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FYI: 500
The Trump Organization is the collective name for a group of approximately 500 business entities of which Donald Trump, the current U.S. President, is the sole or principal owner. Approximately 250 entities use the Trump name.
The Trump Organization - Wikipedia
en.wikipedia.org
6 Corporate Bankruptcies
Trump has filed Chapter 11 bankruptcy for his companies six times. Three of the casino bankruptcies came during the recession of the early 1990s and the Gulf War, both of which contributed to hard times in Atlantic City, New Jersey's gambling facilities. He also entered a Manhattan hotel and two casino holding companies into bankruptcy.

Chapter 11 bankruptcy allows companies to restructure or wipe away much of their debt to other companies, creditors, and shareholders while remaining in business but under the supervision of a bankruptcy court. Chapter 11 is often called "reorganization" because it allows the business to emerge from the process more efficient and on good terms with its creditors.

Personal vs. Corporate Bankruptcy
One point of clarification: Trump has never filed personal bankruptcy, only corporate bankruptcy related to his casinos in Atlantic City. "I have never gone bankrupt," Trump has said.

Six out of approx 500 companies - I would not say 'bankruptcy prone'.

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