The IRS may soon come calling to collect an unpaid debt of more than $100 million in back taxes supposedly owed by former President Donald Trump.

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Trump’s financial woes stem from handling the Trump International Hotel and Tower in Chicago, his most recent major construction project. Built-in 2008 amidst the Great Recession, Trump claimed significant losses from the project, utilizing it as a tax write-off. But get this: the self-proclaimed greatest deal maker initially cited the tower as a “worthless” deduction on his tax return in 2008, emphasizing the overwhelming debt load over any potential profit.

However, the investigation revealed that Trump allegedly claimed the same tower as a loss again in 2010 after transferring it to a new partnership, which was still under his control. This move resulted in an additional $168 million in reported losses over the following decade. Huh? Double dipping? Oh, but this guy owes New York State over $400 million after a judge ruled he defrauded New York widely through his real estate. 


Details of Trump’s IRS audit surfaced in 2020, coinciding with the agency’s investigation into a nearly $73 million tax refund from 2010 — the same year as the establishment of the new Chicago tower partnership.

Trump’s son, Eric Trump, the smart one, defended his father’s tax strategies, stating, “This matter was settled years ago, only to be brought back to life once my father ran for office.” He cited support from various tax experts, including the former general counsel of the IRS.

Despite ongoing audit proceedings, last publicly updated in December 2022, Trump may face substantial tax penalties once the process concludes and any appeals are exhausted. This potential nine-figure bill adds to Trump’s mounting legal troubles, including an $83.3 million penalty from a defamation case by writer E. Jean Carroll and the aforementioned $464 million verdict in a civil fraud suit. Bonds have been secured for both cases, which are currently under appeal. Good luck with that.