This loss would have generated a tax deduction so substantial, according to the Times, that he would be able "to avoid paying any federal income taxes for "up to 18 years".
As to the size of the business loss Trump claimed, the former mayor cited Trump's 1987 bestselling book "The Art of The Deal", which said "every great man has had failures".
According to politifact.com, six Trump businesses have declared bankruptcy, including the Trump Taj Mahal casino in 1991, and the Trump Castle casino, the Trump Plaza and Casino, and the Plaza Hotel, all in 1992. Experts have said that such an audit did not prevent Trump releasing his tax records if he wished. Trump is all smoke and mirrors that one day will blow up in spectacular style when he can no longer service his debts through revenue which has repeatedly happened to numerous such highly indebted characters in the past. Trump lost that fight and had to pay the city taxes on more than $1 million in income.
Bob McIntyre, director of the liberal group Citizens for Tax Justice, said the depreciation allowance allowed Trump to "take losses that really weren't losses", which could enable him to pay no income taxes.
Trump and aides did not provide specifics about his taxes, and did not indicate that he plans to release full tax returns. But if Mr. Trump made $600 million the next year, $600 million of that loss would be wiped out.
The Times explained that it obtained his New York, New Jersey and CT state filings about a month ago, when an anonymous sender sent the documents by mail, with a return address of the Trump Tower.
"The tax experts consulted by The Times said nothing in the 1995 documents suggested any wrongdoing by Mr. Trump, even if the extraordinary size of the loss he declared would have probably attracted extra scrutiny from I.R.S. examiners".
In a statement, the Trump campaign said the GOP nominee has paid hundreds of millions of dollars in other taxes, including property and real estate taxes.
Trump said during the first presidential debate that not paying taxes "makes me smart". But since he announced his candidacy previous year, Trump has refused, bucking a tradition to which presidential nominees have adhered since 1976. And IRS Commissioner John Koskinen, when was asked at a House committee hearing on September 21 whether people under IRS audit are free to release their returns or IRS letters informing them they are being audited, said they are. His son, Donald J. Trump Jr., has seemed to argue the opposite, saying that Trump's tax returns would contain so much information that they would confuse the public and give rise to incorrect armchair analysis.
"So you've got to ask yourself, why won't he release his tax returns?" Other documents show he also didn't pay any federal income taxes in 1978, 1979 and 1984.
The Trump campaign responded with a statement saying the Trump campaign said the Times "illegally obtained" a 20-year-old document and applied a misleading spin.