10 of Donald Trump’s Business That Completely Failed


You may or may not know that a few of Donald Trump’s companies have gone bankrupt. His companies filed Chapter 11 Bankruptcy, which  is considered to be a “reorganization of debt.” Several of his casinos and resorts were in billions of dollars in debt, because the businesses were simply not profitable enough to make up for their losses.

For most humans on this planet, that amount of debt would create a crater so deep, there would be no hope to climb out of it. For Trump, though, all it took was selling some of his shares of those failing companies, and he was squared away. In 2015, he even bragged about this on Twitter, saying that he is simply taking advantage of the way American law works.

The successful real estate business his father started gives him a tremendous safety net. Trump has the luxury of trying as many new business ideas as he wants, no matter how little experience he had in any given industry. Here are just 10 of the many, many failed business ventures Trump has made over the years.

10. Trump Steaks

When you think of buying a quality cut of beef, you would probably go to your grocery store or a butcher. The last place you would even think of shopping for raw meat is the same place that you buy your pillows and blankets, but that’s exactly what Donald Trump did.

In 2007, the future President created a new business called Trump Steaks. Their line of assorted luxury meats included steaks, hamburgers, and hot dogs that were all packaged in black gift boxes. Depending on your choice of meat, they cost anywhere from $199 to $999.  He claimed they were the best tasting steaks in the world. Instead of giving any sort of culinary experience in the commercial, Trump simply says, “I understand steaks. They are my favorite food.”

It shouldn’t take a marketing genius to know that this was a bad idea, but it gets worse, because they were sold at The Sharper Image. If you’re not familiar with The Sharper Image, they normally sell home goods, and they’re basically a more expensive version of Bed, Bath, and Beyond. They were also sold on The Home Shopping Network at $96 per pound.You could either consider a health hazard waiting to happen, or think the idea was years ahead of Amazon Fresh.

According to a one-star customer review of Trump Steaks, titled “Never Again,” they got it for a gift, but they were greasy and gave them a stomach ache. It would seem that everyone else who dared to buy the gift-wrapped meats felt the same, because it didn’t take long for the company to disappear.

9. Trump Ice Bottled Water

Trump Tower in New York City has a snack area where they sell food and drinks. Among them is bottled water called “Trump Ice” with Donald Trump’s face on it. He also sells these at his resorts and casinos. Despite the fact that the bottles look like the cheapest dollar store variety with a new sticker slapped on the front, Trump claimed that his branded water is the “purest” in the world, with superior mineral content that is above all other luxury brands.

According to author and water connoisseur Michael Mascha, the amount of minerals in Trump Ice water is actually much less than many other brands, and it is not sourced from an exclusive location. It is also served in cheap plastic bottles, rather than glass. For all of these reasons, it should not qualify as a luxury product, and yet Trump wants to charge luxury prices simply because his face is on it. Needless to say, no one bought into his claims, and the water never spread to mainstream grocery stores.

8. The New Jersey Generals

You may have never heard of the football team called the New Jersey Generals. They had a short lived lifespan from 1982 to 1986, playing in a lesser-known league called the United States Football League, or USFL. Donald Trump bought the New Jersey Generals for $6 million in 1984. Since the league was just starting out, the team did not get nearly as much time on TV, and was therefore nowhere near as profitable.

Almost immediately after buying the team, Trump wanted to move the team’s schedule from the spring to the fall, so that they would play at the same TV time slot as the more popular NFL games. Then, he pushed the league to  sue the NFL, claiming that they had a monopoly over football in the fall. During this lawsuit, Trump used all of the USFL’s financial resources to pay for the legal fees, in the attempt to win $1.7 billion in damages. Apparently, he was so confident that he would win the case, that the NFL would have no choice but to buy out the teams in the USFL as a compromise. It turns out that the NFL didn’t want to touch Trump with a 10-foot pole.

According to a juror named Patricia Sibilia, who was there to help decide the case in 1984, she and her fellow jury members believed that Trump was shockingly arrogant. It was clear that he was only doing this to as an attempt to create a loophole of buying a football team at a discounted rate, since an official NFL team is closer to $1 billion.

