By the time his master-of-the-universe memoir “Trump: The Art of the Deal” hit bookstores in 1987, Donald J. Trump was already in deep financial distress, losing tens of millions of dollars on troubled business deals, according to previously unrevealed figures from his federal income tax returns.
Mr. Trump was propelled to the presidency, in part, by a self-spun narrative of business success and of setbacks triumphantly overcome. He has attributed his first run of reversals and bankruptcies to the recession that took hold in 1990. But 10 years of tax information obtained by The New York Times paints a different, and far bleaker, picture of his deal-making abilities and financial condition.
The data — printouts from Mr. Trump’s official Internal Revenue Service tax transcripts, with the figures from his federal tax form, the 1040, for the years 1985 to 1994 — represents the fullest and most detailed look to date at the president’s taxes, information he has kept from public view. Though the information does not cover the tax years at the center of an escalating battle between the Trump administration and Congress, it traces the most tumultuous chapter in a long business career — an era of fevered acquisition and spectacular collapse.
The numbers show that in 1985, Mr. Trump reported losses of $46.1 million from his core businesses — largely casinos, hotels and retail space in apartment buildings. They continued to lose money every year, totaling $1.17 billion in losses for the decade.
In fact, year after year, Mr. Trump appears to have lost more money than nearly any other individual American taxpayer, The Times found when it compared his results with detailed information the I.R.S. compiles on an annual sampling of high-income earners. His core business losses in 1990 and 1991 — more than $250 million each year — were more than double those of the nearest taxpayers in the I.R.S. information for those years.
Over all, Mr. Trump lost so much money that he was able to avoid paying income taxes for eight of the 10 years. It is not known whether the I.R.S. later required changes after audits.
Since the 2016 presidential campaign, journalists at The Times and elsewhere have been trying to piece together Mr. Trump’s complex and concealed finances. While The Times did not obtain the president’s actual tax returns, it received the information contained in the returns from someone who had legal access to it. The Times was then able to find matching results in the I.R.S. information on top earners — a publicly available database that each year comprises a one-third sampling of those taxpayers, with identifying details removed. It also confirmed significant findings using other public documents, along with confidential Trump family tax and financial records from the newspaper’s 2018 investigation into the origin of the president’s wealth.
The White House’s response to the new findings has shifted over time.
Several weeks ago, a senior official issued a statement saying: “The president got massive depreciation and tax shelter because of large-scale construction and subsidized developments. That is why the president has always scoffed at the tax system and said you need to change the tax laws. You can make a large income and not have to pay large amount of taxes.”
On Saturday, after further inquiries from The Times, a lawyer for the president, Charles J. Harder, wrote that the tax information was “demonstrably false,” and that the paper’s statements “about the president’s tax returns and business from 30 years ago are highly inaccurate.” He cited no specific errors, but on Tuesday added that “I.R.S. transcripts, particularly before the days of electronic filing, are notoriously inaccurate” and “would not be able to provide a reasonable picture of any taxpayer’s return.”
Mark J. Mazur, a former director of research, analysis and statistics at the I.R.S., said that, far from being considered unreliable, data used to create such transcripts had undergone quality control for decades and had been used to analyze economic trends and set national policy. In addition, I.R.S. auditors often refer to the transcripts as “handy” summaries of tax returns, said Mr. Mazur, now director of the nonpartisan Urban-Brookings Tax Policy Center in Washington.
In fact, the source of The Times’s newly obtained information was able to provide several years of unpublished tax figures from the president’s father, the builder Fred C. Trump. They matched up precisely with Fred Trump’s actual returns, which had been obtained by The Times in the earlier investigation.
Mr. Trump built a business licensing his name, became a television celebrity and ran for the White House by branding himself a self-made billionaire. “There is no one my age who has accomplished more,” he told Newsweek in 1987, adding that the ultimate scoreboard was “the unfortunate, obvious one: money.” Yet over the years, the actual extent of his wealth has been the subject of much doubt and debate. He broke with four decades of precedent in refusing to release any of his tax returns as a presidential candidate, and until now only a few pages of his returns have become public. Last year’s Times investigation found that he had received at least $413 million in 2018 dollars from his father.
The new tax information does not answer questions raised by House Democrats in their pursuit of the last six years of Mr. Trump’s tax returns — about his recent business dealings and possible foreign sources of financing and influence. Nor does it offer a fundamentally new narrative of his picaresque career.
But in the granular detail of tax results, it gives a precise accounting of the president’s financial failures and of the constantly shifting focus that would characterize his decades in business. In contrast to his father’s stable and profitable empire of rental apartments in Brooklyn and Queens, Mr. Trump’s primary sources of income changed year after year, from big stock earnings, to a single year of more than $67.1 million in salary, to a mysterious $52.9 million windfall in interest income. But always, those gains were overwhelmed by losses on his casinos and other projects.
The new information also suggests that Mr. Trump’s 1990 collapse might have struck several years earlier if not for his brief side career posing as a corporate raider. From 1986 through 1988, while his core businesses languished under increasingly unsupportable debt, Mr. Trump made millions of dollars in the stock market by suggesting that he was about to take over companies. But the figures show that he lost most, if not all, of those gains after investors stopped taking his takeover talk seriously.
