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.
Because the documents sent to The Times did not include any pages from Mr. Trump’s 1995 federal tax return, it is impossible to determine how much he may have donated to charity that year. The state documents do show, though, that Mr. Trump declined the opportunity to contribute to the New Jersey Vietnam Veterans’ Memorial Fund, the New Jersey Wildlife Conservation Fund or the Children’s Trust Fund. He also declined to contribute $1 toward public financing of New Jersey’s elections for governor.
The tax documents also do not shed any light on Mr. Trump’s claimed net worth of about $2 billion at that time. This is because the complex calculations of business deductions that produced a tax loss of $916 million are a separate matter from how Mr. Trump valued his assets, the tax experts said.
Nor does the $916 million loss suggest that Mr. Trump was insolvent or effectively bankrupt in 1995. The cash flow generated by his various businesses that year was more than enough to service his various debts.
But fragmentary as they are, the documents nonetheless provide new insight into Mr. Trump’s finances, a subject of intense scrutiny given Mr. Trump’s emphasis on his business record during the presidential campaign.
The documents show, for example, that while Mr. Trump reported $7.4 million in interest income in 1995, he made only $6,108 in wages, salaries and tips. They also suggest Mr. Trump took full advantage of generous tax loopholes specifically available to commercial real estate developers to claim a $15.8 million loss in 1995 on his real estate holdings and partnerships.
But the most important revelation from the 1995 tax documents is just how much Mr. Trump may have benefited from a tax provision that is particularly prized by America’s dynastic families, which, like the Trumps, hold their wealth inside byzantine networks of partnerships, limited liability companies and S corporations.
The provision, known as net operating loss, or N.O.L., allows a dizzying array of deductions, business expenses, real estate depreciation, losses from the sale of business assets and even operating losses to flow from the balance sheets of those partnerships, limited liability companies and S corporations onto the personal tax returns of men like Mr. Trump. In turn, those losses can be used to cancel out an equivalent amount of taxable income from, say, book royalties or branding deals.
Better still, if the losses are big enough, they can cancel out taxable income earned in other years. Under I.R.S. rules in 1995, net operating losses could be used to wipe out taxable income earned in the three years before and the 15 years after the loss. (The effect of net operating losses on state income taxes varies, depending on each state’s tax regime.)
The tax experts consulted by The Times said the $916 million net operating loss declared by Mr. Trump in 1995 almost certainly included large net operating losses carried forward from the early 1990s, when most of Mr. Trump’s key holdings were hemorrhaging money. Indeed, by 1990, his entire business empire was on the verge of collapse. In a few short years, he had amassed $3.4 billion in debt — personally guaranteeing $832 million of it — to assemble a portfolio that included three casinos and a hotel in Atlantic City, the Plaza Hotel in Manhattan, an airline and a huge yacht.
Reports that year by New Jersey casino regulators gave glimpses of the balance sheet carnage. The Trump Taj Mahal casino reported a $25.5 million net loss during its first six months of 1990; the Trump’s Castle casino lost $43.5 million for the year. His airline, Trump Shuttle, lost $34.5 million during just the first six months of that year.
“Simply put, the organization is in dire financial straits,” the casino regulators concluded.
Reports by New Jersey’s casino regulators strongly suggested that Mr. Trump had claimed large net operating losses on his taxes in the early 1990s. Their reports, for example, revealed that Mr. Trump had carried forward net operating losses in both 1991 and 1993. What’s more, the reports said the losses he claimed were large enough to virtually cancel out any taxes he might owe on the millions of dollars of debt that was being forgiven by his creditors. (The I.R.S. considers forgiven debt to be taxable income.)
But crucially, the casino regulators redacted the precise size of the net operating losses in the public versions of their reports. Two former New Jersey officials, who were privy to the unredacted documents, could not recall the precise size of the numbers, but said they were substantial.
Politico, which previously reported that Mr. Trump most likely paid no income taxes in 1991 and 1993 based on the casino commission’s description of his net operating losses, asked Mr. Trump to comment. “Welcome to the real estate business,” he replied in an email.
Now, thanks to Mr. Trump’s 1995 tax records, the degree to which he spun all those years of red ink into tax write-off gold may finally be apparent.
Mr. Mitnick, the lawyer and accountant, was the person Mr. Trump leaned on most to do the spinning. Mr. Mitnick worked for a small Long Island accounting firm that specialized in handling tax issues for wealthy New York real estate families. He had long handled tax matters for Mr. Trump’s father, Fred C. Trump, and he said he began doing Donald Trump’s taxes after Mr. Trump turned 18.
In an interview on Wednesday, Mr. Mitnick said he could not divulge details of Mr. Trump’s finances without Mr. Trump’s consent. But he did talk about Mr. Trump’s approaches to taxes, and he contrasted Fred Trump’s attention to detail with what he described as Mr. Trump’s brash and undisciplined style. He recalled, for example, that when Donald and Ivana Trump came in each year to sign their tax forms, it was almost always Ivana who asked more questions.
But if Mr. Trump lacked a sophisticated understanding of the tax code, and if he rarely showed any interest in the details behind various tax strategies, Mr. Mitnick said he clearly grasped the critical role taxes would play in helping him build wealth. “He knew we could use the tax code to protect him,” Mr. Mitnick said.
According to Mr. Mitnick, Mr. Trump’s use of net operating losses was no different from that of his other wealthy clients. “This may have had a couple extra digits compared to someone else’s operation, but they all benefited in the same way,” he said, pointing to the $916 million loss on Mr. Trump’s tax returns.
In “The Art of the Deal,” his 1987 best-selling book, Mr. Trump referred to Mr. Mitnick as “my accountant” — although he misspelled his name. Mr. Trump described consulting with Mr. Mitnick on the tax implications of deals he was contemplating and seeking his advice on how new federal tax regulations might affect real estate write-offs.