Michael Kruse is a senior staff writer for Politico.

What on earth was Donald Trump up to in the late 1980s? Yesterday’s bombshell report about the president’s tax history—in which the New York Times revealed that Trump in those years may have “lost more money than nearly any other individual American taxpayer”—has quickly focused attention on a chaotic period when he established his glittering national brand as a dealmaker but also sowed the seeds of his near-ruin. POLITICO’s Michael Kruse dove deep into that head-spinning stretch of Trump’s life, capturing this unique portrait of how Trump built, and almost destroyed, his façade of public success.



***


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.”

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.’”

New Window OPTICS: 1988: The Year of Trump (Click to view gallery.)

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.”

If there was a lesson in this failure, Trump did not heed it. He had his eye on the Plaza, New York’s most well-known hotel, the kind of storied property to cement the reputation of an ambitious, arriviste real estate mogul.

Trump was talking to a man named Tom Barrack. Barrack was working for Texas oil heir Bob Bass, who recently had purchased along with a Japanese partner the Westin hotel chain—including the Plaza. Which he wanted to get rid of. It had a regal reputation, but it was old, with an annual net cash flow of a relatively meager $20 million. Bass valued the Plaza at $350 million. “Anything over $350 million is too high,” a hotel analyst told the Wall Street Journal. From Trump, Bass wanted $450 million. Trump scoffed at the big ask, but he and Barrack quickly agreed to split the difference—$400 million. An attorney for Trump who was in his office told him not to agree to that price, according to a detailed, definitive report on the Plaza deal that ran that year in the New York Times. Trump, though, spun around in his chair and looked out his window. He could see the green copper roof of the Plaza. He had lusted after the hotel since he moved in the mid-'70s to Manhattan from Queens. It was perhaps singularly evocative of old money, and would be a way for Trump to assuage his new-money, outer-borough insecurities.

“How can I live without it?” he said.

“You should own it,” Barrack said.

He swiveled back around and said yes.

The Plaza was perhaps singularly evocative of old money, and would be a way for Trump to assuage his new-money, outer-borough insecurities.



“How can I live without it?” he said.

Two weeks later, in the middle of March, Barrack was back, saying Bass wanted more—$410 million now—and Trump asked his attorney to leave his office and agreed to a final figure of $407.5 million. Trump spun the deal publicly, concealing his last-minute concession from reporters to whom he claimed the sale price was $390 million. He wanted, he said, to “upgrade everything” to make the Plaza “the most luxurious hotel in the world.”

He funded the purchase and the refurbishment with a $425 million mortgage from a group of banks led by Citicorp—and rashly personally guaranteed $125 million of it.

“Donald’s purchase of the Plaza was greeted with howls of ridicule in the Manhattan real estate industry,” Harry Hurt III would write in his 1993 biography of Trump, Lost Tycoon.

“The only way the Plaza could possibly make the interest payments on its bank debt out of cash flow,” according to Hurt, “was by filling up all 814 rooms, 365 nights per year at a going rate of $500 a room.” This was at a time when rooms at the Plaza started at $195 a night.

Trump must have known because he paid for full-page ads in the New York Times and New York magazine to explain what he had done. “Why I Bought the Plaza,” read the title.

“I haven’t purchased a building, I have purchased a masterpiece—the Mona Lisa,” he wrote. “For the first time in my life, I have knowingly made a deal which was not economic—so I can never justify the price no matter how successful the Plaza becomes.” He pitched it as practically a public service. “What I have done … is to give to New York City the opportunity to have a hotel which transcends all others!”

Another motivation: He wanted to shift his wife from her role running one of his casinos in Atlantic City to a similar post in charge of the Plaza—he said he would pay Ivana “$1 a year, plus all the dresses she can buy”—partly so he could more easily put up in rooms in his casino hotels his mistress of several months, a blond, buxom, B-movie actress and model, the Georgia-born, 24-year-old Marla Maples.



***

In April, Merv Griffin got on the elevator to the 26th floor of Trump Tower. He had mounted an unexpected challenge to Trump’s takeover of Resorts, offering $35 a share, much more than Trump. But Trump had voting power because of the shares he already held. Now, according to an account in the Los Angeles Times, Griffin headed to the appointment he had requested with Trump, passing a model of Trump’s yacht, a model of Trump’s private helicopter, a model of Trump’s private plane and framed covers of magazines with Trump’s face on the front. Time. Newsweek. BusinessWeek. New York. Manhattan Inc. GQ. Fortune. People. Trump shook Griffin’s hand. He walked him to the window. He wanted him to look at the Plaza.

