Trump’s long-running IRS audit reportedly centers on whether he claimed the same massive Chicago tower losses twice to wipe out taxes.
ProPublica and The New York Times report that the IRS concluded Donald Trump improperly used accounting maneuvers tied to his Chicago hotel and condo tower to generate enormous tax write-offs over multiple years. According to the investigation, Trump first claimed the project was effectively “worthless” in 2008, producing losses that may have reached $651 million.
The dispute centers on what happened next. In 2010, Trump reportedly shifted ownership of the struggling tower into another partnership he also controlled, then claimed an additional $168 million in losses over the following decade. The IRS later argued the maneuver violated rules designed to stop taxpayers from double-dipping on losses. If the agency prevails, the resulting tax bill, penalties and interest could top $100 million.
“I think he ripped off the tax system,” University of Baltimore law professor Walter Schwidetzky told the outlets. Tax experts interviewed for the story reportedly described the accounting strategy as highly aggressive and unlikely to survive scrutiny. The investigation also notes the IRS issued a rare Technical Advice Memorandum during Trump’s presidency to analyze the legality of the transaction.
Eric Trump pushed back on the reporting, saying the matter “was settled years ago” and revived only after his father entered politics. The IRS declined comment because of federal taxpayer privacy laws. Meanwhile, the audit appears to still be unresolved years later, showing once again how slowly massive, complex tax fights move through the system—especially when billionaires and armies of lawyers are involved.
Source: ProPublica investigation
Editor: Somewhere, an average American getting audited over a missing $600 Venmo form is probably wondering why this saga needs a geological time scale to resolve.