Reading Time: 15 minutes A Great Businessman? 26 Of Donald Trump’s Biggest Business Failures (So Far)
This post may contain affiliate links. Read the disclosure.
Donald Trump, a name synonymous with both business acumen and controversy, has navigated through numerous ventures over the decades.
As a child of the 1980s, I remember a few of my uncles on my mom’s side sitting around and playing poker. Then, a few of my uncles on my dad’s side would play some game where they flipped dimes to see who got closest to the wall.
But I was told not to gamble because the house always wins. I wasn’t allowed to play these games. But then again I wasn’t even ten yet.
At the same time there was this guy on the news all the time for bankrupting casinos. But he was also on TV constantly telling people how rich he was.
I remember asking my dad about this Donald Trump guy. I was very confused. How was he rich, yet bankrupting casinos? As a kid, I did not understand.
My dad (who now proudly wears Trump hats and socks), explained that Trump made his money from his dad and from telling people he was rich by writing The Art of The Deal.
That has resonated with me over the three decades as we’ve seen all of his business failures and claims of success. Then, just like The Art of the Deal, he made a lot of money off of The Apprentice.
While some of his endeavors have boasted success, a significant number have stumbled, showcasing the complexities of entrepreneurship and market dynamics.
Here’s a look at 26 of his business ventures that didn’t quite hit the mark.
The original article only contained 20. This version includes a few more that readers pointed out were omitted. If there are still some missing, share them in the comments.
Related Video: Trump’s Tariffs: 23 Things Expected to Cost More With Tariffs #inflation #tariffs
Table of Contents
1. Trump University (2004-2010)
A for-profit education company that ended in a $25 million settlement over fraud lawsuits without admitting wrongdoing.
The venture was criticized for misleading marketing practices, promising to teach Trump’s real estate strategies through programs that failed to deliver.
30 Things Likely To Vanish With Baby Boomers: A Farewell to Yesterday’s Norms
2. Trump: The Game (1989, 2005)
A board game that saw poor sales and was discontinued.
Despite relaunch efforts, the game did not achieve lasting market success. Financial details regarding production and marketing costs versus revenues are limited but reflect a misjudgment in market demand.
24 Things People Over Age 60 Should Never Do Again
3. Trump Vodka (2006-2011)
A luxury vodka brand that failed to meet sales thresholds and was discontinued. Trump Vodka struggled to compete in the saturated premium vodka market.
Discontinued due to failure to meet sales thresholds required to continue the license. The investment in branding and production, given the ambition to dominate the luxury vodka segment, suggests substantial unrecovered costs.
20 Things Millionaires Refuse to Buy, Despite Having Money
4. Trump Airlines (1989-1992)
Acquired for $365 million, the airline defaulted on a $1.1 million loan repayment and was eventually ceased operations, underlining the financial risk in the aviation industry.
Operational costs and eventual default on loan repayments compound the total losses from the venture
Discover the Cheapest Airlines and Save Big on Your Next Flight!
5. Trump Steaks (2007)
An attempt to break into the meat industry that ended shortly after its launch. Sold exclusively through The Sharper Image and QVC, the venture struggled due to poor sales and market reception.
Trump Steaks was pulled from shelves within two months due to low sales. Specific financial losses are not publicly detailed but the quick discontinuation indicates a failure to capture the market.
Join AARP through this link and pay just $12 for your first year with automatic renewal and choose your FREE Gift.
6. GoTrump.com (2006-2007)
A luxury travel search engine shut down after a year due to critique and lack of traction, showcasing the challenges of establishing a new digital platform.
Initial setup and operational costs likely resulted in financial losses due to the short operational period.
13 Pieces of Horrible Financial Advice (That Most People Still Believe)
7. Trump Mortgages (2006-2007)
Launched at the brink of the housing market crash, it folded quickly due to the subprime mortgage crisis, emphasizing the impact of poor timing and market conditions.
Closed doors as the housing market crashed, signaling a poor timing and a significant misread of market conditions, resulting in likely substantial startup costs and operational losses.
