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Donald Trump

The Candidate

About The Book

The revealing story behind Republican presidential candidate Donald Trump’s rise to the top.

In Donald Trump, adapted and updated from The Trumps, bestselling author Gwenda Blair recounts a true-life history with more twists and turns than any television producer could imagine. Towering skyscrapers and glittering casinos, a luxury airline and a football-field-size yacht, steamy affairs and bitter lawsuits, near bankruptcy and stormy feuds—all this and more are part of the life of Trump.

An adaptation and update of her definitive biography, The Trumps, this book provides fresh material on Trump’s brushes with bankruptcy, mammoth construction projects, and ever-expanding place in American life. Blair offers new insight into the man who seems to have it all and making a run for the highest office in the country: the presidency. For the first time, we also get a glimpse of the person who may ultimately decide the fate of the Trump brand: Donald Trump, Jr., the real-life apprentice who hopes to put his own imprint on his father's empire.



On a warm fall afternoon, the world's most famous businessman sat next to a pile of 12-inch-tall male dolls. If this were somewhere other than New York City - the South American jungle, say, or ancient China - they might have been mud-and-twig fetishes designed to ward off evil or ceramic objects destined to accompany him into the afterlife. But it was Times Square in September 2004, and Donald Trump was launching a sales campaign at Toys R Us for a plastic action figure modeled in his likeness - more or less. Laser technology had provided the billionaire's pursed mouth and bushy eyebrows, but a shoe-polish brown pompadour had replaced the famous orange comb-over and there were no genitals.
No matter; despite its single-breasted suit and wing-tip shoes, the Apprentice Talking Donald Trump Doll is not really a replica, or even a toy. Instead, it's a pint-sized, personal mentor for viewers of the hit reality television series, "The Apprentice," on which fresh-faced young contestants compete for a job with the Trump Organization. Embedded in the doll's chest is a digital sound chip that allows it to declare, in Trump's own voice, "Have an ego," "Think big," and other pithy bits of advice similar to those he offers each week on the show.
What the doll doesn't reveal are the sources of Donald Trump's own extraordinary success. These include a number of lucky breaks, among them his father's real estate wealth and political connections, his surname (changed by a prescient German ancestor from "Drumpf" to Trump) and his ex-wife Ivana's gift of a catchy nickname, "The Donald," which became instant newspaper fodder.
But of equal importance are what we might call The Donald's Five Commandments: Do whatever it takes to win. Don't spare the chutzpah. Turn everything into an advertisement for yourself. No matter what happens, claim victory. And above all, always use the superlative. While he's heeded business basics like "Location, location, location," his own personal mantra is "Exaggerate, exaggerate, exaggerate."
Following these guidelines, he's carved out a career in self-aggrandizement that has netted him fortune, fame and enthusiastic fans. Hundreds of them showed up for the one-time-only opportunity to plunk down $26.99 for a doll and The Donald's autograph in metallic gold across the face of the doll's box. They knew him from "The Apprentice" as the archetypal boss: ready to pounce on mistakes, dismissive of excuses and ever aware of the bottom line. What they didn't know was that behind this most recent claim to fame lay a life history with more twists and turns than any television producer could possibly imagine. Nor did they know that Trump himself had been a lifelong apprentice to a powerful man whom he had admired, rebelled against, studied, competed with, and eventually surpassed. "I wanted to do what my father did, but bigger, better, stronger, higher, everything, right?
Fifteen years earlier, that mentor had watched with a bewildered look as Donald sat in another Manhattan toy store, F.A.O. Schwartz, and autographed a Monopoly-like board game with his name and face on it. The man was Donald's father, Fred Trump. Like his son, he was in real estate. Also like his son, he was immensely wealthy. But he had made his money building ordinary homes for ordinary people, not by constructing super-luxury apartments, running casinos, engaging in financial manipulations and turning himself into one of the most celebrated figures of the century. Whereas the erstwhile apprentice lived in the center of photographers' lenses, his master existed outside the media's glare. The two men's lives were vastly different - as different as business in the middle of the twentieth century and at its end, as different as the America of the World War II era had become as the cold war drew to a close.
This apprentice did not always follow his master's advice. When Donald ignored his father's old-fashioned, all-brick aesthetic in favor of modern, glass-walled skyscrapers, he achieved great success; when he disobeyed his father's financial precept s and signed personal financial guarantees for nearly $1 billion, he created a disaster. Only a year after the F.A.O. Schwartz event, Donald's empire lay in shambles. But unlike other magnates of the time, he emerged from financial turmoil to create a second, virtual empire. He would no longer own everything with his name on it; instead, he would market himself as the embodiment of the American dream of wealth and fame. He would be the people's billionaire: the personality brand created by the dark suit, the improbable hair-do, and the over-the-top description of every undertaking as the world's most fantastic, amazing and incredible.
Only a dozen years earlier, many had considered him finished, but his current life seemed to be, quite literally, gold-plated. To the contestants on his show as well as the world at large, he seemed the quintessential man in charge. But the reason he had survived and flourished was that he had, once again, been an apprentice, resolutely adhering to his father's most fundamental rule: No matter what happens, never, ever give up.
November 2004