Griffin asked Trump what he wanted.

The Taj, Trump told him.

Done, Griffin said.

And the steel pier off the boardwalk by the Taj, Trump said.

Trump paid a record fee of $11 million to host Mike Tyson’s boxing championship against Michael Spinks at his Atlantic City Convention Hall, adjacent to the Trump Plaza Hotel on June 8, 1988. | AP Photo

Griffin agreed to that, too. “Is that all?”

“Yes,” Trump answered.

They shook on it. The verbal pact called for Trump to get the Taj and for Griffin to get the rest of Resorts, properties in Atlantic City and the Bahamas. Trump would pay Griffin a little less than $300 million for the Taj, and Griffin would buy him out, for $63 million, from his Resorts management contract. The two men would back out of this, sparring in the press for the better part of the year—that afternoon, though, they had a deal.

“Trump gets the Taj,” a different Trump attorney told Newsday, “which is what he wanted from the day he went into Resorts.” The attorney promised that the Taj would become the “crown jewel” of Atlantic City.

Trump—the man, the name—was everywhere that spring and summer.

In mid-April, he hosted in a ballroom at the Plaza a $1,000-per-plate fundraiser for the vice president’s presidential campaign. “He’s a great gentleman,” Trump said of George H.W. Bush—not quite three decades before he would savage the man’s “low-energy” second son on the campaign trail. Back then, the older Bush reportedly suggested to aides that “someone like Trump” might make good running-mate material. A source told Newsday that Bush considered Trump “certainly a formidable man.”

In May, Trump’s wife, born a Czech, became a naturalized American citizen in a ceremony at a New York court. “By your presence,” the judge told her and 141 others, “America is vastly enriched.”

Trump concurred. “I’m very proud of my wife,” he said to reporters outside the courthouse. “I’m very proud of my country.”

In June, his black helicopter, TRUMP splashed in white letters on the side, landed on a baseball field on the Pennsylvania campus of Lehigh University. He had been invited to give the commencement speech. In his introduction, the president of the school called Trump “a symbol of our age—all the daring and energy that the word tycoon conjures up,” lauding him for his “boldness of vision” and “the splendor of his buildings.”

But in his speech, delivered to 1,126 Lehigh graduates, Trump delivered a dark message, far less glowingly patriotic than when he had spoken after his wife’s naturalization ceremony.

“I love positive thinking,” Trump told them, “but it can only get you in trouble.”

He sounded an alarm about AIDS. “Be very careful,” he said, according to the Morning Call of nearby Allentown, Pennsylvania. “It’s out there.”

He pilloried the nation's politicians. “What kind of clowns do we have representing us?” he asked the liberal arts graduates. “It’s a very sad situation.”

And he relayed a story about a fierce Japanese businessman who had recently visited him in his office in Trump Tower, pounding his fist on the desk, Trump said, demanding property. “We want real estate!”

In the cutthroat New York real estate world, he told the crowd in Lehigh’s basketball gym, “You’re dealing with some rough people. He made them look like babies.” Trump wondered: “What happens when this guy goes to the State Department?”

“I love positive thinking,” Trump told the Lehigh graduates, “but it can only get you in trouble.”

A couple weeks after his Lehigh graduation talk, it was his birthday—on June 14, Trump turned 42—and he threw himself a lavish party at his casino called Trump’s Castle, replete with dancers, a magician and a replica spaceship hovering above Trump and his wife on the stage amid lasers and smoke. There were video birthday cards from people like Liza Minnelli and Billy Crystal.

Later in June, he hosted his second Tyson fight of the year, the bout for which he had paid the boxers’ promoters $11 million. Worth it, Trump told the Los Angeles Times. “I don’t believe in overpaying for anything,” he said.

“Donald Trump don’t mess around,” crazy-haired Tyson promoter Don King told the Chicago Tribune. “He doesn’t procrastinate or vacillate but wants to titillate.”

