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WILL DONALD TRUMP OWN THE WORLD? No, but he's trying -- and an inside look at his operations reveals how. Key elements include shrewd use of copious debt and quite astonishing chutzpah.
By Monci Jo Williams REPORTER ASSOCIATE David J. Morrow

(FORTUNE Magazine) – CONSIDER the novel concept that Donald Trump may only appear to be a self- centered, breast-beating egomaniac. Perhaps he is really just a victim of what pop psychologists call the ''impostor syndrome'': He is successful, but he doesn't really believe he could have done it. Should he? Despite all the publicity, the breast-beating, and even the best- selling book, the story of how Trump really makes all that money has until now never been told. Looking into it reveals not only a no-fooling billionaire, but also an investor with a keen eye for cash flow and asset values, a smart marketer, and a cunning wheeler-dealer given to tough-guy tactics. Yes, Donald, you should believe (presuming you actually have any doubts). Trump's life is a media event, and lately he has kept the press hopping. In October he announced plans to buy the Eastern Shuttle for $365 million and to sell Manhattan's St. Moritz Hotel to Australian beer baron Alan Bond for $180 million. Other press accounts reported that Trump, 42, was angling to sell the West Side rail yards, the undeveloped plot of 78 acres bordering Manhattan's Hudson River on which he had hoped to erect the world's tallest building. His brother, Robert, an executive vice president of the Trump Organization, won't confirm the rumors (''We may sell it, we may not''), but Donald says that if he does, he could get as much as $800 million. Real estate experts say he is more likely to get $500 million to $600 million. Mingled with all this Trump news have been regular progress reports on his plan to divide up Resorts International, the casino company he controls, with Merv Griffin. After several postponements, the deal was scheduled to close in late October, but rumors had it falling through. The speculation: Griffin couldn't come up with the $365 million he had promised, or Trump couldn't come up with his $275 million, or both. Each side denies any problem with financing, but if there were a hangup, it would seem unlikely to be with Trump. His net worth is tough to nail down because it is impossible to determine the debt on his personal holdings -- the 20-acre Palm Beach estate Mar-a-Lago, the three-floor condominium with gold- accented ceilings in Trump Tower, the 300-foot yacht, the 727 jet, and more. But it is possible to estimate the value of Trump's business holdings, the amount of debt attached to them, and their likely cash flow. This can be gleaned from information available through public documents, business associates, competitors, security analysts, and other experts. By FORTUNE's estimate, Trump's two Atlantic City casinos, his commercial real estate in New York and Palm Beach, his hotels, his stock, and his other business holdings are worth $1.575 billion net of debt (see table, page 152). That figure includes his ownership of the St. Moritz Hotel, which he has agreed to sell, and also includes the Eastern Shuttle, which he has agreed to buy. It includes stocks Trump owns, but does not include cash, since the figures are not confirmable. Trump will not divulge the amount of cash he holds. To do so, he says in an uncharacteristic fit of modesty, would be ''too braggadocious.'' But a source very close to Trump claims the man is sitting on $550 million of cash not included in FORTUNE's calculations. If that is true, Trump's business holdings would be worth $2.125 billion. The press usually identifies Trump as a real estate developer, but that description is as narrowly accurate as calling Ronald Reagan a former actor. While real estate was and is the foundation of Trump's fortune, the steadiest gush of cash to the privately held Trump Organization flows from Atlantic City. His two casino-hotels, Trump Plaza and Trump's Castle, will generate about $100 million in operating profits this year. In addition, stock speculation has apparently been a rewarding sideline for Trump. Counting only activity that he has publicly reported, he has earned about $137 million on stock in six companies since 1986 (see table, page 159) and today has paper profits of $300 million in four others. Trump claims to have bailed out of the stock market before last year's crash. (''Other people are schmucks. I am not a schmuck.'') He has certainly been extraordinarily lucky at times, less so at others. He bought about $14.8 million of shares in Federated Department Stores just two weeks before Canadian real estate developer Robert Campeau made his bid for the company last