What were the years and circumstances of each Trump casino Chapter 11 filing?
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Executive summary
Donald Trump’s casino companies sought Chapter 11 protection in multiple waves: the early 1990s (after the costly build-out of Atlantic City properties), a wholesale corporate restructuring in 2004, another collapse amid the 2008 financial crisis in 2009, and a later filing connected to the continued decline of Trump-branded Atlantic City properties in 2014 — though reporting differs on how to count discrete “filings” and corporate entities involved [1] [2] [3] [4].
1. 1991 — The Taj Mahal’s lavish launch and the first Chapter 11
The first major casino-related Chapter 11 tied to Donald Trump came after the $1‑billion construction of the Trump Taj Mahal left the property overleveraged and unable to service its high-interest junk‑bond financing, prompting a Chapter 11 restructuring in 1991 that reflected the broader weakness of Atlantic City and the burden of the Taj’s capital structure [1] [5].
2. 1992 — Trump Castle and the domino effect across Atlantic City properties
Within a year, other Trump casino affiliates followed into Chapter 11 as the Taj’s problems rippled through highly leveraged holdings; Trump Castle (later renamed) entered a prepackaged Chapter 11 in March 1992 and the Plaza/related hotel debts also triggered restructurings in that period as Trump surrendered equity and liquidated personal assets to help stabilize operations [4] [6] [7].
3. 2004 — Corporate reorganization of Trump Hotels & Casino Resorts
In late 2004, Trump Hotels & Casino Resorts — the publicly traded corporate vehicle that had consolidated many of the casino assets — filed for Chapter 11 to implement a negotiated debt‑restructuring after bondholder negotiations failed and a preliminary agreement required drastic dilution of Trump’s equity; the filing was used as a mechanism to reduce Trump’s majority stake from roughly 56% to about 27% and to implement the agreed plan (filed November 21, 2004) [1] [2].
4. 2009 — The recession, missed interest payments, and a defensive filing
Hit hard by the 2008 economic crash and a missed $53.1 million bond interest payment, Trump Entertainment Resorts and affiliated debtors filed Chapter 11 in February 2009 while facing the prospect of involuntary bankruptcy actions by bondholders; court filings show the company entered court after creditors tightened pressure and the group negotiated competing reorganization proposals amid roughly $1.2–$1.74 billion in reported liabilities [3] [8] [1].
5. 2014 (and counting) — Continued decline, a later Trump Entertainment Resorts filing, and why counts differ
Some reporting and corporate histories record an additional 2014 Chapter 11 for Trump Entertainment Resorts or its predecessors tied to continued losses and the closure of Trump Plaza, with the company exiting in 2016 under new ownership, which produces a narrative that the casino group went through multiple court episodes beyond the four widely cited cases; different sources count “four” corporate Chapter 11s while others list 1991, 2004, 2009 and 2014 — the divergence stems from whether separate affiliate filings, successor entities and the 1992 hotel/castle cases are aggregated or treated as distinct matters [1] [2] [4].
6. Context, common ground, and the limits of the record
Across sources there is consensus that these were corporate reorganizations — not personal bankruptcies for Donald Trump himself — and that high leverage, junk‑bond financing, the changing Atlantic City market, and the 2008 recession were recurring causes; however, counting “how many” bankruptcies depends on whether one tallies each entity’s petition, consolidated cases, or the later successor filings, which explains why PolitiFact and ABI list four Chapter 11 events while Wikipedia and some legal histories emphasize filings in 2014 as well [9] [2] [1] [4]. The documentary record in bankruptcy dockets (cited by academic and legal summaries) provides precise filing dates and case numbers, but public narratives often simplify multiple related corporate petitions into a shorter list for emphasis [10] [4].
7. Bottom line
The clearest, commonly cited timeline ties Trump’s casino Chapter 11s to the years 1991 (Taj Mahal), 1992 (Trump Castle/related Atlantic City holdings), 2004 (Trump Hotels & Casino Resorts corporate restructuring), and 2009 (Trump Entertainment Resorts amid the post‑2008 downturn), with an additional 2014 TER filing appearing in some corporate histories; the differences across sources reflect how reporters and analysts group affiliate filings and successor entities rather than a dispute over the underlying financial distress documented in court filings [1] [2] [3] [4].