Donald Trump declared a $916m (£706m) loss on his 1995 income tax returns, which may have allowed him to avoid paying federal income taxes for up to 18 years, according to a report.
The New York Times said it had obtained the Republican presidential nominee's 1995 tax records and that they showed he received the large tax benefits from financial deals that went wrong in the early 1990s.
Tax experts hired by the newspaper to analyse the records said tax rules which are advantageous to wealthy filers would have let Mr Trump use his $916m loss to cancel out an equivalent amount of taxable income over an 18-year period.
The Times said that although Mr Trump's taxable income in subsequent years is as yet unknown, the loss would have been large enough to wipe out more than $50m (£38m) a year in taxable income over 18 years.
Responding to the story, the Trump campaign said the tax document was illegally obtained and claimed the paper was operating as an extension of Democratic rival Hillary Clinton's campaign.
"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."Hillary for America Campaign Manager Robby Mook said: "There it is. This bombshell report reveals the colossal nature of Donald Trump's past business failures and just how long he may have avoided paying any federal income taxes whatsoever.
"In one year, Donald Trump lost nearly a billion dollars. A billion. He stiffed small businesses, laid off workers, and walked away from hardworking communities.
"And how did it work out for him? He apparently got to avoid paying taxes for nearly two decades - while tens of millions of working families paid theirs.
"He calls that 'smart.' Now that the gig is up, why doesn't he go ahead and release his returns to show us all how 'smart' he really is?"
Mr Trump has so far declined to release his tax records, saying his taxes are under a federal audit.
Despite this, experts say he could still release them publicly if he wanted to.
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