It would be his last triumphant moment for a long time—maybe ever—and he knew it. News of his impending financial ruin topped the front page of the June 4 Wall Street Journal, which was even then thudding onto curbsides around the country. In front of a breakfast crowd of 3,000 in Las Vegas, Donald Trump was holding forth on his favorite subject: Donald Trump. It was, of course, the largest audience ever to assemble at the annual American Booksellers Association convention. They had come to hear the megamagnate promote his forthcoming second book entitled, ironically, Trump: Surviving at the Top.

“I said to [my editor], ‘I’m not doing this book. This book is madness. For me to come out with a book at this point, you have to be crazy,’ ” Trump recalled from the podium. “He told me the second one is going to outsell the first [The Art of the Deal, 850,000 hardcovers sold]. He knows how to turn me on, because I want to do that—keep going higher and higher—and then we die, and nobody gives a damn. It is pretty futile when you get down to it.”

Get push notifications with news, features and more.

It was an odd coupling of thoughts: lust for success and expectation of failure. Yet in Donald Trump the two impulses are perhaps inseparable, each drawing power from the other in a fusion reaction that drove him to the greatest heights from which a man could fall. “There is in Donald a genuine need to self-destruct,” says a person who knows him well. “In order to feel real and whole, he had to exceed himself constantly, make more money, build bigger buildings. Underneath there’s despair: Nothing I do is enough, and it never will be. And you can’t outdo yourself forever, so you have to f—- it up and start over.”

What Trump accomplished on the way up continues to amaze. His father, Fred Trump, had built—with his own hands, at first—a substantial fiefdom of low-and moderate-income housing in New York City’s outer boroughs. “If I ever wanted to be known as more than Fred Trump’s son,” Donald once observed, “I was eventually going to have to go out and make my own mark.” Starting, he says, with a patrimony of $200,000, Donald dared to build his fortune where others feared to tread, scarfing up Manhattan property from the ruined Penn Central Railroad in the near-bankrupt New York City of 1974. He bought the rundown Commodore Hotel and, with the help of the enormous tax breaks he demanded, soon turned it into the glittering Grand Hyatt Hotel, the first and last major project he failed to name after himself. Like an attention-starved graffiti artist, he proceeded to emblazon his name on anything that stood still (Trump Tower, Trump Plaza, Trump Pare, Trump Palace, Trump Castle) and some things that didn’t (his Trump Princess yacht and the Trump Shuttle airline).

His grandest edifice to date, the 120,000-square-foot Trump Taj Mahal Casino—with 3½ times the floor space of its namesake in India—opened in April. Yet he planned bigger things. Trump City, to rise on abandoned railway yards on Manhattan’s Upper West Side, was to include 11 60-story buildings grouped around the world’s tallest building, a 150-story skyscraper—”the ultimate symbol,” he called it. When nearby residents objected that they would be shrouded in shadow and choked by traffic, he replied, “What they think doesn’t matter. They have no power.”

He, on the other hand, had everything: a stunning former-model wife, Ivana, and three privately schooled children; the fawning attention of rock stars, celebrity athletes and such shapely young women as Maria Maples; and the adulation of the masses to whom he held himself out as a sort of Messiah of Mammon.

But in this year of his 44th birthday, Trump’s marriage fell apart, and now his empire is crumbling too. Condo sales stalled, the Atlantic City casino business was saturated—by him—and tightening credit markets made it harder to raise money to cover his debt on such high-price properties as the Trump Castle Hotel and Casino. Owing $2 billion to banks and $1.3 billion to bondholders, he missed $73 million in payments due in June. In a last-minute deal to save him from default and bankruptcy, and thus protect their investment in him, the banks last Tuesday extended Trump a new $65 million loan, but there were enough strings attached to permanently moor his 282-foot yacht. Much of his income will flow straight to his creditors, and he must clear important business decisions with them. Particularly irksome is the requirement that Trump limit his personal living expenses to $450,000 a month, which will mean cutting back by more than $100,000 his monthly outlay on such fripperies as $2,000 suits and the ministrations of the staff at his three homes. The $841,000 monthly upkeep of his yacht and the $246,000 monthly expense of his private 727 jet are excluded from the limit, but that is scant comfort, as he immediately put the plane up for lease, and he has been trying to sell the yacht for some time.

Indeed, Wall Street sources say that the purpose of the bailout is not to get Trump up and running, but merely to buy time for the banks to oversee the sale of virtually all of his assets. Donald Trump’s empire, once valued at $3 billion, may be as good as gone, and even his private wealth is at risk. His debt is said to include $500 million in personal loans, and though he claims to be worth more than that, some analysts assay his net worth at less than zero.

