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Rosie O’Donnell Tells the Origin Story of Her Feud with Donald Trump… and Gets It Wrong

To clarify the facts: Donald Trump has never filed for personal bankruptcy. However, several of his business ventures have filed for Chapter 11 corporate bankruptcy, a legal process that allows companies to restructure debt while continuing operations.

Trump has been involved in over 500 business ventures, though the exact number depends on how one defines his role—whether as a founder, owner, or through licensing deals. Among the most well-documented bankruptcies are:

  • Trump Taj Mahal (1991) – A casino in Atlantic City.
  • Trump Plaza Hotel and Casino (1992) – Another Atlantic City property.
  • Trump Castle Hotel and Casino (1992) – Also in Atlantic City.
  • Plaza Hotel (1992) – A luxury hotel in New York City.
  • Trump Hotels and Casino Resorts (2004) – A holding company for multiple casino properties.
  • Trump Entertainment Resorts (2009) – The successor to the previous entity.

These Chapter 11 filings were not liquidations; the businesses continued operating while restructuring debt. Some sources debate whether the number is four or six, as Trump has at times grouped the 1992 filings together. However, legally speaking, each was a separate case.

Compared to his 500+ business ventures, six bankruptcies represent a small percentage—around 1.2%. In high-risk industries like real estate and casinos, such filings are common. Trump has often argued that using bankruptcy laws strategically is a smart business move, not a failure, and that many successful companies have done the same.

P.S. Rosie O’Donnell has often claimed that Donald Trump got his wealth from his father, Fred Trump. In reality, Trump did receive financial support from his father, including a $1 million loan, which Trump has described as “small” in the context of his business career.

Sources: Rosie O’Donnell Tells the Origin Story of Her Feud with Donald Trump , Late Night with Seth Meyers

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