1988: The Year Donald Lost His Mind

1988: The Year Donald Lost His Mind

- in Election 2016

Reviewers trashed Donald Trump’s first book. They dismissed The Art of the Deal as self-promotional pap. They called the author a huckster. “The man’s lack of taste is as vast as his lack of shame,” said the Washington Post. Fortune noted his “shallowness” and “pomposity” and his need for “more money,” more “toys” and “more attention.” The book, said The New Republic, “is a weapon in the continuing public relations war that is Donald Trump’s way of doing business.”

None of it mattered. Shortly after its release, a few weeks into January of 1988, Trump’s book was at the top of the New York Times’ list of best-sellers, surprising even his publishers. “Everyone has been astounded,” the director of publicity of Random House told the Associated Press. The scathing critiques, she said, “don’t seem to be making much of a difference.”

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This was the beginning of a stretch of time that can be seen as peak Trump—at least until this unprecedented and Trump-centric presidential campaign. He had shrugged off his critics and risen to the top of a new field. He had never been hotter, or more famous, than he was at 41 years old, at the start of 1988.

But his response to his surging celebrity was a series of manic, ill-advised ventures. He cheated on his wife, the mother of his first three children. In business, he was acquisitive to the point of recklessness. He bought and sold chunks of stocks of companies he talked about taking over. He glitzed up his gaudy yacht, the yacht the banks would seize less than three years later. He used hundreds of millions of dollars of borrowed money to pay high prices for a hotel and an airline—and his lenders would take them, too. And he tussled for months with game-show magnate Merv Griffin for ownership of his third casino in Atlantic City, the most expensive, gargantuan one yet, the Trump Taj Mahal, which led quickly to the first of his four corporate bankruptcy filings.

The man who now says he would be a good president because of his ability to make good deals made bad deals; 1988 was the year in which the candidate whose pitch is success sowed the seeds of many of his signature failures.

“Deals are my art form,” Trump had written in his book. “I aim very high, and then I just keep pushing and pushing and pushing to get what I’m after.” He claimed he believed in “spending what you have to” but also “not spending more than you should,” never letting “personal preferences affect my business judgment.”

That spring, though, he purchased the Plaza Hotel because he openly coveted the Manhattan landmark, so much so that he paid more for it than anybody anywhere ever had spent on a hotel—$407.5 million—a hotel that wasn’t turning enough profit to service the debt to which Trump committed.

And in the fall, he agreed to buy the Eastern Airlines Shuttle, which he wanted to rename the Trump Shuttle, for a sum that analysts and even his own partners considered excessive—more than the airline itself thought the shuttle was worth.

“I went to him,” Frank Lorenzo, the former Texas Air chairman, who sold Trump the shuttle, diplomatically told me in an interview. “I think our number was 375, 385”—million—“and he negotiated it down”—to $365 million. “Your offering price is always higher than you think you’re going to get,” Lorenzo said. From Trump, he almost got it, anyway.

“The price was too high,” said Bruce Nobles, the former president of Trump Shuttle, who was involved in the negotiations—and Lorenzo, not Trump, set the tone. “He said, ‘This is what I want.’

“It was not a lengthy financial analysis,” added Nobles, describing it as “back-of-the-envelope” and “very quick.” “Lorenzo said, ‘I really want to sell it,’ and Donald said, ‘I really want to buy it.’”

The haggling, meanwhile, that got Trump the abandoned, half-built, already wildly over-budget Taj took longer. He bragged that he had bested Griffin. Others weren’t convinced.

“He called me on the telephone, and he said to me, ‘Don’t you think I did a fantastic deal?’” said Marvin Roffman, who then was working in Philadelphia as a casino industry analyst. “And I think he started to dislike me then, because I said to him, ‘I think you made a mistake.’”

“He was just buying up things with loans, and that’s what caught up with him,” Barbara A. Res, a Trump Organization vice president at the time, told me last month. “There was never enough for him. Nothing satisfied him.”

If Trump’s current campaign is the culmination of a lifelong effort to turn his name into a brand, his brand into money and all of it into power, 1988 was the first sustained look at what the man who is the shocking favorite to be the Republican Party’s nominee does when he gets ahold of it. It was the year Trump’s insatiable appetites and boundless ego—this early, spectacular show of success—nearly did him in.


Trump’s frenzied 1988 matched the country’s ostentatious and indulgent mood at the end of the Reagan administration.

In the first three months of the year, Trump christened his $29 million, 282-foot yacht the Trump Princess, changed the name of his large, dormant tract of land on the Upper West Side of Manhattan from TV City to Trump City and bought bunches of Federated department store stock and MCA movie company stock and vowed to buy more. He was reportedly interested in owning the New York Post and the National Football League’s New England Patriots—rumors that went nowhere. He got the U.S. patent office to revoke the trademark of two brothers in the real estate business in New York also named Trump because they were using “his” name. He got the appraiser’s office in Palm Beach, Florida, to lower the property taxes at his Mar-a-Lago estate by $86,000—five months after Forbes estimated his net worth at $850 million. He hosted at his Trump Plaza casino Wrestlemania IV and a Mike Tyson championship boxing match and paid by far a then-record price of $11 million for rights to host another. He debuted a pair of Trump-branded limousines equipped with wet bars, paper shredders and hidden safes and launched a “super luxury,” “super modern,” “totally first- class” helicopter service from New York to Atlantic City. He dubbed it Trump Air.

He tried to take private the public Resorts International casino company with a lowball bid of $15 a share to gobble up the stock he didn’t already own. He wanted to control the Taj so he could have a third casino in the small, struggling city. Griffin hadn’t gotten involved yet. Some members of New Jersey’s casino control board thought the maneuvering felt fishy. They worried Trump had disparaged the company to drive down its value. Trump upped his bid to a still low $22 a share. One commissioner called Trump’s testimony “laced with hyperbole, contradictions and generalities.” Eventually, though, the board relented—thanks in part to a backhanded assist from an independent investment banker, who testified that the notion of some sort of planned-out scheme by Trump gave him too much credit. “I think Trump is more impulsive than that,” he said.

In a recent interview, Goldberger told me he saw Trump at the time as an amalgam of Greek mythology’s Icarus and Narcissus.

Paul Goldberger, the architecture critic of the New York Times, linked in print the rise of Trump with a survey showing that a higher-than-ever number of college freshmen wanted to be rich more than they wanted to develop a “meaningful philosophy of life.” In a recent interview, Goldberger told me he saw Trump at the time as an amalgam of Greek mythology’s Icarus and Narcissus.

“He was just sort of pushing harder and harder and less and less aware of the risks he was taking,” Goldberger said. “In one sense, ’88 was kind of a high point—but it was also clear he was flying a little too close to the sun, already.”

In March, Trump got what many other men might have considered a warning.

A federal appeals court affirmed a ruling from 1986, saying essentially that the upstart United States Football League had failed due to self-inflicted wounds and not an NFL monopoly. The judge in his 105-page ruling blamed in particular one owner—“notably Donald Trump of the New Jersey Generals”—who unwisely and impatiently urged the league to start playing games in the fall to go head-to-head with the NFL in hopes that such a strategy would lead to a merger with the NFL for the USFL’s teams from bigger cities. Like Trump’s Generals. “Courts,” the judge wrote, “do not exclude evidence of a victim’s suicide in a murder trial.”

Michael Kruse is a senior staff writer for Politico.


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