As his world unraveled, Trump maintained a reflective composure. “You know,” he told PEOPLE in April, “there was an old Twilight Zone episode: It was about a man—he wasn’t a good man—killed in an accident. Then somebody came up to him and said, ‘You can have any wish you want.’ And he said, ‘I want to win all the time. I want to win, win, win. Everything I want, I want to get. I want to get the most beautiful women. I want to get the most beautiful this and that. I want to never lose again.’ ” Trump paused, remembering. “Then they showed him playing pool. He was winning every time. Everything he did, he won, won, won. And the person came back to him, and this man said, ‘If this is Heaven, let me go to Hell.’ And the person said, ‘You are in Hell.’ This was sort of interesting.” Trump let out an exhalation that in a less upbeat person might have been taken for a sigh. “I’ve had a lot of victories,” he went on. “I fight hard for victory, and I think I enjoy it as much as I ever did. But I realize that maybe new victories won’t be the same as the first couple.”

Diminishing thrills in the dominion of victory need no longer concern Donald Trump. His course is now set for the terra incognita of defeat. How did he come to this pass? Those who know him offer an abundance of causes.

Just Desserts

Trump was never a serious contender for the title of Most Venal New York Developer. Indeed he was often generous, donating about $4 million a year to such causes as AIDS research and a New York State Vietnam Veterans Memorial. But in his business dealings, he could be brutal.

To demolish the stately Bonwit Teller building on Fifth Avenue to make way for Trump Tower, a pending lawsuit alleges, Trump’s contractor utilized 200 Polish laborers, most of them undocumented aliens, to work for as little as $4 an hour—union scale was $11. Then the workers weren’t even paid all of the meager sum they had earned. Trump denied any knowledge of what went on. “It was disgusting how he used people,” recalls Daniel Sullivan, then a labor-relations consultant to Trump. “I said, ‘Don’t exploit them like that. Don’t try to f— these poor souls over.’ It baffled me then, and it makes me sick even now that he knowingly had these Poles there for the purpose of Trump Tower at starvation wages. He couldn’t give a s—-because he’s Donald Trump and everybody is here to serve him. Over time he became more and more monstrous and arrogant. I asked myself, ‘How long is it going to take for all of this to catch up with him?’ ”

Actor Christopher (Superman) Reeve, a resident of Manhattan’s Upper West Side, once met with Trump to suggest that rather than erect a 150-story palace for the wealthy, he might consider building some affordable housing for the homeless sleeping on the neighborhood’s streets. “I said, ‘You’re going to build this tremendous monument to yourself, and you’re going to make the rest of us live in your shadow,’ ” Reeve recalls. “He said, ‘Well, I respect your opinion.’ With an ego that size, an hour’s conversation with me was not going to make a dent.” Perhaps Trump should have listened. Community opposition has stymied his attempts to secure zoning and building permits, and the plot still lies fallow five years after he bought it.

Social Climbing

Many who know him believe that Trump’s reach exceeded his grasp because he was striving for something his new money could never buy: acceptance by New York City’s high society. “He’s very insecure,” says a close personal and professional acquaintance. “He’d tell about how when he first moved to New York he was shunned by a lot of people—hardly any invitations to the Hamptons for the weekend and all that. Although he claims he doesn’t care, you know deep down it bothers him.”

Trump avows that the old-line rich are frivolous and boring. For their part, the upper crushes consider him arrogant and coarse. It apparently never occurred to either side that they might both be right. So the lines were drawn, and Trump took up the challenge of joining the club that wouldn’t have him. “He thought they would accept him if he built the biggest building or if he owned the most important landmarks,” says the acquaintance. “The tragedy is they never wanted to accept him, and the harder he tried the more they laughed at him after they left his parties. He doesn’t see that he has had everything a man could hope for: a beautiful wife, three perfect kids and enough money to last them all their lives. Unfortunately he’s just out to impress.”

Palm Beach society still titters about the Trumps” fruitless attempt to get into the exclusive Palm Beach Bath & Tennis Club shortly after they bought their 118-room Florida estate, Mar-a-Lago, five years ago. Hoping to be at least invited to a club luncheon, they flew some 40 New York City-based club members on the Trump jet for a weekend bash at Mar-a-Lago. His guests feasted and drank and cut the blue-and-gold rug late into the night, but left without offering a reciprocal invitation to lunch.

