In 1991, Donald Trump faced a precarious financial situation as a mid-level real estate developer with approximately $900 million in debt. His casino businesses were failing, and his high-profile split from his wife, Ivana, was dominating headlines. Desperate for cash, Trump relied on unconventional support, with his father reportedly purchasing $3.
35 million in casino chips without using them, helping Trump make a significant bond payment the previous year. Many of Trump’s financial challenges originated in the 1980s, when he overpaid on acquisitions like the Eastern Air Lines Shuttle for $365 million and the Plaza Hotel for $400 million. According to his associate, Barbara Res, these costly purchases were poor choices.
The financial pressure intensified in the early 1990s recession, with Trump’s debts reportedly totaling $3.4 billion, of which he personally guaranteed over $800 million. Massive Losses and Tax Implications In 1995, Donald Trump’s state tax returns showed a staggering loss of $916 million, as revealed by a New York Times investigation.
Although the source of this figure is unclear due to limited documentation, such a large loss would have allowed Trump to potentially avoid paying federal income taxes for years. Trump’s legal representative, Alan Pomerantz, noted that while Trump anticipated profits from his acquisitions, they proved to be highly risky ventures with losses largely affecting his investors. The Trump Taj Mahal: A Risky Gamble One of Trum.