While Trump has promoted himself as a great businessman who has made a tremendous amount of money, he has had his share of business disasters. Trump University was found to be a sham (Trump settled the case out of court); he was found guilty of 32 felonies by a Manhattan, New York jury (as a conspirator - he was aware of and approved the plan); and, he has filed for business bankruptcy 6 times under chapter 11 of the bankruptcy code (business re-organization).

 

Business re-organizations can be a good thing for a business. However, the underlying question is why the re-organization necessary.

 

According to a New York Times article republished by the Tampa Bay Times on June 13, 2016 see article below), [Trump's] audacious personality and opulent properties brought attention — and countless players — to Atlantic City as it sought to overtake Las Vegas as the country's gambling capital. But a close examination by the New York Times of regulatory reviews, court records and security filings leaves little doubt that Trump's casino business was a protracted failure. ... In reality, [Trump] was failing in Atlantic City long before Atlantic City itself was failing.

 

... [E]ven as his companies did poorly, 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.

 

Here is the list of Chapter 11's filed by Trump:

Bankruptcy No. 1: The Trump Taj Mahal, 1991

Bankruptcy No. 2: Trump Castle, 1992

Bankruptcy No. 3: Trump Plaza and Casino, 1992

Bankruptcy No. 4: Plaza Hotel, 1992

Bankruptcy No. 5: Trump Hotels and Casinos Resorts, 2004

Bankruptcy No. 6: Trump Entertainment Resorts, 2009

 

Below articles by ThoughtCo. and Politifact describe why each bankruptcy occurred as well as how Trump, himself, was affected.