Donald Trump may face a $100 million-plus tax bill if he loses IRS audit fight over Chicago tower: report

Donald Trump faces potential $100 million IRS bill for alleged tax scheme involving Chicago skyscraper, per NYT report.

Former U.S. president Donald Trump may face an IRS bill in excess of $100 million after a government audit indicates he double-dipped on tax losses tied to a Chicago skyscraper, according to a report by The New York Times and ProPublica that drew on a yearslong audit and public filings.

The report’s findings could put renewed focus on Mr. Trump’s business career as the presumptive Republican nominee tries to regain the White House after losing in 2020.

Mr. Trump used his cachet as a real estate developer and TV star to build a political movement, yet he has refused to release his tax filings as past presidential candidates have. The tax filings that the public does know about have come from past reporting by the Times and a public release of records by Democrats on the House Ways and Means Committee in 2022.

Mr. Trump’s presidential campaign provided a statement in son Eric Trump’s name saying the IRS inquiry “was settled years ago, only to be brought back to life once my father ran for office. We are confident in our position”. The tax records cited by the report indicate that Mr. Trump twice deducted losses on the Trump International Hotel and Tower, which opened in 2009 near the banks of the Chicago River that cuts through that city’s downtown.

The report said Mr. Trump initially reported losses of $658 million in his 2008 filings under the premise that the property fit the IRS definition of being “worthless” because condominium sales were disappointing and retail space went unfilled amid a deep U.S. recession.

But in 2010, the published report said, Mr. Trump transferred the ownership of the property to a different holding company that he also controlled, using the move to save money on taxes by reporting an additional $168 million in losses over the next decade on the same property.

The report did not have any updates on the status of the IRS inquiry since December 2022, but said Mr. Trump could owe more than $100 million, including penalties, if he were to lose the audit battle.