1. Mr. Trump was deep in the red even as he peddled deal-making advice
“Trump: The Art of the Deal” came out in 1987. It became a best seller — and a powerful vehicle for the self-spun myth of the self-made billionaire that would ultimately help propel him to the presidency.
Mr. Trump has long attributed his first run of business reversals and bankruptcies to the recession that hit three years later, in 1990. But the new tax information reveals that he was already in deep financial distress when his master-of-the-universe memoir hit the shelves.
For Mr. Trump, the 1980s were a frenzy of acquisition and construction, buoyed by hundreds of millions of dollars of borrowed money. In 1985, for the first time, Forbes’s “rich list” included Mr. Trump individually, independent of his father. But his estimated net worth according to the magazine, $600 million, included the real estate empire Fred Trump still owned.
With Mr. Trump’s vast debt and other expenses on his properties — among them Trump Tower and the Grand Hyatt hotel in Manhattan, and two Atlantic City casinos — his fortunes were already on the way down. In 1985, his core businesses reported a loss of $46.1 million; they also carried over a $5.6 million loss for earlier years.
Because those businesses were generally created as partnerships, they did not pay federal income taxes themselves. Instead, their gains, and their losses, flowed onto Mr. Trump’s ledger. To put his results in perspective, The Times compared them with detailed information that the I.R.S. compiles on an annual one-third sampling of high earners. Most of them appeared, like Mr. Trump, to be businessmen who received what is known as pass-through income.
For 1985, the I.R.S. information indicates this: Only three individual taxpayers in the sampling reported bigger losses than Mr. Trump.
2. In multiple years, he appears to have lost more money than nearly any other individual taxpayer
The tax results for the years that followed trace an arc of continued empire building — and gathering loss.
ADVERTISEMENT
He bought the Eastern Airlines shuttle for $365 million; it never made a profit, and he spent more than $7 million a month to keep it flying. His new Trump Taj Mahal Hotel and Casino, opened in 1990 with more than $800 million in debt, sucked revenue from his other casinos, pulling them along into the red.
And so, year after year, Mr. Trump appears to have lost more money than nearly any other individual taxpayer, according to