Which of Donald Trump's businesses have filed for Chapter 11 bankruptcy protection?

1. The businesses most commonly named as Chapter 11 filers

Contemporary summaries and legal reviews list six Trump-linked hotel and casino entities that sought Chapter 11 protection: Trump Taj Mahal (Atlantic City), Trump Plaza Hotel and Casino (Atlantic City), Trump Castle/Trump Castle Associates (Atlantic City), the Plaza Hotel (New York), Trump Hotels and Casino Resorts (the publicly traded casino company), and Trump Entertainment Resorts (a later iteration of his casino holdings) — filings that span the early 1990s through a final wave in 2009 ^{[3] [1] [4]}.

2. The alternate accounting that yields “four” bankruptcies

Fact-checking outlets and political summaries often report “four” Chapter 11 bankruptcies because they treat multiple corporate filings as part of the same restructuring or focus only on the major consolidated corporate bankruptcies (not every subsidiary case) — for example, PolitiFact and related summaries attribute four Chapter 11 reorganizations to Trump’s casino operations (noting the Taj Mahal in 1991, Trump Plaza in 1992, Trump Hotels and Casino Resorts in 2004, and Trump Entertainment Resorts in 2009) and explicitly differentiate business filings from personal bankruptcy ^{[2] [5]}. This methodological difference — whether to count each subsidiary case or only the headline corporate reorganizations — explains the gap between “four” and “six” in public statements and campaign messaging ^{[2] [1]}.

3. The timeline and context of the filings

The bulk of the distressed filings date to the early 1990s when several Atlantic City properties — financed with heavy, high-interest debt — restructured under Chapter 11 amid a downturn in gaming and broader economic pressures, and later corporate entities of Trump’s casino business filed again in the 2000s as debt burdens resurfaced; a final federally filed proceeding tied to Trump’s casino interests culminated in 2009 ^{[3] [1] [4]}. Multiple sources emphasize that these were corporate reorganizations: the businesses remained operating during court-supervised restructurings rather than being liquidated under Chapter 7 ^{[4] [1]}.

4. What Chapter 11 meant in practice for Trump and his creditors

Legal and reporting accounts underline that Chapter 11 is a reorganization tool that lets companies renegotiate debt and continue operations — and that Trump himself avoided personal bankruptcy while his equity stakes and control were often diluted through restructurings, asset sales, or concessions to bondholders and lenders ^{[4] [6]}. Analysts and fact-checkers note this is a common corporate strategy and that the public debate often conflates political rhetoric with the technical legal reality: Trump’s name and brand survived even as ownership and financial arrangements were altered in court-supervised reorganizations ^{[2] [6]}.

5. Why the count matters politically and for accurate reporting

Counting “four” versus “six” bankruptcies has become shorthand in political messaging; campaign actors and opponents lean on whichever figure best serves their narrative, while legal sources and bankruptcy experts focus on docket-level detail and consolidated cases ^{[5] [7]}. Reporting that cites four filings generally references consolidated headline reorganizations and aims to distinguish corporate rescue from personal financial failure, whereas sources that list six are cataloging each subsidiary or related entity that formally entered Chapter 11 ^{[1] [3]}.

Conclusion

The verifiable core: Donald Trump himself has not filed personal bankruptcy, but his companies—primarily casino and hotel operations—used Chapter 11 multiple times between 1991 and 2009; authoritative summaries count six distinct Trump-linked corporate filings when subsidiary cases are enumerated, while prominent fact-checkers and political summaries often report four headline reorganizations depending on their counting method ^{[1] [2] [3]}.