How many times has Donald Trump or his businesses filed for bankruptcy and what were the outcomes?
Executive summary
Donald Trump’s corporate empire has been through multiple Chapter 11 restructurings; legal and industry sources disagree on whether to count four distinct “bankruptcies” tied directly to Trump or up to six filings by affiliated companies, but all agree these were business reorganizations (not personal bankruptcies) that ended with debt restructurings, asset concessions and, in some cases, closures [1] [2] [3]. The dispute over “four vs. six” reflects different counting methods—whether one counts only the primary, widely cited filings or every affiliated corporate filing consolidated in later proceedings [1] [2].
1. The commonly cited four: the headline narrative and its basis
Many mainstream and legal summaries list four Chapter 11 bankruptcies widely associated with Trump’s casino business: Trump Taj Mahal , Trump Plaza Hotel , Trump Hotels & Casino Resorts , and Trump Entertainment Resorts ; each was a Chapter 11 corporate reorganization rather than a personal bankruptcy for Donald Trump [1] [4]. These four events are the ones most often referenced in campaign attack lines and fact checks because they were major, publicly reported reorganizations of high-profile, brand-name properties [4] [1].
2. The larger count of six: how counting changes the story
Other timelines and legal analyses count as many as six corporate bankruptcies linked to Trump by including additional affiliated filings and later reorganizations—examples include separate Chapter 11 cases for Trump Castle/Trump Castle Associates and a 2014 filing by TERH LP, Inc./Trump Entertainment Resorts that led to additional closures such as the shuttering of Trump Plaza [3] [2]. These more granular counts treat each legal entity’s bankruptcy case as a separate “filing,” which produces the higher total often cited by critics and some legal timelines [2] [3].
3. What “filed” actually meant: Chapter 11 outcomes in plain terms
Every disputed filing referenced in the record was a Chapter 11 business reorganization that allowed companies to renegotiate debt, convert obligations to equity, or hand over stakes to lenders while continuing operations in some form; for example, reorganizations resulted in Trump relinquishing large ownership stakes (such as in the Plaza) or giving up equity in casinos, and in at least one case closing an asset later on [4] [3]. Chapter 11’s practical outcomes ranged from refinancing and reduced debt burdens to forced equity concessions, delisting and share-value collapses for outside shareholders [5] [3].
4. The personal angle: Trump himself was not personally bankrupt
Across the sources, a clear factual line is that these were corporate Chapter 11 proceedings for affiliated companies, not personal Chapter 7 or 13 filings by Donald Trump himself; commentators and lawyers have emphasized that Trump used corporate structures to isolate personal liability while permitting businesses to restructure [6] [7]. That distinction is central to defenders’ arguments that he “used the law” rather than admitting personal insolvency, and critics counter that the restructurings shifted costs onto creditors, bondholders and some employees or shareholders [6] [8].
5. Why the count matters: politics, messaging and legal nuance
Campaign material and partisan press have incentives to pick the lower or higher count: supporters cite four to downplay scale and frame the filings as standard corporate strategy, while opponents cite six (or emphasize repeated filings) to portray a pattern of risky leverage and harm to creditors and workers; both frames rely on the same court records but apply different rules for what constitutes a separate “bankruptcy” [4] [2]. Legal observers and bankruptcy professionals stress that the accurate technical description is “multiple Chapter 11 reorganizations by Trump-linked companies,” and note that outcomes varied—some assets survived under restructured debt, some were sold or closed, and shareholders and some creditors lost value [1] [3] [5].
6. Bottom line — a precise answer grounded in the reporting
Depending on how one counts discrete corporate Chapter 11 cases, Trump-linked businesses filed for bankruptcy four times in the four-major-filings account commonly used in political debate, or up to six times when counting additional affiliated entity filings and later reorganizations; in all cases the filings were Chapter 11 corporate reorganizations that reorganized debt, cost Trump equity or control in properties, and in at least one instance culminated in closures—while Donald Trump himself did not file for personal bankruptcy [1] [2] [3] [6].