Former President Trump faces a potential tax bill exceeding $100 million as the I.R.S. investigates his questionable tax breaks from the Chicago tower. The investigation revealed that Trump's maneuver of claiming losses twice through improper deductions may result in significant financial consequences.
Trump's initial move in 2008 to declare his investment in the Chicago tower as worthless, resulting in reported losses of up to $651 million for the year, is being scrutinized by the I.R.S. for potential double write-offs.
In 2010, Trump attempted to extract further tax benefits by shifting ownership of the tower, which the I.R.S. is investigating. The maneuver involving declaring additional losses totaling $168 million over the next decade raised eyebrows and triggered prolonged scrutiny.
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