The New York Times has not been able to pry loose Donald Trump's tax returns, but in a new feature they say they were able to verify some of the bottom line numbers of his returns from 1985 to 1994. This is the period of time when a high-flying Trump was still casting himself as a business genius—but was, according to the times, hemorrhaging money at an astonishing rate. At no point during the ten-year period did Trump post anything but a negative income; by the end of the decade, his reported losses were $1.17 billion dollars.
The overall takeaway of the Times piece is that Donald Trump appears to be one of the worst businessmen in the history of business. He didn't just manage to bankrupt a casino, a business in which the general public literally walks in your doors and hands you their money, but similarly failed in alternate personas as real estate speculator and would-be corporate raider.
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.
That $53 million in "interest" income in a single year is especially curious, as the Times was able to find nothing in Trump's then-portfolio that would have even come close to generating that number.
The Times story reveals only the roughest topline numbers of Trump's returns, however, and they don't cover the later period when Trump, reeling from debts, began to tiptoe towards Russian organized crime and other new benefactors—topics long of keen interest to federal investigators and Congress alike. The only thing the Times story reveals with certainty is that Donald Trump has been bleeding his inherited money for a very long time, and in astonishing amounts: By 1991, skas the Times, Trump's financial losses "had grown to nearly $418 million, accounting for fully 1 percent of all the losses that the I.R.S. reported had been declared by individual taxpayers that year."
[Y]ear 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.
Even during the most "successful" years of his career, it appears the self-described world's greatest businessman was in reality one of the biggest failures in U.S. taxpayer history.