In 1985, two years before releasing his book The Art of the Deal, President Trump purchased several properties, including his Mar-a-Lago club in Florida, and reported losses of $46.1 million from his casinos, hotels, and retail space in apartment buildings, The New York Times reports.
The Times obtained tax information from 1985 to 1994 that shows Trump's businesses lost more than $1 billion over the decade. Trump spent the 1980s boasting about his business talents; the figures show that in 1985, he borrowed hundreds of millions of dollars in order to purchase a $351.8 million casino, $60 million hospital, and $85 million undeveloped railroad yards. He also borrowed $10 million to buy Mar-a-Lago.
The Times reports that it took Trump 10 years to make any money off Mar-a-Lago; it cost $18.7 million a year to carry the rail yards; and it took five years to turn the hospital property into a building with apartments that could be sold. In 1985, Trump also owned a United States Football League team, the New Jersey Generals, but the league soon folded. He did have one win that year: He purchased the Hotel St. Moritz in Manhattan for $73.7 million, and sold it in 1989 for $180 million.
Because most of his businesses were not created as partnerships, Trump was on the hook for federal income taxes. In addition to losing $46.1 million in 1985, his tax information shows he also carried over $5.6 million from earlier losses, the Times reports; in fact, IRS data on one-third of high-income tax returns shows that for 1985, only three other taxpayers had greater losses that year. Under the tax code, business owners can use their losses to keep from paying taxes on future income. This is known as a net operating loss, and by 1991, the Times says, Trump's net operating losses had grown to almost $418 million, or 1 percent of all the losses reported to the IRS by individual taxpayers that year.
For more on Trump's heavy losses in other years — including 1989, when he purchased an airline that never made any money, and 1990, when he opened his debt-laden Taj Mahal Hotel and Casino in Atlantic City — visit The New York Times.