The judge agreed that the NFL did have a monopoly over the airwaves for live coverage of football on TV, but he disagreed with the claim that they somehow owed the USFL nearly two billion dollars. While Trump technically won the case, he was awarded just three dollars. This brilliant master plan backfired even further, because it  exposed the fact that the USFL was breaking the laws with player contracts, which forced them to fay hefty fines.

All of this drama drained the league’s bank accounts so much, the entire USFL had to shut down in 1986. A reporter for the Los Angeles Times named Chris Dufresne explained that thousands of people, including his wife, lost their jobs all because of Trump’s ego.

Even today, Trump is clearly still very salty about the NFL, and he continues to bash them on Twitter whenever he can.

7. The TourDeTrump Bike Race

When you look at Donald Trump, you don’t exactly see a great example of physical fitness, even if he does go golfing every single weekend. But he seemed utterly determined to succeed in the world of sports. In the 1986, he moved on from football and decided he would have a “tremendous” long distance American bike race that would rival the Tour de France. When the press asked why he called it the “Tour De Trump,” he said the name would make it more successful.

During an interview, he said that he had not ridden a bike since he was 7 or 8 years old, and like most Americans, he wasn’t really a fan of watching cycling, either. His interest most likely came from the fact that in Europe, the Tour de France gets hefty sponsorships worth millions of dollars. As he would later learn, the only reason why the Tour de France is so profitable is because people in Europe actually watch cycling on TV.  

The race began in Albany, New York and ended in Atlantic City, New Jersey. Some of the best cyclists in the world gathered to compete in the race, because Trump offered a generous cash prize. The race was broadcast on NBC, and they tried their best to get American audiences interested in cycling by having one-on-one interviews to help get them invested in the competitors, but it simply was not enough.

Trump sponsored a second race three years later in 1989, which failed to make a return on the investment. He pulled out of the race, and the DuPont family took over, renaming it the Tour DuPont. After a couple years, though, even the DuPonts decided it wasn’t worth the trouble, and they stopped having the race in 1996.

6. ACN and The Trump Network

ACN was a digital phone service provider, and Donald Trump agreed to be the face of the company. Despite the fact that laptops and smartphones already have webcams, ACN claims that their cutting-edge technology is years ahead of everyone else.

Donald Trump spoke in front of stadiums filled with over 20,000 people in training seminars for ACN, encouraging them to buy more phones to sell to their family and friends. Their top sales people, brothers Michael and Patrick Maser, spoke on a regular basis about how ACN made them millionaires. In reality, it turns out that they were actually running a drug ring to make millions, and used their ACN business for money laundering.

The vast majority of people who signed up to become ACN sales people lost money in the process, and the true average income has been estimated at just $700 per year. Even after all of these problems were exposed, Trump still endorsed the company, calling it a better investment than real estate. This was clearly a pyramid scheme, and they are illegal in the United States. Montana was the first state to bring ACN to court, and many other states followed suit. Unfortunately, this global company is so powerful, it still exists to this day.

You may want to give Trump the benefit of the doubt on this one. Maybe he wasn’t aware that this company was a pyramid scheme when he chose to become their spokesperson. Not so much. He was actually inspired to make his own multi-level marketing company called The Trump Network in 2009. They requested that customers send them urine samples so they could give custom vitamin supplements in return. He even mentioned the recession in the commercial for the company, playing on the hopes and dreams of desperate Americans by promising that it would be the answer to all of their financial problems. Thankfully, not enough people fell for it, and The Trump Network disappeared.

5. Trump: The Game

Donald Trump decided that he could make a better board game than Monopoly, so he came out with Trump: The Game. Each of the players starts off with millions of dollars at their disposal, and the object of the game is to buy New York real estate and become the richest person by the end. Milton Bradley made 2 million copies of the game in 1989, but only 800,000 sold in stores across the country. According to consumers who tested the game, the rules made the players feel anxious, rather than having fun, and many people kept it sealed as a novelty item.

That same year, a fellow casino owner named Bob Stupak bet Trump $1 million that he would win a one-on-one match playing his own board game against him. Trump turned down the challenge, admitting that it was always possible to lose.

It wasn’t until The Apprentice aired on TV in 2004 that Milton Bradley decided to give the game another go. Instead of improving the rules or gaming experience, the second edition added in “You’re Fired” cards that could block another player from buying a property. There are also cards with Donald Trump’s face on them that can beat absolutely anything else a player tries to do, which makes him the hero of the game every time.

