IE 11 is not supported. For an optimal experience visit our site on another browser.

Trump's true apprentices: his two children

There are two souls Donald Trump trusts, the ultimate apprentices: his two oldest children.  Enough that they are gradually assuming day-to-day responsibilities in the Trump property empire.
Donald Trump Jr. speaks during news conference in Chicago
Donald Trump Jr., right, talks to reporters as his sister, Ivanka, and his father, Donald Sr., look on.Stephen J. Carrera / Reuters file
/ Source: Forbes

Donald Trump, famous for his wealth, infamous for his ego, has a dim view of the world. To the real estate mogul and TV star, most people are either “enemies,” “bastards,” “sleazebags” or “stone-cold losers.” He isn’t acting when a little glee creeps into his curt dismissal of contestants on The Apprentice: “You’re fired.”

But there are two souls Trump trusts, the ultimate apprentices: his oldest children, Donald Jr., 28, known as Don, and Ivanka, 24. Enough that they are gradually assuming day-to-day responsibilities in the Trump property empire, which has four developments of its own and, as a label for hire, is a consultant and front for dozens of buildings that others construct. The Trumps, that is, run a franchising operation for condo vendors.

At 60, Donald J. Trump remains firmly in control of his real estate company, the Trump Organization, overseeing things great and small. But as his kids jet around the world to check on his projects, he’s devoting even more time to his public appearances (he was at Hugh Hefner’s 80th birthday party this spring). And he’s eyeing new reality TV shows now that The Apprentice is fading in the ratings. One idea: a knockoff of the Monopoly board game, apt for a man whose casinos are fixtures on the Atlantic City boardwalk.

Ivanka and Don embody two sides of their father. Ivanka, a former model, is the spotlight-loving Ms. Outside, and her brother is the detail-obsessed Mr. Inside. The family dynamics are on view on a recent Sunday evening when Donald Trump walks onto the stage of the Los Angeles Convention Center to the din of an adoring crowd. The audience of 54,000 would-be real estate millionaires has been whipped into a frenzy by two dozen hiphop dancers gyrating to the slick theme music from The Apprentice. Trump, who is getting $1 million for the speaking gig, says he looks forward to their questions. “Ideally, to be sexually oriented,” he says. Not about “real estate, which is boring.”

Don Jr. is not present. He is spending an unglamorous weekend back in the family’s New York base, fielding phone calls from project managers, builders and lawyers. “I know the entertainment stuff helps us,” he says. “But somebody’s got to stay here to remind everybody that we build buildings.”

Ivanka is decidedly present in L.A. An audience member asks her father for a date with her. “On The View, I said she was so beautiful that if she weren’t my daughter, I’d date her myself,” he says, then beckons Ivanka to the stage to further rev up the crowd.

“Okay, honey, now sit down — get the hell outta here,” he says. She feigns offense, then flashes a bulletproof smile.

Learned lessons from his father
Donald Trump learned the business from his father, Fred, a housing developer in New York’s outer boroughs of Queens and Brooklyn. “One advantage my father had was that he knew what everything cost,” Trump wrote in a memoir. Well versed in Fred’s hard-negotiating style, the ambitious young Donald Trump made his mark in the mid-1970s by invading Manhattan. After bare-knuckled bargaining with the city, he won tax breaks to refurbish a rundown hotel near Grand Central Terminal.

Trump has been an exacting tutor to his offspring, whether the subject is how concrete is mixed or how the celebrated surname is marketed. They now are in the post-grad phase. While Trump still gets a last word on every deal Don Jr. and Ivanka arrange, a large number of details are in the kids’ hands. “I’m very proud of my children,” he says. “They’re doing a terrific job.”

Give the man his due: Beyond his operatic personal life and tempest-tossed business career, the truth is that he understands how to make good deals, build good buildings and make good money. “People say he’s not worth this or he doesn’t really own that,” says New York developer Richard LeFrak. “But measure him by what he gets built. It’s impressive.”

Trump has made a handsome recovery from the early 1990s, when he was on the brink of insolvency because he borrowed too much and real estate tanked. The last vestige of that bloody era played out two years ago with the bankruptcy filing of his publicly traded casino company, which is separate from the privately held Trump Organization. Trump Entertainment Resorts emerged from Chapter 11 in mid-2005 with Trump’s equity stake reduced from 47% to 31%.Trump was shorn of the chief executive role; he remains chairman. Don Jr. and Ivanka aren’t involved in running the casinos.

Through it all Trump has nurtured a valuable brand name that has withstood the scorn of his many critics. Dumped from the Forbes 400 during his down spell, he returned in 1996. We estimate Trump’s fortune at $2.9 billion (see box, p. 60). Trump insists he is worth $6 billion.