January. Thanks in great part to the bidding war for the company that erupted between Campeau and Macy's, Trump made at least $22 million on the investment (he says the figure is higher, but won't say how much). He bought into another takeover target, Gillette, after Coniston Partners had launched its raid, and made only about $2 million on an investment of some $14.9 million. REAL ESTATE developments, particularly the luxury condominiums in Manhattan, have been far more lucrative for Trump than most people realize. By FORTUNE's estimate, roughly $100 million has rolled into the Trump Organization from Trump Tower, the Fifth Avenue complex of condos, offices, and shops that opened in 1982 and that made Trump's name. Trump's partner in the deal was the Equitable Life Assurance Society. Wally Antoniewicz, senior vice president of Equitable Real Estate Investment Management, says that Equitable realized a gross profit of about $90 million and that Trump's gross profit was about $100 million, a figure with which Trump agrees. But while Trump and Equitable sold off most off the condominiums in the building, Trump kept a big chunk of the office and shopping space for himself. As a result, Trump Tower continues to pay him a handsome annuity. Besides a three-floor condominium, which serves as one of his homes, he bought five floors of condos to rent. He also bought 180,000 square feet of office space and about 150,000 square feet of retail space, which he leases to Bonwit Teller and other merchants in the rose-marbled shopping atrium. Trump paid $45 million for all this space, and it pays him about $30 million a year. When a man grows rich as quickly as Trump has, especially in real estate, he is inevitably rumored to be in debt up to his eyeballs. Trump has certainly borrowed a lot of money, yet he seems to be a more conservative borrower than one might expect. He usually makes sure that the cash flow from a property he buys will be enough to service his debt with a considerable safety margin. Even when he builds condominiums, Trump rarely dips into cash from other investments to finance the project. For Trump Parc, a luxury condominium on Manhattan's Central Park South that Trump began in 1986, he took out a $40 million mortgage to buy the land and another $50 million to finance construction, development -- and carrying costs. Like a Latin American country, he uses some of his loan to pay the interest on itself. Last year, with only about 30% of the units sold, he paid off the debt with part of the proceeds. A rare exception to Trump's rule that each deal pay for itself is the Plaza Hotel, which he bought in August from Robert Bass and Aoki Corp., a Japanese construction company, for $400 million, all borrowed. Trump has since reduced the debt to $325 million, but the Plaza will still lose about $5 million this year. Hotel analysts say he overpaid, but Trump contends he can reduce his cost by converting part of the property into condos and selling them. Besides, there's an extra consideration with the Plaza. As Trump says, ''For me this is like owning the Mona Lisa. It's not just an investment, it's a work of art.'' To keep the ferocious deal machine running, Trump leans heavily on a few other people. Younger brother Robert, 40, is an executive vice president who keeps an eye on Atlantic City operations. Harvey Freeman, 50, a precise, dry- humored fellow, is a former real estate lawyer and developer who analyzes the financial fundamentals of Trump deals. Alan ''Ace'' Greenberg, chairman of Bear Stearns, is the closest thing Trump has to an investment banker. But like most successful people, Trump is obsessive about work and cannot help sticking his fingers into everything. He recently considered 52 types of doorknobs for a condominium before making his choice. Blanche Sprague, the whirlwind in charge of developing and selling Trump condominiums, recalls the time he called her to check on the details of a building. She could hear water thundering in the background. ''Where are you, under a waterfall?'' asked Sprague. ''No,'' replied the always working developer, ''I'm in the bathtub with ((son)) Donny.'' TRUMP has acquired a reputation for tough-guy tactics in business dealings with contractors, lawyers, architects, competitors, and even state and local regulators. He has been known to refuse to pay all or part of a bill if he is unhappy with the work provided, and he will take the matter to court rather than negotiate a settlement. A standard Trump negotiating stance is, ''You need me more than I need you.'' He will bargain suppliers down to prices that a Trump aide says are ''fair but not overly generous'' by telling them that plenty of people are lining up to work for Donald Trump for free. Apparently