The New York Times says Donald Trump avoided paying potentially hundreds of millions of dollars in taxes in a way even his own lawyers considered questionable. The newspaper says the maneuver may explain how Trump posted a one-year loss of more than $900 million in 1995, enabling him to avoid paying federal income taxes on as much as $50 million a year for 18 years.
At issue is how Trump canceled hundreds of millions of dollars of debt as his Atlantic City casinos went broke. The Times says it obtained documents showing that Trump claimed his creditors’ losses as his own, a strategy that his lawyers said the IRS would likely not allow. Congress later explicitly banned the maneuver in 2004. Trump spokeswoman Hope Hicks said Trump’s approach was appropriate.