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Fact check: How many times did Donald Trump's companies file for Chapter 11 bankruptcy?

Checked on August 20, 2025

1. Summary of the results

The analyses reveal conflicting information about the number of Chapter 11 bankruptcies filed by Donald Trump's companies. Two distinct counts emerge from the sources:

Four bankruptcies are reported by multiple sources [1] [2], which consistently list:

  • Trump Taj Mahal [3]
  • Trump Plaza Hotel [4]
  • Trump Hotels and Casinos Resorts [5]
  • Trump Entertainment Resorts [6]

Six bankruptcies are reported by other sources [7] [8], which include the above four plus:

  • Trump Castle [4]
  • Trump Entertainment Resorts [9]

The sources citing six bankruptcies provide more comprehensive documentation, with one source [8] offering "a detailed breakdown of each filing" and another [7] specifically addressing the discrepancy between four and six filings.

2. Missing context/alternative viewpoints

The original question lacks important contextual information that emerges from the analyses:

  • Corporate structure complexity: The analyses reveal that these were filings by Trump's casino and hotel companies, not personal bankruptcies by Donald Trump himself [1] [7] [8]
  • Timeline concentration: Most bankruptcies occurred during specific periods - the early 1990s and 2000s - suggesting industry-wide challenges in the casino sector rather than isolated business failures
  • Political implications: One source [2] appears to be from a "Rubio Campaign Press Release," indicating this information has been used in political contexts, potentially with selective presentation of facts
  • Legal distinction: Chapter 11 bankruptcy is a reorganization process, not liquidation, allowing companies to continue operating while restructuring debt

3. Potential misinformation/bias in the original statement

The original question itself is neutral, but the conflicting source information reveals potential bias in how this information is presented elsewhere:

  • Selective counting: Sources reporting four bankruptcies [2] may be deliberately omitting the Trump Castle [4] and Trump Entertainment Resorts [9] filings to minimize the total count
  • Political motivation: The involvement of campaign materials [2] suggests this information is being used strategically, with political operatives benefiting from presenting lower numbers to defend Trump or higher numbers to criticize him
  • Definitional ambiguity: The discrepancy may stem from how sources define "Trump's companies" - whether they include all entities with Trump's name or only those he directly controlled
  • Temporal bias: Without publication dates for most sources, it's unclear whether some analyses were conducted before the 2014 Trump Entertainment Resorts filing, which could explain the four versus six discrepancy

The most comprehensive sources [8] [7] support the six bankruptcy count, suggesting that claims of only four filings may represent incomplete or politically motivated reporting.

Want to dive deeper?
What were the specific circumstances surrounding each of Donald Trump's Chapter 11 bankruptcy filings?
How did Donald Trump's companies recover from Chapter 11 bankruptcy?
What role did Donald Trump play in the financial management of his companies during bankruptcy proceedings?
How many of Donald Trump's business ventures have filed for bankruptcy since his presidency?
What are the long-term financial implications of Chapter 11 bankruptcy on a company's credit and reputation?