Donald’s chances might have improved had he listened to his Mar-a-Lago maids. “I just couldn’t take it anymore,” recalls Reidun Torrie, who says she quit after three months. “When the Trumps came, they put plastic Trump Castle ice buckets in each of the guest bedrooms. Well, you just don’t do those things.” What’s more, says Torrie, “they weren’t very nice to the help. I never did like Donald or Ivana. She has steel rods up her nose—and a hot temper. She ain’t no lady. I’m sorry they bought Mar-a-Lago, and to be very honest I hope they don’t get to keep it. It just doesn’t suit the Trumps. They have no class.”

Now that Trump’s in the dump, the envious and resentful are in full cry. Says New York City society pianist Christopher Mason, “High society is saying, ‘Thank God it happened. Why did it take this long?’ People are dancing in the streets.” Yet, notes columnist James Revson, society women rallied around Ivana after Donald left her in February amid the clangor of publicity over what Trump calls his “friendship” with model Maria Maples. By flaunting his apparent relationship with Maples and insisting that after a divorce Ivana would get only their Connecticut mansion and $25 million, Trump fell further from social grace. “People thought he behaved like a true cad,” says Revson. “He treated her like garbage, and that doesn’t play well.”

The Question of Maria

Maria Maples, who appeared at a dinner for Trump at the booksellers’ convention in June, stands by her man. “Donald has an incredible inner strength which helps him to maintain control and focus even in the most pressured times,” she says. “Donald is an extremely intelligent man, and as long as he trusts himself and does what he knows is appropriate he will succeed.”

Such earnest support draws only scorn from the ladies who lunch, who claim they’ve seen it all before. “Maria’s a cheerleader,” says one. “At this point in his life, where he’s in his 40s, it’s the same old story. It’s the young woman cheerleader who spends the whole day fixing her body up and he comes home and her arms are open and there’s no intellectual challenge. It’s just a big smile, a giggle and a cheer.”

If that sounds like a scene from a mid-life crisis, Trump denies it. “I don’t believe in mid-life crisis,” he insists. “I’m not sure there is such a thing, and I’m not sure I’m in mid-life.” But he is in crisis, and some lay the blame on l’affaire Maria. “For three years this has been going on, and it has blown his judgment on everything,” continues the socialite. “The things he has done have been disastrous financially. In those years he was cheating, lying, betraying, manipulating and maneuvering so that Ivana wouldn’t find out and people within his organization wouldn’t find out. It takes a lot of energy to cheat, and that energy should have been in his business.”

Says another Trump observer, “With Maria, I don’t think he understood that we are still a very puritanical society. Bankers of all people—they may be screwing around too—but they don’t want to lend billions of dollars to somebody who’s behaving like a kid in high school. It says to them that he’s immature and he can’t control himself.”

The 80’s Are Over

In the booming ’80s, Trump’s lack of restraint—fiscal, not physical—only helped him. He was buying into a rising market, and even if a property’s income didn’t cover interest expenses, demand for real estate would drive its price up. Then he would borrow against its rising value to buy more. “It’s funny what’s happened,” he wrote in The Art of the Deal, “bankers now come to me, to ask if I might be interested in borrowing their money. They know a safe bet.”

Now those bets are off. “Trump was the perfect character for the ’80s,” says New York Times architecture critic Paul Goldberger, a longtime observer of the Manhattan real-estate market. “He was mainly smoke and mirrors, very highly leveraged in every way. In the ’90s there’s not room for that.” But Trump, apparently assuming the boom would never end, forgot the very rules he set out for himself in his own book. “If you plan for the worst—if you can live with the worst—the good will always take care of itself…. The point is that you can’t be too greedy…. What you should never do is pay too much…sometimes your best investments are the ones you don’t make…. I try never to leave myself too exposed.” Famous last words.

“Money was never much of a motivation for me,” Trump has said, “except as a way to keep score.” Now it’s the bottom of the ninth, and he’s so far down, the crowd is leaving the ballpark. Of course, some hopeful fans remain. Insists Roger Stone, a longtime business associate: “He’s audacious, he’s imaginative, and given a fair chance he’ll kick ass again.” Even some of his critics hope he can rally, but not to resume his old ways. “I think Donald Trump should be given room to live and to transform,” says Christopher Reeve, who wonders whether a financial Armageddon might prove a morally bracing experience for the deal maker. “Some people would like to crush him like a bug, but that doesn’t help anybody. What would be great would be for Donald Trump to use his money and his energy and his talent to help people. He’d become a hero if he’d do that.” Stranger things have happened, but few foresee Trump donning sackcloth and ashes. “The minute he steps out of bed in the morning it’s important for him to say, ‘I’m the best, I’m the greatest,’ ” says Ned Schnurman, who’s working on a documentary about Trump. “He can’t say that now.”

What can Trump say? Perhaps he could quote himself. “Sometimes,” he said in The Art of the Deal, “not often, but sometimes, less is more.”