From lending his name to all sorts of flop products to the companies that crashed and burned, read on as we look at some of Donald Trump and his organisation's worst past business moves over the years. All dollar amounts in US dollars.

Aged just 24, Trump attempted to break into the Manhattan entertainment elite by investing $70,000 (£29k) to bag a co-producer’s position on the Broadway comedy Paris Is Out! It was an unlikely move at the start of a career in property. Despite good reviews, the play closed after just 96 performances.

Trump’s business acumen took a huge hit when he bought the New Jersey Generals of the United States Football League (USFL) for $9 million (£6m) in 1983, losing $30 million (£20m) by the fall. Some even accuse Trump of folding the entire USFL.

Trump’s lawyers filed a $1.69 billion (£1.1bn) lawsuit against the NFL over its monopoly of the TV networks. It backfired spectacularly, with the jury ruling that the NFL did have a monopoly but the USFL had caused its own downfall by overspending. 

Trump had started building his Atlantic City casino empire by borrowing money at high interest rates, and when he opened another casino and started pouring money into the new Trump Taj Mahal rather than existing casinos such as Trump Plaza, the debt began to balloon. Just one year later Trump was $3 billion (£1.6bn) in debt, and ended up in the bankruptcy court for his Taj Mahal, Trump Marina, and Trump Plaza casinos. Four years later, having reorganised the casino holding company, Trump Entertainment Resorts missed another interest payment on a $53.1 million (£33.5m) bond, and had to declare bankruptcy again. But that wasn't the end of it...

In 2009, Trump Entertainment Resorts filed for Chapter 11 bankruptcy following the Great Recession. Then in 2014 the Resorts holding company was forced to file for bankruptcy again, which saw the closure of Trump Plaza, as well as the departure of Trump and his daughter Ivanka from the company's board. The company finally emerged from bankruptcy in 2016, and billionaire Carl Icahn's Icahn International company took over Trump's old Atlantic City properties, including the Taj Mahal, and the closed Trump Plaza.

But even though he tried to have his name removed from the casinos, Trump doesn't see all of his work in Atlantic City as a failure. In fact, in a 2016 interview with The New York Times he boasted about the "growth" the city gave him, and how "the money [he] took out of there was incredible". Perhaps success is a question of perspective...

Although his books proved entertaining, Trump’s board game Trump: The Game was, by all accounts, a failure. It launched in 1989 with the tagline, "It's not whether you win or lose, it's whether you win!" Trump starred in a TV commercial, anticipating it would sell over two million copies. It sold only 800,000 – which Trump put down to it being “too complicated” – and was pulled.

It seems that 1989 was not Trump’s year, with another fortune lost on a failed business venture: the Trump Shuttle. In an attempt to have his own slice of luxury air travel, Trump secured a $245 million (£150m) loan to buy air carrier Eastern Air Shuttle for $365 million (£224m). Within two years, and after a very expensive rebrand and upgrade, he was unable to make his $1.1 million (£630k) loan interest payments and the company lost $128 million (£73m).  

In another unsuccessful departure from real estate, Trump trademarked two beers, a lager and an American pale ale, both of which failed to materialise into anything profitable. Despite this, he tried his luck in the beverage market again a few years later, with soft drinks called Trump Fire and Trump Power, neither of which got past the planning stages.

Trump University is perhaps the most well-known and controversial of Trump’s business failures. In 2010, four former students sued Trump University for “offering classes that amounted to extended ‘infomercials’” and employing convicted felons as educators. The New York Attorney General sued Trump $40 million (£25.3m) for allegedly defrauding students. Trump tried to leave the incident behind, renaming the business The Trump Entrepreneur Initiative, but operations soon ended.

Although he wasn’t directly involved with the business, Trump’s brand and wallet took a hit when he leant his name to a condo tower that went bankrupt. This was just one of many lost investments during the housing market crash. The Tampa developers declared bankruptcy with only $3,500 (£1.9k) in assets.

Clearly Trump could renovate and run a highly successful hotel, but a travel website was a different matter. With the industry worth $80 billion (£57bn) a year, Trump sought his own slice of the cake by launching his GoTrump travel website. The experiment flopped, and the address now redirects to his current website.

When launching his mortgage business at the height of the housing market boom, Trump boasted to CNBC: “Who knows more about financing than me?” Yet the man Trump selected to run the business had worked on Wall Street as a registered broker for only six days. Trump’s anticipated first-year profits of $3 billion (£1.6bn) was quickly revised to $1 billion (£535m). With outstanding debts of $298,274 (£146,150) to a former employee and $3,555 (£1,745) owed in unpaid taxes, the entire enterprise was out of business by September 2007 as the housing market headed south. 

Unfortunately for Trump, 2006 was about to become one of his worst years in business. The complete failure of his first attempt at running a publication, Trump World, should have served as a warning of things to come. But ever the optimist, Trump re-launched the magazine as Trump in 2006, attempting to advertise luxury living even as the global financial crisis took hold. With $7.3 million (£4.6m) in debt, the magazine had folded entirely by 2009.

Trump’s brand took yet another hit in this shaky business move. Despite being teetotal and having no previous success in the alcohol business, Trump fancied his luck as the face of a vodka brand. As the slogan suggested, this was supposed to be “Success Distilled”. However, after poor sales the business folded five years later.

Next up he decided to launch a line of steaks. Strange move? Not when you consider that his beef was sourced from Buckhead Beef, to whom he owed $715,240 (£350k) after his Atlantic City properties filed for bankruptcy. Sales were abysmal and the company was discontinued, as was the Trump Steakhouse in Las Vegas due to 51 health code violations. 

Trump's flagship hotel is located in the Old Post Office in Washington DC, bought by the former president in 2012. It was a controversial move. According to sources quoted by Buzzfeed, Trump won the contract by promising to employ an architect who championed the historic building's restoration – a promise he swiftly reneged on. The construction of the hotel cost $170 million (£126.5m) and it's bled money ever since, with reports that it lost $70 million (£52m) during Trump's presidency.

In 2021, the Trump Organization announced that it would be selling the building for $375 million (£279m) to CGI Merchant Group. The deal came amid an investigation into Trump's leasing of the hotel from the federal government, which critics have described as a conflict of interest given his ongoing presidential campaign at the time. 

A new "communications" website Trump launched last year permanently shut down after less than a month. Following his permanent ban from Twitter and suspension from other platforms such as Facebook in early January 2021 after he was accused of inciting violence at the Capitol, Trump revealed his newsfeed-style blog – called From the Desk of Donald J. Trump – on donaldjtrump.com in early May as a "space to speak freely and safely". The website's closure came at the same time Facebook extended Trump's suspension from its platform for two years. There were reports that the blog had low traffic, which Trump called "wrong". He told his Desk followers to "stay tuned" for his new "platform", which has turned out to be new social network Truth Social.

Now take a look at the products and brands Donald Trump loves