Donald Trump Campaign: 10 ‘Deplorable Don’ Business Failures

More than one observer of the Donald Trump campaign for president has noted that for all of the Republican nominee’s braggadocio, he has been involved with a seemingly high number of failed ventures, which have been the subject of features by Time, Newsweek, and Rolling Stone, among other media outlets.

This morning, the Huffington Post named the GOP candidate “Deplorable Don” due to his boasts that he “called” the weekend New York City bombings.

Donald Trump has been bankrupt four times, as reported by Politifact.

“Hundreds of companies have filed for bankruptcy,” Donald Trump was quoted at a 2015 Republican debate. “I used the law four times and made a tremendous thing. I’m in business. I did a very good job.”

1. Donald Trump Is An Average Investor At Best

Objectively, given that her life began in humble circumstances compared to Donald Trump, Hillary Clinton’s net worth, estimated between $31.3 and $45 million, as previously reported by the Inquisitr, could be seen as evidence that she is a better investor and businessperson than the GOP nominee.

How many daughters of curtain manufacturers have gone on to have a net worth of tens of millions of dollars?

“He expected to be paid when he showed up,” Clinton was quoted with regard to her father in August by CTV News. “He did the work. He paid for the supplies and the labour he often hired to help him on big jobs. I can’t imagine what would have happened to my father and his business if he had gotten a contract from Trump.”

A conservative estimate of the size of the inheritance Donald Trump received from his father has been reported to be $40 million. The Inquisitr has previously reported that if Trump had invested with Warren Buffett’s Berkshire Hathaway Inc. (NYSE: BRK-A, BRK-B) in the early 1970s, his net worth would be over $200 billion, compared to the $4.5 billion Forbes currently estimates.

The growth of Donald Trump’s net worth has been compared to that experienced by average Americans who own index funds by Massachusetts Senator Elizabeth Warren, as reported by the Inquisitr.

Lifelong Republican and former Nixon speechwriter Ben Stein called Donald Trump a “pauper” when compared to Warren Buffett, as reported by the Inquisitr.

2. Donald Trump’s Public Company Lost More Than 90 Percent Of Investors’ Money

On top of a demonstrated inability to choose the shares of businesses set to rise, the one time Donald Trump brought a company public and convinced investors to buy his stock, he failed miserably on their behalf, while at the same time pocketing close to $40 million himself, as reported by CNN Money.

Trump chose the symbol DJT for the shares of Trump Hotels & Casino Resorts Inc., which were listed on the New York Stock Exchange and came public for $14 a share in 1995, as reported by the New York Times.

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On top of earning $20 million through “salary, bonus, and options” from Trump Hotels, Trump was also paid $18.5 million in other compensation.

CNN Money calculated that investors who bought $100 worth of DJT stock in 1995 were left with $8.72 by 2000. By comparison, $100 invested in the S&P 500 Index (^GSPC) would have grown to $232 over the same period.

3. Trump University Faces Fraud Allegations, Three Federal Lawsuits

Stories of students being pressured at the hands of Trump University instructors to enroll in high-priced real estate courses abound, which has led to three lawsuits being brought against Donald Trump in federal courts.

The Inquisitr has previously featured the story of Trump University student Sheri Winkelmann being denied a refund at the end of the first day of a $1,495 three-day introductory course that was described as a high-priced up-selling exercise for premium $34,995 courses.

Donald Trump Campaign: Ten business failures on the part of 'Deplorable Don' and how Hillary Clinton may be a better businessperson.

The Trump University student also described instructors focusing their efforts on students who had revealed their ability to pay such high fees after showing the instructors personal financial information under the guise of crafting a real estate career plan.

Winkelmann’s story matches that of a former sales manager with Trump University, Ronald Schnackenberg, who testified in Southern California U.S. District Court with regard to being reprimanded by the school after he failed to push a couple struggling with financial difficulties to enroll in a $34,995 course, as reported by the New York Times.