some are; among decorators, for example, to have worked on a Trump building can be a valuable credential. He is often impolitic. Trump says he has not met with the New York community group that has opposed his plan to build the world's tallest building on the West Side rail yards site. Why not? ''What they think doesn't matter. They have no power.'' Trump has also run afoul of various regulators. In April he agreed to pay a fine of $750,000 levied by the Justice Department for failing to report ownership of stock in Holiday Corp. and Bally Manufacturing that he bought through Bear Stearns in 1986; he had accumulated enough to require reporting under Securities and Exchange Commission rules. The violations, says Trump, resulted from a ''technical misunderstanding.'' (The government also fined First City Financial Corp., controlled by Canada's Belzberg family, another Bear Stearns client, for a similar infraction.) THE MASTER PROMOTER says that any accounting of his net worth should assign a value to the Trump name. That may sound like more of the familiar braggadocio, but the man has a point. There is undeniably a Trump mystique. Some people love him, others despise him, but everybody talks about him. He has become a cult hero for many people around the world, who seem to regard this flamboyant billionaire as the most heartening example of the American dream come true since Ross Perot. Trump wasn't born poor. He was born rich. His father, Fred, 82, is a tough, self-made man who amassed about $20 million by building and running rent- controlled apartments in the New York City boroughs of Brooklyn and Queens. (Donald started out assisting his father but went off on his own in his 20s; he says little about the extent to which his father helped him get going.) Socially, however, Trump sprouted from decidedly unglitzy roots. Bad enough that dear old dad was a New York landlord. Trump grew up in Queens, and snobbish Manhattanites dismiss the unfortunates who hail from the Bronx, Brooklyn, and Queens as lowly BBQs. Like those snobs at the center of the universe, Trump saw Manhattan as the be-all and end-all, the only place to want to be. He is in some ways the ultimate wanna-be, and that is a key ingredient in his success, for one of Trump's chief appeals is to people who wanna be too. He speaks simply, colloquially, and with much profanity. He seems to have little sense of humor, particularly about himself, but he does enjoy his money and fame. Squealing ''Oooh, you're bad,'' he will let a reporter tug on his hair to test the rumor that he wears a rug. (He doesn't seem to; he does use hair spray.) When Trump appeared at a Palm Beach bookstore to promote his book, Trump: The Art of the Deal, so many autograph seekers showed up that the session stretched from a scheduled one hour to six. At one point the crowd pressed forward with such force that the security guards panicked and rang down the steel gates that protect the store windows at night. The people cared not, and shoved hands and arms through the gates to try to touch the author. HE IS NOT merely a self-promoter in the style of P. T. Barnum. He is an instinctive marketer. Prime example: Trump Tower. Little known when he began the project in 1979, Trump picked a site next door to Tiffany on Manhattan's Fifth Avenue, where important people and wanna-bes from all over the world flock to shop till they drop. Wealthy people in France, South America, and Japan might not have heard of Donald Trump, but Fifth Avenue and Tiffany they knew. The condos not only sold -- to those buyers and others -- they blew the ceiling off the market. High-end apartments and condominiums in Manhattan (of which there were then relatively few) were going for about $350 per square foot. Trump's condos, in an ultraluxurious building at one of the world's great locations, fetched an average of $700 per square foot. The enormous success of Trump Tower enabled Trump to introduce a brand name to a class of products that previously had no brands, a textbook marketing strategy. That name indisputably adds value. Blanche Sprague says that the standard question from prospective buyers -- even the rich and famous -- is, ''So tell me, is Trump around here a lot?'' Though brother Robert says real estate will always be a primary business of the Trump Organization, Trump has been casting his eye on other horizons. He says he is ''getting ready to do something very big in the corporate area'' and claims to be hoarding cash so that he can finance his deals if interest rates rise. But whether he is hankering to bite off just a morsel, as he did with the Eastern Shuttle, or to gobble up a whole company, he will not say. If Trump does buy a company, it will be a first. He has taken positions