Donald Trump Used Legally Dubious Method to Avoid Paying Taxes.
Moreover, the tax experts said the maneuver tramplAs that empire floundered in the early 1990s, Mr. Trump pressured his financial backers to forgive hundreds of millions of dollars in debt he could not repay. While the cancellation of so much debt gave new life to Mr. Trump’s casinos, it created a potentially crippling problem with the Internal Revenue Service. In the eyes of the I.R.S., a dollar of canceled debt is the same as a dollar of taxable income. This meant Mr. Trump faced the painful prospect of having to report the hundreds of millions of dollars of canceled debt as if it were hundreds of millions of dollars of taxable income.
But Mr. Trump’s audacious tax-avoidance maneuver gave him a way to simply avoid reporting any of that canceled debt to the I.R.S. “He’s getting something for absolutely nothing,” John L. Buckley, who served as the chief of staff for Congress’s Joint Committee on Taxation in 1993 and 1994, said in an interview.
The new documents, which include correspondence from Mr. Trump’s tax lawyers and bond offering disclosure statements, might also help explain how Mr. Trump reported a staggering loss of $916 million in his 1995 tax returns, portions of which were first published by The Times last month.United States tax laws allowed Mr. Trump to use that $916 million loss to cancel out an equivalent amount of taxable income. But tax experts have been debating how Mr. Trump could have legally declared a deduction of that magnitude at all. Among other things, they have noted that Mr. Trump’s huge casino losses should have been offset by the hundreds of millions of dollars in taxable income he surely must have reported to the I.R.S. in the form of canceled casino debt.
By avoiding reporting his canceled casino debt in the first place, however, Mr. Trump’s $916 million deduction would not have been reduced by hundreds of millions of dollars. He could have preserved the deduction and used it instead to avoid paying income taxes he might otherwise have owed on books, TV shows or branding deals. Under the rules in effect in 1995, the $916 million loss could have been used to wipe out more than $50 million a year in taxable income for 18 years.
Mr. Trump declined to comment for this article.
“Your email suggests either a fundamental misunderstanding or an intentional misreading of the law,” Hope Hicks, Mr. Trump’s spokeswoman, said in a statement. “Your thesis is a criticism, not just of Mr. Trump, but of all taxpayers who take the time and spend the money to try to comply with the dizzyingly complex and ambiguous tax laws without paying more tax than they owe. Mr. Trump does not think that taxpayers should file returns that resolve all doubt in favor of the I.R.S. And any tax experts that you have consulted are engaged in pure speculation. There is no news here.”
Mr. Trump financed his three Atlantic City gambling resorts with $1.3 billion in debt, most of it in the form of high interest junk bonds. By late 1990, after months of escalating operating losses, New Jersey casino regulators were warning that “a complete financial collapse of the Trump Organization was not out of the question.” By 1992, all three casinos had filed for bankruptcy, and bondholders were ultimately forced to forgive hundreds of millions of dollars in debt to salvage at least part of their investment.
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