Donald Trump has filed for business bankruptcy four times, though he has not filed for personal bankruptcy. All four business bankruptcies were chapter 11, which allowed him to get rid of his corporate debt and continue operating as a business.
The first bankruptcy was filed in 1991 for the Trump Taj Mahal. During this bankruptcy filing, Donald Trump sold a yacht and the Trump Shuttle, which was a private airline he owned. In 1992, he filed bankruptcy for Trump Castle Associates, which owned other casinos in Atlantic City. He filed again in 2004 for the Trump Hotel and Casino Resorts. He got rid of $500 million in debt during this bankruptcy. The final filing was in 2009 for Trump Entertainment Resorts, following a $53.1 million bond payment that was never paid.