It’s interesting that Trump Mortgages struggled as a lender, given Trump’s history as a borrower.
The Best Mortgage Housing Hack, Despite Rates Rising
8. Trump Ice (2004-2010)
Originally launched as part of Donald Trump’s array of branded products, Trump Natural Spring Water, marketed under the “Trump Ice” brand, promised one of the purest bottled waters.
Despite its discontinuation in 2010, it remains exclusively available at Trump-branded properties, emphasizing the luxury and exclusivity associated with the Trump name.
The brand, known for its low mineral content and being bottled in plastic, has been critiqued as more of a vehicle for Trump’s image than a testament to water quality.
Stop Wasting Money! 22 Things You’re Buying That You Can Get for Free
9. Trump Magazine (2007-2009)
Shut down after two years amid a challenging advertising market for luxury publications, underlining the tough media landscape.
The venture’s shutdown suggests significant unrecouped investment in publication and distribution.
Is the Economy Failing Us? 20 Financial Moves to Survive the Next Recession
10. Trump Tower Tampa (2006-2007)
A real estate venture shelved due to financing and market challenges, indicating significant investment losses.
The proposed luxury condo project was canceled amid the real estate market downturn, leading to lost deposits and investments, highlighting the financial risks in speculative real estate ventures.
🙋♀️If you like what you are reading, then click like and subscribe to my newsletter. We share tips to waste less time and money.
11. Trump SoHo Hotel (2008-2017)
Faced legal challenges and struggled with occupancy rates before being rebranded, showing the competitive nature of the luxury hotel sector.
Initial investment and operational losses, compounded by legal fees, mark this as a financial misstep.
Must-Know Investment Property Upgrades, From A Landlord
12. Trump Taj Mahal (1990-2016)
Opened with grandeur but faced immediate financial distress and multiple bankruptcies, reflecting the complexities of large-scale casino operations.
The scale of investment versus accumulated debt and operational losses underscores a significant financial failure.
Are You Earning Enough? Here’s How Much You Need to Live Comfortably in Your State
13. Trump Marina (originally Trump’s Castle)
Opened in 1985 in Atlantic City as Trump’s Castle, this casino resort was renamed Trump Marina in 1997. Despite the rebranding efforts and strategic location, the property struggled with financial stability and competition from newer, more modern casinos.
By 2011, Donald Trump had sold the property after multiple challenges, including a near foreclosure in the late 1990s.
17 Financial Traps You Should Avoid If You’re Over 50
14. Trump’s World Fair at Trump Plaza
Trump’s World Fair, another casino venture in Atlantic City, was opened in 1996 as an addition to the existing Trump Plaza. It aimed to provide a unique entertainment experience with its fair-like atmosphere.
It failed to draw the expected crowds and revenue, leading to its closure in 1999. This venture further highlighted the difficulties in maintaining profitability in the volatile casino market.
Join AARP through this link and pay just $12 for your first year with automatic renewal and choose your FREE Gift.
15. Trump Baku Hotel (Never opened)
A luxury hotel project in Azerbaijan that faced legal and financial issues, highlighting the risks of international real estate ventures.
Legal and financial issues halted this project, suggesting sunk costs in development and planning without the realization of potential revenues or returns.
20 States Fighting for Higher Minimum Wages (Despite Legitimate Concerns)
16. Trump Plaza Hotel and Casino (1984-2014)
Once a landmark in Atlantic City, it went through multiple bankruptcies before closing, demonstrating the challenges of maintaining profitability.
Multiple bankruptcies before its closure, indicating substantial financial losses over its operational life due to declining revenues and competitive pressures.
How To Get A Cheaper Hotel Room: Ways To Save On Hotel Stays
17. Trump International Hotel and Tower Dubai (Never realized)
Shelved following the 2008 financial crisis, illustrating the global impact of economic downturns on luxury real estate.
The failed venture reflects lost investments in planning and pre-development stages.