Donald Trump's unrelenting focus on his own accomplishment alienated many people; others, drawn to winners, found his self-absorption appealing. No matter the occasion, he was always competing, always concentrating on how to make whatever he was doing seem bigger and better than what anyone else had ever done. When he lost, he would say he won; when he won, he would say he won more. He called such behavior "truthful hyperbole." Broker Ed Gordon labeled it "diarrhea of the mouth." Barbara Corcoran, founder and chairman of one of the largest residential real estate companies in Manhattan, may have put it best: "He's got a gift that's good in good times and really good in bad times," she said. "It's called bullshit, and he uses it unabashedly. We've all gone to high school with someone like that - the only difference is most people have to let it go."
But as Donald Trump would be the first to say, he wasn't like most people. In The Art of the Deal, he claims that business deals are what distinguish him; by all accounts, he is indeed an artful negotiator, with his father's skill at walking into a meeting without notes or a calculator because he's got the numbers and deal points in his head. But his most original creation is the continual self-inflation that has made him a touchstone of excess. Early on, it made him his father's favorite child and treasured apprentice, a choice that sheds a certain light on the journey taken by this family - indeed, this nation - over the past century.
Despite obvious differences in lifestyle and affect, grandfather Friedrich, father Fred and Donald were similar types. All three were energetic men who would do almost anything to make a buck; all three possessed a certain ruthlessness; all three had a free and easy way about the truth and a wide range of solid, practical skills. But how these traits played out in different eras is, in its own way, a vest-pocket history of America.
During Friedrich's first two decades in the New World, he made a living by providing services that were as concrete as could be imagined. They ranged from haircuts to food to sex, and customers returned because they were satisfied with his work, not because he was the vendor. When he purchased older businesses, he did not change the sign over the door; when he started new ones, he named them after their locations. Even when he moved into real estate, near the end of his life, his intention was to create value not through his name but by buying plots of land and building homes.
Friedrich's son Fred followed in his father's footsteps but created value in his own way. By establishing a network of political contacts, he managed to obtain government housing subsidies, then released a stream of press releases designed to give a special shimmer to what were in fact conventional developments. A man of his era, he gave them innocuous generic addresses, like Shore Haven and Beach Haven. Only on the last, Trump Village, did he place his name, a precedent that his son Donald would expand on in ways that Fred never dreamed of.
Donald shared much with his father and grandfather. He, too, knew how to frame a building and retar a roof. But Friedrich's grandson would not employ this practical knowledge to build anything with his own hands; instead he would use it to hire and fire those who put up his structures and to connect with the construction crews, maintenance men and retired blue-collar workers who played his slot machines in Atlantic City. Although these skills would be helpful in negotiating contracts, the special value he would add to his projects would be his name. Seemingly the simplest of acts, it was actually quite arduous, for keeping that name going, constantly protecting and buffing it, required vigilance and intensity of the highest order.
By 2005, 14 buildings in Manhattan bore the name, although he had provided little or no financing for more than half. To all appearances, he held equity in only three or four, but rather than offering proof of more extensive ownership, he simply insisted, sometimes ferociously, that he owned practically everything labeled Trump. One perennially sore spot involved Trump Place, the vast West Side complex financed by a Hong Kong consortium. When the New York Times Magazine asked about Trump's holdings there, the consortium's lawyer delicately described him as "a major partner" who was "not merely receiving a fee" - seemingly a roundabout version of the near-unanimous belief that Trump's portion was a management fee plus a share of the profits.
Donald was less delicate. "I'm not a fucking flunky," he said. "I'm a 50/50 owner, owner, owner of the job. Okay, do you have that? I get 50 percent of the profits because I own 50 percent of the job, and it turned out to be one of the most successful jobs ever done in Manhattan." Afterward, in a Trump-style clarification, he added that he did get fees for building and managing the project. "I own that job, can I get it through your head? I own the West Side. I'm the largest owner. I own it. I'm not just a person that works, you know, for a fee. Do you understand? I'm an owner. I own a big chunk of that job, a big portion of that job. Off the record, I own 50 percent of that job. Five-Oh. You said I didn't own it, I got fees, but that's bullshit."

