Donald Trump was never a successful businessman. By any measure.
By Cody Andrus
Donald Trump has long portrayed himself as a brilliant and successful businessman, but the reality of his career paints a different picture. Despite his fame and wealth, Trump’s business ventures often end in failure, with multiple bankruptcies, financial losses, and a reputation for not paying workers and contractors. His ability to market himself as a success is a testament more to his skills as a promoter than his talents as a businessman.
One of the most glaring indicators of Trump’s business failures is his string of bankruptcies. Over the years, Trump has filed for corporate bankruptcy six times, largely to restructure debt from his casinos and hotels. His Atlantic City casinos, once part of a booming empire, collapsed under heavy debt, with Trump repeatedly borrowing more money than the businesses could repay. The Trump Taj Mahal, once billed as the “eighth wonder of the world,” was one of the most high-profile failures, eventually closing its doors after years of financial struggles. These bankruptcies not only damaged his reputation but also left many creditors and workers unpaid.
Another example of Trump’s business mismanagement was his ill-fated attempt to enter the airline industry. In 1988, Trump purchased Eastern Air Shuttle and rebranded it as Trump Shuttle. Despite his bold claims that the airline would dominate the market, it struggled to turn a profit from the start. The airline's failure, like many of Trump’s ventures, was due to a combination of over-expansion, poor management, and a failure to understand the complexities of the industry. After just a few years, Trump Shuttle was forced to shut down, adding yet another failure to his record.
Trump’s reputation for not paying workers and contractors is another troubling aspect of his business dealings. Numerous lawsuits have been filed against him by small businesses and contractors who claim they were not paid for services rendered. These include painters, carpenters, and even dishwashers who worked on Trump properties but were never compensated in full. Trump often justified this by claiming dissatisfaction with the work, but the sheer volume of complaints suggests a pattern of behavior rather than isolated incidents. This practice not only hurt small businesses but also tarnished Trump’s reputation in the construction industry.
In addition to his bankruptcies and unpaid workers, Trump’s financial losses have been staggering. According to a New York Times investigation, Trump reported over $1 billion in business losses from 1985 to 1994. These losses were so significant that they allowed him to avoid paying federal income taxes for several years. While Trump has often boasted about using tax loopholes to his advantage, such massive losses raise serious questions about his competence as a businessman.
Trump’s ventures into other areas, such as Trump University, also ended in disaster. Trump University, which promised students valuable real estate education, was sued for fraud, with many students claiming they were misled and left with little to no useful knowledge. Trump ultimately settled the lawsuit for $25 million, another blow to his credibility as a businessman.
The Washington Post - "Trump's History of Bankruptcies and Business Failures", The New York Times - "The Decade of Trump’s Business Losses", NBC News - "Lawsuits Against Trump for Unpaid Work", Forbes - "Trump's Failed Businesses and Financial Struggles", CNN - "Trump University Fraud Settlement"
