Trump casinos filed for bankruptcy four times between 1991 and 2014

Donald Trump began acquiring Atlantic City properties in the early 1980s, opening Trump Plaza in 1984, acquiring Trump's Castle (later Trump Marina) in 1985 for $325 million, and building the Trump Taj Mahal — a $1 billion casino that opened in April 1990. Trump Hotels & Casino Resorts (THCR) was formed as a public company in 1995. By the late 1990s, Trump controlled three of Atlantic City's twelve casinos.

The Trump Taj Mahal, financed largely with junk bonds, was in trouble from the start. It filed for Chapter 11 in 1991, unable to service its debt amid the early-1990s recession. Trump personally guaranteed much of the debt and nearly went bankrupt himself. A restructuring with bondholders kept the casino operating and Trump retained a stake, but he was forced to cede some control and sell assets including the Trump Shuttle airline.

THCR filed again for Chapter 11 on November 21, 2004, after bondholders rejected a restructuring deal. Donald Trump's ownership stake was reduced from 56% to 27%. The company renamed itself Trump Entertainment Resorts (TER). In February 2009, TER filed Ch.11 again with $1.2 billion in debt — Beal Bank held $500 million. Carl Icahn partnered with Beal to propose a competing restructuring plan. Trump received 5% stock plus 5% for use of his name.

The fourth bankruptcy came in September 2014. Trump Plaza closed that month and was demolished in 2021. TER became a subsidiary of Icahn Enterprises in February 2016. Trump Taj Mahal closed in October 2016, sold to Hard Rock International and reopened as Hard Rock Atlantic City in June 2018. Trump Marina had been sold to Landry's in 2011 for $38M and became the Golden Nugget. The casino empire that was built on junk bonds and the Trump brand was dissolved under Icahn.