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IRS Audit of Trump Could Cost More Than $100 Million

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May 11, 2024

Pro Publica and New York Times

Former President Donald Trump used a dubious accounting maneuver to claim improper tax breaks from his troubled Chicago tower, according to an IRS inquiry uncovered by ProPublica and The New York Times. Losing a yearslong audit battle over the claim could mean a tax bill of more than $100 million.

The 92-story, glass-sheathed skyscraper along the Chicago River is the tallest and, at least for now, the last major construction project by Trump. Through a combination of cost overruns and the bad luck of opening in the teeth of the Great Recession, it was also a vast money loser.

But when Trump sought to reap tax benefits from his losses, the IRS has argued, he went too far and in effect wrote off the same losses twice.

The first write-off came on Trump’s tax return for 2008. With sales lagging far behind projections, he claimed that his investment in the condo-hotel tower met the tax code definition of “worthless,” because his debt on the project meant he would never see a profit. That move resulted in Trump reporting losses as high as $651 million for the year, ProPublica and the Times found.

There is no indication the IRS challenged that initial claim, though that lack of scrutiny surprised tax experts consulted for this article. But in 2010, Trump and his tax advisers sought to extract further benefits from the Chicago project, executing a maneuver that would draw years of inquiry from the IRS. First, he shifted the company that owned the tower into a new partnership. Because he controlled both companies, it was like moving coins from one pocket to another. Then he used the shift as justification to declare $168 million in additional losses over the next decade.

The issues around Trump’s case were novel enough that, during his presidency, the IRS undertook a high-level legal review before pursuing it. ProPublica and the Times, in consultation with tax experts, calculated that the revision sought by the IRS would create a new tax bill of more than $100 million, plus interest and potential penalties.

An IRS spokesperson said federal law prohibited the agency from discussing private taxpayer information.

The audit represents yet another potential financial threat — albeit a more distant one — for Trump, the Republicans’ presumptive 2024 presidential nominee. In recent months, he has been ordered to pay $83.3 million in a defamation case and an additional $454 million in a civil fraud case brought by the New York attorney general, Letitia James. Trump has appealed both judgments.