Donald Trump: The Illusion of Success in Business and Government

By: Donald V. Watkins

Copyrighted and Published on October 19, 2025

An Editorial Opinion

The commercial success of Trump Tower and The Apprentice TV show created a public perception that Donald Trump was a marketing genius and superstar businessman.  A closer look at Trump's record in business paints a totally different portrait. Much of Trump's success in business was illusory. This is also true with respect to how Trump is running the federal government as the nation's 47th president.

Today, President Trump has: (a) immersed the government in high-risk ventures, (b) increased the national debt to an unsustainable $40 trillion, (c) imposed $1 trillion in new taxes upon American businesses and consumers in the form of Trump tariffs on imported goods, equipment, and merchandise, (d) cut taxes for millionaires and billionaires, (e) engaged in nonstop legal entanglements, (f) shutdown the government (with no end in sight), (g) stiffed and/or fired tens of thousands of federal employees, and (h) grifted on a scaled never before seen in America politics.

These actions mirror what Trump did with his most notable business failures. Judge for yourself.

Bankruptcies (Chapter 11 Filings).

Trump’s companies filed for Chapter 11 bankruptcy protection six times -- a record for a single business owner. These restructurings allowed the businesses to continue operating while shedding debt, often leaving creditors and contractors unpaid or underpaid.

1. Trump Taj Mahal (1991)

   • Opened in 1990 as the "eighth wonder of the world," this Atlantic City casino cost over $1 billion to build. It filed for bankruptcy less than a year later in 1991 due to overwhelming debt and inability to cover interest payments.

2. Trump Plaza Hotel and Casino (1992)

   • Purchased in 1988 for $400 million, this Atlantic City property filed for bankruptcy in 1992. High debt and competition in the casino market led to its failure. The property was eventually repossessed by lenders.

3. Trump Castle/Trump Marina (1992)

   • Acquired in 1985 as the Hilton Atlantic City Hotel and rebranded, it also filed for bankruptcy in 1992 alongside Trump Plaza. Excessive borrowing and operational losses doomed the venture. It was later sold off in 2011 for $38 million, a fraction of its original cost.

4. Trump Hotels and Casino Resorts (2004)

   • This parent company, encompassing Trump Taj Mahal, Trump Plaza, and Trump Marina, filed for bankruptcy again in 2004 with $1.8 billion in debt. Trump reduced his ownership stake but stayed on as chairman until 2009.

5. Trump Entertainment Resorts (2009)

   • The successor to Trump Hotels and Casino Resorts filed for bankruptcy in 2009 with $1.2 billion in debt. Trump resigned from the board but retained a 28% stake. The company emerged from bankruptcy in 2010 under new ownership.

6. Trump Entertainment Resorts (2014)

   • The company filed for bankruptcy yet again in 2014, closing Trump Plaza that year. The Trump Taj Mahal shut down in 2016, marking the end of Trump’s direct casino operations in Atlantic City.

Failed Ventures Outside of Bankruptcy

These are businesses that closed, were abandoned, or otherwise failed without necessarily filing for bankruptcy, often due to poor performance, legal issues, or lack of market interest.

7. Trump Shuttle/Trump Airlines (1989–1992)

   • Trump purchased Eastern Air Shuttle in 1989 for $365 million, rebranding it as a luxury service with gold fixtures and maple interiors. It never turned a profit due to high debt, rising fuel costs, and lack of customer demand for the upscale experience. The business defaulted on loans and was sold to USAir in 1992.

8. Trump Vodka (2006–2011)

   • Launched with the slogan “Success Distilled,” Trump aimed to compete with premium brands like Grey Goose. Poor sales led to its discontinuation by 2011, with Trump himself not drinking alcohol possibly undermining its appeal.

9. Trump Mortgage (2006–2007)

   • Started in 2006 with Trump claiming, “Who knows more about financing than me?” The company shut down within 18 months amid the housing market crash. Its CEO, E.J. Ridings, had exaggerated his credentials, having only six days of Wall Street experience.

10. Trump Steaks (2007–2014)

    • Launched in partnership with Sharper Image and QVC, this venture promised premium meat tied to Trump’s luxury brand. It flopped due to lackluster sales and was discontinued by 2014, with negative reviews highlighting poor quality.

11. Trump University (2005–2010)

    • Marketed as a real estate training program, it faced lawsuits alleging fraud and misrepresentation. New York forced it to drop “University” from its name in 2010 for lacking accreditation. In 2016, Trump settled three lawsuits for $25 million without admitting wrongdoing.

