From 1986 to 1988, he purchased significant blocks of shares in various public companies while suggesting that he intended to take over the company and then sold his shares for a profit,[66] leading some observers to think he was engaged in greenmail.[67] The New York Times found that he initially made millions of dollars in such stock transactions, but "lost most, if not all, of those gains after investors stopped taking his takeover talk seriously".[66]

According to a review of state and federal court files conducted by USA Today in 2018, Trump and his businesses had been involved in more than 4,000 lawsuits,[87] liens, and other filings, often filed for nonpayment against him by employees, contractors, real estate brokers, and his own attorneys.[88] While Trump has not filed for personal bankruptcy, his over-leveraged hotel and casino businesses in Atlantic City and New York filed for Chapter 11 bankruptcy protection six times between 1991 and 2009.[33] They continued to operate while the banks restructured debt and reduced his shares in the properties.[33] During the 1980s, more

than 70 banks had lent Trump $4 billion.[89] After his corporate bankruptcies of the early 1990s, most major banks, with the exception of Deutsche Bank, declined to lend to him.[90] After the January 6 Capitol attack, Deutsche Bank also decided not to do business with him or his affiliated company in the future.[91]