4. His record of bankruptcy and business failure. Trump’s braggadocio about his business acumen masks a long record of failure and ruin. His real talent seems to be for fleecing his investors and then walking away when the crash hits. While he makes grandiose promises, he repeatedly underdelivers and underperforms, which is why his hotels and casinos have wound up in bankruptcy time and time again. In one memorable instance, his rich father temporarily bailed out one of his struggling casinos with a suitcase full of chips:
But a close examination of regulatory reviews, court records and security filings by The New York Times leaves little doubt that Mr. Trump’s casino business was a protracted failure. Though he now says his casinos were overtaken by the same tidal wave that eventually slammed this seaside city’s gambling industry, in reality he was failing in Atlantic City long before Atlantic City itself was failing.
But even as his companies did poorly, Mr. Trump did well. He put up little of his own money, shifted personal debts to the casinos and collected millions of dollars in salary, bonuses and other payments. The burden of his failures fell on investors and others who had bet on his business acumen.
…By December 1990, when Mr. Trump needed to make an $18.4 million interest payment, his father, Fred C. Trump, sent a lawyer to the Castle to buy $3.3 million in chips, to provide him with an infusion of cash. The younger Mr. Trump made the payment, but the Casino Control Commission fined the Castle $65,000 for what had amounted to an illegal loan.
—How Donald Trump Bankrupted His Atlantic City Casinos, but Still Earned Millions, New York Times, 11 June 2016
3. His record of stiffing people who worked for him. However many of Trump’s businesses collapsed, you can say that most of his investors were wealthy, sophisticated people who should have known what they were getting into by investing with him. But you can’t say the same for the many, many working people and small business owners who did work for Trump that he then refused to pay for:
At least 60 lawsuits, along with hundreds of liens, judgments, and other government filings reviewed by the USA TODAY NETWORK, document people who have accused Trump and his businesses of failing to pay them for their work. Among them: a dishwasher in Florida. A glass company in New Jersey. A carpet company. A plumber. Painters. Forty-eight waiters. Dozens of bartenders and other hourly workers at his resorts and clubs, coast to coast. Real estate brokers who sold his properties. And, ironically, several law firms that once represented him in these suits and others.
…Just last month, Trump Miami Resort Management LLC settled with 48 servers at his Miami golf resort over failing to pay overtime for a special event. The settlements averaged about $800 for each worker and as high as $3,000 for one, according to court records. Some workers put in 20-hour days over the 10-day Passover event at Trump National Doral Miami, the lawsuit contends.
…Trump’s Doral golf resort also has been embroiled in recent non-payment claims by two different paint firms, with one case settled and the other pending. Last month, his company’s refusal to pay one Florida painter more than $30,000 for work at Doral led the judge in the case to order foreclosure of the resort if the contractor isn’t paid.
—Hundreds allege Donald Trump doesn’t pay his bills, USA Today, 9 June 2016