The Worst Business Deals Donald Trump Has Made

Love him or hate him, there’s no denying that Donald Trump has had a prolific and high-profile business career. Even as president, he’s still making money from his various businesses (whether or not that’s legal is a different debate).

Trump has worked hard his whole life and has a vast business empire to show for it. Yet not every move he’s made has been a rousing success. He likes to present himself as a savvy businessman and master dealmaker, but his business history paints a somewhat different picture. One of his mistakes cost $3.4 billion, but that wasn’t the only misstep. We’ll start out with some his more pedestrian misses before working our way to the massive disasters (including one at No. 13 that crash landed).

1. Trump Tower Tampa

Trump Tower Tampa sign

He just slapped his name on it. | Wikimedia Commons

Trump lent his name to a condo tower in Tampa in 2005 and received a nice payday up front plus money on the back end. Or he would have if the project didn’t go bankrupt. Donald Trump wasn’t directly involved with the project, but its failure is not a good look for him. He was involved with small-time developers, the housing market bubble burst, and dozens of people lost huge down payments on property that was never built. When the developers declared bankruptcy, they had just $3,500 in assets.

Next: A business idea that only exists on paper.

2. Trumpnet

This one didn’t cost him too much. | iStock/Getty Images

Donald Trump has dabbled in just about every business possible. Telecommunications was almost one of them. He trademarked the name Trumpnet in 1990 with the idea of getting into the corporate telecom game. Nothing ever came of it, but this misstep didn’t cost him much. It costs no more than $400 to file a trademark request.

Next: A website that went nowhere.

3. GoTrump.com

Airplane at Seattle Tacoma aiport

He was hoping to get a cut of the travel industry. | David_Johnson/iStock/Getty Images

Hoping to carve out his piece of an $80 billion a year industry, Donald Trump launched the GoTrump travel website in 2006. The idea was to jump in the ring and take on Expedia, Hotels.com, and other travel websites. It didn’t last long, and now the URL directs you his current website.

Next: This wasn’t the wisest roll of the dice.

4. Trump: The Game

Trump board game

The game was eventually pulled. | Youtube

Long before he was the boss man on TV show The Apprentice, Donald Trump entertained people with a board game. Or at least he tried entertaining people. The underwhelming Trump: The Game was far from a hit  — 800,000 copies sold vs. 2 million expected — and in 1989 and was pulled. It came back later in an effort to ride his The Apprentice popularity, but apparently, it wasn’t any better.

Next: He tried to sip on success in the 1990s and early 2000s.

5. Beverages

Beer into glass on wooden surface

Trump was briefly looking to get into the beer business. | grafvision/iStock/Getty Images

One of Donald Trump’s business ideas that never got off the ground was a series of beverages. In 1997, he trademarked two beer ideas, a golden lager and an American pale ale. A few years later, he was back at it with Trump Fire and Trump Power, which were to be carbonated fruit juice drinks. These ideas never got past the initial planning stages. We’ll cover another foray into the beverage business, and one that was a complete disaster, later in item No. 11.

Next: An utter failure in his area of expertise

6. Trump Mortgage

Trump at a campaign rally

The mortgage business went under less than two years later. | Alex Wong/Getty Images

At the peak of the housing market, Donald Trump launched a mortgage company in 2006. His expertise is in real estate and financing, but this was not one his smartest moves. Hoping for $3 billion in business in the first year, it did $1 billion. Less than two years later, the entire enterprise was out of business.

Next: In the end, this business venture ended up well done.

7. Trump Steaks

Considering he likes his steaks well done, this business failure wasn’t a surprise. | Trump Steaks

Real estate is more Donald Trump’s forte. Restaurants and food, not so much. That didn’t stop him from launching a line of steaks in 2007. They were sold by QVC and Sharper Image, though not for long. The steaks weren’t a hit at all, and by 2014 the business was just the same as Trump likes his steaks — well done.

Next: You could say there wasn’t much fine print with this next deal.

