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Donald Trump once called it “the eighth wonder of the world.” But just one year after it opened in 1990, the Trump Taj Mahal casino filed for bankruptcy. Trump had borrowed over $800 million to build the massive casino in Atlantic City. It was the most expensive casino ever built at the time—complete with chandeliers, gold decor, and Trump’s name in giant letters. But behind the glamor was a financial mess. The casino couldn’t earn enough money to pay back the debt. In 1991, Trump’s Taj Mahal entered Chapter 11 bankruptcy, a legal process that lets companies restructure debt. Trump gave up a large part of his ownership in the casino to keep it afloat, but it wasn’t the end. Over the next decade, Trump’s casino empire—including the Trump Plaza and Trump Marina—went bankrupt multiple times. Trump often said the bankruptcies were smart business moves, letting him reduce debt while keeping his brand. Critics called it financial failure on repeat—hurting investors, workers, and the city of Atlantic City. While Trump himself never declared personal bankruptcy, his companies did four times before 2010—most of them tied to casinos. The bankruptcies didn’t end his career, but they showed a pattern: big risk, big debt, and walking away when it all crashes down.

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