Trump's Business Failures and Controversies
A historical overview of major business ventures and controversies prior to Trump's first term
What happened with Trump Shuttle?
Trump purchased the airline in 1988 for $365 million, but it failed to turn a profit and ceased operations by 1992 after defaulting on loans. The venture was plagued by high debt service and declining air travel during the Gulf War period.
What was the Trump University controversy?
Trump University was a for-profit educational venture launched in 2005 that closed in 2011 amid lawsuits alleging fraud. In 2013, the New York Attorney General sued Trump for $40 million, and Trump eventually settled a class-action lawsuit for $25 million after his election in 2016.
How many times did Trump's businesses file for bankruptcy?
Trump's businesses filed for Chapter 11 bankruptcy six times between 1991 and 2009, including Trump Taj Mahal (1991), Trump Plaza Hotel (1992), Trump Hotels & Casino Resorts (2004), and Trump Entertainment Resorts (2009). These bankruptcies were due to over-leveraging and financial mismanagement.
| Year | Business | Details |
|---|---|---|
| 1991 | Trump Taj Mahal | Filed for bankruptcy after being open for one year, with $3 billion in debt |
| 1992 | Trump Plaza Hotel & Casino | Filed Chapter 11 with over $550 million in debt |
| 1992 | Trump Castle Hotel & Casino | Filed for bankruptcy protection |
| 2004 | Trump Hotels & Casino Resorts | Filed for bankruptcy with $1.8 billion in debt |
| 2009 | Trump Entertainment Resorts | Filed for bankruptcy after missing a $53.1 million bond interest payment |
Which Trump-branded products failed?
Trump Vodka (2006–2011), Trump Steaks (discontinued after two months), and GoTrump.com (a travel site shut down in one year) are examples of ventures that failed due to lack of demand and poor market positioning.
Trump Mortgage (2006–2007)
Launched at the peak of the housing bubble, just before the market collapsed. Closed after one year of operation.
Trump Magazine (2007–2009)
A luxury lifestyle publication that ceased operations after two years due to poor advertising revenue.
Trump Network (2009–2012)
A multi-level marketing company selling urine tests and vitamins. Sold off after three years of operation.
Trump Ice (bottled water)
Failed to gain significant market share and was eventually limited to Trump properties only.
What real estate projects failed before the presidency?
Several Trump-branded real estate developments faced significant issues prior to his presidency, including projects that collected millions in deposits but were never built.
- Trump Tower Tampa (2005–2008): Announced but never built. Deposits of $40 million were eventually refunded after lawsuits.
- Trump Ocean Resort Baja Mexico (2006–2009): Collected $32 million in pre-construction deposits but was never built. Lawsuits followed.
- Trump International Hotel & Tower Fort Lauderdale: Announced in 2005, abandoned after the 2008 financial crisis, leaving buyers without their deposits.
- Trump SoHo (2008–2017): Rebranded as The Dominick after poor performance. The Trump Organization was bought out of its contract amid criminal investigations.
How many lawsuits involved Trump before 2016?
By the time of his first presidential campaign in 2016, Trump or his companies had been involved in over 3,500 lawsuits, including cases as both plaintiff and defendant. These ranged from contract disputes to employment issues and allegations of fraud.
Housing Discrimination (1973)
The Justice Department sued Trump Management Corporation for discriminating against Black rental applicants. The lawsuit was eventually settled with a consent decree requiring the Trump company to change its rental practices.
Trump University Settlement (2016)
After extensive litigation, Trump agreed to pay $25 million to settle fraud allegations related to Trump University. The settlement covered two class-action lawsuits and a civil case filed by the New York Attorney General.
Trump Foundation (2016)
The Donald J. Trump Foundation faced scrutiny for alleged misuse of charitable funds. The foundation was eventually dissolved under judicial supervision, with assets distributed to approved charities.
Where can I find sources on Trump's business record?
Major news outlets and legal databases have documented Trump's business failures, bankruptcies, and lawsuits over several decades. The list below includes key reporting and archival references.
- Los Angeles Times, "A List of Trump's Disastrous Business Deals" (2022)
- Time, "Donald Trump's Biggest Business Failures" (2015)
- The Ticker, "Donald Trump's Failed Business Ventures" (2024)
- ABI, "Examining Donald Trump's Chapter 11 Bankruptcies"
- Miller Center, "Donald Trump: Life Before the Presidency" (2025)
- The Washington Post, "The Business Disasters That Trump Doesn't Want You to Know About" (2016)
- The Washington Post, "Trump Foundation Faces Scrutiny for Donations" (September 13, 2016)
- Forbes, "How Donald Trump Turned Around His Business Failures" (2018)
- The New York Times, "Justice Department Sues Trump Firm for Bias" (October 16, 1973)
- The New York Times, "Trump Agrees to Pay $25 Million in Trump University Settlement" (November 18, 2016)
- The New York Times, Multiple Articles (2010–2016), "Trump University Investigation"
- The Wall Street Journal, Coverage of Trump's Business Disputes and Casino Fines
- Wikipedia, "Business Career of Donald Trump" (2025)
Note: Full articles can be accessed via ProQuest, LexisNexis, or newspaper archives like nytimes.com/archives.