![]() ![]() Trump’s surprise victory in 2016 paralleled the arrival of the brash upstart in Atlantic City more than 30 years earlier. Trump’s 6th bankruptcy was the Plaza Hotel, which he bought in 1988. The company that emerged from that restructuring declared bankruptcy in 2009. Lenders restructured the debt rather than liquidate and Trump put his casino holdings into a new company that went bankrupt in 2004. The Taj Mahal declared bankruptcy in 1991, the Trump Plaza and the Trump Castle in 1992. ![]() He acquired three casinos that by 1991 couldn’t pay their debts. In the 1980s, Trump was a swashbuckling real-estate investor who bet big on the rise of Atlantic City after New Jersey legalized gambling there. As the president running for a second term, Trump is repeating some of the mistakes he made as a businessman and risking the downfall of yet another venture: his own political operation. As a businessman, Donald Trump ran 6 businesses that declared bankruptcy because they couldn’t pay their bills.
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