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.
Pictures of Hillary Clinton and Donald Trump on the side of a campaign bus
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."
Brian Fallon, Mrs Clinton's press secretary, wrote on Twitter: "BOMBSHELL: Trump's returns show just how lousy a businessman he is AND how long he may have avoided paying any taxes."
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.
BY: NEWS SKY
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