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2019-05-07 — nytimes.com

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...

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Mr. Trump was able to lose all that money without facing the usual consequences -- such as a steep drop in his standard of living -- in part because most of it belonged to others, to the banks and bond investors who had supplied the cash to fuel his acquisitions. And as The Times's earlier investigation showed, Mr. Trump secretly leaned on his father's wealth to continue living like a winner and to stage a comeback.

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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.

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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.

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At his nadir, in the post-recession autumn of 1991, Mr. Trump testified before a congressional task force, calling for changes in the tax code to benefit his industry.

"The real estate business -- we're in an absolute depression," Mr. Trump told the lawmakers, adding: "I see no sign of any kind of upturn at all. There is no incentive to invest. Everyone is doing badly, everyone."

... [But] While Donald Trump reported hundreds of millions of dollars in losses for 1990 and 1991, Fred Trump's returns showed a positive income of $53.9 million, with only one major loss: $15 million invested in his son's latest apartment project.

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