f0Such diligence had its rewards. In the early 1990s, when Donald's empire was in trouble, the carefully tended glow attached to his name persuaded holders of the junk bonds underwriting his casinos to cut deals leaving him in place as owner. In 1995, Several years later, his renown allowed him to take the casinos public and load them with still more junk bonds. But a decade later, the casinos faced stiff competition: neighboring Pennsylvania had legalized slot machines, and right in Atlantic City there was a new kid on the block: the $1.1 billion Borgata, the first casino built since the Trump Taj Mahal. A sleek, sumptuous Las Vegas-style resort with high-end retail shops, celebrity-chef restaurants and a popular spa - the wait list for facials was eight weeks - the Borgata was blowing the doors off every casino in town, but the dilapidated Trump properties were hit especially hard.
tThe remedy was obvious: refurbishment and more hotel rooms. But staggering interest payments on high-interest bonds had left Trump's thepublic company too strapped to replace worn upholstery and repaint scuff marks on walls - a serious no-no in an industry that relies on glitz and glamour to lure customers. Worse, there was no money in the till for. - much less to finance a much-needed expansion. Because Trump was always strapped, said Jacques Cornet, a casino analyst for CIBC World Markets, the developer had never been able to "right-size" his casinos with enough hotel rooms - a critical gap given that overnight customers spend an average of $325, compared to only $100 for someone who drives down for the day. "The logic was that if Donald could double the room count, the returns would finally be adequate," Cornet said. "It makes sense, but there's a tremendous leap of faith involved."
Evidently, the Trump name continued to give the bondholders that faith. In late October 2004, just weeks before another interest payment that many predicted THCR would not be able to make, they "took a haircut." But once again, the Trump name convinced bondholders to "take a haircut." In exchange for the right to keep using that name and likeness, plus an equity stake and a modest cash payout, they accepted a prenegotiated bankruptcy that reduced their rate of return and gave Donald yet another lease on his ever more highly leveraged financial life.
This time, the man who had insisted that he owned "mostly 100 percent of everything" declared that reducing his own equity by more than half was not such a bad thing after all. "I'll own 27 percent of a great company as opposed to 56 percent of a company that had a lot of debt," Trump said. "Which would you rather own? It's a great deal, no one else has ever done such an amazing deal. The casinos have always been a great deal for me. How much have I made off the casinos? Off the record, a lot. And nobody's ever understood that. They think, oh, gee, he hasn't done that well. But I've made a lot of money with the casinos over the years and now I'm going to make it a great company. I put a lot of debt on them and I took the money out and I bought a lot of real estate in New York. So I'm very happy at how things have turned out."
It was a remarkable turnaround for a man facing seemingly inexorable death by interest payments. "He has staved off a ticking time bomb," one long-time Trump critic, casino analyst Marvin Roffman, told Newsday. "He should go home tonight and take out his cashmere Trump bathrobe and crack open some Dom Perignon and celebrate."
But there would be another reckoning, and soon. According to the terms of the agreement with bondholders, by the following spring, Trump, who would still be the largest shareholder, would have to kick in an investment of $71.4 million, including $55 million in cash. "People are talking about whether the check will appear," said one industry observer. "Will some bank lend him more on a building in New York? Or against future expected fees on his TV show, "The Apprentice"? He can get creative - and historically, he has."
* * * *

