How Trump Invented Trump
Inside the empire
Past Trump Tower’s bow-tied doorman, through a shiny revolving door, toward the 60-foot waterfall, up a dim elevator, after glass doors and smiling assistants, Donald J. Trump, chairman of the Trump Organization, sits with pictures of himself to his left, to his right, in front of, and behind him. A gun he got at an awards dinner this year in Charleston, S.C., is mounted above his desk.
Trump is three days away from his first debate with the nine other Republican presidential candidates who made the cut, the ones he’s pulverizing in polls. He’s taking a break from a campaign that, though he has no experience in government, has him zooming toward the White House. We’re talking business rather than politics—after all, that’s his central qualification for the job he’s seeking.
When Trump is asked to name a leader he looks to for advice on managing his company, his mouth, just as acrobatic as his more famous hair, pulls tight, snaps open, and lets out its most important syllable.
“Me,” Trump says.
“Mirror,” says one of the two deputies in the room. “The mirror.”
“I look at me,” says Trump.
Does he admire any other business leaders?
“I,” Trump says, “don’t like the word admire.”
Trump isn’t exactly self-made—he inherited substantial wealth from his father—but he is definitely self-invented. There’s no model in the political world for how he transformed himself into a campaign megastar without preparation, politeness, policy, or public service. To wander around inside Trump’s kingdom with his deputies, children, lenders, and former executives is to find a New York real estate mogul who stopped building Manhattan real estate and a global hotelier who doesn’t own most of his foreign hotels. Long before he was ignoring basic political rules, he was sailing far beyond the limits of his industry, steering an empire that’s as similar to most corporations as his run is to most presidential campaigns. In the same way that his campaign is post-politics, his company is post-business.
Trump is selling himself to America as the king of builders, a flawless dealmaker, and masterful manager. But he isn’t really any of those things. Trump has built few skyscrapers this century, stumbling twice when he’s tried, and struggled with an array of other projects. Meanwhile, his corporate leadership is a kind of teenager’s fantasy of adult office power. From his Trump Tower desk in Midtown Manhattan he controls the teensiest details, rejects hierarchy, and picks top deputies by following his own recipe for promotion.
None of those things means he’s a sham. The story of how he came to be what he is now—above all else a landlord and a golf bigwig—is even weirder than his charge to the White House. Trump rose in the glitzy 1980s on borrowed money, survived early 1990s disasters that nearly brought him down, then transformed himself and his business. His organization is still successful, just not in the way he’s claimed.
“We evolve very much in this company,” Trump says. “See that? I’m just looking while I’m talking to you. See that record?” There’s a plaque across from his desk. “That’s a platinum, that was sent. Mac Miller, did you ever hear of Mac Miller? He’s a rapper. He did a song called Donald Trump—100 million hits!” He takes a breath and goes back to his company. “I tell you what,” he says a few minutes later. “Someday before I kick the bucket, somebody is going to get what a great business I built. People don’t know.”
Four days later, the morning after the debate, Matthew Calamari’s eyes are misting. Trump’s chief operating officer has the mustache and bulk of a late-1970s linebacker because he was one in college. That was before he tackled hecklers at a 1981 US Open women’s semifinal, won the attention of a young real estate star who happened to be there, got hired as his bodyguard, and rose to become one of his top executives.
“I love the guy,” Calamari says. “My thing is, I’ve always promised I would, knock on wood, never let anything happen to him.” His voice wobbles. Lately, if you catch the right Trump speech and look carefully, you see Calamari. He likes to watch over his boss on the trail. “I just enjoy it. It’s not the money. I enjoy working for the man.”
A commemorative Secret Service knife keeps him company in his office, along with a poster of Tony Soprano, snapshots of his Shih Tzus, and a photo his brother took of the moment his knee was wrecked in a game. “You know what?” Calamari says. “If I would have made it in football, I would not be working for Donald Trump.”
Calamari gets up from his chair to show how he escorted his boss in the early days, just behind and slightly to the side. “Being able to walk with him to these other job sites, I saw his eye for detail,” he says. Calamari tried to emulate Trump when he hired other security guards. Besides security, Calamari’s responsibilities now include building management, construction, and insurance. “He promotes you until you fail,” he says. “There are no boundaries.”