A pre-fight gala for VIPs offered 1,200 pounds of lobster tail and filet mignon. A headline in the Washington Post called the scene “a monument to a decade of greed.” In the packed arena attached to the Trump Plaza casino, it took almost an hour to introduce all the celebrities in the stands—Chuck Norris, Bruce Willis, Elizabeth Taylor, Malcolm Forbes, Muhammad Ali—while Trump and his wife sat next to Democratic presidential hopeful Jesse Jackson. The fight itself lasted a minute and a half. Tyson put Michael Spinks on his back with two punches to his face.

In July, a few days after new cable channel TNT announced plans to make a movie about Trump’s life—“I want a very good-looking guy to play me,” Trump told the New York Post—Trump called a news conference on Independence Day because he wanted to show reporters his yacht, which he had bought, he said, without ever having boarded the boat.

“I’m not into them,” he told a reporter from New York. “I’ve been on friends’ boats before and couldn’t get off fast enough.”

This one, though, he said, was an “incredible toy,” the “ultimate toy”—“a masterpiece,” too, “a work of art.”

“It’s very hard to explain the level of quality.”

Trump kept trying.

He took the reporters around the yacht to get them to look at the disco, the theater, the pool, the helipad, the bulletproof deck, the onyx-laden and gold-plated interiors. He opened a closet and pulled out a collection of white golf caps that shouted TRUMP PRINCESS. “Anybody want some hats?” he said.

Also that month, the gossip pages of the New York Post ran the first public report suggesting Trump’s ongoing infidelity. A brief with no byline said a “shapely blonde” was dating “one of New York’s biggest tycoons, a married man,” and that the woman had been spotted in stores in Trump Tower saying, “Charge it to Donald.”

It was probably the biggest construction disaster I had ever seen.”

“It was no coincidence that these misbegotten deals came one after another in what was now the Marla Maples phase of Donald’s life,” Wayne Barrett would write in 1992 in Trump: The Deals and the Downfall, the first Trump biography. “She was just another symptom of the recklessness and arrogance that had seized him.”

Trump’s top executives began to fret about his decision-making overall. He was using the Trump Princess as a marketing tool for his casinos, making Trump’s Castle lease the yacht for $400,000 a month, which helped him avoid paying sales tax in New Jersey but made it an exorbitant line item for the underperforming casino. He paid $1 million to have the channel by the casino dredged so the mammoth vessel could motor in without scraping the bottom.

The back-and-forth with Merv Griffin dragged on, and Trump’s advisers tried to tell him to cut bait—just let Griffin have it all, Resorts plus the stalled, half-built Taj, they said. “It was probably the biggest construction disaster I had ever seen,” former Trump construction manager Tom Pippett told Hurt for his book. “The building was open to the ocean right through to the beach. Everything had been sitting there for years open to and exposed to the weather and the salt air. There were birds nesting in the sheet metal ducts.

Trump forged ahead.

“Everything is much bigger than it should be,” he told Manhattan Inc., describing the vision in his mind for the Taj. “It’s built as a dream.”

It was late in the summer that Lorenzo, the Texas Air boss in charge of Eastern Airlines, started searching in earnest for a potential buyer for Eastern’s shuttle service. Eastern as a whole was hemorrhaging money; its shuttle, flying from Boston, to New York, to Washington, was its only profitable entity.

Trump had purchased the yacht. He had purchased the Plaza. He was attempting to hammer out the purchase of the Taj. He was on a buying binge, and the banks were giving him virtually unlimited loans. And he loved elite, New York-associated properties—and the Eastern Airlines Shuttle fit the bill, ferrying upper-middle-class businesspeople up and down the East Coast power corridor for higher-than-average fares. Fortune had just labeled Trump a billionaire for the first time, estimating his net worth at $1.3 billion. One of his attorneys had just announced to Forbes that Trump’s “appetite for companies and his ability to feed it are both enormous.”

Trump, Lorenzo told me, “was an obvious candidate.”

Lorenzo met Trump in the Oak Room at the Plaza. Ignoring the advice of his two closest attorneys, according to Gwenda Blair’s book on Trump, to pass on the chance to get involved in any shuttle sale—Harvey Freeman didn’t return my calls; Jerry Schrager said he had no comment—Trump set up a meeting with Nobles, who at the time was slated to become president of the Eastern Airlines Shuttle.

