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Manhattan and Chicago developments

Trump attracted public attention in 1978 with the launch of his family's first Manhattan venture, the renovation of the derelict Commodore Hotel, adjacent to Grand Central Terminal. The financing was facilitated by a $400 million city property tax abatement arranged for Trump by his father who also, jointly with Hyatt, guaranteed a $70 million bank construction loan. The hotel reopened in 1980 as the Grand Hyatt Hotel, and that same year, Trump obtained rights to develop Trump Tower, a mixed-use skyscraper in Midtown Manhattan. The building houses the headquarters of the Trump Corporation and Trump's PAC and was Trump's primary residence until 2019.

In 1988, Trump acquired the Plaza Hotel with a loan from a consortium of sixteen banks. The hotel filed for bankruptcy protection in 1992, and a reorganization plan was approved a month later, with the banks taking control of the property. In 1995, Trump defaulted on over $3 billion of bank loans, and the lenders seized the Plaza Hotel along with most of his other properties in a "vast and humiliating restructuring" that allowed Trump to avoid personal bankruptcy. The lead bank's attorney said of the banks' decision that they "all agreed that he'd be better alive than dead."

In 1996, Trump acquired and renovated the mostly vacant 71-story skyscraper at 40 Wall Street, later rebranded as the Trump Building. In the early 1990s, Trump won the right to develop a 70-acre (28 ha) tract in the Lincoln Square neighborhood near the Hudson River. Struggling with debt from other ventures in 1994, Trump sold most of his interest in the project to Asian investors, who financed the project's completion, Riverside South.

Trump's last major construction project was the 92-story mixed-use Trump International Hotel and Tower (Chicago) which opened in 2008. In 2024, the New York Times and ProPublica reported that the Internal Revenue Service was investigating whether Trump had twice written off losses incurred through construction cost overruns and lagging sales of residential units in the building Trump had declared tto be worthless on his 2008 tax return.