IRS Challenges Trump's $100 Million Tax Deductions Linked to Chicago Tower

Former President Donald Trump faces a potential $100 million tax bill over controversial deductions from his Chicago real estate project, as IRS audits reveal possible double-dipping.

Trump initially claimed a $651 million loss in 2008, labeling his investment in the Chicago tower as 'worthless' due to significant debt.
In 2010, Trump restructured the company owning the tower, leading to an additional $168 million in claimed losses over the next decade.
IRS scrutiny intensified during Trump's presidency, focusing on a 2010 merger meant to prevent double-dipping on tax reductions.
Tax experts and IRS memos suggest the maneuvers may not withstand legal scrutiny, potentially leading to hefty penalties and back taxes.
The ongoing audit and legal challenges highlight broader issues with tax law enforcement and the need for clearer regulations.