In Washington, the struggle over access to Mr. Trump’s tax returns and other financial information has sharpened in recent days, amid partisan warfare over the findings in the Mueller report. On Monday, the Treasury secretary, Steven Mnuchin, said he would not deliver the tax returns to the Ways and Means Committee. And after vowing that “we’re fighting all the subpoenas” from House Democrats, the president has filed lawsuits against his banks and accounting firm to prevent them from turning over tax returns and other financial records.
In New York, the attorney general’s office is investigating the financing of several major Trump Organization projects; Deutsche Bank has already begun turning over documents. The state attorney general is also examining issues raised last year by The Times’s investigation, which revealed that much of the money Mr. Trump had received from his father came from his participation in dubious tax schemes, including instances of outright fraud.
The first of the two previous glimpses of the president’s tax returns came from his 1995 filings, pages of which were anonymously mailed to The Times in 2016. They showed that Mr. Trump had declared losses of $915.7 million, giving him a tax deduction so substantial that it could have allowed him to legally avoid paying federal income taxes on hundreds of millions of dollars of income for almost two decades. Several months later, the journalist David Cay Johnston was mailed pages of Mr. Trump’s 2005 returns, which showed that by then he had significant sources of income and was paying taxes.
The year was 1985, and Mr. Trump appeared to be on top of the world.
He was still riding high from the completion of his first few projects — the Grand Hyatt Hotel, Trump Tower and another Manhattan apartment building, and one Atlantic City casino. He also owned the New Jersey Generals of the United States Football League.
As the year played out, he borrowed hundreds of millions of dollars to fuel a wave of purchases, acquiring a second casino ($351.8 million), a Manhattan hotel ($80 million), the Mar-a-Lago property in Florida ($10 million), a New York hospital he intended to replace with an apartment building ($60 million) and an undeveloped expanse of railroad yards on the West Side of Manhattan ($85 million), where he planned to construct an entire neighborhood, including a 150-story tower envisioned as the world’s tallest.
For the first time, Forbes’s ranking of the wealthiest Americans listed Mr. Trump individually, independent of his father — with an estimated net worth of $600 million that included the real estate empire Fred Trump still owned.
“What I have done is build the most beautiful buildings in the best locations,” Donald Trump told the magazine.
But what the newly revealed tax information makes clear is that, with his vast debt and other expenses on those properties, Mr. Trump’s fortunes were already on the way down.
His yearly carrying costs on the rail yards would rise to $18.7 million. He would not be able to convert Mar-a-Lago into a moneymaking club for another decade. The apartments on the hospital site would not be ready for sale, as Trump Palace, until 1990, and another residential project would be stalled for years. The football league would soon fold.
Because his businesses were generally created as partnerships, the companies themselves did not pay federal income taxes. Instead their results wound up on Mr. Trump’s personal ledger.
Beyond the $46.1 million loss that his core businesses logged in 1985, Mr. Trump’s tax information shows that he carried over $5.6 million in losses from prior years. The I.R.S. data on one-third of high-income tax returns that year lists only three taxpayers with greater losses.
In his letter, Mr. Harder, the president’s lawyer, took issue with comparing the tax returns of “a real estate developer to the returns of all taxpayers.” But most of the high-income taxpayers appeared, like Mr. Trump, to be business owners who received what is known as pass-through income. (That data does not include businesses, like most large corporations, that pay their taxes directly.)
The next years were a time of continued empire building. The information also documents, year by year, a time of gathering loss. Here is how it added up.
In 1986, he bought out his partners in Trump Tower and the Trump Plaza Hotel and Casino. He bought an apartment building in West Palm Beach for $43 million. His business losses for the year: $68.7 million.
A Deal Maker in Financial Distress
Every year from 1985 through 1994, Donald J. Trump reported a negative adjusted gross income on his tax returns. That number grew as new losses were combined with those from prior years. The New York Times previously found that Mr. Trump declared an adjusted gross income in 1995 of negative $915.7 million.
About two weeks before the stock market crash of Oct. 19, 1987, he spent $29 million on a 282-foot yacht. Months later he bought the Plaza Hotel for $407 million. He recorded $42.2 million in core business losses for 1987, and $30.4 million for 1988.
In 1989, he bought a shuttle operation from Eastern Airlines for $365 million. It never made a profit, and Mr. Trump would soon pump in more than $7 million a month of his dwindling cash to keep it airborne, New Jersey casino regulators, who closely monitored his finances in those years, found.
Mr. Trump’s business losses that year soared to $181.7 million.
Then came the Trump Taj Mahal Hotel and Casino, which opened in April 1990 saddled with more than $800 million in debt, most at very high interest rates. It did not generate enough revenue to cover that debt, and sucked revenue from his other casinos, Trump’s Castle and Trump Plaza, pulling them deep into the red.
“In fact, year after year, Mr. Trump appears to have lost more money than nearly any other individual American taxpayer, The Times found when it compared his results with detailed information the I.R.S. compiles on an annual sampling of high-income earners. His core business losses in 1990 and 1991 — more than $250 million each year — were more than double those of the nearest taxpayers in the I.R.S. information for those years.”
