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News organizations have reported that Trump claimed huge financial losses twice — first on his 2008 tax return, when he said the debt-ridden building was “worthless,” and again in 2010, when he also transferred ownership of it to a new partnership controlled by Trump.
The 2008 claim led Trump to report losses of up to $981 million for the year and there is no indication that it has prompted an IRS challenge, the sources said.
Trump’s lawyers then allowed additional claims for losses in 2010 by transferring the Chicago tower to another partnership, DJT Holdings LLC, The Times and ProPublica reported.
In the coming years, other Trump businesses, including golf courses, would be transferred to the same partnership — which his lawyers are using as a basis to claim more tax-cut losses from the Chicago tower.
The move sparked an IRS investigation. Those losses totaled $253 million over the next decade, the report said.
The outlets estimated that the revision requested by the IRS could result in a tax bill of more than $150 million.
The only public mention of an IRS audit of Trump’s Chicago Tower loss claims came in a December 2022 congressional report that The times and ProPublica reported that they made an unexplained reference to the section of tax law at issue in the case.
That mention, the outlets reported, confirms that the audit is still ongoing.
“This issue was settled years ago, only to be brought back to life after 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,” said Trump’s son Eric Trump, executive vice president of the Trump Organization The times and ProPublica in a statement.
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