Donald Trump double-dipped on tax breaks stemming from losses on his Chicago skyscraper, an ill-conceived move now sending him further into the hole.
Per ProPublica and New York Times reporting on an Internal Revenue Service inquiry, Trump International Hotel and Tower, completed in 2009, opened amidst economic downturn and led to massive losses for Trump. But he engaged in accounting maneuvers to effectively double the tax benefits stemming from those losses, the report says.
Trump allegedly wrote off the losses once, then transferred the building’s holding company into a new entity, declaring $168 million more in losses through the new company. The move sparked IRS interest, with a legal probe into the move beginning during his presidency.
Per ProPublica and the New York Times, Trump could owe more than $100 million to the IRS for the evasive move, though they note that IRS actions in investigating and collecting on the sum have been unclear since 2022.
In a statement from Eric Trump, the former President’s son and Trump Organization executive, the organization denies all wrongdoing.
“This matter was settled years ago, only to be brought back to life once my father ran for office,” Eric Trump said. “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, who has a history of tax mishaps and underpayment, paid no federal taxes at all for a decade leading up to his presidency.
The tax bill, with potential penalties, could add to Trump’s mounting financial challenges, including a nearly half a billion dollar fine stemming from other Trump Organization valuation fraud in New York.