that range from 0.4% of a corporation's shares (in Pillsbury) to 88.1% (Resorts International). He usually buys stock in companies because they own a hard asset -- a hotel, a casino, a piece of real estate -- that he might like to own. Sometimes, as with Pillsbury, he invests in corporations that are rumored takeover targets. The management of the company in which Trump invests, not to mention the stock market, usually reacts as if Trump is a big, bad raider who will huff and puff till he blows the house down, adopting poison pill defenses and occasionally paying greenmail. But Trump has yet to swallow a company whole. Trump's largest and newest gamble centers on Atlantic City. If his deal to split Resorts International with Merv Griffin falls through, Trump could resume his earlier plan to take Resorts private. If the deal closes, Trump will get as his share a half-finished casino-hotel called the Taj Mahal. Trump's interest in the Taj seems curious, since it has been a sinkhole for Resorts' management. Resorts had poured $467 million into land and construction of the Taj when Trump took control of the company in 1987, and Trump has filed a junk bond offering through Merrill Lynch to raise another $675 million to get it up and running. WHAT TRUMP will have when the Taj is completed is the tallest building in New Jersey (42 stories) and by far the biggest gambling den in Atlantic City, with a casino bigger than two football fields. Competitors worry that if Trump can't fill the huge casino and turn a profit, he could default on his bonds, making it harder for other Atlantic City casino operators to raise money at reasonable rates. But where they see danger, Trump, the cash flow investor, sees opportunity. He believes he can make the Taj profitable by applying Nevada's success formula: Reel in the high rollers and bring on the conventioneers. The Taj would be the first casino hotel in Atlantic City with enough rooms and meeting space to be a convention host. Robert Trump says it will serve as a magnet for regional conventioneers; Trump's two other casino-hotels can handle the spillover. Air service to Atlantic City is still spotty, but the Eastern Shuttle -- to be renamed the Trump Shuttle if the deal goes through -- could ferry conventioneers from up and down the East Coast. As for the high rollers, Trump has been wooing them for a while, with some success. He flies them down from New York City on helicopters labeled Trump Air. And because fans of boxing also tend to be big gamblers, he has added to his crowded resume the role of fight promoter. When Trump staged the heavyweight championship fight between Mike Tyson and Michael Spinks at the Atlantic City Convention Center, conveniently situated next to Trump Plaza, betting at the casino that weekend increased 250%. Since the sale of tickets at up to $1,500 a pop covered the $11 million Trump had put up to stage the fight, the casino's winnings on all that extra betting were pure, incremental profit -- a $15 million bonus, Trump says. No appraisal of Trump's moneymaking abilities would be complete without noting the man's quite astonishing chutzpah. Consider the case of a management contract that plays a seemingly small role in the Resorts deal. Soon after Trump won control of the company, he persuaded the board to award him a management contract that would pay him $100 million over five years to run the company and oversee completion of the Taj. Since completing the Taj was ostensibly his principal goal in buying Resorts, it isn't clear why he would need a $100 million inducement. But the board nevertheless acquiesced. Then, when Merv Griffin came along and topped Trump's offer to take Resorts private, he agreed to pay Trump $63 million to buy out the management contract. If the deal with Griffin goes through, Trump in effect will receive $63 million for an agreement he cooked up as an incentive to himself to do something he wanted to do anyway. Trump professes to be amazed at how easy it is for him to make money sometimes. As he says, ''I will be getting $63 million for a piece of paper that didn't exist six weeks earlier. Just say I'm very happy with the deal Merv made with me.'' A gaming executive sums up his competitor nicely: ''Donald Trump can pull a rabbit out of a hat when the hat doesn't exist.'' Now if only Trump believed it, we could all get some peace.

CHART: NOT AVAILABLE CREDIT: NO CREDIT CAPTION: HOW TRUMP MAKES HIS MONEY Trump got rich developing hotels and condos, but casinos account for about half his current cash flow. These estimates -- which Trump says are too conservative -- exclude cash and personal holdings. DESCRIPTION: Color.

CHART: NOT AVAILABLE CREDIT:NO CREDIT CAPTION: TRUMP'S PICKS OF THE PAST DESCRIPTION: Color.