Donald Trump’s Failed Businesses: The Body Count

Trump’s Casinos: The Atlantic City Debacle

If you ever wanted proof that leverage plus ego equals bankruptcy, look no further than Trump’s Atlantic City casinos.

• Trump Taj Mahal (1990–2016)
  Trump called it the “Eighth Wonder of the World,” then watched it file for Chapter 11 just a year after opening, crushed under more than $3 billion in debt.
  
  “He literally wrote a chapter called ‘I built the casino in Atlantic City, I’m a business genius.’ Then the casino went bankrupt, and the chapter became a Yelp review.”
• Trump Plaza Hotel & Casino
  Bought for $390 million, it piled up around $550 million in debt and joined the bankruptcy parade in 1992. The building later reopened under new owners and finally shut for good in 2014.
  
  “Trump Plaza was like that one friend who shows up to the party with a fake Rolex and leaves with a DUI: flashy, expensive, and ultimately a liability.”
• Trump Marina (Trump Castle)
  Another Atlantic City property that went under Trump’s bankrupt casino‑holding companies, later sold off and rebranded.
  
  “Trump Marina was less ‘marina,’ more ‘marina‑debt‑sink.’ The only thing that stayed afloat was the lawsuits.”
• Trump Hotels & Casino Resorts (THCR)
  The corporate parent of several casinos filed for Chapter 11 in 2004 with over $1.8 billion in debt, wiping out much of Trump’s equity.
  
  “THCR was the corporate equivalent of a guy who refinances his mortgage to buy a jet‑ski. The jet‑ski looks great; the bank owns your house.”
• Trump Entertainment Resorts (TER)
  The renamed successor went bankrupt again in 2009 during the financial crisis, cementing Trump’s four‑time casino‑bankruptcy hat‑trick.
  
  “Trump Entertainment Resorts: where the only thing more bankrupt than the balance sheet was the idea that this was a good business model.”

Trump Airlines and the Trump Shuttle

Trump once tried to turn air travel into a walking billboard for his ego. It did not go well.

• Trump Shuttle Inc. (1989–1992)
  Trump bought Eastern Air Lines’ shuttle service between New York, Washington, and Boston, slapped his name on the planes, and promised luxury. He defaulted on a $1.1 million loan, and the operation was folded into a merger by 1992.
  
  “The Trump Shuttle was like a guy who buys a private jet and then realizes he can’t afford the fuel. So he sells the jet and calls it a ‘strategic retreat.’”

Trump University: The “Get Rich Quick” Scam That Got Richer in Court

Trump University was less “university,” more multi‑level‑marketing‑style seminar with a side of lawsuits.

• Trump University (2005–2011)
  Marketed as a real‑estate “school,” it charged thousands for seminars and mentorship packages. After years of investigations and class‑action suits, it shut down in 2011 and Trump later settled multiple cases for millions.
  
  “Trump University: where the only thing you learned was how to lose money in a seminar and then lose more money in court.”

Trump‑Branded Consumer Products That Vanished

Trump licensed his name to a string of short‑lived products that made more headlines than sales.

• Trump Vodka (2005–2011)
  A “super‑premium” vodka launched under license; sales were weak and the brand was discontinued in 2011.
  
  “Trump Vodka: proof that even when you put his name on a bottle, people still didn’t want to drink it.”
• Trump Steaks / Trump Meats (2007–2007)
  A steak line sold at Costco that lasted about two months before sales collapsed. Trump later tried a broader “Trump Meats” concept that also flopped.
  
  “Trump Steaks: the only thing more rare than the meat was the customer.”
• Trump Bottled Water
  Trump claimed his bottled water came from a “secret spring,” but it turned out to be ordinary Pennsylvania tap water; the company collapsed around 2010.
  
  “Trump Bottled Water: the only thing ‘premium’ about it was the price.”
• Trump Mattresses
  A mattress line sold through retailers like Costco; it quietly shut down due to low sales and became a meme‑worthy business failure.
  
  “Trump Mattresses: where the only thing softer than the foam was the demand.”
• Trump Fragrance
  A line of perfumes and colognes that never became a major brand and faded from shelves.
  
  “Trump Fragrance: the only thing it left behind was a faint smell of regret.”

Trump’s Financial and Tech Side Hustles

Trump also tried to conquer finance and tech, with predictable results.

• Trump Mortgage, LLC (2006–2007)
  A mortgage‑brokerage company launched just before the housing crash; it ceased operations in 2007 as the market imploded.
  
  “Trump Mortgage: the only thing it financed was the crash.”
• GoTrump.com (2006–2007)
  A travel‑booking website meant to sell Trump‑branded vacations; it shut down in 2007 after failing to compete with Expedia‑style giants.
  
  “GoTrump.com: the only thing that went ‘Trump’ was the traffic.”
• Trump Net / Trump Telecom
  A telephone‑and‑internet venture that reportedly ran out of money before it properly launched.
  
  “Trump Net: the only thing it connected was the dots between hubris and bankruptcy.”

Trump’s Media and Publishing Flops

Trump tried to turn his brand into a magazine empire and a board‑game dynasty. Spoiler: it didn’t stick.

• Trump Magazine (2006–2007)
  A luxury‑lifestyle magazine tied to the Trump name; it folded after only a few issues due to poor circulation and ad sales.
  
  “Trump Magazine: the only thing more exclusive than the content was the audience of one—Trump.”
• Trump: The Game (board game)
  A Monopoly‑style game released in the 1980s; sales were so weak that Milton Bradley pulled it from shelves. A re‑release during The Apprentice era also flopped.
  
  “Trump: The Game: the only thing it taught you was how to lose money in a board game.”

Other Trump‑Branded Busts

Trump’s brand‑licensing machine produced a few more head‑scratchers.

• Trump Wines and Spirits (beyond vodka)
  Various Trump‑branded wines and spirits were launched under license but never became major brands and were quietly discontinued.
  
  “Trump Wines: the only thing they aged was the lawsuits.”
• Trump‑Branded Hotels and Resorts (international)
  Several Trump‑branded international hotels and condos were announced with fanfare but later scaled back, rebranded, or abandoned as partners distanced themselves from Trump’s politics.
  Jon‑Stewart‑style line:
  “Trump‑branded hotels: the only thing more unstable than the buildings was the brand.”
• Trump‑Branded Golf Courses and Clubs
  Some Trump‑branded golf ventures struggled with membership declines and political backlash, leading to rebranding or sale of certain properties.
  
  “Trump‑branded golf courses: where the only thing more toxic than the water hazards was the politics.”

Truth Social: The SPAC‑Powered Train Wreck

Trump’s social‑media platform, Truth Social, was taken public via a SPAC deal that became a case study in overhyped, under‑delivered tech ventures. The company’s filings even list Trump’s prior failed businesses as part of its risk disclosures.

“Truth Social: the only thing more bankrupt than the platform was the idea that people would pay for it.”

Why This Matters for Voters

Trump’s four major Chapter 11 bankruptcies and dozens of shuttered side ventures show a pattern: high‑leverage debt, aggressive branding, and short‑lived fads rather than durable business building. This catalog of failures undercuts the “self‑made billionaire” myth and highlights how much of his fortune has relied on family money, tax strategies, and licensing deals rather than operational success.