Donald Trump wasted no time in being Donald Trump. “I’ve brought some things for you,” he said, handing me a sheaf of papers as he boarded his private 727. These included some glossy brochures and a copy of New York Construction News, which, it seemed, had named Trump owner and developer of the year for 1999. “Owner and developer of the year,” he pointed out with his uncommonly stubby fingers, “which is unusual.”
It was early January, and the plane was headed for Minnesota, where Trump was to meet with Governor Jesse Ventura to discuss running for President on the Reform Party ticket. Onboard were a handful of journalists, Trump’s son Donny Jr., and his political adviser, Roger Stone, a former Nixon and Reagan handler who favors three-piece pinstriped suits and a pocket watch. Also onboard were some gold-plated sinks, a double bed, and gilt-framed works of art with signatures like “Renoir.” Nobody I asked seemed to know if they were real, or to care.
“We’ve done internal polls that have been amazing,” Trump was saying, ensconced in a red-velvet seat while Stone sat nearby in his Jay Gatsby getup. “If I feel I could win—win—then I’d run. I think I have a good chance.” He explained why. “Hey, I’ve got my name on half the major buildings in New York,” he said. “I went to the Wharton School of Finance, which is the No. 1 school. I’m intelligent. Some people would say I’m very, very, very intelligent.” Plus, he had written three best-selling books. “Not bestsellers,” Trump clarified. “No. 1 bestsellers.” Another thought occurred to him: “You know I am the highest-paid speaker in the country?”
Trump had inked a deal with Tony Robbins, the frighteningly upbeat motivational speaker, by which Robbins would pay Trump $1 million to give ten speeches at his seminars around the country. Crucially, Trump had timed his political stops to coincide with Robbins’ seminars, so that he was “making a lot of money” on those campaign stops. “It’s very possible that I could be the first presidential candidate to run and make money on it,” Trump said, adding that “there’s no way a good businessman” would have blown the kind of money Steve Forbes had. I wondered whether Trump was proposing his own special version of campaign finance reform here. I also wondered where he was planning to come up with the $100 million he was promising to spend if nominated, considering that his cash flow seemed much more precarious than he claimed.
But talk turned to Trump’s women, prompting a reporter from the New York Post to ask whether he found Monica Lewinsky attractive. Trump screwed up his face and stuck his tongue out slightly, as if to gag.
“There’s a John F. Kennedy-type charisma that’s very hard to put your finger on,” Stone told me later on, when I asked him to describe Trump the politician. “He’s probably the best speaker on the circuit.” Once on the ground in Minneapolis, Trump was greeted on the frozen tarmac by a passel of Reform Party officials, who whisked him off by limousine to the hotel conference center.
After the Jesse Ventura action figures went on sale in the lobby, and not long after Ventura insisted he once saw Muhammad Ali levitate—no kidding, levitate!—off somebody’s kitchen floor, Trump took the stage to address an audience of Ventura backers. Though he dispensed with his usual critiques of Pat Buchanan (“a Hitler lover”), Bill Bradley (“a total disaster”), George W. Bush (“no Einstein”), Fidel Castro (“a bad guy”), North Korea (“run by some very bad people”), and Russia (“totally mixed up”), Trump did tell an unflattering joke about his second wife, Marla Maples, and crescendoed from a story about Jay Leno to the oblique observation that he’d count on people’s support “if I decide to do the thing that I very well might decide to do.” This, it turned out, was the applause line. “It was awfully disjointed,” one of Ventura’s people worried afterward. “Does he speak better than that?” But by then Trump had already headed out the door, past the “Trump 2000” posters, for a weekend of golf at Mar-a-Lago, his Palm Beach estate.
At age 53, a good decade and a half after he came to national prominence, Donald Trump is possibly the most famous businessman in America. According to the Gallup Organization, fully 98% of Americans know who he is. Bill Gates and Ross Perot also score in the high 90s. None of the other grandees of American business—not Jack Welch, not Warren Buffett, not Steve Jobs, not Ted Turner—even come close.