These days the Trump Organization is more careful. It oversees the building of residential condo towers that it does not own. Other people, ranging from little-known developers to magnates like Forbes 400 member Jorge Perez of Miami, put up the money and hire the contractors. Then the attention-drawing “Trump” moniker gets slapped on the project. The Trumps promote the project and advise on planning, architecture and marketing in exchange for fees and a cut of the gross sales.

An impressive 33 such Trump franchise projects now are under way, seven of them “condo hotels,” where investors buy a room from the Trumps and their backer, getting the right to cream off rental income in the still burgeoning lodging sector. The others are apartment condos. The housing units are packed to their custom crown molding with high-style kitchen appliances, elegant-looking bathroom sinks and enough marble to renovate the Taj Mahal.

Not a risk-free industry
Of course, real estate development is hardly risk-free, even when the Trumps get someone else to cough up the capital. Don Jr. and Ivanka are haunted by the possibility that some of their projects might go wrong. Housing is softening nationally. In South Florida, where 3,000 Trump condos are under construction, the threat of an oversupply looms. With typical Trumpian bravado, Don insists the brand name will carry them through, even in a bad market. Still, Ivanka wonders, “How will the headlines read if Trump has to cut prices?”

Knowing Trump and his seething temper, some close friends wonder how forgiving he will be to the kids should any deals collapse. “He can be an extremely mean guy, even to people very close to him,” says a former business partner.

Now with 300-plus developers per year approaching the Trumps hoping to partner up, Don Jr. and Ivanka are in charge of safeguarding the brand. Don’s small office in Trump Tower, on Fifth Avenue, is cluttered with proposals from possible partners. His job is to vet the paperwork. Then he and Ivanka put the winning projects in motion. Real estate pros seem to respect them as their father’s surrogates. “When developers are talking to Ivanka and me, they know they’re not talking to some flunky,” says Don.

Tall like their 6-foot-2 father — Don is an inch shorter, Ivanka 5-foot-11 — they exude dad’s self-confidence, yet little of his braggadocio. They work well together and finish each other’s sentences.

Like their dad, they both graduated with bachelor’s degrees from the Wharton School.

Don went right to work for his old man. Ivanka, who was summa cum laude, joined the company in 2005 after a stint with developer Forest City Ratner and works for her older brother, technically. “I wanted to ward off any pretensions that I am Don’s equal,” she says, but the two usually work like equal partners.

One sign of the torch passing is the launch last fall of Trump Mortgage, a loan brokerage that is Don Jr.’s brainstorm. “This one’s really my baby,” he enthuses. Thus far Trump Mortgage has arranged $1 billion in loans. It bags a fee of 1 percent to 2 percent of the loan amount.

The brokerage serves as the middleman between lenders and buyers; the buyers are 50 percent commercial types (offices, retail, etc.), and commercial real estate has yet to see a slowdown, as housing has. Don remains confident that the brand name will keep the high-end residential borrowers who make up the rest of the clientele coming, even in a real estate slump. “Try naming a mortgage broker,” he says. “You can’t.”

Don and Ivanka are products of Trump’s first marriage to Czech Olympic skier Ivana, now known for her clothing and jewelry lines sold on TV shopping channels. A third child from the Ivana union, Eric, 22, just graduated from college and joined the business in August. Their childhoods coincided with some of Trump’s better years in the 1980s, when he built Trump Tower, a mixture of residential, retail and offices.

Don Jr. was born on New Year’s Eve in 1977. “I like to joke I started working for my dad the minute I was born,” he says. “My dad wanted to be able to claim me as a dependent on his taxes for 1977, so he told my mom she had to have me before midnight, and if she didn’t, he’d make her take a cab home.

“I’d be going to work with my dad when I was 5 or 6 years old,” recalls Don. “Besides telling me again and again not to drink, not to smoke and not to chase women, he always told me: ‘Never trust anybody.’ Then he’d ask me if I trusted anybody. I’d say, ‘No.’ ‘Do you trust me?’ he’d ask. I’d say, ‘Yes.’ And he’d say: ‘No! Don’t even trust me!’ ”

Affair makes tabloid headlines
Prophetic. In 1990, Don and Ivanka learned of Trump’s affair with model-actress Marla Maples. Ivana confronted Maples on a ski slope in Aspen. Donald moved from the family’s Trump Tower apartment to another unit in the building, and headlines of the affair with Maples began running on the front pages of the New York tabloids.

Hurt on behalf of his mother and outraged by his schoolmates’ ribbing, Don didn’t speak to his father for a year. “I was a brat,” he says. “I’d hang up on him.” Don turned to his Czech grandfather, Ivana’s dad, who introduced the lad to outdoor sports and encouraged him to make peace with his father.