To his grandfather and his father, Trump had been a name, a signifier of family and history. But to Donald, it meant something more. When he'd hoisted it on one undertaking after another, it wasn't simply a matter of advertising; he was turning himself into a brand. In turn, when investors backed his ventures and the public patronized them, they weren't merely making financial choices; they were buying into "Donald Trump," the personality brand created by consistently making the same extravagant claims and having the same look - including, apparently, the dark suit, the smirk, and the ever-more-improbable hairdo. "He was an early mover in this kind of personal branding," said brand guru Bernd Schmitt, a professor at Columbia Business School. "Like Bill Gates and Steve Jobs in computers, he became the most well-known brand in real estate - in public awareness and notoriety, no one else even comes close."
It was a strategy that paid off handsomely. In the early 1990s, when he was in his late forties, Donald was nearly $1 billion in the red; by the fall of 2004, when he was approaching his sixties, the Forbes 400 pegged his wealth at $2.6 billion. Along with film director Steven Spielberg and Yahoo cofounder David Filo, Trump was in a five-way tie for being the 74th richest American. Such a spot would have been more than enough for others on this exclusive list, who tended to be reticent about their means. But modesty was not Donald's way, and he continued to insist that the real number was actually $6 billion. Whether anyone believed him was unimportant; what mattered was that he sparked still more press attention.
For years, Donald had looked to such coverage to keep his name in the public eye. But in 2004, there would be, literally, a dramatic change. The hit reality television show "Survivor" had rented Wollman Rink, the skating arena in Central Park that Trump had renovated nearly twenty years earlier, for the live broadcast of its season finale. When Donald dropped by to watch, a sandy-haired man with a hybrid British-Australian-American accent introduced himself as Mark Burnett, the show's producer. Back when he'd been hawking t-shirts on Venice Beach, he said, he'd been inspired by The Art of the Deal, and now he wanted to talk about a new idea.
Although Trump courted attention every waking moment, he'd already turned down other pitches for day-in-the-life-style reality shows. "Can you imagine 15 cameras in the middle of an important meeting?" he said later. "I don't want to do that, and neither do the people I do business with. It would freak them out." But Burnett, a famously persuasive sort - CBS chairman Leslie Moonves called Burnett's pitch for "Survivor" the best he'd ever heard - proposed a elimination-style format in which the contestants, divided into teams, would compete on a demanding business task and each week Donald would fire someone. Intrigued at the prospect of a show set not in a jungle hideaway, a la "Survivor," but in New York's real-life business world, Trump said yes. Later he explained his decision: "The combination of Mark Burnett, who did Survivor, which was the number one show, and Trump, the number one developer in New York, was a great combination. It would be terrific, amazing, totally amazing."
It was a rare understatement. In Jacques Cornet's phrase, real estate jargon, television "right-sized" Donald, translating his over-the-top mannerisms and exaggerations into entertainment and turning his sometimes grating behavior into something engagingly camp. "He's a pull-me-in, push-me-back personality," said Michele Greppi, national editor of TelevisionWeek. "Seeing the show is like going to the zoo, where there are some things you watch between the fingers of your hand. I wouldn't want to be his employee, but I've got to know who he's going to fire or praise."
Television also seemed to exert a humanizing effect on the developer. As the would-be apprentices schemed and backstabbed their way to the grand prize of a one-year, $250,000 job with the Trump Organization, he consoled one contestant whose mother had cancer, winced while addressing another competitor named Ivana and made fun of his own much-ridiculed hair. In this medium, even his own brush with financial disaster was an asset, for it showed that he, too, was mortal, and his comeback fit perfectly into the ever-popular genre, tales of redemption.