4. Trump University

After trying and failing at so many different industries, Trump University was the one idea that should have actually worked. Most of Donald Trump’s financial success came from the real estate business he inherited from his father, and he gained a lot of notoriety after being the star of The Apprentice. It would have actually made a lot of sense for him to follow through, but of course, he wasn’t actually trying.

Trump University promised to give students courses that were taught by some of the leaders in the real estate industry that would help them become successful. It turns out that this was not an actual accredited university, and the teachers were not licensed real estate agents, either. He didn’t even plan a curriculum for the school. Instead, the school hired charismatic salespeople who pushed students to pay upwards of $35,000 for tuition, where they ultimately learned nothing of value in the real estate industry.

He was sued not just once, but three times over Trump University. One lawsuit was brought by the New York Attorney General in 2013 for the fact that the school was a fraud. There are two separate cases demanded that he give refunds to former students. During interviews, Trump’s lawyers claimed that loads of people were happy with the classes. In reality, nearly 7,000 notices were sent out to former students about the lawsuit, and only two of them claimed that they thought their experience was worth the money.

In the end, Trump could not continue to fight the legal battle when he became President, and he was forced to pay $25 million to 6,000 students who were part of the class-action lawsuit. After it was over, Trump refused to acknowledge any wrongdoing, saying that he only lost the case because the judge was Mexican.

3. Trump Magazine

Even after becoming President of the United States, Donald Trump has had no qualms about attending a party hosted by Playboy. So it should come as no surprise to learn that in 1990, Donald Trump was on the cover, and this experience is probably what inspired him to make his own men’s publication called Trump Magazine in 2007. The content he included in the magazine was mostly advertising for luxury products like yachts, cigars, and liquor, often with a sexy woman on the cover, of course. Basically, Trump made the perfect magazine for himself.

According to the former managing editor, most of the articles that were written for the magazine were just meant to glorify his achievements and advertised his own businesses so much that it could rival propaganda from North Korea. The magazine was not allowed to be printed until he had the final say-so, marking any issues he found with a sharpie. The company flopped in 2009, because the audience for the magazine turned out to be so small, they simply didn’t sell enough copies to pay for the expense of running a print publication.

2. Trump Vodka

While Trump Vodka promised to be success distilled in liquid form, the liquor company failed almost as quickly as it went on the market. The man who was in charge of creating the vodka is J. Patrick Kenny, who was a former employee of Seagram’s. After Kenny pitched the idea to Trump, he agreed to let him use his name in exchange for 50% of the profits made by selling the vodka. Kenny set off straight away, creating a corporation called Drinks America, and found a distillery in… the Netherlands.

One of the biggest downfalls for the company was in 2006, when Trump admitted during an interview with Larry King that he doesn’t even enjoy drinking Trump Vodka, despite the fact that his name was on the label. The brand tanked soon afterwards, which completely screwed over Kenny’s career. He said that “the company cratered,” and there is not a single bottle of Trump Vodka left… except, of course, for the ones selling on eBay.

1. Trump Airlines

Yet again, Donald Trump tried to dive head-first into an industry that he had absolutely no experience with. He bought the company formerly known as Eastern Airlines, and decided to slap his name on the side of 21 Boeing 727 airplanes. Unfortunately, he knew nothing about fuel costs, repairs, or what to charge for ticket prices. Like everything else, he simply promised everyone that it would be the “best” flight experience in the world.

A travel writer from Conde Nast named Barbara Peterson experienced what it was like to fly on a Trump Shuttle back in 2011. She says the staff was pleasant, and the food and drinks were great, but she couldn’t get over how Trump’s attempts to insert luxury into such old planes just didn’t fit. In her own words, it was like “having the 21 Club cater a Greyhound bus.”

If you’re wondering why Trump Airlines failed… well, he couldn’t pay his bills. The company took out a $245 million loan from Citibank, and the company wasn’t making any profit. They were $1.1 million behind in their bills. When he couldn’t make the payment, a so-called “rescue package” was gathered by some of his banker friends to cover the bill for him. Y’know, because what’s a million dollars between friends?  

He was not able to keep the company afloat, even after getting that help from friends. When asked about his experience running the airline, Trump said, “The airline business is a tough business… but I did great.”

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