Passive Real Estate Investing – How To Get Started
18. Trump International Hotel and Tower New Orleans (Never realized)
Abandoned after Hurricane Katrina, indicating initial investment losses and unrealized potential in a recovering market.
The project was abandoned due to the city’s extensive rebuilding challenges.
The 10 Best and Worst States for Financial Literacy in 2024
19. Trump Tower Palm Beach (Never realized)
Faced local opposition and environmental concerns, quickly scrapped, underscoring the influence of community and environmental considerations.
🙋♀️If you like what you are reading, then click like and subscribe to my newsletter. We share tips to waste less time and money.
20. Trump Tower Charlotte (Never realized)
Encountered economic uncertainties and financing challenges, leaving the ambitious mixed-use development uncompleted.
This is another example of Trump experiencing financial losses related to planning and initial development efforts without achieving fruition.
What Poverty Really Feels Like: 15 Things Poor People Don’t Think You Understand
21. Trump Institute
A separate business from Trump University offering real estate seminars under a licensing agreement until 2009. Trump endorsed the program through infomercials despite not being involved in its operations.
While Trump endorsed the program, financial details on the scale of investment or revenue share are not public, suggesting a venture that did not meet its expected potential.
Mass Exodus: The States People Are Fleeing From and Where They’re Flocking To
22. Professional Football and Social Media Forays
Trump’s business interests have also spanned professional sports and social media.
These endeavors, while not detailed in financial outcomes here, signify his diverse portfolio and his readiness to take on high-risk ventures, demonstrating his approach to business and entrepreneurship.
Stop Doing These 30 Activities If You Are Over 75 (With Video)
23. Trump Foundation (Fraudulent Charity) (1988-2018)
A private foundation started by Donald Trump, dissolved by court order in 2018 following a series of legal violations. The foundation was scrutinized for unethical and illegal activities, including self-dealing and unauthorized campaign contributions.
Investigations led by the New York State Attorney General culminated in Trump being ordered to pay $2 million in damages for misusing charitable funds for political gains. This payment was distributed among eight different charities as restitution.
The settlement also mandated that the foundation be dissolved under court supervision, highlighting the misuse of charitable organizations for personal benefit.
20 Retirement Mistakes That Could Wipe Out Your Savings
24. Trump Winery (2011-)
Established following Donald Trump’s acquisition of the Kluge Estate Winery and Vineyard in 2011, Trump Winery has floated in and out of headlines due to both controversy and success.
Situated in Charlottesville, Virginia, near Thomas Jefferson’s historic Monticello estate, the winery underwent a significant transformation under the Trump family’s ownership.
Despite initial skepticism, Trump Winery has achieved a measure of acclaim within the wine industry. The winery, now managed under Eric Trump’s name, has produced award-winning wines recognized in prestigious competitions.
For instance, its 2014 Sparkling Reserve won Best in Class-Brut, Double Gold, 97 points at the 2020 San Francisco International Wine Competition, outscoring competitors from renowned wine regions including Napa, Sonoma, and even Champagne.
Despite claims of being the largest winery on the East Coast, Trump Winery is not the largest either by volume of wine produced or acreage under vine in Virginia, let alone the East Coast.
It produces around 36,000 cases of wine annually, with around 200 acres under vine, making it a significant player in Virginia’s wine scene but not the largest as previously claimed.
The winery’s product lineup includes a mix of sparkling, white, red, and rosé wines, with several of its offerings garnering critical acclaim for their quality. Notably, the Trump Winery Chardonnay and the Sparkling Blanc de Blanc have received positive reviews and multiple awards, affirming the winery’s commitment to leveraging Virginia’s terroir.
The winery has also been subject to criticism from wine experts who have had mixed reviews about the quality of its wines. Moreover, despite Donald Trump’s well-known abstention from alcohol, his name remains synonymous with the winery, illustrating the complex interplay between his business interests and personal life.
Are You Aging Faster? 20 Everyday Habits You Need to Break Now
25. Trump Cologne (2004-2015)
Donald Trump’s venture into the fragrance market began with “Donald Trump, The Fragrance” in 2004, a partnership with Estée Lauder.
