He ran a casino into bankruptcy
From Gnomon Chronicles

The Trump Taj Mahal casino broke anti-money laundering rules 106 times in its first year and a half of operation in the early 1990s. The casino repeatedly failed to properly report gamblers who cashed out $10,000 or more in a single day. Trump’s casino was a money laundering concern shortly after it opened (22 May 2017).
People laugh: "He ran a casino into bankruptcy!"
But perhaps this was the plan all along:
• Launder money constructing casino • Launder money operating casino • Continue until authorities close in, transfer assets to insiders and declare bankruptcy
- Trump’s casino was a money laundering concern shortly after it opened @ CNN (22 May 2017)