This embarrassing state of affairs might be likened to the time when Betty Crocker polled as the second-most-admired woman in America (behind Eleanor Roosevelt, who had the advantage of being a real person) or when kids voted Hulk Hogan their favorite athlete a few years back. For Donald Trump is to business what professional wrestling is to sports: part of it, certainly, but also a cartoonish parody of it. Which is why Fortune decided it was necessary to investigate and uncover, once and for all, why it is we feel compelled to write about Donald Trump in the first place.
The most impressive aspect of Trump’s celebrity, to begin with, is not its grandeur but its durability. Not only has he far outlasted the decade that produced him, but—unlike other products of the 1980s who’ve managed to stay in the limelight through self-reinvention a la Michael Milken—Trump has done it without any discernible personal growth. Like a cryogenically frozen Austin Powers, he stands as an almost perfectly preserved specimen of the era, an unreconstructed hedonist who persists in calling the plantings on his new golf course the “Rolls-Royce of oak trees.”
That changelessness, no doubt, is partly to account for his appeal. In an age when wealth is paper, assets move electronically, and moguls wear jeans, Trump’s mandarin tastes and almost sensual love of money can seem a refreshing throwback. “I, personally, like feeling the asset,” he said during a stop in Silicon Valley. “With the dot-com, it’s nothing that you see so easily.”
It’s one of the paradoxes of Trump that this aura of exclusivity goes over best with some of the most excluded elements of society. In an 800-person survey conducted by Democratic pollster Rob Schroth, Trump scored a 67% favorable rating among blacks (vs. 21% unfavorable), 62% among Hispanics, and 66% among whites earning under $25,000, substantially higher than either Al Gore or Bill Bradley in each category. Real estate agents say Trump is also big among immigrants, many of whom flock to his buildings. Admiring rap artists have recorded odes like “Black Trump” and “Trump Change.” “I think people say, ‘If I won the lottery, that’s how I’d want to live,’ ” says Roger Stone. “The plane, the boat, the estate in Florida, the beautiful girls—our polling showed that people identified with it.” Trump is, in short, a workingman’s plutocrat: a nonbusinessman’s idea of what a businessman should be. (Supporters standing in line at a Trump Tower book signing included a Greenwich Village artist who was “attracted to the power of myth in our society,” an Orthodox rabbi who “heard he loves the Jews,” and a soccer mom who noted, optimistically, that “he’s never been indicted.”)
Among Trump’s theoretical peers, which is to say other rich business people, the situation is different. When Fortune asked several thousand of them to rank 469 companies for its 1999 list of Most Admired Companies, they put Trump’s casino company dead last. More specifically, they ranked it worst in quality of management, use of corporate assets, employee talent, long-term investment value, and social responsibility.
Trump tries to shrug off such opinions, noting in his new book, The America We Deserve, “Rich people who don’t know me never like me. Rich people who know me like me.” But deep down, the disrespect clearly rankles. “I was a little surprised Fortune hadn’t done a cover on me in the last year and a half, because I’m the biggest developer in New York,” he said on the plane. “Now I’m getting a story not because I’m the biggest real estate developer but because I’m running for President. There’s something about that that I don’t really like.”
Did he mean he doesn’t get the recognition he deserves as a businessman? “I don’t think anybody knows how big my business is,” Trump replied. “People would rather talk about my social life than the fact that I’m building a 90-story building next to the U.N….They cover me for all sorts of wrong reasons.”
For more on Donald Trump, watch this Fortune video:
Right or wrong, his presidential dalliance had generated coverage and then some; Trump recounted how Don King, the furious-haired boxing promoter, called up to declare, “This is the single greatest promotion I have ever seen!” It was widely presumed, of course, that Trump’s political noodlings were just that: a promotion, a cynical ploy to sell books and condos—politics as the continuation of salesmanship by other means, if you will. But after spending time with Trump over several weeks, I became convinced otherwise. The man seriously wanted to seek the American presidency—to win, as he put it, “the whole megillah.”