Aimed at capturing the essence of the luxury and success associated with his persona, this line expanded with “Trump Success” in 2012 and “Empire by Trump” in 2015, broadening his brand’s reach into personal grooming and luxury lifestyle products.
Declutter Now: 39 Things You Need to Get Rid of Today
26. Truth Social
Truth Social, the social media platform launched by Donald Trump’s Trump Media & Technology Group (TMTG), has faced significant financial challenges since its inception.
The platform reported substantial financial losses, amounting to $31.6 million from its launch until mid-2023. In 2023 alone, regulatory filings and company reportshighlighted losses of $58 million.
A key issue for Truth Social has been generating sufficient revenue, particularly from advertising, a challenge amid stiff competition from established social media giants.
The platform generated only about $3 million in revenue over the first nine months of 2023, contrasting sharply with its significant operating losses.
The platform’s financial struggles are compounded by its limited user base and engagement levels, which are crucial for attracting advertisers and sustaining operations. Truth Social has an estimated 2 million active users, substantially lower than larger platforms like Instagram or TikTok, making it challenging to draw significant advertising revenue.
The stock of TMTG, listed as Truth Social, has also seen volatile movements, reflecting investor skepticism about the platform’s viability and the broader financial sustainability of Trump’s media venture. The stock experienced sharp declines due to ongoing financial losses and uncertainties about its future profitability.
22 Uncomfortable Truths: How Technology Is Quietly Making Life Worse
Is Marriage A Business?
Trump hasn’t limited his financial failures to business. Donald Trump has been married three times:
Seniors Are Seperating. “Gray Divorce” Is Changing Senior Life in America
Ivana Trump
They married in 1977 and divorced in 1992. Ivana was a significant figure in the Trump Organization, notably in interior design and managing the Plaza Hotel.
The divorce settlement with Ivana Trump was one of the most talked-about in the early ’90s. It was reported that Ivana received a settlement that included $14 million, a mansion in Connecticut, an apartment in Trump Plaza, and use of Mar-a-Lago for one month a year.
Stop Feeling Entitled: Why More Boomers Are Choosing Not to Pass Down Their Wealth
Marla Maples
The marriage took place in 1993, following their affair that began while Trump was still married to Ivana. They have one daughter, Tiffany, and divorced in 1999.
The divorce from Marla Maples was less costly in comparison. Reports suggest that Maples received around $2 million in the divorce settlement.
6 Reasons You Should Have a Living Trust
Trump: A Lesson Learned
This comprehensive overview of Donald Trump’s less successful ventures showcases the challenging nature of entrepreneurship.
Each venture, from educational endeavors like Trump University to ambitious real estate projects like Trump Tower Tampa, underlines the importance of market timing, financial management, and the complexities of navigating various industries.
Trump’s widespread interests, spanning from luxury goods to online platforms and professional sports, highlight his entrepreneurial spirit but also the potential pitfalls of extending one’s brand across too diverse a range of sectors.
These failures not only represent financial losses but also offer lessons on the importance of ethical business practices, market research, and strategic planning.
Despite these setbacks, Trump’s career continues to be a subject of study for understanding the dynamics of business success and failure in the modern economic landscape.
Time to Let Go? 24 American Traditions We Probably Need to Leave Behind
In Conclusion
Each of these ventures illustrates not just the ambition and breadth of Trump’s business interests but also the inherent risks of entrepreneurship and market speculation.
The financial figures, where available, help to illuminate the scale of investment and the magnitude of losses involved, offering a cautionary tale about the complexities and challenges of business ventures across diverse industries.
If you liked what you read, then after you click like, be sure to follow us on Flipboard.
- Save Time and Money with These Expert Approved Travel Sites
- 12 Reasons Companies Secretly Refuse To Hire Workers Over 60
- Discover 11 Secrets to Booking Last-Minute Flight Deals
- Discover the Cheapest Airlines and Save Big on Your Next Flight!
- Are They Really Upper Class? 24 Ways to Spot the True Elite from the Pretenders