Calamari won his job when the hecklers interrupted Martina Navratilova and Chris Evert. “I took one guy immediately right down,” he says. Then someone else started getting rude. “I ran right at him, I picked him up, I slammed him to the ground, I carried him down,” he says. He remembers Trump’s wife at the time, Ivana, asking for his name on her husband’s behalf. Navratilova won.
Calamari isn’t the only bodyguard Trump has promoted. The man who manages his Las Vegas hotel “used to drive us to school every day,” middle son Eric Trump says. “If you go down to Wall Street, that’s not happening.” Eric, like his sister Ivanka and their brother Donald Jr., is a senior executive at the company. Allen Weisselberg, who grew up in Brownsville, worked as an accountant for Trump’s dad before joining the son, and hasn’t shaken his terrific Brooklyn honk, is now his chief financial officer. Amanda Miller, who was a teenage waitress when Trump spotted her at his Westchester club, is his head of golf marketing.
“I like taking people that I know,” Trump says. “They don’t have drug problems, they don’t have alcohol problems. They’re family. I would rather take guys at a lower level and move them up than hire people that you have no idea who they are.”
Trump’s empire is almost moving if you spend time with the deputies who admire him, alarming if you focus on its messier deals, and astounding if you remember how close it came to ruin. If you’re Donald Trump, it’s totally underrated.
It’s not a gargantuan company. The $605 million revenue that Weisselberg says it took in last year (though the months shift depending on the business line) makes it, for purposes of comparison, roughly the size of a company called NN, based in Johnson City, Tenn., which produces tiny steel balls.
The $605 million is almost double the revenue he reported in his financial disclosure for candidates, which Weisselberg says was bogged down by federal rules on what they could include. The profit on that revenue was somewhere between $275 million and $325 million, the CFO says.
That margin is extraordinary. Weisselberg points out that Trump’s licensing businesses, even if they’re smaller than his real estate and golf portfolios, are essentially all profit and help make the margin so wide. Trump squeezed about 13 times more profit than the Tennessee company got from the same revenue.
Trump is about to describe the most profitable parts of his business when Michael Cohen walks into the office.
“What do you have, Mike?” Trump says. Cohen, an executive vice president and special counsel to Trump, became famous a week earlier. He said he would do something “disgusting” to a Daily Beast reporter if the website published Ivana Trump’s accusation in a deposition that Trump had violated her in 1989, when they were married. Cohen added that a wife can’t be raped by her husband, legally speaking, which isn’t true. (Ivana has said the story was “without merit.”)
Cohen is upbeat, naming a television anchor who just called.
“His comments to me just now on the phone—” Cohen says.
“He can’t believe it, right?” Trump interrupts. “Because he saw the new polls?”
“He actually thinks you really could be the nominee. He said, ‘If you asked me the same question six weeks’—I’m sorry to interrupt—‘if you would have said this to me six, seven weeks ago,’ ” Cohen says. “He goes, ‘If Donald wants to come on, love to have him.’ They’re running 24/7 on just the debate.”
“I’ll talk to him,” Trump says. He corrects himself. “I’ll see if I can talk to him.”
The two other deputies in the room are sitting quietly on either side of me as we face their boss. On my left is Chief Legal Officer Jason Greenblatt. Trump tells me he’s there “not to sue you, just because he knows a lot about the company.” Weisselberg is on the right.
When Cohen leaves, the boss turns his attention back to the lucrative parts of his company. Or, rather, to parts that might be more lucrative should he decide to unlock the riches therein. “I think one of the things you have to think of is that the golf land is not just golf land; it’s land that if I want I can close up and build into thousands and thousands of units. And not one person has ever mentioned it.” He moves on to something else. “Let me just show you these real fast,” he says, picking up plans for his renovation of the Old Post Office Pavilion, soon to be Trump International Hotel, Washington, D.C.
The city he’d like to make his home comes up again when he describes some of those golf courses, one outside Washington and another in New Jersey. “Bedminster, in New Jersey, which is amazing, which you have to go see,” he says. “Have you been there? Have you seen it?”
