Trump’s business past appears to be predicting the USA democratic, economic, and foreign policy future, as well as the self enrichment constant.

Six businesses controlled by Donald Trump filed for Chapter 11 bankruptcy between 1991 and 2014. These were:

1. **Trump Taj Mahal (1991)**: Atlantic City casino, burdened by $675 million in junk bond debt at 14% interest, filed for bankruptcy due to insufficient revenue during a recession.

2. **Trump Plaza Hotel and Casino (1992)**: Atlantic City casino, struggled with operational costs and filed for bankruptcy alongside other properties.

3. **Trump Castle Hotel and Casino (1992)**: Atlantic City casino, faced similar financial difficulties and filed for bankruptcy.

4. **Plaza Hotel (1992)**: New York hotel, acquired for $390 million, accumulated $550 million in debt, leading to bankruptcy.

5. **Trump Hotels and Casino Resorts (2004)**: Holding company for Trump’s Atlantic City casinos, filed for bankruptcy with $1.8 billion in debt.

6. **Trump Entertainment Resorts (2009, 2014)**: Successor to Trump Hotels and Casino Resorts, filed for bankruptcy twice due to ongoing financial struggles, with liabilities between $100 million and $500 million in 2014.

These bankruptcies involved corporate entities, not personal bankruptcy, and were primarily tied to over-leveraged casino and hotel ventures in Atlantic City and New York. Trump used Chapter 11 to restructure debts, often retaining partial ownership or management roles while shifting losses to bondholders and creditors.