“Simply put, the organization is in dire financial straits,” New Jersey casino regulators concluded after reviewing his business balance sheet woes in 1990.

The 1995 tax documents, which were anonymously mailed to a New York Times reporter, were 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. They did not include any pages from Mr. Trump’s 1995 federal return.

Mr. Trump was correct when he said he benefited from a provision that had been used by other wealthy families.

Known as net operating loss, it allows an 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 people like Mr. Trump. In turn, those losses can be used to cancel out an equivalent amount of taxable income.

With a $916 million net operating loss in 1995, Mr. Trump could have avoided paying more than $50 million a year in taxable income over 18 years.

Mr. Trump appears to have embraced other elements of the tax code.

In 1991, he lobbied federal lawmakers to relax tax rules that he claimed had strangled the real estate industry. And in less than two years, as part of a wide-ranging budget deal, Congress passed a set of provisions sought by developers that could have helped Mr. Trump avoid large tax bills linked to his enormous debt racked up by the early 1990s, while also allowing him to spin other real estate losses into valuable offsets on his future earnings in licensing, television and other ventures.