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Trump’s Legal Troubles * Case Tracker * Hush-Money Trial * Fact-Checking Trump’s Defenses * What if Trump Is Convicted? * Trump on Trial Newsletter The I.R.S. believes that former President Donald J. Trump violated a law meant to prevent double-dipping on tax-reducing losses.Credit...Jamie Kelter Davis for The New York Times Skip to contentSkip to site indexSearch & Section NavigationSection Navigation TRUMP MAY OWE $100 MILLION FROM DOUBLE-DIP TAX BREAKS, AUDIT SHOWS A previously unknown focus of an I.R.S. audit is a dubious accounting maneuver that effectively meant taking the same write-offs twice on a Chicago skyscraper. The I.R.S. believes that former President Donald J. Trump violated a law meant to prevent double-dipping on tax-reducing losses.Credit...Jamie Kelter Davis for The New York Times Supported by SKIP ADVERTISEMENT * Share full article * * * 1.5k * Read in app By Russ Buettner and Paul Kiel This article was published in partnership with ProPublica. Russ Buettner of The New York Times has spent years reporting on the former president’s finances, including decades of his tax returns. Paul Kiel of ProPublica has reported on the I.R.S. and the ways the ultrawealthy avoid taxes since 2018. * May 11, 2024Updated 4:37 p.m. ET Former President Donald J. Trump used a dubious accounting maneuver to claim improper tax breaks from his troubled Chicago tower, according to an Internal Revenue Service inquiry uncovered by The New York Times and ProPublica. Losing a yearslong audit battle over the claim could mean a tax bill of more than $100 million. LISTEN TO THIS ARTICLE, READ BY ERIC JASON MARTIN Listen 21:35 The 92-story, glass-sheathed skyscraper along the Chicago River is the tallest and, at least for now, the last major construction project by Mr. 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 Mr. Trump sought to reap tax benefits from his losses, the I.R.S. has argued, he went too far and in effect wrote off the same losses twice. Advertisement SKIP ADVERTISEMENT The first write-off came on Mr. 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 Mr. Trump reporting losses as high as $651 million for the year, The Times and ProPublica found. There is no indication the I.R.S. challenged that initial claim, though that lack of scrutiny surprised tax experts consulted for this article. But in 2010, Mr. 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 I.R.S. 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. Subscribe to The Times to read as many articles as you like. Russ Buettner is an investigative reporter. Since 2016, his reporting has focused on the finances of Donald. J. Trump, including articles that revealed tax avoidance schemes evidenced on several decades of his tax returns. In 2019, he shared a Pulitzer Prize for work that revealed the vast inheritance Mr. Trump had received from his father. More about Russ Buettner A version of this article appears in print on May 12, 2024 of the New York edition with the headline: Audit of Trump Zeroes In On Disputed Accounting. Order Reprints | Today’s Paper | Subscribe See more on: Donald Trump, U.S. Politics * Share full article * * * 1.5k * Read in app Advertisement SKIP ADVERTISEMENT COMMENTS 1469 Trump May Owe $100 Million From Double-Dip Tax Breaks, Audit ShowsSkip to Comments Share your thoughts. The Times needs your voice. We welcome your on-topic commentary, criticism and expertise. Comments are moderated for civility. SITE INDEX SITE INFORMATION NAVIGATION * © 2024 The New York Times Company * NYTCo * Contact Us * Accessibility * Work with us * Advertise * T Brand Studio * Your Ad Choices * Privacy Policy * Terms of Service * Terms of Sale * Site Map * Canada * International * Help * Subscriptions Enjoy unlimited access to all of The Times. See subscription options