The Trump campaign, in a statement responding to the Times report, said that the tax document was obtained illegally and that the New York Times is operating as an extension of the presidential campaign of Democratic rival Hillary Clinton.
The Times said it had obtained Trump's 1995 tax records and that they showed he received the large tax benefits from financial deals that went bad in the early 1990s.
The newspaper said that tax experts it hired to analyse Trump's records said tax rules which are especially advantageous to wealthy filers would have let Trump use his $916 million loss to cancel out an equivalent amount of taxable income over an 18-year period.
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The Times said that although Trump's taxable income in subsequent years is as yet unknown, a $916 million loss in 1995 would have been large enough to wipe out more than $50 million a year in taxable income over 18 years.
Trump has declined to release his tax records, unlike previous presidential nominees in modern history, saying his taxes are under a federal audit. Experts say he could still release them publicly if he wished.
"Mr. Trump is a highly-skilled businessman who has a fiduciary responsibility to his business, his family and his employees to pay no more tax than legally required," the Trump campaign statement said.
"That being said, Mr. Trump has paid hundreds of millions of dollars in property taxes, sales and excise taxes, real estate taxes, city taxes, state taxes, employee taxes and federal taxes, along with very substantial charitable contributions," it said.
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