TIME Executives

Donald Trump’s 16 Biggest Business Failures and Successes

<> on July 30, 2015 in Ayr, Scotland.
Jeff J Mitchell—2015 Getty Images Donald Trump on July 30, 2015 in Ayr, Scotland.

Ventures that went belly-up and plenty that made it big

Donald Trump promised to “take the brand of the United States and make it great again” when he threw his hat into a crowded ring of 2016 GOP presidential candidates. Trump has since consistently cited his credentials as businessman, as well as his (disputed) $10 billion fortune, when asked how, exactly, he would “Make America Great Again.” But it’s not just Trump’s immigration comments that are landing him in hot water; even his business deals have come under scrutiny, most recently in the August 7 GOP debate. The candidate deflected questions about how he plans to run America’s economy when his own companies have filed for bankruptcy multiple times. Here’s a closer look at some of his biggest success and failures in business.

Not-so-Succesful

Trump Airlines

In 1988, Trump bought Eastern Air Shuttle, an airline service that ran hourly flights between Boston, NYC and DC for 27 years prior, for $365 million. He turned the airline, once a no frills operation, into a luxury experience, adding maple-wood veneer to the floor and gold-colored bathroom fixtures. The company never turned a profit and the high debt forced him to default on his loans. Ownership of the company was turned over to creditors. It ceased to exist in 1992.

Trump Vodka

Trump unveiled his own vodka line in 2006 paired with the characteristic slogan “Success Distilled.” Advertising for the product claimed that the vodka would “demand the same respect and inspire the same awe as the international legacy and brand of Donald Trump himself.” Trump had high hopes for his liquor brand, predicting that the T&T (Trump and Tonic) would become the most ordered drink in the country and stating on Larry King Live that he got into the vodka business to outdo “his friends” at Grey Goose. The company stopped production in 2011, reportedly due to a lack of interest.

Trump Casinos

Trump Entertainment Resorts, which is composed of three Trump-owned casinos, all in Atlantic City, filed for bankruptcy for the fourth time in 2014. Trump has distanced himself from the company, saying that besides the company having his name, he has “nothing to do with it,” despite the fact that he owned 28% of its stock.

Trump: The Game

Trump launched a Monopoly-like board game in 1989, which was discontinued a year later due to lack of interest. He tried his hand at game making once again in 2005, when he launched an updated version tied to The Apprentice. It was also discontinued.

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.

Trump Steaks

Donald Trump was featured on the June 2007 cover of the Sharper Image catalogue 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.

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.

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.

Trump Mortgage

In 2006, Trump forayed further into the real estate industry, launching a mortgage company. The Donald had high hopes for the company, asking CNBC, “Who knows more about financing than me?” Trump Mortgage shut down within a year and a half, in part because Trump selected E.J. Ridings, a man who claimed to be a top executive at a prestigious investment bank but had actually only worked on Wall Street as a registered broker for six days, to run the company.

Successful

Grand Hyatt Hotel

Trump bought the former Commodore Hotel, which had fallen into relative disrepair, from Penn Central Railroad in 1974 and after six years of construction, the Grand Hyatt Hotel debuted. Smack dab in the heart of New York City, with the image of Grand Central reflected off its glass façade, the 34-story hotel is still booming business today.

Trump Tower

Trump broke ground on his now-famous 48-story Trump Tower in 1980. The luxury high-rise opened in 1983 and, with upscale restaurants and stores located in the mostly residential building, is still highly sought after real estate.

Wollman Rink

Trump renovated Wollman Rink in 1986 after contacting Mayor Ed Koch and offering to complete the renovation for $3 million. He finished the project on time and $750,000 under budget. Wollman Rink remains a Central Park fixture with more than 5 million annual visitors.

40 Wall Street

Trump purchased the building in 1995 for $1 million and renovated it for $35 million. Today, 40 Wall Street, one of the tallest office buildings in downtown New York, is worth over $500 million.

Trump Place

After years of negotiations, Trump finally broke ground on Trump Place, the gargantuan housing development along the Hudson River. The development includes 25 acres of open space and 5,700 apartments housed in 18 residential buildings.

The Apprentice

The Apprentice premiered on NBC in 2004 to great ratings. Trump served as not only the host but also the executive producer, raking in $1 million per episode. The show was successful enough that it inspired a spinoff, The Celebrity Apprentice.

Trump International Tower Chicago

Trump bought the former Chicago Sun-Times headquarters in 2005 for $73 million and converted it into the second tallest building in Chicago. It houses a hotel, condos, restaurants and shops, and was named Travel+Leisure’s best large city hotel in North America in 2010.

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