In 1988, Trump purchased the unfinished Taj Mahal property from Resorts International for $230 million after negotiations with Merv Griffin in which the two men divided the assets of the failing company.

Trump completed the project using junk bonds, a decision that hurt the company afterward as the gaming industry struggled in a recession and interest rates became unmanageable.

[5][6] The company was shaken by the deaths of three key executives in an October 10, 1989 helicopter crash in northern New Jersey while they were returning from a New York press conference promoting an upcoming Atlantic City boxing event.

[15] The bid was ultimately dropped from consideration because of Mayor Dennis Archer's doubts about the company's financial condition.

According to a report by Newsweek, the consulting firm Seven Arrows Investment and Development instructed THCR on how to evade the embargo by linking the money to a charitable effort.

In 2004, Trump Hotels & Casino Resorts explored various options for restructuring its debt, amid speculation that it might file for bankruptcy.

On October 27, the company announced that Morgan Stanley would be the joint lead arranger for a $500 million financing as part of the restructuring plan.

[26] In 2007, the company attempted to negotiate a buyout with several public and private firms, but on July 2, it announced that it could not reach a deal, and would take itself off the market.

The bankruptcy court eventually sided with the Trump/Avenue partnership, favored by bond holders who believed that Trump's brand would result in a stronger company after reorganization.

[32] In 2011, TER sold the Trump Marina to Landry's Restaurants, which also operates the Golden Nugget in Las Vegas.

[39] On a motion made by union UNITE HERE Local 54,[40] relating to the bankruptcy action, the United States Court of Appeals for the Third Circuit ruled in Trump Entertainment's favor on January 15, 2016, and held that Trump Entertainment could reject the continuing terms and conditions of a collective bargaining agreement with the union, an agreement that had already expired by its terms.

On December 14, 2018, the deadline for demolishing it officially passed, meaning Trump Plaza would remain standing through the winter.

[46] Later that month, Icahn terminated the deed restriction on the property and bought out a complicated lease, making a sale more attractive.

The building was declared a hazard by the city in March 2020;[47] demolition began that summer, and the main hotel tower was imploded on February 17, 2021.