It was early October. Trump had all but decided he was buying it. Now he wanted to hire Nobles.

“I met him at 4 o’clock,” Nobles told me. “At 5 o’clock, he offered me the job; at 6 o’clock, he said he wouldn’t let me leave the office until I accepted; at 7 o’clock, I accepted.”

A week later, there was a news conference, in a ballroom at the Plaza, announcing Trump had agreed to buy 17 planes, the routes and the landing rights at the airports in the three cities. It would be renamed, of course, Trump Shuttle. “Trump to Buy Eastern Shuttle for $365 Million Cash,” said the headline from the Associated Press—a year after Eastern’s own analysis had appraised this part of the company at $300 million at the most, for a shuttle service that had seen its profit of $28.2 million in 1985 dip to $16.8 million in 1987 on account of increasingly stiff competition from Pan Am’s version of the shuttle. The assessment from Standard & Poor’s? “A generous price.” From respected airline analyst Robert Joedicke? “Top dollar.” Lorenzo “really made out well on this deal,” Morgan Stanley airline analyst John W. Mattis told the Los Angeles Times. The deal also barred Trump from selling the shuttle to an independent owner for five years and to another airline for 10 years, according to Tim O’Brien’s 2005 book, TrumpNation.

He borrowed an additional $405 million from another cluster of banks—the balance earmarked for improvement to the planes that would include gold-plated faucets in the lavatories—and this time he personally guaranteed $100 million.

“I was astounded,” Nobles told me last month. “I had banks calling me. ‘How can we get in on this deal?’ People were throwing money at him.”

“None of the debt is personally guaranteed,” Trump lied to the Globe. “If the world goes to hell in a handbasket, I won’t lose a dollar.”

True, Lorenzo said. “He was able to negotiate with the banks to land him far in excess what he paid to us,” he told me.

“I like collecting works of art,” Trump told the Washington Post, echoing the language he used in his ads to justify the steep Plaza price. “This is a work of art.”

“I like playing real-life Monopoly,” he told the New York Times.

But in late October, the casino analyst who had told Trump the Taj was a mistake was quoted in a story in the Boston Globe. “Trump has only experienced an economy that is growing,” Roffman said. “Let’s see how he does in a real turndown.”

Trump sniffed.

“None of the debt is personally guaranteed,” he lied to the Globe. “If the world goes to hell in a handbasket, I won’t lose a dollar.”



***

“Is there any way a guy like you could go broke?” David Letterman asked Trump on his show that November.

The audience laughed.

Trump grinned.

“I think it’s a great time to really save as much money, in dollars, as you can,” he said.

It was a curious answer to the question. Anybody who had read the best media coverage of Trump’s business activities up to that point in 1988 knew the extent of the loans he had taken to get what he wanted. Forbes in May had pointed out that Trump was one of the few individuals on the publication’s annual list of the 400 richest people who routinely called to “insist we have greatly undercounted his wealth. But there are reasons to believe he is not as liquid as he would like us to think.” The magazine reminded readers his two casinos—not yet counting the Taj—were being floated on “100 percent borrowed money.” That was before the Plaza acquisition, and the story about it that ran in the New York Times in September said the hotel did not bring in sufficient funds to even cover the interest payments on Trump’s loans. Then came the eye-popping Shuttle sale. Trump was going to spend “tremendous amounts of money on each individual plane,” he had told the Associated Press. How? “I’m just going to do it.”

If the world goes to hell in a handbasket, I won’t lose a dollar.”

Maybe, sitting next to Letterman’s desk, Trump had in mind his Upper West Side rail yards land. He had started telling reporters he could sell it for as much as $900 million. New York real estate insiders laughed at that inflated figure. “Unmitigated baloney,” one of them told Newsday. Trump unquestionably could have sold it for a lot—he rejected offers of $550 million and $600 million, Barrett reported in his book—but Trump sat on it. He allowed himself, though, in the presence of a reporter from the Boston Globe, to think out loud: “Wouldn’t it be nice to have some cash for a change?”

He did, however, sell the St. Moritz hotel, to Australian billionaire Alan Bond, for $150 million—a significant profit he nonetheless exaggerated by saying he had bought the St. Moritz in 1985 for $31 million when, in fact, according to Blair in her book, he had spent $73.7 million.