But perhaps dearest to Trump's heart, the show presented him as he had always seen himself: the most stupefyingly successful man in the world. Contestants gaped with wonder at a Trump helicopter, golf course and casino, and they turned ashen when he pointed his index finger at 20one of them and uttered the show's catchphrase, "You're fired." Spending 10 minutes alone with The Donald (and, of course, a camera crew) seemed tantamount to a papal audience. "I show this apartment to very few people," he said grandly when one week's winning team visited his residence in Trump Tower. "Presidents, kings - let me give you a little tour." In fact, his opulent penthouse has appeared multiple times in print, television and film, but there was nary a snicker from the awestruck contestants.
From the start, the show held an enviable position on the schedule: directly after the hugely popular sitcom "Friends," then in its last season. But almost immediately it was clear that "The Apprentice" was a hit. Each week it attracted an average of 20 million viewers, had an audience of 40 million people for the final episode and scored particularly well with the affluent viewers that advertisers crave. Although the show did not consistently top the charts, such niggling details did not prevent Donald from making the usual claims: "You see the ratings are through the roof, bigger than ever," he chortled. "The show is now number one in demographics and I think in two weeks it's number one overall. It's a big monster. I'm in Los Angeles, I get out of my limo to be on Jay Leno and both Jay and [NBC Entertainment president] Jeff Zucker greet me at the door, and you know they only do that if you're number one in the ratings."
He was equally jubilant about press coverage: "I was on the cover of TV Guide last week, and it was their most successful magazine in three years. I was on the cover this week of Newsweek and they say you cannot buy Newsweek on the stands. So something's happening, right? I don't know what it is, but I just got a call from Rick Smith of Newsweek, you know, he's the head guy. He said we cannot put this magazine out there fast enough, there's some crazy phenomenon here."
Evidently the craziness was catching. After the first season was over in the U.S., networks in two dozen other countries purchased broadcast rights, and production companies in more than a dozen more began work on their own broadcasts. Long before the first U.S. season was over, the contestants had become celebrities in their own right, netting interviews, magazine covers, job offers, and, in some cases, their own books. "We had a chance at everything from tv to film to business," said Nick Warnock, a regional Xerox manager who was fired in the next-to-last round of competition. "Modeling ourselves after Donald Trump, we used being celebrities as capital."
At auditions for the first season, more than 250,000 people had appeared; for the next season, one million hopefuls showed up. "Even if I didn't win the job, I could milk this thing," said Rob Flanagan, a Texan who markets mouse pads and pens for distribution at trade shows and ended up being the first candidate fired on the second season. "I'd pull on those udders until the powder comes out."
0By 8 a.m. on the morning of the New York try-outs, held at the Trump Building on Wall Street, there was a line of several thousand, despite the frigid winter weather. Among them was Victor Btesh, a high school dropout from New Jersey who owned his own company, Hot Records, which produced and marketed trendy products, including a line of Osborne family action figures. Btesh had managed to get the name of the casting director and used it to get out of the cold and into a line of only several hundred apprentice wannabes. "All of a sudden I hear all this noise," he said. "Donald Trump was coming up an escalator and there were all these cameras and paparazzi and all this excitement." Outside, when Donald had paused for a moment at the top of the steps, the crowd had started chanting his name; now they began screaming it. "It was like when people were screaming for the Beatles," Btesh said. "These were his people, his fans, people who love the show and just want to be connected to him."

