Strategic Chapter 11 corporate bankruptcies: Between 1991 and 2009, Trump’s companies filed for Chapter 11 bankruptcy protection six times (mostly involving Atlantic City casinos). By exploiting loopholes in corporate restructuring laws, he largely protected his personal wealth while shifting large losses to banks, bondholders, and contractors, all while keeping his name on the buildings.
The net operating loss tax loophole: As revealed by his own tax disclosures, Trump reported a staggering $916 million loss on his 1995 tax returns. Exploiting tax codes regarding net operating losses (NOL), this massive single-year business loss allowed him to legally avoid paying any federal income taxes for up to 18 subsequent years. Similarly, those tax returns reveal that Trump and his family minimized their estate taxes by transferring wealth through various legal structures, such as setting up a family-controlled contracting firm to divert profits from the Trump Organization.
Emoluments Clause ambiguity: During his presidency, Trump retained ownership of his many businesses. While the Constitution’s Emoluments Clauses forbid a president from taking gifts or profits from foreign or domestic states, the lack of a clear statutory definition or enforcement mechanism allows his businesses to legally do business with foreign governments in spades.