Weisselberg, the CFO, is wearing a golf shirt when I meet him in his office four days later for a trip to New Jersey. We head downstairs and out a Trump Tower side door, driving uptown before turning west at Central Park, where Trump’s New York rise was boosted by his quick renovation of the city’s long-suffering Wollman ice rink in the 1980s.
By then, Trump had already emerged in Manhattan as a fully formed version of himself. When barely 30 he was being chauffeured around town in a Cadillac with his initials on the license plate, and newspapers were noting his dazzling grin and model companions. By the end of the 1970s he had brought his father’s outer-borough apartment company into Manhattan, transforming the Commodore Hotel on grimy 42nd Street into what would become the glassy Grand Hyatt New York. He had political connections helping him nab a new kind of tax deal to save him millions of dollars. He fought the government when the U.S. Department of Justice sued his family company for discriminating against black tenants in Brooklyn and Queens, a case he eventually settled.
Trump’s ego has its own origin story. On a cold November afternoon in 1964, the year he graduated from the New York Military Academy, he went with his dad, Fred, to watch the opening of the Verrazano-Narrows Bridge. He saw, he said later, its 85-year-old designer standing like a sap, with his name unspoken at the ceremony. “I realized then and there something I would never forget,” he told the New York Times in 1980. “I don’t want to be made anybody’s sucker.” It didn’t matter that the master of ceremonies, Robert Moses, had introduced the designer as “one of the significant great men of our time,” or that the man, Othmar Ammann, was applauded by 1,000 guests. Moses hadn’t remembered his name.
“Everybody thought Donald was just this brash young kid who was going to ride along on his father’s money,” says Louise Sunshine, one of his first deputies. “And I just thought, Oh boy. This was my opportunity in life.” Sunshine was also a top fundraiser for Governor Hugh Carey, an early connection to the officials who bestowed tax deals and zoning changes.
Despite saying he’d give them to the Metropolitan Museum of Art, Trump got rid of some of the old Bonwit Teller building’s limestone reliefs when he demolished it to make way for Trump Tower. “When I knew Donald, he lived half in the Trump world and half in the real world,” Sunshine says. “The only thing that makes Donald different today from the Donald that I knew is that I think he listened more in those days.”
The 1980s was a steroidal decade. Trump bought an airline, a vast Palm Beach estate called Mar-a-Lago, and a yacht so big it inspired a song by the band Queen. He proposed the world’s tallest building and was considered for a job to build a City of God for Hare Krishnas in New Jersey, according to a news report at the time. He became an Atlantic City tycoon instead, calling his Trump Taj Mahal the world’s most expensive casino ever built. He took over a pair of buildings on Central Park South, renamed them Trump Parc and Trump Parc East, and offered to house homeless people in one of them to pressure rent-controlled tenants to leave.
Weisselberg and I drive by those buildings, and by the Plaza Hotel, which he bought near the end of that decade for about $400 million—borrowing every dollar. Citigroup and other banks loaned him more than the hotel actually cost, throwing in money for renovations, and Trump had to personally guarantee more than $100 million of it. He said he’d give Ivana $1 and all the dresses she wanted to run the hotel.
That kind of debt exposure wasn’t rare. He borrowed so much that he ended up guaranteeing, altogether, close to $1 billion, which meant that the banks could have ruined him if something went wrong. Before his run ended, he opened the Taj Mahal in 1990 with a giant genie named Fabu declaring Trump its master and a green laser shooting out to cut the building’s red ribbon. It beat the Verrazano’s opening ceremony. The curtain came down on that era of Trump a year later when the Taj went bankrupt.
Before this year’s presidential race, the grandest triumph Trump had managed was staying on his feet during his 1990s disaster as the economy fell out from under him. He lost the Plaza, the yacht, and the airline, and the casinos filed for bankruptcy—but he himself didn’t, as he reminds his crowds on the campaign trail. In Trump: The Art of the Comeback, a book with two chapters on his prenuptial agreements and one on his collapse, he chalks up his survival to the timing of his debt negotiation, playing hardball with his lenders, and teaching one holdout banker a better golf grip.
What saved him is that those bankers believed he was worth more to them above water than under it. He fought to buy time until the real estate market could rebound. By 1995, with some but not all of his debt wiped out and a pair of big projects that would use his name under way, limousine mogul Bill Fugazy handed him a boomerang encased in glass at a lunch marking his comeback.