If that sounds far-fetched, it may be because you haven’t yet grasped the governing principles of the Trumpian universe. Consider, for instance, his beef with America’s trade representatives: It’s that they have low name recognition. “Who are these people?” Trump sputtered at one point. “Nobody’s ever heard of them!” As for candidates who had made less money than he: “They’re losers. Who the hell wants to have a person like this for President?” More famous, more money: To those who objected that he had no obvious qualifications for politics other than a Bob Dole-like tendency to refer to himself in the third person, Trump offered the vaguely articulated but firmly held notion that he was, like, the top guy, and therefore worthy of the nation’s top office. He even noted at several points that he was good at sports in high school. “Because I’ve been successful, make money, get headlines, and have authored bestselling books,” he wrote in his new book, “I have a better chance to make my ideas public than do people who are less well known.”
Just so. But it all raised the question: Just how successful a businessman is he?
A couple of weeks after the Minnesota trip I was sitting in the Trump Tower offices of the Trump Organization, surrounded by magazine covers featuring Donald Trump and flanked by two of Trump’s lieutenants. In front of me sat Donald Trump. He was wearing a blue suit, cuff links, and one of his famous red ties; his hair, as usual, seemed to be levitating slightly above his skull in a baroque swirl. “People liked the speech,” Trump began. “You even liked it, I heard. Did you like my speech?” I mumbled something polite, then turned the conversation to the task at hand: figuring out what Trump’s empire actually consisted of.
Easier said than done. Trump delights in the sort of elaborate shell games and impenetrably complex deals that frustrate the most conscientious efforts to assess a person’s true worth. “It’s always good to do things nice and complicated,” he once told an interviewer, “so that nobody can figure it out.”
That difficulty is compounded by Trump’s astonishing ability to prevaricate. No one’s saying Trump ought to be held to the same standards of truthfulness as everyone else; he is, after all, Donald Trump. But when Trump says he owns 10% of the Plaza hotel, understand that what he actually means is that he has the right to 10% of the profit if it’s ever sold. When he says he’s building a “90-story building” next to the U.N., he means a 72-story building that has extra-high ceilings. And when he says his casino company is the “largest employer in the state of New Jersey,” he actually means to say it is the eighth-largest.
The predictable result is the steady stream of articles debunking Trump’s exaggerated claims—particularly his oft-repeated assertion that he’s worth $5 billion. Trump and his aides are so used to their veracity being questioned that they went to almost laughable lengths to assure me they weren’t lying, as when Abe Wallach, Trump’s finance man, produced a letter from a company offering $120 million for a piece of Trump property. “This is not concocted,” Wallach told me, though I’d never suggested such a thing. “This is real.” And to assure me that Trump had received many, many offers on his building at 40 Wall Street, Wallach summoned his assistant Diane to tell me about a recent call from a potential buyer, “just so you know I’m not making this up.”
“What did he want to know?” Wallach asked Diane.
“If it was for sale,” Diane responded.
“What did I say?”
“No.”
Turning to me, Wallach added, “This is unrehearsed.” That bit of office theater complete, Wallach pulled out the partnership agreements for several of Trump’s properties so that I could check, among other things, whether Trump’s ownership stakes in them were in fact what he said they were.
But here’s the weird thing about Donald Trump: Try as he might to be a figure of ridiculous fun, lie as he might about things large and small, Trump appears to be an enormously skilled developer. Associates describe an unfailing knack for spotting and ferreting out waste; a memory like a Zip drive; a grasp of byzantine zoning laws so detailed that he routinely requires the city to close loopholes only he had the wherewithal (many would say gall) to exploit. There’s Trump walking the construction sites every day, yelling that the concrete is the wrong kind, that the marble isn’t flat enough, that the ceiling should be ripped out and redone. “He can look at a type of window glass and tell you what type it is and its energy-efficiency rating,” says a former employee.
