Photo: AP

In 1995, the New York Times reports, Donald Trump declared a $916 million loss on his income tax returns—a deduction so great it might have entitled him to wait as long as 18 years before paying any federal income taxes. Three pages of Trump’s tax returns were sent to a Times reporter in the mail.

A declared loss of that size does not necessarily suggest that Trump was insolvent or bankrupt, as the revenue generated by his various holdings would have covered the debts. However, the tax 1995 records, obtained by the Times, show how Trump’s accountants exploited loopholes in the tax code to allow the real estate developer protect his wealth at a time when casino regulators described the Trump Organization as being in “dire financial straits.”

Tax experts hired by The Times to analyze Mr. Trump’s 1995 records said that tax rules especially advantageous to wealthy filers would have allowed Mr. Trump to use his $916 million loss to cancel out an equivalent amount of taxable income over an 18-year period.

Although Mr. 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.

The $916 million loss certainly could have eliminated any federal income taxes Mr. Trump otherwise would have owed on the $50,000 to $100,000 he was paid for each episode of “The Apprentice,” or the roughly $45 million he was paid between 1995 and 2009 when he was chairman or chief executive of the publicly traded company he created to assume ownership of his troubled Atlantic City casinos. Ordinary investors in the new company, meanwhile, saw the value of their shares plunge to 17 cents from $35.50, while scores of contractors went unpaid for work on Mr. Trump’s casinos and casino bondholders received pennies on the dollar.

In the early ‘80s, as part of an application for a New Jersey casino license, Trump submitted his 1978 and 1979 tax returns to gambling regulators—he had paid nothing in federal income tax those years. The same appears to have been true a decade later. “Welcome to the real estate business,” he quipped to Politico in an email.

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Trump was less flippant at last Monday’s debate when Democratic presidential nominee Hillary Clinton theorized that he has refused to release his tax returns so that voters won’t find out “He’s paid nothing in federal taxes.” In a huffy statement to the Times, the Trump campaign claimed that “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.”

(The Times also received a threatening letter from Trump’s lawyer, claiming that publication of the records would “prompt initiation of appropriate legal action,” as Trump had not authorized their disclosure. Also: If the tax document was illegally obtained, and also Trump has not authorized its disclosure, then it’s not really an “alleged” tax document at all, is it?)

Anyway, this is all interesting enough, so far as it goes, but ultimately these three pages of tax records—the first page of a New York state resident income tax return; the first page of a New Jersey nonresident tax return; and the first page of a Connecticut nonresident tax return—are confirmation of little more than the fact that Trump, like many wealthy people, has a very good accountant. Enter Jack Mitnick, the man who handled the Republican presidential nominee’s taxes for more than three decades, until 1996. From the Times:

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Mr. Mitnick, 80, now semiretired and living in Florida, said that while he no longer had access to Mr. Trump’s original returns, the documents appeared to be authentic copies of portions of Mr. Trump’s 1995 tax returns. Mr. Mitnick said the signature on the tax preparer line of the New Jersey tax form was his, and he readily explained an obvious anomaly in the way especially large numbers appeared on the New York tax document.

A flaw in the tax software program he used at the time prevented him from being able to print a nine-figure loss on Mr. Trump’s New York return, he said. So, for example, the loss of “-915,729,293” on Line 18 of the return printed out as “5,729,293.” As a result, Mr. Mitnick recalled, he had to use his typewriter to manually add the “-91,” thus explaining why the first two digits appeared to be in a different font and were slightly misaligned from the following seven digits.

“This is legit,” he said, stabbing a finger into the document.

Mitnick actually makes an appearance in The Art of the Deal: Trump shares an anecdote, describing him as “my accountant” and spelling his name wrong. (“Mitnik.”)