toymaker. It's on sale now and retails for about $24.99, according to Hasbro. (AP Photo/Hasbro Inc.)
Victoria Arocho—AP

Trump: The Game

In 1989, the Donald teamed up with Milton Bradley to release Trump: The Game, a Monopolyesque board game in which three to four players must buy and sell real estate and try to trump one another in business deals. A year later Trump admitted the game was vastly underselling the predicted 2 million units he and the toy company had hoped for. Not one to abandon ideas, Trump revived the game 15 years later after his success on The Apprentice, making sure to incorporate the series catchphrase “You’re fired!” into the game. Other updated features included a sterner-looking Trump on the box cover, somewhat simpler rules and cards with business tips.

clothing label made in china cheap
Getty Images

The China Connection

"The problem with our country is we don't manufacture anything anymore," Donald Trump told Fox News a year ago. "The stuff that's been sent over from China," he complained, "falls apart after a year and a half. It's crap." That very same Donald Trump has his own line of clothing, and it's made in ... China. (O.K., O.K. — not all of it. Salon, which reported this intriguing, head-scratching fact, notes that some of his apparel is from Mexico and Bangladesh.)

Atlantic City, UNITED STATES: The Trump Plaza hotel and casino in Atlantic City, New Jersey, is pictured 25 May 2007. Gambling has been legal in Atlantic City, one of the few such cities in the United States, since the first casino opened in 1978. AFP PHOTO/SAUL LOEB (Photo credit should read SAUL LOEB/AFP/Getty Images)
Saul Loeb—AFP/Getty Images

Trump Casinos

Donald Trump’s gambles don’t always go as planned. Especially when that gamble is gambling itself. In February 2009, Trump Entertainment Resorts Inc. filed for Chapter 11 bankruptcy protection for the third time in a row — an extremely rare feat in American business. The casino company, founded in the 1980s, runs the Taj Mahal, the Trump Plaza and the Trump Marina. All three casinos are located in Atlantic City, N.J., where the gambling industry has faced a decline in tourists who prefer gambling in Pennsylvania and Connecticut instead. Trump defended himself by distancing himself from the company, though he owned 28% of its stock. “Other than the fact that it has my name on it — which I’m not thrilled about — I have nothing to do with the company,” he said. He resigned from Trump Entertainment soon after that third filing, and in August of that year he, along with an affiliate of Beal Bank Nevada, agreed to buy the company for $100 million. The company reported it emerged from bankruptcy in July 2010.

Donald Trump during Launch of Trump Steaks at The Sharper Image at The Sharper Image in New York City, New York, United States.
Donald Trump during Launch of Trump Steaks at The Sharper Image at The Sharper Image in New York City, New York, United States.Stephen Live-in—WireImage for Hill & Knowlton

Trump Steak

Donald Trump was featured on the June 2007 cover of the Sharper Image catalog hunched over a platter of meat to kick off his line of premium steaks that he dubbed the “world’s greatest.” The company has since been discontinued—maybe it had something to do with the Trump Steakhouse in Las Vegas being closed down in 2012 for 51 health code violations, including serving five-month old duck.

NEW YORK - SEPTEMBER 20: Donald Trump poses at the Trump Magazine celebration on September 20, 2006 in New York City. (Photo by Gustavo Caballero/Getty Images)
Donald Trump poses at the Trump Magazine celebration in New York City on Sept. 20, 2006.Gustavo Caballero—Getty Images

Trump Magazine

Trump launched an eponymous magazine in 2007 that, in a press release announcing the publication’s arrival, was described as “[reflecting] the passions of its affluent readership by tapping into a rich cultural tapestry.” A year-and-a-half after the launch, the magazine ceased publication.

Donald Trump at the Marquee in New York, New York (Photo by Bennett Raglin/WireImage)
Donald Trump at the GoTrump.com launch party at the Marquee in New York City on Jan. 24, 2006.Bennett Raglin—WireImage/Getty Images

GoTrump.com

Trump launched this luxury travel search engine in 2006, only to shut it down a year later, despite being powered by booking giant Travelocity.

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Real estate mogul Donald Trump holds a media conference announcing the establishment of Trump University May 23, 2005 in New York City.Thos Robinson—Getty Images

Trump University

In 2005, Trump opened the non-accredited, for-profit Trump University. In 2010, four students sued the university for “offering classes that amounted to extended ‘infomercials.’” Following the suit, the “university” changed its name to “The Trump Entrepreneur Initiative,” before ending operations one year later. In 2013, the New York Attorney General sued Trump and the “university” for $40 million for allegedly defrauding students.

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