“Other people are schmucks,” Trump told Fortune in late November, when he was asked about how he had said he had gotten out of the stock market before the crash of October 1987—even though, as Blair reported, too, he actually had suffered a $22 million paper loss because of some Alexander’s Department Stores shares he hadn’t unloaded.

“I am not a schmuck,” Trump said.



***

Trump could have backed out of the Shuttle deal at the end of 1988 and into 1989. Contractually, he had the right. Certainly, he had the reason. First the unions of the employees sued—saying the sale to Trump was tantamount to a union-busting tactic—and then, they struck. Pan Am took advantage, steadily upping its share of the shuttle market.

“I really see this as an eroding asset,” Trump said in testimony he insisted on giving in federal court in Washington.

By the end of March, Trump and Nobles had reached a conclusion. “We just couldn’t go forward,” Nobles told me. “We looked at each and said, ‘This just isn’t going to work.’”

The next day, Nobles said, his dad died. He flew to Arizona for the funeral. As he got off the plane in Phoenix, he heard his name over the loudspeaker. Trump was paging him. Nobles called.

“Listen,” Nobles heard Trump say, “sorry about your dad, but Frank Lorenzo has called and he still wants to do the deal.”

“OK,” Nobles said. “What do you want to do, Donald?”

The response Nobles heard from Trump: “I really want this property.”

But due to the delays and the devaluation of the Shuttle, Trump asked Lorenzo for five additional planes, extra assets—but extra airplanes, say aviation experts, are not ideal. Airplanes that aren’t in the air are airplanes that aren’t making money. “Lorenzo must have been laughing all the way to the bank,” former Trump casino executive John R. O’Donnell would write in his book, Trumped!.

Nobles told me it was helpful at times to have the additional planes so they could keep the routes full while having some planes refurbished to make them look the way Trump wanted them to look, with red, black and gold stripes and big Trump T’s on the tails and fancier seats and amenities inside. Trump’s airline struggled, though; as the economy slipped into recession in late 1989 and 1990, Trump pressed Nobles on ways to save money. He told him, among other things, to fly the planes with two pilots instead of three, Nobles said. He had to tell him that was impossible in a 727. Hampered by debt, the Shuttle never turned a profit.

Same with the Plaza.

The Taj, which ended up costing approximately $1 billion, rushed to open in the spring of 1990. It filed for bankruptcy the following year. The Trump Plaza casino did so a year after that. “The more casinos you had, the more cash registers you had,” Roger Gros, publisher of Global Gaming Business, told me. “He got in over his head.”

In 1990 and 1991, as Trump came out with the sequel to The Art of the Deal, titled Surviving at the Top, as his affair with Maples and his divorce from his wife became a major tabloid story, and as his total debt topped $3 billion, $900 million of which he had personally guaranteed, his lenders took back the yacht, the shuttle, the Plaza Hotel. The only thing that saved Trump from personal bankruptcy and permanent financial ruin: loans from his rich father and his siblings, and the severity, strangely, of his fiscal straits. The money was so big, the loans so brazen, that not only was he beholden to the banks—the banks were beholden to him. “Leverage: Don’t make deals without it,” Trump has said, and here his leverage was we’re in this together. The banks had been just as irresponsible as he had.

“I have a great relationship with the banks,” he told Time in 1991.

In 2005, two years into his revitalization as a reality TV star as the boss on The Apprentice, he sat for an interview with O’Brien, who was working on his book, TrumpNation, and he was asked what he had learned from his mistakes of the late ’80s and his Houdini act of the early ’90s. Judging from his record, what he learned was to build and buy less and market and license more. Image over assets. But that’s not what he said.

“I had a great string (of deals), and I think it was BusinessWeek, and they had a great story: Everything he touches turns to gold,” Trump told O’Brien. “The fact is, you do feel invulnerable. And then you have the tendency to take your eye off the ball a little bit and hunt around for women. And hunt around for models. And hunt around for shit instead of maybe doing what you’re supposed to do. Because you really feel it is easy. I mean, you feel it’s easy. Let’s put it this way: I’m much more cautious today than I was in the ’80s. Much more cautious. Because I can see what can happen. And I appreciate it much more today. In the ’80s, I didn’t even appreciate it. I figured, this is the easiest fuckin’ thing.”