Audit: Trump may owe $100 million from double-dip tax breaks

Former U.S. President and Republican presidential candidate Donald Trump attends a campaign rally Saturday in Wildwood, N.J. (REUTERS/Evelyn Hockstein)

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 The New York Times and ProPublica. 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’s reporting losses as high as $651 million for the year, the Times and ProPublica found.

There is no indication that the IRS challenged that initial claim, although 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. The Times and ProPublica, 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.

Trump’s tax records have been a matter of intense speculation since the 2016 presidential campaign, when he defied decades of precedent and refused to release his returns, citing a long-running audit. A first, partial revelation of the substance of the audit came in 2020, when the Times reported that the IRS was disputing a $72.9 million tax refund that Trump had claimed starting in 2010. That refund, which appeared to be based on Trump’s reporting of vast losses from his long-failing casinos, equaled every dollar of federal income tax he had paid during his first flush of television riches, from 2005 through 2008, plus interest.

The reporting by the Times and ProPublica about the Chicago tower reveals a second component of Trump’s quarrel with the IRS. This account was pieced together from a collection of public documents, including filings from the New York attorney general’s suit against Trump in 2022, a passing reference to the audit in a congressional report that same year and an obscure 2019 IRS memorandum that explored the legitimacy of the accounting maneuver. The memorandum did not identify Trump, but the documents, along with tax records previously obtained by the Times and additional reporting, indicated that the former president was the focus of the inquiry.

In response to questions for this article, Trump’s son Eric, executive vice president of the Trump Organization, said: “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.”

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

Beyond the two episodes under audit, reporting by the Times in recent years has found that, across his business career, Trump, the Republicans’ presumptive 2024 presidential nominee, has often used what experts described as highly aggressive — and at times, legally suspect — accounting maneuvers to avoid paying taxes. To the six tax experts consulted for this article, Trump’s Chicago accounting maneuvers appeared to be questionable and unlikely to withstand scrutiny.

“I think he ripped off the tax system,” said Walter Schwidetzky, a law professor at the University of Baltimore and an expert on partnership taxation.

The worthlessness deduction serves as a way for a taxpayer to benefit from an expected total loss on an investment long before the final results are known.

It occupies a fuzzy and counterintuitive slice of tax law. Three decades ago, a federal appeals court ruled that the judgment of a company’s worthlessness could be based in part on the opinion of its owner. After taking the deduction, the owner can keep the “worthless” company and its assets.

Subsequent court decisions have only partly clarified the rules. Absent prescribed parameters, tax lawyers have been left to handicap the chances that a worthlessness deduction will withstand an IRS challenge.

The tax experts gave the weakest chance of surviving a challenge for a worthlessness deduction based on borrowed money for which the outcome was not clear. It reflects a doubly irrational claim — that the taxpayer deserves a tax benefit for losing someone else’s money even before the money has been lost, and that those anticipated future losses can be used to offset real income from other sources. Most of the debt included in Trump’s worthlessness deduction was based on that risky position.

Including that debt in the deduction was “just not right,” said Monte Jackel, a veteran of the IRS and major accounting firms.

A second bite at the apple

Trump continued to sell units at the Chicago tower, but still below his costs. Had he done nothing, his 2008 worthlessness deduction would have prevented him from claiming that shortfall as losses again. But in 2010, his lawyers attempted an end-run by merging the entity through which he owned the Chicago tower into another partnership, DJT Holdings LLC. In the following years, they piled other businesses into DJT Holdings.

Those changes had no apparent business purpose. But Trump’s tax advisers took the position that pooling the Chicago tower’s finances with other businesses entitled him to declare even more tax-reducing losses from his Chicago investment.

His financial problems there continued. More than 100 of the hotel condominiums never sold.

Sales of all units totaled only $727 million, far below Trump’s budgeted costs of $859 million. And about 70,000 square feet of retail space remained vacant because it had been designed without access to foot or vehicle traffic. From 2011 through 2020, Trump reported $168 million in additional losses from the project.

It’s unclear when the IRS began to question the 2010 merger transaction, but the conflict escalated during Trump’s presidency.

The IRS explained its position in a memorandum, released in 2019, that identified Trump only as “A.” Such memos are reserved for cases where the law is unclear.

The document is dense with footnotes, calculations and references to various statutes, but the core of the IRS’ position is that Trump’s 2010 merger violated a law meant to prevent double dipping on tax-reducing losses. If done properly, the merger would have accounted for the fact that Trump had already written off the full cost of the tower’s construction with his worthlessness deduction.

In the IRS memo, Trump’s lawyers vigorously disagreed with the agency’s conclusions, saying he had followed the law.

The only public sign of the Chicago audit came in December 2022, when a congressional Joint Committee on Taxation report on IRS efforts to audit Trump made an unexplained reference to the section of tax law at issue in the Chicago case.

That the IRS did not initiate an audit of the 2008 worthlessness deduction puzzled the experts in partnership taxation.

“I think the government recognized that they screwed up,” and then audited the merger transaction to make up for it, Jackel said.

The agency’s difficulty in keeping up with Trump’s maneuvers, experts said, showed that this gray area of tax law was too easy to exploit.

“Congress needs to radically change the rules for the worthlessness deduction,” Schwidetzky said.