An expose in the New York Times revealed that Trump is a financial flop.

“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.”

James Hohmann of the Washington Post writes about this Times’ story:

 

The most fascinating passage of the lengthy Times article, deep in the second half, focuses on the three years Trump spent “posing as a corporate raider” from 1986 through 1988. He had overleveraged himself by taking out huge loans at high interest rates and making questionable spending decisions. Two weeks before the stock market crashed in October 1987, for example, Trump bought a 282-foot yacht for $29 million.

The president recognized as a relatively young man – still in his early 40s – that he could profit off his celebrity and perceived business acumen. This was around the time that his book “The Art of the Deal” came out in 1987. He didn’t have the assets to purchase large publicly traded companies, but he knew that other people didn’t know that – especially after he successfully bamboozled Forbes Magazine into wildly overestimating his wealth. He expressed interest and spread rumors that he was looking to acquire companies he knew he couldn’t and wouldn’t.

“Trump made a total of $57 million by briefly presenting himself as a takeover threat to, among others, Hilton Hotels, the Gillette razor company and Federated Department Stores … In all, from 1986 through 1989, Mr. Trump declared $67.3 million in gains from stocks and other assets bought and sold within one year,” Russ Buettner and Susanne Craig report. “As with many things Trump, his adventures in the stock market were more image than substance, helped greatly by news reports quoting anonymous sources said to have knowledge of Mr. Trump’s actions. An occasional quote from an associate — including his stockbroker, Alan C. Greenberg — helped burnish the myth. ‘He has an appetite like a Rocky Mountain vulture,’ Mr. Greenberg, the legendary chairman of Bear Stearns, told the Wall Street Journal in 1987. ‘He’d like to own the world.’ In his actions, Mr. Trump was more like a peacock.”

Investors grew wise to Trump’s game – eventually – so it caught up with him and stopped working. In 1989, Trump bought up American Airlines stock and then announced he was thinking about buying the huge company. “I’m very skeptical of everything this man does,” Andrew Geller, then an airline analyst at Provident National Bank in Philadelphia, told the Associated Press.