A new empire rose out of the wreckage of the first. The reimagined Trump relied more on partners than on personally guaranteed debt, at least most of the time. His name on a building didn’t necessarily mean that he owned or built it. When our car gets to Columbus Circle, we pass the skyscraper that was remade in 1997 from the Gulf + Western Building into Trump International Hotel & Tower. General Electric put up the money to transform it, but the GE International Hotel & Tower probably wouldn’t have attracted as many guests. A year later, on the other end of Central Park South, even though Trump put in only $11 million to buy the General Motors Building with insurer Conseco, his name went up in 4-foot letters on the white-marble tower. They were taken down overnight and the building was sold off after Conseco’s fall a half-decade later.
“I think that a healthy bit of fear got into him, and that was good,” says Brian Harris, whose company Ladder Capital is Trump’s biggest lender, according to his campaign filings. “Like a lot of very heavy hitters, they get older, they get a little more conservative, they start thinking about the kids.”
New York disappears, New Jersey highways ooze by, and after an hour’s drive from Midtown Manhattan we pull into the Trump National Golf Club in Bedminster. It’s a monument to the Trump style. At the front of the clubhouse is a fountain with lions around a pedestal below a pool, then more lions up above, another pool, even more lions, and a third pool, topped by a statue of a woman, high above our heads, holding buckets. She towers over a Lamborghini, a Maserati, a Mercedes, and a Bentley, keeping watch. Merely nice cars park elsewhere.
Stepping into the Trump world is like taking a long soak, or huffing new car smell, or doing both at the same time. We start in the main clubhouse, beneath chandeliers chosen by Trump. Mark Sanchez lived in a villa by the swimming pool when he was a New York Jets quarterback. A couple of his more prominent peers have reserved spaces near Trump’s in the glistening men’s locker room, where salves and lotions are lined up as far as the eye can see. A framed TV Guide list of catchphrases hangs by the door, with “You’re fired!” from his show The Apprentice highlighted in yellow, near gigantic urns also picked out by Trump.
The Trump Organization is not the kind of place where employees can always tell you what colleagues are working on or what their titles are. What they agree on is Trump’s immersion in the minutest of details, from the fountain and urns to the marble of lobby floors.
“Not in a compulsive way, or sick way, but in a caring way,” says David Schutzenhofer, Bedminster’s manager. When asked about it, Trump says he pays attention to details, even though he has good managers who should be able to handle them. It’s hard to imagine how Trump’s management style would or could translate to government, where hierarchies are impenetrable, micromanagement ineffective, and expensive urns susceptible to congressional scrutiny.
Bedminster has 400 members, and new ones are expected to fork over $150,000 to join on top of $24,000 a year. It’s a dreamy place, except when a player who’s facing us on one of the two golf courses a few yards away swings hard at a ball. It dribbles forward a few inches.
“We could have been killed,” Schutzenhofer says.
“That,” Weisselberg says, “was a terrible shot.”
We turn a corner and come to a spot overlooking the first hole of the club’s new course. Trump has suggested this could be his final resting place, with space for 548 more graves nearby.
“It’s funny, because when we bring it up to members, their initial reaction is they question it,” Schutzenhofer says. “But then when you ask them, ‘Where would you like to be buried?’ they kind of get it.”
Trump was connected to the land even before he bought the course. When gull-wing car magnate John DeLorean was going bankrupt in 1999, he announced plans to turn his estate into two golf courses, saying he could pull off a Trump-like comeback. He couldn’t; Trump himself bought it three years later. Trump’s website now lists a dozen U.S. clubs, two in Scotland, one in Ireland, and a licensed course planned for Dubai, leaving out the licensed Trump golf course in Puerto Rico that went bankrupt in July.
Schutzenhofer expects his club to make a $5 million profit this year. It will host the PGA Championship in 2022.
When we’re driving home, New York rises across the Hudson River in the afternoon sun. Manhattan’s skyline grows taller and ganglier by the day. Trump Tower has been dwarfed by a new generation of skyscrapers sprouting around it, skinny and strange.