For the public, the question was which contestant Donald Trump would finally select as his apprentice. But for the broadcast industry, it was whether the new show could deliver a changed economic model for television advertising. Because of the rise of new technologies like TiVo that allow viewers to skip over conventional ads, broadcasters were eager to find a format that incorporates products directly into programming. Although Burnett had done so in crude but effective fashion on "Survivor," where the rewards to weekly winners were sponsors' sodas and snack foods, major marketers were still wary of the concept and hesitant to tie themselves to an untried new version.
But when Marquis Jet, an unknown company which sells time on luxury private planes, participated in an "Apprentice" episode and became a nationally recognized name overnight, "placement" fees that ranged up to $1 million began to seem like a bargain. By the second season, there were a near-record number of product placements, and familiar names, including Mattel, Petco and Levi's, had moved front and center in almost every episode. Apparently the association with The Donald worked its usual magic; two hours after the broadcast of an episode in which contestants vied to launch Crest Refreshing Vanilla Mint toothpaste, the Proctor & Gamble website received a record 800,000 hits asking for samples and offering ideas for how to create more buzz for the new product.
* * *
As such legendary failures as the Ford Edsel and New Coke bear eloquent witness, branding isn't everything. In order to last, a brand has to be associated with a product that the public wants to buy. Not what people used to want, or what some marketer thinks they should want, but what they do want right now. For Donald Trump, this product was real estate with the showy, expensive look and luxurious amenities that an elite market segment craved and for which it would pay top dollar. He was remarkably successful in this endeavor: apartments in Trump properties were among the most expensive listings in Manhattan and he was working on luxury projects in Toronto, Phoenix, Las Vegas, and Palos Verdes, California. Condominiums in his 90-story skyscraper in Chicago, not due to be completed until 2007, were already setting new price records.
Financial arrangements for the Chicago International Hotel & Tower had been protracted, in part because local banks had been leery of involvement in the project, the city's largest in thirty years. Ultimately, a New York-based hedge fund, Fortress Investment Group, put up a high-interest $130 million "mezzanine" loan to supplement a $640 million construction loan from Deutsche Bank. "What made the difference wasn't 'The Apprentice,'" said Bob Horowitz, a commercial real estate investment broker in New York who has handled financing on Trump projects for a decade. "Donald is a very, very sharp guy and he is always financeable. The only question is the price."
But with the success of "The Apprentice," Donald Trump had once again reinvented himself. Already famous for being famous, he had become the apotheosis of wealth. At one time his name had been synonymous with real estate; now it had become a free-floating brand that could sell anything. Or so it seemed; weeks before the national roll-out, the Apprentice Talking Donald Trump Doll was on's list of top-selling new action figures. Other manufacturers were plastering the mogul's name and face on bottled water, men's cologne, a new clothing line, a magazine and an updated version of the 1989 board game. Meanwhile, Trump himself was recording syndicated radio commentaries, appearing in commercials for Visa and Verizon, plugging two new insta-books, How to Get Rich and Think Like A Billionaire, penning forwards for other books by "Apprentice" veterans and making frequent public appearances with Melania, now his fiancée, and her 12-carat diamond engagement ring.
Which raised the obvious question: Could anyone, even The Donald, keep this up? "I'm cautious and skeptical," said Columbia professor Bernd Schmitt. "Even a very successful brand can get diluted by being extended into other products." Taking a more dire view, John Allen, senior partner at the New York-based consultancy Lippincott & Margulies, warned that overexposure could damage or even kill the brand. "If you were managing the brand," he told a reporter, "You'd say, 'No, Don, it's not for you."
Other marketing experts were more sanguine. "If your business is exposure, there's no such thing as overexposure," said Advertising Age columnist Randall Rothenberg. "He's beyond anything like shame or embarrassment. He's created a brand that's about shamelessness and out-there-ness, so why couldn't he keep going forever?"