Then, too, Trump brings the sheer power of his persona to bear. He negotiates with subcontractors himself instead of relying on a purchasing department and isn’t opposed to using his celebrity to better the terms. To seal one deal, Trump agreed to call the subcontractor’s mother and wish her a happy birthday. “He has this ability to relate to the doorman, to the guy who’s carrying the iron or steel, and make that guy feel good and important,” says Colony Capital CEO Tom Barrack.
And while Trump’s lifestyle hasn’t changed much since the 1980s, his dealmaking approach has. Chary of the sort of leverage that pushed him close to bankruptcy in the early 1990s, he refrains from putting up large sums, instead partnering with financial backers—General Electric’s pension fund among them—that want to tap the power of his name and retain him as a sort of jungle guide. (Yes, people do pay more to live in Trump buildings: The Corcoran Group, a New York real estate agency, estimates his condos command an 80% premium.) In one extreme instance, developers paid Trump a flat $5 million licensing fee for the right to brand a Trump Tower in Seoul.
Trump’s rivals seize on such deals to label him a mere front man for financial interests—a brand slapped on buildings he doesn’t own—which in turn sends Trump into paroxysms of outrage. “I own at least 50% of everything I do,” he says, not quite accurately. “I’m the biggest developer in the hottest city in the world.”
In truth, Trump’s strategy resembles less a Potemkin village than a fast-expanding game of SimCity, which is to say he has a lot of big projects in the works. On Manhattan’s East Side, he and partner Daewoo are erecting Trump World Tower, the “90-story” colossus that is going to cast a shadow on the United Nations and block Walter Cronkite’s view. Over on the West Side, he and a group of Hong Kong investors are two buildings into an 18-building residential project along the Hudson River, the creatively titled Trump Place, which will fill up Manhattan’s last big parcel of undeveloped land. Condo sales from both are benefiting from the hottest real estate market anyone can remember. As for the three trophy properties Trump calls “my other children”—Trump Tower, 40 Wall Street, and the General Motors Building, which he purchased in 1998 with insurance company Conseco—he has lately succeeded in jacking up rents.
Trump’s partners seem pleased. “We were never projecting the numbers that he’s producing routinely now,” says Conseco executive vice president Ngaire Cuneo. “His attention to detail and to what potential tenants will want has been uncanny,” adds CEO Steve Hilbert. “The results have been stunning for us at Conseco.”
Colony Capital’s Barrack, who hired Trump to convert the Mayfair Regent Hotel into condos, has similar words: “Bottom line is, the project came in under budget, four months ahead of schedule, and at sales prices that were 40% above what we had pro forma’d. We didn’t have one work stoppage, not one strike, not one city red tag. Everything was perfect.” Even former New York mayor Ed Koch, a Trump hater if there ever was one, told me he is a great builder.
If only Trump were content to leave it at that. For the rest of the story is much darker. Nowhere are Trump’s self-defeating tendencies more evident than with his casino company, Trump Hotels & Casino Resorts, which he took public in 1995 under the monogram ticker symbol DJT. It was Trump’s salvation at the time, raising $140 million that he used to pay off creditors. “Without the casino company, Donald would not be alive today,” one of his employees says. The stock climbed to $34—then headed straight for the toilet. These days it’s hovering somewhere above $3, and Trump’s 42% stake in the company has shriveled from more than half-a-billion dollars to $53 million.
Surprisingly, the underlying assets are in good shape. Trump’s three New Jersey casinos command nearly a third of all gaming revenues in Atlantic City, a slow-growing market that has nonetheless withstood challenges from Connecticut’s new megacasinos. All are well-run operations with top-drawer management; the New Jersey Casino Control Commission says they all have clean records. The flagship Taj Mahal, an onion-domed complex with some 4,500 slot machines, throws off nearly $100 million in cash annually; the smaller Trump Marina has almost doubled its own cash flow to $53 million in three years. Add in Trump Plaza and a riverboat outside Gary, Ind., and the company generates more than $240 million in cash a year. “Donald is not blowing smoke when he says there is a lot of money in that business,” says Barrack.
