Exploring Donald Trump's failed business ventures – from board games to bottled water

Before he became the 45th president of the United States – and then returned to the White House in 2025 – Donald Trump built his name as a businessman.

From skyscrapers and casinos to golf courses and hotels, his brand was everywhere. He even became a household name as the host of The Apprentice, where he played the role of a master dealmaker.

But not every business venture carrying the Trump name lived up to his larger-than-life image. Here, we take a look at some of Trump’s biggest business failures, from universities to bottled drinks.

One of his earliest missteps was Trump: The Game, a board game released in 1988 through Milton Bradley. Trump had high hopes, but the game sold just 800,000 copies – less than half of the expected 2 million. He later claimed it was “too complicated” for consumers. Hasbro attempted to revive it in 2004 to capitalize on The Apprentice’s success, but the reboot quickly vanished from store shelves.

At the same time, he had more serious issues going on. After meeting Eastern Air Lines chairman Frank Lorenzo at a party and learning of the company’s financial woes, Trump invested $365 million on the airline’s fleet of 17 Boeing 727s, then creating the Trump Shuttle.

The company started the operation of hourly flights between New York City, Boston, and Washington D.C., with promises of a luxurious experience on board. Trump Shuttled never proved to be profitable, especially in a scenario when the region went through a recession and the 1990 Iraqi invasion of Kuwait doubled jet fuel prices. Trump ultimately defaulted, surrendering ownership of the airline to his creditors, and in between $25 and $35 million of debt.

By the early ’90s, his Atlantic City casinos went bankrupt not once, but three times. The first came in 1991 when the Trump Taj Mahal collapsed under $3 billion in debt after just one year in operation.

In 2004, Trump Hotels and Casino Resorts filed for bankruptcy again, this time affecting the Taj Mahal, Trump Marina, Trump Plaza, and a riverboat casino in Indiana, which together carried about $1.8 billion in debt. After restructuring as Trump Entertainment Resorts, the company still struggled. After missing an interest payment on a $53.1 million bond, it declared bankruptcy once again. This time, Trump resigned as chairman.

In 2003, Trump was ready to enter the mortgage business, confidently telling CNBC, “Who knows more about financing than me? The real estate market is going to be very strong for a long time to come.” That optimism led to the launch of Trump Mortgage in 2006. The company was licensed to operate in 25 states and claimed to be the fastest-growing mortgage company in the country. But just a year later, it shut down, citing a “poor economic market.”

Reports later revealed that its CEO, E.J. Ridings, had exaggerated his credentials, and the company left behind unpaid debts, including a $298,274 judgment to a former employee and $3,555 in unpaid taxes.

While that was happening, in 2004, the Trump University was founded. Despite its name, it was not an accredited university or college, never conferred college credits, grant degrees or grade students. Instead, it offered a real estate training program, which consisted of three- and five-day seminars (often called “retreats”), promising to teach students the secrets of his success, with mentorship programs costing as much as $34,995. Instead of the hand-picked experts Trump had promised, many instructors were motivational speakers, some with criminal records. The program was later hit with multiple lawsuits, including a $40 million suit from New York Attorney General Eric Schneiderman. Trump ultimately settled for $25 million in 2016.

While that controversy brewed, Trump made another attempt at branding his name in real estate. Trump Tower Tampa, a planned 52-story luxury condo project, wasn’t his development – he simply licensed his name to it for $2 million. Developers used the Trump brand to collect down payments from eager buyers, but when the project collapsed in 2008, it had no real assets, just two scale models and some office furniture worth $3,500. Buyers sued Trump for misleading them, and he settled, sometimes for as little as $11,115, despite some investors losing hundreds of thousands.

His food and beverage ventures fared no better. Trump Steaks, launched in 2007, were supposed to bring a taste of luxury to American households, sold exclusively through The Sharper Image. But as CEO Jerry Levin later admitted, “We literally sold almost no steaks.” Within two months, the product was pulled from stores.

Trump Vodka, launched in 2006 with the slogan “Success Distilled,” was meant to dominate the liquor market. Trump confidently predicted that the “T&T” (a Trump and Tonic) would become America’s most popular cocktail. But the brand failed to gain credibility and was discontinued by 2011.

Other Trump-branded products quietly disappeared over the years. Trump Ice, his bottled water brand, made some profit, but his attempts at energy drinks – Trump Fire and Trump Power – never made it past their trademark applications before being abandoned in 2006. His Trump American Pale Ale, trademarked in 2007, suffered the same fate.

His cologne line, including Success by Trump and Empire by Trump, was once sold at Macy’s but was later discontinued, along with his Trump-branded menswear line and mattresses, both of which had generated millions in royalties before being pulled from stores.

The financial crisis of 2008 also doomed Trump’s luxury magazine. Originally called Trump Style and Trump World, it was relaunched as Trump Magazine in 2007, hoping to profit from high-end advertising targeting yachts and luxury goods. But the timing was disastrous. The magazine folded by 2009.

That same year, GoTrump.com, a travel booking site launched in 2006, shut down after failing to attract users. The site had been marketed as a high-end alternative to platforms like Travelocity, but it never gained traction.