According to the report, Trump made significant financial loss claims twice related to the Chicago tower. The first instance occurred on his 2008 tax return, where he stated that the building, burdened with debt at the time, was essentially "worthless." Despite reporting losses as high as $651 million that year, there is no indication that the IRS challenged these claims.

Trump's lawyers provided further opportunities to claim losses in 2010 by shifting the ownership of the Chicago tower into a new partnership called "DJT Holdings LLC," which Trump also controlled. Subsequently, other Trump businesses, such as golf courses, were incorporated into the same partnership, enabling his legal team to assert additional tax-reducing losses tied to the Chicago tower. This move triggered the IRS inquiry.

Over the next decade, these claimed losses on the Chicago tower amounted to a staggering $168 million, according to the investigation. As a result, the IRS is seeking a revision that could potentially result in a tax bill exceeding $100 million for Trump.

The IRS audit into Trump's claims of losses for the Chicago tower was not publicly acknowledged until a December 2022 congressional report. The report made an enigmatic reference to the specific section of tax law under scrutiny in the case, confirming that the audit was still ongoing.

Responding to the revelations, Eric Trump, the executive vice president of the Trump Organization, released a statement to The Times and ProPublica, saying, "This matter was settled years ago, only to be brought back to life once my father ran for office. We are confident in our position, which is supported by opinion letters from various tax experts, including the former general counsel of the IRS."

The potential tax liability stemming from the IRS inquiry adds a significant financial burden to the list of legal challenges faced by the former president. The investigation sheds light on the complex strategies employed by Trump and his legal team to reduce tax bills, emphasizing the ongoing efforts by authorities to scrutinize the financial practices of public figures.