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Legal affairs and bankruptcies
Main article: Legal affairs of Donald Trump
As of 2016, Trump and his businesses had been involved in more than 3,500 state and federal legal actions. He or one of his companies was the plaintiff in 1,900 cases and the defendant in 1,450. With Trump or his company as plaintiff, more than half the cases have been against gamblers at his casinos who had failed to pay off their debts. With Trump or his company as a defendant, the most common type of case involved personal injury cases at his hotels. In cases where there was a clear resolution, Trump's side won 451 times and lost 38.[166][167]
Trump has never filed for personal bankruptcy, but his hotel and casino businesses have been declared bankrupt six times between 1991 and 2009 in order to re-negotiate debt with banks and owners of stock and bonds.[168][169] Because the businesses used Chapter 11 bankruptcy, they were allowed to operate while negotiations proceeded. Trump was quoted by Newsweek in 2011 saying, "I do play with the bankruptcy laws – they're very good for me" as a tool for trimming debt.[170][171]
The six bankruptcies were the result of over-leveraged hotel and casino businesses in Atlantic City and New York: Trump Taj Mahal (1991), Trump Plaza Hotel and Casino (1992), Plaza Hotel (1992), Trump Castle Hotel and Casino (1992), Trump Hotels and Casino Resorts (2004), and Trump Entertainment Resorts (2009).[172][173] Trump said, "I've used the laws of this country to pare debt ... We'll have the company. We'll throw it into a chapter. We'll negotiate with the banks. We'll make a fantastic deal. You know, it's like on The Apprentice. It's not personal. It's just business."[141]
A 2016 analysis of Trump's business career by The Economist concluded that his "... performance [from 1985 to 2016] has been mediocre compared with the stock market and property in New York", noting both his successes and bankruptcies.[174] A subsequent analysis by The Washington Post concluded that "Trump is a mix of braggadocio, business failures, and real success", calling his casino bankruptcies the "most infamous flop" of his business career.[175]