When it launched in 2006, advertised Donald Trump’s first-ever email address and a website powered by Travelocity as Trump’s introduction to the then-$80 billion online travel industry, as reported by Business Wire.

Sales and revenue figures from do not appear to be available. The site was quietly shuttered in 2007.

5. Trump Steaks

During one of Donald Trump’s bankruptcies related to his Atlantic City properties, it was found that he owed Buckhead Beef of Georgia more than $700,000. In 2007, a deal was struck that led to steaks bearing the Trump name being offered for sale at retailer Sharper Image.

“[W]e literally sold almost no steaks,” Jerry Levin with the Sharper Image was quoted about Trump Steaks by Rolling Stone. “If we sold $50,000 of steaks grand total, I’d be surprised.”

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Not faring much better in his restaurant business, it was reported that the Trump Steakhouse in Las Vegas was temporarily closed after facing 51 health code violations in 2012, including serving 5-month-old caviar and expired yogurt, as reported by the New York Daily News.

6. Trump Vodka

In 2006, Donald Trump announced that a line of vodka would be marketed using his name and that the drink Trump and Tonic would become the most popular in the United States. Sales figures for the product remain elusive.

Production and distribution of Trump Vodka ended by 2011 due to a reported “lack of interest.”

7. Trump Airlines

Referred to as both Trump Shuttle and Trump Airlines, Donald Trump’s foray into aviation began in 1988.

Using a borrowed $245 million to purchase Eastern Air Shuttle for a total of $365 million, Trump attempted to attract customers with regular flights between Washington, D.C., Boston, and New York and planes decorated with “maple-wood veneer” and “gold-colored bathroom fixtures.”

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After less than three years, Trump was reportedly unable to make interest payments on his loan and forced to hand the airline over to creditors. It ceased operations in 1992.

8. Trump Mortgage

“I think it’s a great time to start a mortgage company,” Donald Trump was quoted by Crain’s in 2006 after opening his mortgage company.

“Who knows about financing better than I do?”

Trump Mortgage was reported doing less than $1 billion in business its first year after analysts had predicted mortgage sales exceeding $3 billion.

Much has been reported about the profits generated by hedge fund managers Michael Burry and Steve Eisman, who were able to successfully predict the collapse of the subprime mortgage-backed securities market, as featured in the book The Big Short by Michael Lewis and the film of the same name starring Steve Carrel and Brad Pitt, as reported by IMDb, just as Donald Trump’s mortgage business was getting started.

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Trump Mortgage closed in September of 2007. A judgment for $298,274 in favor of a former employee, as well as a $3,555 tax bill, has reportedly been left unpaid by the company.

9. Trump Magazine

Trump Magazine was described by its publisher in 2007 as reflecting “the passions of its affluent readership by tapping into a rich cultural tapestry.”

Carey Purcell, a former Trump Magazine receptionist, spoke with Joy Reid with MSNBC in August.

Purcell described starting with the publication right out of college, in the fall of 2006, and the problems that presented themselves within the first six months, including a bounced paycheck — for which no explanation was offered.

The receptionist also remembered signing eviction notices on behalf of the magazine and coming to work to find the electricity and internet service turned off. She reminisced over being provided with credit card numbers to pay utility bills and the numbers being declined, as well as being paid with paper bags containing cash to make up for paychecks she was advised would bounce.

Trump Magazine stopped publication after its first one and a half years in business.

10. Trump: The Game

Donald Trump has twice attempted to bring his board game to the public and twice the public has answered with seemingly bored indifference.

Trump: The Game was first released by Milton Bradley in 1988, which, despite being promoted with flashy television commercials, only sold 800,000 copies. The company had expected to sell 2 million copies.

With the beginning of his run on The Apprentice on NBC in 2004, an updated version of Trump: The Game was offered to fans, which Trump himself predicted would sell more copies than the original. The updated Trump game was also quickly discontinued.

[Featured Image by Mark Wilson/Getty Images]