Trump, Debt, and the Art of Losing Other People’s Money

Company Profile

Donald J. Trump (DJT) Hotels & Casinos was an entertainment company that owned and operated the Trump Plaza Hotel and Casino, Trump Taj Mahal Casino Resort, Trump’s Castle Casino Resort and Trump Indiana.

Besides revenues from gambling, the properties offered other forms of entertainment. The Taj Mahal was an experience unto itself. Just the entrance had $1 million in 24-karat gold leaf… and, millions of dollars worth of German crystal chandeliers sparkled over the lobby’s Carrera marble-floor.

I’m an economist. In the 1990s, I conducted a moral and ethics experiment involving the stock DJT for a widows and orphans fund, during which Trump misappropriated the funds. A business bankruptcy impacts more people than a personal bankruptcy and is seen as a more significant violation of business ethics and morals.

The original stock with the ticker symbol DJT belonged to Trump Hotels & Casino Resorts (THCR), a company founded by Donald Trump in the 1990s. It operated various casinos and resorts, including Trump Plaza, Trump Taj Mahal, and Trump Marina in Atlantic City. THCR faced ongoing financial difficulties, which eventually led to four major bankruptcies. In 1995, the company went public under the ticker DJT, aiming to raise funds to refinance debts and expand its casino ventures. However, the company quickly became over-leveraged with high-interest debt, which plagued its operations.

The first bankruptcy in the timeline occurred in 1991, before DJT went public, when Trump’s Taj Mahal casino filed for Chapter 11 bankruptcy after failing to generate enough revenue to service its over $1 billion debt from junk bonds. Trump had to give up half of his ownership in the Taj Mahal but retained control of the casino. In 2004, Trump Hotels & Casino Resorts (by then public under DJT) filed for bankruptcy a second time due to its massive debt load and struggling casino operations. During this bankruptcy, Trump gave up more control of the company to creditors, though he stayed on as chairman.

In 2009, the company, rebranded as Trump Entertainment Resorts, filed for Chapter 11 again, marking the third bankruptcy. Trump resigned as chairman and left the board of directors, maintaining only a small ownership stake. Despite these efforts, the financial situation worsened, and in 2014, the company filed for bankruptcy a fourth time, leading to the closure of the Trump Plaza and Trump Taj Mahal casinos. This final bankruptcy signaled the end of Trump’s casino ventures, though his name remained on some properties through branding agreements.

The successive bankruptcies decimated the value of DJT stock, and Trump’s stake in the company dwindled over time. By the time of the 2014 bankruptcy, Trump had little control over the company. Eventually, DJT stock ceased to exist as the company’s assets were sold off. The bankruptcies are often cited as part of Trump’s controversial financial history, where he used bankruptcy laws to restructure debts, often at the cost of shareholders and creditors.

Conclusion

It’s difficult to determine the exact number of corporate bankruptcies associated with Donald Trump’s business ventures, in part because of how some analysts count them. In this particular case, there were four separate bankruptcy filings, though many analysts count them collectively as a single event. Broadly, most sources agree that Trump’s companies have filed for bankruptcy at least six times, with some estimates — depending on how repeat filings by the same entity are treated — placing the total closer to 12 to 14.

In each instance, critics have argued that Trump personally profited despite the financial losses borne by shareholders, lenders, and employees. These allegations typically focus on patterns of aggressive debt use, questionable fiscal management, and the transfer of risk from Trump to investors and creditors.

Now, he is doing it worldwide.

As one economist put it:

“Trump didn’t just pick a trade war — he picked one with the entire planet.”

A Crisis of This Magnitude Has Not Been Seen in Nearly 100 Years

While past recessions were driven by financial collapses (such as 2008’s mortgage crisis or the dot-com bubble in 2000), this economic crisis is entirely policy-driven. The sheer scale of the tariffs, combined with global retaliation and the isolation of the U.S., has created a trade collapse not seen since the 1930s. If history is any guide, the consequences could be severe, with prolonged economic hardship, market instability, and lasting damage to U.S. credibility in global trade.

Capital Preservation During Trumpenomics

Trumpenomics: The Decline of the US

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