Market Data 
Former President Donald Trump could owe more than $100 million in taxes as a result of a yearslong Internal Revenue Service inquiry into claims of huge losses on his Chicago skyscraper, The New York Times and ProPublica reported Saturday.
The news organizations reported Trump claimed massive financial losses twice — first on his 2008 tax return, when he said the building, then mired in debt, was “worthless,” and again after 2010, when he had shifted its ownership into a new partnership also controlled by Trump.
The 2008 claim resulted in Trump reporting losses as high as $651 million for the year, and there is no indication it drew an IRS challenge, the outlets reported. Then, Trump’s lawyers enabled further claims of losses in 2010 by shifting the Chicago tower into another partnership, “DJT Holdings LLC,” The Times and ProPublica reported.
In the years that followed, other Trump businesses, including golf courses, would be shifted into that same partnership — which his lawyers used as the basis to claim more tax-reducing losses from the Chicago tower. That move sparked the IRS inquiry. Those losses added up to $168 million over the next decade, the report said.
The outlets calculated the revision sought by the IRS could result in a tax bill of more than $100 million.
The only public mention of the IRS audit into Trump’s Chicago tower loss claims came in a December 2022 congressional report that The Times and ProPublica reported made an unexplained reference to the section of tax law at issue in the case. That mention, the outlets reported, confirmed the audit was still underway.
“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,” Trump’s son Eric Trump, the executive vice president of the Trump Organization, told The Times and ProPublica in a statement.