0 When Donald was asked if he worried about overexposure, he seemed almost baffled by the question. He didn't believe there was any such thing as overexposure. As far as he was concerned, the ubiquity of his name, his face and his voice was as it should be. When, as happened pretty often now that he thought about it, like when he was sitting at a screening of an episode of "Sex In The City" and one of the characters mentioned him, or when he was reading Parade one Sunday and learned that he was listed in the Guinness Book of Records for having the greatest financial comeback in financial history, which he didn't even know about, or he saw himself quoted in an article and he had never talked to the writer, in other words when he saw himself or people talking about him, it was the craziest thing, but okay, that was cool, it wasn't anything to worry about.
"A lot of people sit down and discuss their lives, things like are they happy, but it's not like that with me." he said in one interview. "I don't think positively, I don't think negatively, I just think about the goal. But it's not like I sit down and write goals. I just do things." As for the idea of worrying about anything, he said on a later occasion, it simply never comes up. "I don't worry and I don't give up. My father was a worker, not a worrier. He got things done, like I do. We get things done. Some people worry about things, but I get things done."
* * *
On an overcast day in October, the man who would ultimately determine the fate of the brand stood next to a bridge over the Chicago River. Although his name was Donald Trump and he had been working at the Trump Organization since his own graduation from Wharton, in 2000, he bore none of the features usually associated with his famous name. His hair was thick and brown and his eyes were dark, giving him a marked resemblance not to his father but to his mother, Ivana, in the long-ago days before she turned into a blonde.
His manner was low key and modest, for he was by nature what the family called a Boston Trump, referring to the wing of the family headed by Fred's brother, a physics professor at MIT. Don Jr., as he called himself, did not refer to his bachelor apartment, located on a mid-building floor in a Trump condominium, as a penthouse, nor did he turn every conversation into a checklist of his own attributes and achievements. But as this day made apparent, perhaps his most striking deviation from the path carved out by his father was that instead of rushing to claim the spotlight, he actively avoided it.
The occasion was a press event for the new Trump tower slated for Chicago, and the first speaker before the audience of politicians, local real estate interests, Donald, Don Jr. and several hundred on-lookers was "Apprentice" winner, Bill Rancic. For his year on the Trump payroll, he had chosen assignment to this project, and he had often declared that he was intent on learning the real estate trade. But so far, Rancic, a lanky 33-year-old with a crewcut, seemed more focused on how to exploit his newly acquired fame - like his new master, he had quickly churned out an advice book titled You're Hired - and he opened with a crowd-pleasing reference to his experiences at a different Trump-owned enterprise, the recent Miss Universe contest in Quito, Ecuador.
Then Donald, dressed in his signature black business attire, strode to the microphone and said that the city planning commissioner, the mayor, the Trump team and the architect, Adrian Smith, a principal in the firm Skidmore, Owings & Merrill, were all amazing. "Chicago is a truly great city and we're going to make it a little greater," he vowed. Then he veered off to a more immediate concern: "Is everyone going to watch "The Apprentice" tonight?"
The cue was not lost on Smith, a portly figure with a sheaf of white hair, who spoke next. "People ask me what it's like with The Donald," he said. "He's a strong client, who wants the best building, the best views and the best prices, and you have to give it to him or else" - a well-timed pause - "you're fired!"
Smith's initial sketches for the Trump project, scheduled for presentation on September 11, 2001, had showed a 2000-foot-tall monument that would have fulfilled Donald's lifelong dream of erecting the world's tallest building. But the events of that day had taken their toll on his seemingly impervious ego, not to mention the potential market for super-luxury apartments, and Smith ended up whittling the design down to a still-enormous 1,100 feet. It would be the tallest project the developer had ever done and the highest new skyscraper in Chicago since the Sears Tower (1,450 feet), built in 1974, but only the fourth-tallest structure in the city. "As Donald put it," Smith said, "after 9/11, fourth-highest sounded just right."
