In a story published online late Saturday, The Times said it anonymously received the first pages of Trump's 1995 state income tax filings in New York, New Jersey and Connecticut. The filings show a net loss of $US915,729,293 in federal taxable income for the year.
"Mr Trump, the developer who came to epitomise opulent wealth during the '80s before tumbling into deep financial trouble, has managed to erase much of his debt and is moving ahead with major projects at a time other developers are idling," the newspaper wrote.
But in the story published over the weekend, the newspaper alleged the losses revealed in the leaked document potentially allowed Trump to avoid paying taxes for years, possibly until the end of the last decade.
'THE GREAT DEPRESSION OF 1990'
The fact that Trump was losing money during the early to mid-1990s was already well established. Trump wrote about his financial woes in what he called the "Great Depression of 1990" in his 1997 book The Art of the Comeback.
And in 1995, in a story titled 'Crowning the Comeback King', The New York Times reported how business and government leaders honoured Trump for pulling off "the comeback of the decade".
His campaign said that Trump had 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" over the years.
"The only news here is that the more than 20-year-old alleged tax document was illegally obtained, a further demonstration that The New York Times, like establishment media in general, is an extension of the Clinton Campaign, the Democratic Party and their global special interests," his campaign said in a statement.
"What is happening now with the FBI and DOJ on Hillary Clinton's emails and illegal server, including her many lies and her lies to Congress are worse than what took place in the administration of Richard Nixon - and far more illegal.
"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 incredible skills Mr Trump has shown in building his business are the skills we need to rebuild this country. Hillary Clinton is a corrupt public official who violated federal law, Donald Trump is an extraordinarily successful private businessman who followed the law and created tens of thousands of jobs for Americans."
DID TRUMP LEAK THE DOCUMENTS?
According to the journalist who wrote the story, the leaked tax return arrived in an envelope with a New York City postmark and Trump Tower listed as the return address.
The news sparked speculation of a mole within the businessman's inner circle, but some Trump supporters have floated the idea that Trump himself leaked the documents.
"Most Americans don't know much about tax law, which is a problem for entrepreneurs like Trump," wrote lawyer and prominent Trump supporter Mike Cernovich.
"Tax law advantages those who create jobs by giving us access to all sorts of tax deductions. Many entrepreneurs have trouble getting a home mortgage because our income tax returns reveal little personal income.
"If Trump had released all of his tax returns at once, the 1995 carry forward loss would have been lost. Now everyone knows about the loss."
Cernovich speculated that leaking his 1995 tax returns would allow Trump to tell the "comeback story of his massive losses in 1995". "Trump is using the power of metaphor to link himself and his own story arc to America's," he wrote.
Dilbert creator Scott Adams, another outspoken Trump supporter, also believes it was a "either a Trump leak or the luckiest thing that has happened to him in the past year".
"Thanks to Trump, today smart people all over the country are explaining to their dumb friends how taxes work," Adams tweeted.
The theory is not outside the realm of possibility, given Trump's history of manipulating the media. In the 1990s, Trump regularly pretended to be his own spokesman, "John Miller", in interviews with journalists about his love life.
Earlier this year, audiotapes from one such interview in 1991 were leaked to The Washington Post. In the tapes, "John Miller" discusses the billionaire's divorce from his first wife Ivana.
But Sue Carswell, the reporter who conducted the original interview, said she lost the tapes years ago, claiming on Fox News that Trump leaked the audio himself to create headlines and distract from controversy over his tax returns.
CLINTON USED SAME 'LOOPHOLE'
And according to Clinton's own tax returns, released by her campaign, she herself used a $US700,000 ($916,000) loss to avoid paying taxes in 2015.
Neither New Jersey Governor Chris Christie nor former New York City Mayor Rudy Giuliani, both top Trump supporters, disputed the report that said Trump's loss in 1995 was big enough that he could have legally avoided paying taxes for as many as 18 years.
On Fox News Sunday, Christie declared it "a very, very good story for Donald Trump". Giuliani called him "a genius at how to take advantage of legal remedies that can help your company survive and grow" on ABC's This Week.
"Don't you think a man who has this kind of economic genius is a lot better for the United States than a woman? And the only thing she's ever produced is a lot of work for the FBI checking out her emails," Giuliani said.
Trump did not appear publicly on Sunday, but weighed in on social media, saying he was singularly qualified to fix the nation's tax system.
"I know our complex tax laws better than anyone who has ever run for president and am the only one who can fix them," Trump tweeted.
Clinton made no mention of Trump's taxes during her events in North Carolina on Sunday. But the Democratic presidential nominee reposted a tweet from Trump, who wrote in 2012 that "HALF of Americans don't pay income tax despite crippling govt debt..." "Now that's pretty rich coming from a guy who paid $0 in taxes for 18 years," Clinton tweeted.