A cash cow it may be, but most of the cash goes toward the care and feeding of another beast: the $1.8 billion in high-yield debt that has saddled the company almost since its inception. The debt servicing eats up $216 million of the cash flow, leaving the company precious little capital to reinvest in its properties and even less in the way of earnings for shareholders. The company lost $134 million after depreciation and special items in 1999, and S&P recently lowered Trump’s bond rating from junk to junkier.
Trump denies misusing company funds and says he’ll repay the $26 million when it comes due May 15. Two sources close to Trump say that to raise the money, he is trying to mortgage Mar-a-Lago. Trump confirms that he is considering a $25 million to $30 million mortgage on that property, but insists he has the money to meet the obligation. “Our cash flow has been tremendous,” Trump says. He is sensitive on this point: Trump had his lawyer send a letter threatening to sue Fortune and me, saying, “It is our information that the article will contain false and misleading material concerning, among other things, the net worth and cash flow of The Trump Organization and/or Mr. Trump.” During one of our telephone discussions (which Trump later admitted he had begun taping), Trump said he would “sue the ass off of Fortune” if I were to “disparage [his] cash flow.” But one of Trump’s senior executives confirmed that Trump is seeking a mortgage on Mar-a-Lago, and possibly on Trump Tower, to pay back the $26 million.
Meanwhile, a shareholder has sued for breach of fiduciary duty. And as if all this weren’t enough to undermine Trump’s Street cred, the company was accused of overstating last year’s third-quarter results when it failed to disclose that $17 million in revenues came from a one-time event.
A couple of people close to Trump and otherwise sympathetic to him suggested to me that he’s unfit to be running a public company. Given that the low stock price seems partly a function of Wall Street’s allergic response to Trump’s flamboyance—analysts call it “the Donald factor”—the obvious solution would be for Trump to remove himself from management. One industry executive estimates that step alone would bring a 30% bump in the stock.
Trump has started by firing Taj Mahal President Rudy Prieto the day before Christmas Eve. He may soon be searching for a new CEO too: Recent word is that the highly capable Nick Ribis, tired of having his hands tied by restrictive debt covenants and his stock options several million dollars underwater, is on his way out. And in February, Trump settled his five-year feud with Mirage Resorts’ now former boss Steve Wynn—a feud that had Trump flinging lawsuits to stop Mirage from entering Atlantic City, Wynn countersuing for restraint of trade, both men throwing around words like “imbecile,” and a Mirage operative allegedly wearing a “modified jockstrap” equipped with listening devices. The settlement should save Trump $3.5 million a year in legal fees.
Now it appears Trump will attempt to deleverage the company by unloading one of the casinos within the next six months; the Indiana riverboat seems the likely candidate. If that doesn’t goose the stock price, well, there are already internal discussions about taking the company private.
Another puzzling aspect of Trump’s public image is that even though he runs two companies that together employ 22,000 people, one never gets the sense of an organization underneath him. Indeed, one could easily come to the conclusion that he’s not only a sole proprietor but a sole employee. But in fact Trump has assembled an extremely loyal crew within his 50-person corporate office: CFO Allen Weisselberg began working for Trump’s father in 1973; Nick Ribis began as Trump’s lawyer in 1977. Both current and former employees describe Trump as a loyal if not especially well-paying boss, citing stories of birthdays remembered, of sick relatives visited in the hospital. Yet some of them bristle at the popular perception of Trump as a one-man show. “He’s got a very good team. It’s not just a show front,” says Abe Wallach. “This is a professionally run real estate organization.”
His point is perhaps blunted by the I <3 DONALD TRUMP bumper sticker on his office wall, but then theirs is a complex relationship. Around 1990, when Trump’s empire seemed on the verge of collapsing under its own weight, Wallach—then a senior vice president at New York real estate firm First Capital Management but a stranger to Donald—began speculating to the press about Trump’s fate, telling the Washington Post that people would soon be saying “Donald who?” On the MacNeil/Lehrer Newshour, he said of Trump, “If your ego is as large as his is and you just buy everything in sight, part of the blame has to squarely rest in your own lap.”