After the speeches were over, the crowd trooped over the bridge to the site, currently occupied by the squat, seven-story former home of the Chicago Sun-Times. Surrounding by workers in hardhats, Donald nodded his head and the operator of a large yellow backhoe began taking big, noisy bites out of the now-empty building's entrance canopy. It was a perfect photo opportunity, but Don Jr., who was accompanied by his fiancé, a model and actress named Vanessa Haydon, stayed out of the picture.
As might be expected, there were certain echoes of the father in the son: "Me and Russell Ticker [a senior Trump Organization executive] have been pretty well running this operation," Don Jr. declared, passing over the well-publicized involvement of construction supervisor Greg Cuneo. "And I guess Trump Park Avenue [an $85-million makeover of the old Hotel Delmonico in Manhattan] is pretty much my baby." There were also reminders of the relationship between 0Donald and Fred: Although Don Jr. loved his father, he sometimes found him a stubborn guy with a one-track mind. "I'm the one person who can stand up to him," the younger man said, "who's not afraid to pull him aside and say here, take a look at the larger picture."
But what stood out were the differences. At 26, Donald had been itching to take over the company, but Don Jr. seemed content to wait his turn. "I'm on my way," he said, "but right now I'm still learning." He worked hard, but not 24/7; he was, he said, "more grounded" than Donald because "I can lay back in my personal life." Even more dissimilar, the one person on whom he lavished praise was not himself but his father. "He's always hands-on and one step ahead," Don Jr. said with evident admiration. "People see him as famous, but they don't know that he knows how to do all this stuff."
In his quiet way, this apprentice was his own man. He might eventually be joined by his sister Ivanka, who had been a successful model in her teens and was now working for a competing real estate developer based in Brooklyn, or his young brother Eric, a student at Georgetown University. But for the present, Don Jr. had his own plans for where to take the brand next.
He'd experienced its power firsthand - "It's not easy at 12 to walk out of school and see the front page of every newspaper talking about your parents' divorce" - and he'd long since learned the necessity of bracing himself whenever he had to tell someone his name. "It would be nice not to have people prejudge you because they see your father a certain way and there's no chance you might actually be different," he said. "And every time you check in at an airport, it's oh, my god, you're Donald Trump's son."
After working at a minimum-wage job as a dock attendant at the Trump Marina in Atlantic City and on Trump construction sites, he also understood what the brand could do. When he'd started working for his father, the company had still been "very New York-centric," but now Don Jr. was working on projects all over the country. "That's not entirely my doing," he said, "but these are things I've helped pushed. It's such a huge brand, it could be global." Although he was open to almost anything, there was one possibility he'd ruled out: "I have no desire to go on television, so you're unlikely to have 'The Apprentice, Jr.'"
For the moment, though, control of the brand remained firmly in the hands of his father. As was so often the case, the Chicago event, meant to be about the soaring silver skyscraper in the large photograph propped on an easel, had ended up being about The Donald. The men and women who stood listening to the speeches seemed to welcome this new addition to their city's skyline, but their real focus was on the man who was building it. They had greeted him with hand-lettered signs; one read "Donald," and another said "Sing Hallelujah, next Apprentice challenge." And when he had finished speaking, they crowded around him, waving dollar bills and asking him to autograph them.

About The Author

Photograph by Matthew W. Stolper

Gwenda Blair is the author of the bestselling Almost Golden: Jessica Savitch And The Selling of TV News, and she has written for Politico, The New York Times, New York, Newsweek, the New York Daily News, Esquire, Smart Money, The Village Voice, Chicago Magazine, and other newspapers and magazines. She lives in Chicago and teaches at Columbia University’s Graduate School of Journalism. Follow her @GwendaLBlair.

Product Details

  • Publisher: Simon & Schuster (October 3, 2007)
  • Length: 320 pages
  • ISBN13: 9781416546542

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