12. Trump: The Game (1989–1990, relaunched 2004)

    • A Monopoly-style board game launched with Milton Bradley, it sold only 800,000 units against a projected 2 million. A 2004 relaunch tied to The Apprentice also failed to gain traction and was discontinued.

13. GoTrump.com (2006–2007)

    • A luxury travel search engine, it lasted just one year before shutting down, unable to compete with established players like Expedia despite its 120% price guarantee promise.

14. Trump Ice (2004–unknown, effectively defunct)

    • A bottled water brand tied to The Apprentice, it was sold briefly in Trump properties and select stores. It faded from the market with no clear end date, overshadowed by Trump’s other failures.

15. Trump Magazine (2007–2009)

    • Aimed at wealthy readers with features on yachts and luxury watches, it launched during the 2007 recession. It folded by 2009 due to poor timing and lack of sustained readership.

16. Trump Power and Trump Fire (Trademarked 2004, abandoned 2006)

    • These carbonated fruit juice drinks never made it to market. Trademark applications were abandoned in 2006, leaving no evidence of production or sales.

17. Trump American Pale Ale (Trademarked, canceled 2007)

    • Another beverage venture that never launched, its trademark was canceled in 2007, suggesting it failed to materialize beyond planning.

18. Trump Tower Tampa (2005–2007)

    • A planned 52-story condo project in Florida, Trump licensed his name for $2 million but wasn’t the developer. It collapsed in 2007 amid the housing crash, leaving investors suing to recover losses.

19. Trump Ocean Resort Baja Mexico (Announced 2006, abandoned 2009)

    • A proposed luxury condo-hotel in Mexico, Trump licensed his name but didn’t invest capital. It fell apart in 2009 after developers failed to deliver, prompting lawsuits from buyers.

20. Trump International Hotel & Tower New Orleans (Proposed 2000s, never built)

    • A planned high-rise in New Orleans stalled and was abandoned, with no construction ever started despite initial announcements.

21. Trump International Hotel & Residence Phoenix (Proposed 2000s, withdrawn 2005)

    • Trump pulled his name from this project in 2005 before construction began, leaving it to fizzle out under other developers.

22. Elite Tower (Proposed 2000s, abandoned)

    • A planned skyscraper in Germany, it never progressed beyond the planning stage and was dropped.

23. Trump Tower Europe (Proposed 2000s, abandoned)

    • Another unbuilt project in Stuttgart, Germany, it remained a concept without execution.

24. New Jersey Generals (1983–1985)

    • Trump bought this USFL football team in 1983, pushing for a merger with the NFL. The league folded in 1985 after an antitrust lawsuit against the NFL failed, ending the team’s run.

25. Trump Fragrances (Various launches, discontinued)

    • Brands like “Success by Trump” and “Empire by Trump” were sold at Macy’s but discontinued due to low sales, with no clear end date but no longer available by the mid-2010s.

26. Trump Mattress (Launched 2000s, discontinued)

    • A Serta-partnered line of mattresses tied to Trump’s hotel brand, it was dropped due to poor sales, with no specific end date but absent from markets by the 2010s.

27. Trumpnet (Trademarked 1990, abandoned 1992)

    • A proposed corporate telephone service, its trademark was abandoned in 1992, indicating it never launched.

Additional Context

• Licensing Deals: Many of Trump’s “failures” (e.g., Trump Tower Tampa, Trump Ocean Resort) were licensing arrangements where he lent his name but didn’t manage operations. These still reflect poorly on his brand when they collapsed.

• Unpaid Contractors: Across ventures like his casinos and Trump University, reports indicate thousands of workers and contractors were stiffed, though exact numbers vary and are disputed.

• Scale of Failures: The New York Times analyzed 61 Trump projects from the 2000s to 2012, rating 40% as failures, suggesting a broader pattern beyond this list.

Today, Trump has the federal government swimming in $40 trillion in debt. There are no checks and balances on his spending. Trump has reduced the two other co-equal branches of government -- Congress and the Supreme Court -- to cheerleader status. Trump has also fired or weakened the federal watchdog agencies that monitor government spending, job market data, and public corruption.

Finally, the U.S. dollar is weak against other benchmark currencies because of rising deficits, political polarization, and a leveraged financial system. The U.S. stock markets are operating inside of a bubble where stock valuations are often based upon hyperthetical future value rather than actual revenues.

Thanks to Donald Trump, the U.S. now operates in a "fake it until you make it" paradigm. That's what Trump did during his entire career in business.