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Repair Windows errors before they cause bigger problemsFix Now →Fix the driver behind crashes, sound loss and screen glitchesFind Drivers →Clear out junk files and repair common Windows errorsFree Scan →Donald Trump’s most consequential business failures were concentrated in highly leveraged Atlantic City casinos, but his record also includes a failed airline, a shuttered real-estate training venture, and short-lived consumer and media brands. This list selects 13 repeatedly documented cases; it is an editorial list, not an official ranking. The count changes if related casino companies and later corporate restructurings are grouped together or counted separately.
The 13 businesses and ventures
| Business or venture | Sector and timing | What happened |
|---|---|---|
1. Trump Taj Mahal |
Atlantic City casino; filing in 1991. | Built with very high-cost debt, the casino filed for Chapter 11 protection in 1991. The Washington Post reported that by March of that year Trump was in noncompliance on $1.1 billion in loans across his business empire, including the Taj (2016 account). A U.S. House committee document says the Taj required $1.3 million per day in interest payments (2020). |
2. Trump Plaza Hotel and Casino |
Atlantic City hotel and casino; filing in 1992. | A Trump-owned company filed for bankruptcy protection in 1992, according to the Miller Center and the Washington Post’s chronology. |
3. Trump Castle, later Trump Marina |
Atlantic City casino; separate operating entity within the casino portfolio. | The Washington Post and contemporary summaries describe the Castle as part of the overleveraged casino empire. It can be counted as a separate casino failure or grouped with the Atlantic City cluster; the cited summaries do not establish a separate filing date here. |
4. Trump Hotels & Casino Resorts |
Casino holding company; restructuring in 2004. | The company’s 2004 bankruptcy and restructuring was a later corporate event involving the casino portfolio, distinct from the earlier filings by individual casino companies. |
5. Trump Entertainment Resorts |
Casino company; bankruptcy in 2009. | The Los Angeles Times records that the renamed company declared bankruptcy in 2009. |
6. Trump Shuttle |
Airline; loan default in 1990 and disappearance by 1992. | The Los Angeles Times records a 1990 loan default and says the airline had disappeared by 1992. TIME reports that it never turned a profit, defaulted on loans, and ceased to exist in 1992. |
7. Trump University |
For-profit real-estate training venture; ceased operations in 2011. | It was not an accredited university. The Los Angeles Times says it ceased operations in 2011 amid lawsuits and investigations. TIME describes the lawsuits and the venture’s name change to The Trump Entrepreneur Initiative. |
8. Trump Mortgage |
Mortgage business; launched in 2006 and shut down roughly a year and a half later. | TIME reports the launch and closure. In TIME’s 2015 account, Trump asked CNBC, “Who knows more about financing than me?” |
9. Trump Vodka |
Vodka brand; introduced in 2006 and discontinued in 2011. | TIME’s business-failure chronology records the product’s introduction and discontinuation. |
10. Trump Steaks |
Premium steak line; launched in 2007. | The product line was later discontinued, according to TIME’s business-failure chronology; that account does not give a discontinuation year. |
11. GoTrump.com |
Luxury-travel search engine; launched in 2006. | TIME says the site shut down about a year after launch. |
12. Trump Magazine |
Magazine; launched in 2007. | TIME reports that it ceased publication roughly 18 months after launch. |
13. Trump: The Game |
Monopoly-style board game; launched in 1989. | TIME says the original game was discontinued after about a year. A 2005 Apprentice-linked relaunch was also discontinued. |
Why the Atlantic City casinos dominate the story
The casino cases are not five interchangeable bankruptcies. The list includes individual properties, a casino company, and later corporate restructurings of the portfolio. They are related episodes in a highly leveraged casino business, and the same financial strain can appear across more than one entity. That is why a simple count of “bankruptcies” can mislead: the answer depends on which companies and restructuring events are included.
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The clearest evidence of the financing pressure is the Taj Mahal’s reported interest burden: the House committee document put its required interest payments at $1.3 million a day. The Washington Post’s 2016 account, looking back to March 1991, reported $1.1 billion in loans in noncompliance across the wider empire, including the Taj and other named businesses. Those figures describe different measures—the Taj’s daily interest requirement and empire-wide loans in noncompliance—not two estimates of the same debt.
How to interpret the bankruptcy count
Trump-linked companies filed for Chapter 11 protection; Trump did not file personal bankruptcy. Chapter 11 is a corporate reorganization process, and a company filing does not mean its owner personally filed. The Washington Post explains that the apparent count varies because related corporate filings can be grouped differently. The 2004 Trump Hotels & Casino Resorts restructuring and the 2009 Trump Entertainment Resorts bankruptcy are corporate events, not additional personal bankruptcy filings.
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Business losses in the broader record
Separately from the individual venture closures, Axios summarized New York Times tax records showing $46.1 million in reported business losses in 1985 and $1.17 billion in cumulative reported business losses through 1994 (Axios, 2019). These are reported losses over specified periods, not a measure of the value lost on each business in this list or proof that every venture listed produced a loss of a particular amount.
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