8. Trump magazine

Trump magazine cover

It was done by 2009. | Trump Magazine

The mid-2000s were not a good time for the Donald. First, it was the utter failure of Trump Mortgage. Then came Trump magazine. A publication named Trump World started and quickly folded in 2002. The magazine relaunched as Trump in 2006, but by the end of 2007 it was $7.3 million debt and it was gone for good by 2009.

Next: A big bill for the family man

9. Divorce

Donald Trump

Trump has five children with three different wives. | Dave Kotinsky/Getty Images

Donald Trump touts himself as a family man, and in a way it’s true. It’s just that he’s never been able to settle with one woman to start a family with. He has five children with three wives. His first wife, Ivana, is the mother of Donald Junior, Ivanka, and Eric Trump. When they divorced, she hoped for half of the estimated $5 billion Trump was worth at the time. She had to settle for $14 million and other assets. As we will see a bit later, $14 million is far from the biggest financial misfortune the man has suffered.

Next: Trump’s very high-profile business failure.

10. Trump University

donald trump and trump university press conference

He settled the lawsuit before taking office. | Thos Robinson/Getty Images

This might be the most well-known failure associated with the Donald. Trump University was a for-profit endeavor that was basically a sham. Felons and frauds were instructors, and students were bilked out of money in a high-pressure bait-and-switch scheme. Then came the lawsuits. In the end, he settled the lawsuits for $25 million without having to admit any wrongdoing.

Next: A curious product for a teetotaler

11. Trump Vodka

Trump Vodka

The whole thing was over in five years. | Quality Liquor Store

If there is money to be made in a business, Donald Trump will take a stab at it. That includes alcohol, even though he doesn’t drink. He lent his name to a brand of vodka in a licensing deal, so while he didn’t actually distill it himself he is still linked to its failure. Similar to the condo building in Tampa that never opened, it seems Trump didn’t do his research. The company making it was something of a startup with a shaky foundation. The first bottles appeared in 2007, but by 2012 the whole enterprise was done for.

Next: He really punted his chance at succeeding in this business.

12. USFL

USFL football

He ran the USFL into the ground. | Mike Russell/Wikimedia Commons

Before becoming president, Donald Trump tried buying the NFL’s Buffalo Bills. That’s wasn’t his first foray into professional football. He was the owner of the New Jersey Generals of the United States Football League. He paid $6 million for the team in 1983. By 1986 the league was gone, and he is considered the person who ran the league into the ground. That’s a major business fumble right there.

Next: Next up are two of Trump’s most notable and costly failures.

13. Trump Shuttle

Trump shuttle airlines

He lost $128 million in a year and a half. | JetPix/Wikimedia Commons

Opulence on the ground is one thing. Luxury in the air is something else. Donald Trump tried his hand at owning an airline in 1989, and it eventually crash-landed. He secured a $245 million loan to buy regional air carrier Eastern Air Shuttle for $365 million. He rebranded it Trump Shuttle and upgraded the fleet, but not the bottom line. By 1990 he couldn’t make his $1.1 million loan interest payments. In 18 months the company lost $128 million, and by the end of 1991, he was out of the airline business for good.

Next: The most glaring failure on Trump’s ledger.

14. Casinos

The casino failures caused him to file for bankruptcy. | Craig Allen/Getty Images

Donald Trump may be a master negotiator and businessman, but that doesn’t necessarily make him a successful one. Just look at his Atlantic City casinos. A New York Times article goes into great detail, but the short story is he racked up $3.4 billion in total debt on his Atlantic City properties. Just three months after it opened in 1990 the Taj Mahal, his flagship casino, lost $14 million. Six months in and he couldn’t make his loan payments and multiple trips to bankruptcy court followed.

Next: It hasn’t been all bad news

15. Despite the failures, there have been some wise decisions

donald trump in a dark suit and red tie giving thumbs up

Despite some failures, he’s still in business. | Alex Wong/Getty Images

While Donald Trump’s business failures are noteworthy, he’s also made several good decisions along the way. There are numerous Trump products that are actually worth your money. And despite the failures, he always finds some financial stability and forges ahead with a new idea.

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