Trump once wanted to be the biggest. Halfway through his 1980s climb, he tried to build the world’s tallest tower, a 150-story skyscraper on an East River landfill. A year later he zoomed across town, proposing to go just as high on the long stretch he controlled along the Hudson. Instead, after his 1990s fall, he sold 70 percent of the project, called Trump Place, to Hong Kong investors. A decade later, with only some of the towers up, they sold off the whole thing, including his stake, without his approval. He sued. Peace came when the Hong Kong investors used the money from that sale to buy two towers in New York and San Francisco, and then sold their 70 percent chunk to Vornado Realty Trust, a more acceptable partner for Trump.
That’s how he ended up with about a third of two huge Vornado office towers. He didn’t get to build higher than everyone else, he gave up control of his West Side dreamland, and sued over its sale, but ended up with a stake that the Bloomberg Billionaires Index estimates is worth $640 million, his most valuable holding. (Trump says it’s worth even more.) And it’s just one part of the real estate portfolio he owns that Weisselberg says is Trump’s biggest business, along with office building 40 Wall Street, Trump Tower, the NikeTown store connected to it, and shiny resorts. One of them is Trump National Doral Miami, where the spa menu includes a 35-minute beard shave, an 80-minute hydrating cocoon, a 100-minute antigravity face-lift, and a two-hour foot and hand treatment with salt exfoliation.
Landlords—and Trump is a major one—have a very good business. But builders capture the city’s imagination because they move brick, soil, money, government, and men. And only losers give up when they try and fail twice to put up the world’s tallest skyscraper. In 2001, before construction began on Trump International Hotel & Tower Chicago, he said he’d love to make it the tallest building ever. It ended up as that city’s second-highest, after Willis Tower, and in a flashback to his old ways he personally guaranteed $40 million on a Deutsche Bank construction loan to build it. It was still going up when the 2008 financial crisis struck. With sales slow and the German bank asking for its money, Trump claimed that the credit crunch was the kind of random catastrophe that allowed him to delay. They sued each other and announced a year later they would settle privately.
He built one other skyscraper with a big investment of his own in the past decade, and it suffered the same bad timing. His partner at Trump International Hotel Las Vegas, fellow billionaire Phil Ruffin, tells me they would have made a fortune if the economy hadn’t crashed as they opened in 2008. For now, Ruffin says, they still owe about $12 million out of the $560 million they borrowed.
Trump, such a proud erector of towers that he once promised to put up “the stiffest building in the city,” hasn’t built his own skyscraper since.
“Here’s the thing,” he says in his office. “What I’m doing now—I’ve been building all my life. I built a lot of buildings.” His voice hushes, serious and nostalgic, and he ticks through Trump Tower, the Trump Palace condos on Third Avenue, the Trump World Tower across from the United Nations, and Trump Park Avenue, which he converted from the Hotel Delmonico into apartments. “All over the city I built.”
Trump didn’t leave Atlantic City after his ugly fall. He doubled down, winning control of his casinos from his lenders, opening another, and turning down at least one offer to sell. He even said he’d build the world’s biggest yacht, a few yards longer than the royal Britannia, and dock it by the Trump Castle casino. “I’ve always wanted a boat bigger than the queen’s,” he said. Atlantic City continued its slide, and Trump didn’t leave until more than a decade later, though his name stayed on his old casinos even after he gave them up. He said last year he’s thinking about buying back in.
In 2005 he became an education entrepreneur, founding Trump University. “The problem with school is that school is a little academic,” said Roger Schank, its chief learning officer, when the online program started. Trump U gave out no degrees, wasn’t accredited, changed its name to the Trump Entrepreneur Initiative, and was sued by New York’s attorney general for cheating students. Trump denied the allegations and countersued.
The parts of his company that slap his name on other people’s things help explain how Trump can make all that profit from such a modest amount of revenue. Trump can earn millions of dollars when he licenses out his five sparkling letters, that unbeatable verb, to new towers in the Philippines, Panama, India, Uruguay, Brazil, Canada, and the U.S., too. And he doesn’t have to worry about spending money on stuff like concrete.
“It’s not conventional, traditional real estate, but it’s real estate,” says Richard LeFrak, another billionaire son of an outer-borough New York developer. “I mean, if you think about it, his brand is his real estate.”