In college Don got into strenuous sports—and strenuous partying. He also developed into a serious drinker. In 2000 he spent a year as a ski bum in Aspen. He has twice broken ankles, while skiing and paragliding. After coming to work for Trump, he quit drinking entirely. “Drinking in moderation wasn’t something I was good at,” admits Don, now settled down with wife, Vanessa Haydon, a model.

Ivanka also has zest for adventure. She insists that her modeling, done as a teenager, was just a lark, an excuse to get in some European travels on somebody else’s dime. Her height and looks made her perfect for the runway. “She’s taller than 80 percent of the men in any room,” says Panamanian builder Roger Khafif, who is planning a 2.5-million-square-foot development that will bear Trump’s name on reclaimed land in Panama City. “And she’s a tough person.”

As a teen she endured an agonizing ski weekend trying to save face by ignoring the pain of a badly broken thumb. “I really take pride in my skiing, and I was embarrassed that I fell in front of my friends,” she says. “My friends kept looking at it, saying, ‘I think it’s broken,’ but I kept saying it was ‘no big deal.’ ”

Brother and sister regard Trump with a measure of awe. When showing him a possible deal, Don says, “He always zeros in on the three things you don’t know.” Here’s what the two siblings have learned about doing business, Trump-style:

Put on the squeeze
If you’re a real estate know-it-all, you may not like Donald Trump. You may think another developer, like New York’s Stephen Ross or Irvine, Calif.’s Donald Bren, builds condos or houses or hotels that are better. But thousands disagree. In fact, buyers consistently pay a premium —  brokers say it’s usually 20 percent to 30 percent of what other comparable properties fetch — for a condominium with the Trump name on it. Ivanka and Don Jr. take full advantage of that.

The Trump Organization occupies a unique position as the lone residential real estate franchiser. The Trumps’ arrangement is similar to what is common in the hotel industry, where big outfits like Hilton, Starwood and Marriott license their names and expertise to others. Prospective partners pay Trump an initial fee (usually, $1 million to $2 million) and agree to pay 8 percent to 15 percent of the gross sales of their condos. If the Trump name produces the 20 percent-plus premiums, both parties make out.

Finally, the Trumps get as much as half of every dollar paid exceeding a benchmark, typically  20 percent above what they and their development partners agree is fair market value of a property. For all this, Trump generally puts no money down. “When it comes to money, most people are too afraid or embarrassed to haggle. Maybe they think it’s tacky. My dad doesn’t,” says Don.

Be creative
Don recalls how his father found a clever way to add 12,000 square feet of space to the Hotel Delmonico on Park Avenue, which he converted to high-end condos. Built in 1929, the building had 200 suites, suitable as hotel rooms but lacking the square footage that the target buyers would demand. The zoning code forbade adding any square feet to the property. Trump told his son: “If you go by the status quo, you’ll never get anything done.”

Trump, who’d purchased the property for $115 million and was spending $85 million on renovations, wanted to add space by extending the building’s upper floors. So he gutted 12,000 square feet of old commercial space at the structure’s base, leaving open dirt beneath a corner of the building away from the street.

Then, putting a twist on the sort of trade that is common in New York zoning, he transferred the space upstairs to make bigger apartments by erecting a steel-and-glass extension above the existing roof. All units at what now is called Trump Park Avenue are sold except for the penthouse, priced at $32 million.

Use the media
Although Donald Trump on occasion gets trashed in the press, most recently for the casino bankruptcy, he is a master at generating positive publicity. “We can do a building in the middle of nowhere, and it makes national news,” says Don. He and Ivanka spend hours on the phone with reporters in cities where new Trump properties are being developed.

Know your timbers
The elder Trump is a perfectionist. For years he has lectured the kids on what was right and wrong with buildings. On one recent Saturday morning Donald Trump visited the construction site of his housing development, one of the few undertakings he owns 100 percent and for which he is putting up all the money. It adjoins his seaside golf course in Palos Verdes, Calif., south of Los Angeles.

Trump and his construction managers look over samples of patio bricks for the driveways. Then they go into the master bedroom of one of the houses. Ivanka, Trump is told, toured this house yesterday and said a window should be moved to get a better view. “She’s right,” Trump says.

Another Trump project is rising in Jersey City, N.J., a once dowdy industrial burg that’s now rallying. New Jersey developers Dean Geibel and Paul Fried are shouldering the $415 million cost of the twin-tower condo structure. Called Trump Plaza and due to open in 2008, it promises to be the tallest residential building in the state.

Don Jr. is on the phone with Geibel about the construction work at least twice a week. Originally Geibel wanted the building to have “eyebrows,” concrete slabs on each floor that poke out from the exterior walls, dividing the facade into one-story sections. But Don convinced him that these protrusions disguised the complex’s height, its big selling point. Eliminating the eyebrows, Don argued, would add just $2 per square foot to the construction cost of $400.

Once all the units sell, the Trumps will stay on as property managers. After all, their name is on the building.