Twenty-five years ago, Donald Trump had already achieved no small measure of success. His unmistakable buildings speckled the sprawls of Manhattan and Atlantic City. He owned an airline. He vacationed on a 282-foot yacht, the Trump Princess. He was likely worth $1 billion. Maybe $3 billion.
So what did the high-flying dealmaker think of his kids’ prospects for the future? "Statistically, my children have a very bad shot,” Trump told Playboy in 1990. “Children of successful people are generally very, very troubled, not successful. They don't have the right shtick.”
Presidential campaigns aren’t just a test for candidates but for families too. Just ask Bill Clinton or Columba Bush. As Trump’s "right shtick" has vaulted the reality-television host to the tops of early Republican primary polls, a new challenge faces a clan that's already seen its fair share of them.
After surviving their parents' divorce, endless tabloid attention and what they have described themselves as an absentee father, the Trump children have entered the latest chapter of what has been an upbringing unlike any other. Now in this summer of Trump, their father's campaign-trail antics are testing their peculiar inheritance like little before.
DEAL MAKERS Given their father's reputation for bluster and braggadocio, the three adult Trump scions—Donald Jr., age 37; Ivanka, age 33; Eric, age 31—have a habit of surprising people. People who know them say they can be down-to-earth and easy-going, descriptors that would not apply to their father unless he was trying to close a deal. They lack his hunger for publicity for its own sake and his flair for the outrageous.
They work for their father as executive vice presidents of development and acquisition. (Trump also has two younger children, one each by his second and third wives.) As for their specializations: Don Jr. manages the existing property portfolio, Ivanka oversees the family's hotels, and Eric manages the family's golf assets. The Trump Organization has a reported 22,000 employees, with nine luxury hotels, 17 golf courses and 18 luxury residential properties worldwide. The company also makes millions from extensive licensing deals on real-estate developments it does not own or manage.
"To be honest," says Richard Huckestein, a principal in T&G Constructors' Miami office who served as a project executive on the Trump renovation of the Doral Golf Resort and Spa, as though preparing to break bad news, "I really like Eric. I didn't know anything about the family other than what I read about them beforehand. But they were straight shooters and honest."
"Ivanka is very smart and meticulous. She'd be successful anywhere in New York," says Michael Ashner, whose Winthrop Realty Trust sold the Trumps Doral for $170 million in 2011. "In a room full of testosterone, she can keep her cool."
People who have worked with Trump's children say that they handle the details of many of the company's deals and projects. (A representative for the Trump organization declined on behalf of the children to participate in this story.) The Trumps—both this generation and their father—are said to be more hands-on than many developers, weighing in on design and construction matters that others might delegate.
"As negotiators, the boys are very fair, very ethical. They make a deal on a handshake and they stick to it," says Jeff Lichtenberg, an executive vice president at Cushman and Wakefield who works as a leasing agent for the Trumps and is especially close with Don and Eric.
Ben Coster—Camera Press/Redux; Gilbert Carrasquillo—Getty Im
RAISING THEMSELVES Growing up a Trump was tumultuous even by the standards of the truly wealthy. Donald and Ivana’s marriage had fascinated the tabloids even when it was intact. (To wit: Her broken-English coinage "the Donald" has outlasted much of the so-called popular culture of the 1980s.)
"I look at my brothers and myself and I'm, like, really proud of the fact that nobody's, like, totally f--ked-up," Ivanka told an interviewer in 2007. "Nobody's a drug addict, nobody's driving around chasing women, snorting coke. There's something amazing about that. And you know, this isn't to pat myself on the back, but I could be a lot worse."
Neither parent was especially present. The kids grew up in the close company of nannies and security guards who worked for the family. Ivana's parents lived with them when they were young; the boys' interest in hunting and fishing came from grandfather Milos. (In 2011, Donald and Eric went trophy hunting in Zimbabwe, killing an elephant and cheetah among other large animals and facing scorn from the press upon the photos' surfacing.)