A year after the university opened, he launched Trump Mortgage with a press release, saying in all-caps it would put the “SUIT AND TIE BACK IN THE MORTGAGE BUSINESS.” His CEO’s work experience, posted on the company’s website, turned out to be embellished, and within a year the company shut down.
Trump began endorsing a multilevel-marketing firm called ACN around that time. “Hey, if you want a nice, easy, OK life, you can be in the pack ... but if you really want to do something, you do have to get out of the pack,” he said in a promotional video. “We do a lot of research on companies before we agree to do something like I’m doing for you, and ACN’s a great company.” ACN, which charges new members $499 to join a system that rewards them for selling digital phone service and natural gas, was featured on 2009 and 2011 episodes of The Celebrity Apprentice, where contestants promoted a video phone. In between, Montana’s securities commissioner accused ACN of running a pyramid scheme, dropping a cease-and-desist order when the company agreed to better training programs. Trump got $1.35 million for three recent speeches to the company.
Trump, a teetotaler, launched his liquor the same year as his university. The spirit, which was billed as the World’s Finest Super Premium Vodka, lasted until at least 2008. A phone number for the company that made it, Drinks Americas Holdings, leads to the answering machine for a hair design studio.
There’s also Trump tea, a Trump energy drink for the Israeli and Palestinian markets, Trump coffee, and Trump colognes called Success and Empire. And those are only the liquids.
He found more success with NBC’s The Apprentice, which his campaign says made him more than $200 million over 14 seasons. He also rolled out Trump-brand menswear sold at Macy’s and Serta’s Trump Home® iSeries® mattress with Cool Action™ Dual Effects® Gel Memory Foam. The clothing and mattress deals each brought in between $1 million and $5 million last year, according to Trump’s filings—and all three companies announced they were cutting ties with him after he said in June’s campaign kickoff at Trump Tower that some Mexican immigrants are rapists. The speech, a loud amplification of The Apprentice’s insult drama, cost him some sponsors while hurtling him into the Republican stratosphere.
Antagonizing enormous swaths of North America, mocking women, and startling anyone tuned in to a few minutes of his speechifying wouldn’t be a wise business move if those products were all he had, because he’d be alienating precious customers. But there’s more to Trump’s business, and not just because he has the real estate and golf portfolios. His brand isn’t kindness and inclusiveness; it’s aggression and extravagance and power. It’s a self-rendered notion of an elite man who controls and wins, even when he loses.
That doesn’t mean you can take the boasts about his empire literally.
“I’m the biggest developer in New York, by far,” he told Larry King in 1999. “I’m the biggest developer in New York, and I’m not looking for additional work,” he told the New York Post in 2003. “My name’s Donald Trump, and I’m the largest real estate developer in New York,” he said in 2004’s Apprentice pilot, introducing himself in a limo. “Here I am, the biggest developer in New York,” he told a reporter from Scotland in 2007. “The greatest builder is me, and I would build the greatest wall you have ever seen,” he said this May, invoking his plan for Mexico’s border at a speech in South Carolina. He pointed at his chest while rolling his head around. The crowd went wild.
Trump isn’t the biggest New York developer. He isn’t really a skyscraper developer anymore, and he hasn’t been for years. He put up huge buildings and casinos, borrowed to do it, nearly wiped out, came back as a brand name that often needed bigger partners, was smacked by the financial crisis when he tried to again take massive risks, and ended up with a profitable business anyway.
The lesson from the 150-story building he craved is the same one you get from stepping inside the company. It’s not the hugest in the whole world, and it’s not what it was supposed to be, but it’s something. And, like his politics, it can seem much, much bigger than it is.
Trump has crushed his presidential competition by presenting himself as the finest businessman ever to don a suit. Will his career’s blemishes hurt him? Could Americans who love the great, amazing, terrific, perfect version of Trump accept the flawed one? In his office, he tells me that someone said the cool thing about his race to be the leader of the free world is that if he loses he gets to go back to being Donald Trump again—only an even vaster version.
“So win, lose, or draw, I’m glad I did it,” he says. “Although it’s too early to say that yet.” 