This revelation comes after a yearslong audit and examination of public filings related to Trump's tax losses linked to a Chicago skyscraper.

The findings of the report have the potential to cast a renewed spotlight on Trump's business career as he seeks to make a comeback and regain the White House following his defeat in the 2020 election. While Trump capitalized on his status as a real estate developer and television personality to build a political movement, he has steadfastly refused to release his tax filings, a move that has raised questions among past presidential candidates.

Details revealed from past reporting by the Times and the public release of records by Democrats on the House Ways and Means Committee in 2022 shed light on Trump's tax filings. The records indicate that Trump claimed tax deductions twice for losses incurred by the Trump International Hotel and Tower in Chicago, which opened its doors in 2009 along the city's downtown area near the banks of the Chicago River.

According to the report, Trump initially declared losses of $658 million in his 2008 tax filings, citing the underperformance of condominium sales and unoccupied retail space due to the deep U.S. recession at the time. However, in a move to save on taxes, the report reveals that in 2010, Trump transferred ownership of the property to another holding company under his control. This allowed him to report an additional $168 million in losses over the following decade for the same property.

The report does not provide updated information on the current status of the IRS inquiry but suggests that if Trump were to lose the battle against the audit, he could potentially owe more than $100 million, including penalties. Trump's camp, represented by a statement from his son Eric Trump, asserts that the IRS inquiry was resolved years ago and attributes its revival to his father's political pursuits.

In addition to the IRS audit, Trump is currently appealing a ruling from a New York judge in February which stated that he, his company, and top executives had misled financial institutions and insurers about his wealth on various financial statements. Consequently, Trump had to post a $175 million bond in early April to halt collection of the more than $454 million he owes according to the judgment. This move also prevents the state from seizing his assets while he appeals the ruling.

President Joe Biden has been critical of Trump's tax practices and has emphasized the need for wealthy individuals to pay their fair share. His administration has allocated increased funding to the IRS to enhance tax compliance and audits of the ultra-wealthy. However, the Trump campaign opposes this additional funding, with Trump himself highlighting the importance of extending his 2017 tax cuts to prevent the potential destruction of the United States.

The developments surrounding the IRS audit and ongoing legal battles are sure to keep Trump's financial matters in the forefront as he navigates his political ambitions. The potential outcome of the audit and its implications for Trump's financial standing remain to be seen.