Never one to sit idly by and take that sort of treatment, Trump decided he wouldn’t. According to one account, Wallach opened his door one day to find himself served with a $250 million lawsuit. When Trump and Wallach got in touch to discuss the situation, the story goes, they ended up hitting it off, and Trump eventually hired Wallach instead of suing him. Trump says he never threatened litigation but confirms the rest of the story. Wallach at first denied it altogether, saying he met Trump in a cordial fashion through Trump’s father, then admitted it was all true. Whatever.
Oddly enough for a man who all but lives in the media, Trump has no public relations machinery to speak of. In a day when even petty tycoons insulate themselves with platoons of spokespeople and media consultants, he relies only on his longtime assistant Norma Foederer and returns most reporters’ calls personally, making him one of the most accessible businessmen anywhere. Sometimes overbearingly accessible: When Fortune once assembled a list of billionaires, Trump called so many times to haggle over his net worth that an intern was assigned to field his calls.
All the while, Trump takes pains to maintain a pretense of exclusive access, at one point summoning Foederer into his office so that she could show me the stack of requests for interviews (59 last week alone!). “Half of the press corps in the country is upset that they’re not on this plane,” Trump assured me on the way to see Ventura, which may not have been entirely untrue: Given the alternatives of covering Steve Forbes’ robodork routine in New Hampshire or living it up on Air Trump, political reporters seemed all in favor of the latter.
It occurred to me, though, that for a guy who seems to value “loyalty” so much, Trump’s media-soaked life must feel like a series of betrayals, as journalist after journalist chooses to accept his advances and then turns on him. While at first blush Trump can come off as a thick-skinned believer in the adage that there’s no such thing as bad publicity, that doesn’t quite hit the mark: Like a true publicity-holic, Trump repeatedly indulges in publicity and then rails against the consequences. “A lot of reporters are scum,” he told me, denouncing “that little moron” from such-and-such financial publication and the “piece of shit” from another. Recently, he threatened to sue George after the magazine seemed to suggest that he had filed for personal bankruptcy in the early ’90s. This got me thinking that the cause of his behavior perhaps wasn’t so much egotistical as medical. I even called a psychiatrist to get his clinical assessment of Trump. (He suggested an overmastering need to escape the shadow of his father, Fred, a successful outer-borough developer who died last year and whom Trump rarely mentions.)
But even while Trump complains he’d like to be covered “more in business and less in social,” he can’t seem to help himself. In the end, one is simply humbled before the awesome insularity of his logic. “I own a lot of things that I don’t have my name on,” he explained at one point. “But when I don’t put my name on it, nobody knows that I own it. That’s one of the reasons I like putting my name on things.”
Outside the General Motors Building, Trump and I paused by his limo for a few seconds to stare up at the huge trump lettering on the facade. “See how understated that is?” he said in a rare outburst of irony. A foreign-sounding woman on the street recognized him. “Are you going to be a President?” she asked. “Absolutely,” said Trump. “No doubt about it.”
Three weeks later (after Fortune had flown with him to St. Louis for some final politicking and, yes, a Tony Robbins speech) Trump announced he wasn’t running. The proximate cause was the Reform Party meeting that ended with red-faced delegates screaming and jostling one another for microphones, and Jesse Ventura’s subsequent secession from the “dysfunctional” party. Privately, I wondered if Trump had begun to doubt his own constitutional capability for certain political rituals, notably the concession speech. But the final nail in the coffin was John McCain’s surprise surge in the polls. Roger Stone felt robbed: “He’s running on Trump’s message.”
“One more thing,” he said one time just before hanging up. “Did you know that New York Construction News named Donald Trump the developer and owner of the year?”
Reporter Associate: Theodore Spencer
A version of this article was originally published in the April 3, 2000 issue of Fortune.