"My father is a very hardworking guy, and that's his focus in life, so I got a lot of the paternal attention that a boy wants and needs from my grandfather," Donald Jr. told a reporter in 2004.
In the same story, Trump Sr. said, "I'm a really good father, but not a really good husband. You've probably figured out my children really like me—love me—a lot. … The hardest thing for me about raising kids has been finding the time. I know friends who leave their business so they can spend more time with their children, and I say, 'Gimme a break!' My children could not love me more if I spent 15 times more time with them."
"Donnie's always been my friend, a mentor," Eric Trump said of his older brother in 2006. "In a way, he raised me. My father, I love and I appreciate, but he always worked 24 hours a day."
When, in 1990, after 12 years of marriage, Donald and Ivana's union came apart—precipitated in part by a skirmish between Ivana and Trump's new flame, Marla Maples, on the Aspen slopes—then the vultures really flocked. The Daily News's Liz Smith had the inside story of Ivana's broken heart; the Post had Maples boasting "Best Sex I Ever Had." The story ruled the headlines for three months. Donald Jr., who was 12 at the time of the divorce, told New York: "You're not quite a man, but you think you are. You think you know everything. Being driven into school every day and you see the front page and it's divorce! THE BEST SEX I EVER HAD! And you don't even know what that means. At that age, kids are naturally cruel."
All three would eventually enroll in boarding school—the boys at Pennsylvania's Hill School and Ivanka at Choate, in Connecticut—where they were largely sequestered from the family's fortune and notoriety. Donald Jr. would afterward attend the Wharton School of Finance at the University of Pennsylvania, as would Ivanka (she graduated cum laude) after spending two years at Georgetown, the school from which Eric would graduate.
Growing up, they did odd jobs for their father's businesses—Don, for instance, as an attendant at the docks at the former Trump Marina in Atlantic City—to earn pocket money. "We were spoiled in many ways, but we were always taught to understand the value of the dollar," Don Jr. once said.
And even though Don Jr. went through a rowdy phase in college, drinking to excess and starting fights, he said that the life of a trust-fund kid wasn't for him. He spent a year in Aspen and gave it up. "I had a great time, but your brain starts to atrophy. It just wasn't enough for me."
FAMILY DEALS "I knew my children were competent. I just never knew they were this competent," the eldest Trump said in 2007, before he had handed off so many operational responsibilities to the three.
Apart from their Trump Organization duties, all three have built up genuine side gigs. Eric Trump runs Trump Winery, the Charlottesville vineyard that once belonged to billionaire heiress Patricia Kluge, and a foundation that has pledged millions to St. Jude's Children's Research Hospital. Donald Jr. hosts a syndicated business TV show. And Ivanka has had perhaps the most success spinning the family brand into her own—she has released jewelry, shoe and clothing lines and publishes a lifestyle website.
Ivanka sprung on the scene before her brothers. She modeled as a teenager, covering Seventeen (at age 15, but who's counting?) in 1997. All three would become more prominent thanks to the success of The Apprentice and The Celebrity Apprentice, on which they appeared regularly.
Although the eldest Trump did not arrange his children's marriages, it wasn't for lack of trying. Trump once said, "Ivanka is a great, great beauty. Every guy in the country wants to go out with my daughter." He later said, "If Ivanka weren't my daughter, perhaps I'd be dating her." And in 2006, Vanessa, the model who is now married to Donald Jr., recalled how the couple first met. "I'm at this fashion show. Donald Trump comes up to me with his son: 'Hi, I'm Donald Trump. I wanted to introduce you to my son Donald Trump Jr.'" At intermission, the Trumps, to Vanessa's surprise, returned. "Donald comes back up to me again, 'I don't think you've met my son Donald Trump Jr." The pair reencountered one another, for good, at a party months later.
Ivanka's marriage, for all the money involved, seems quite domestic. She has two young children, whose photos she posts lovingly online. For her husband Jared Kushner, another scion of a New York real estate family, she converted to Judaism, and she keeps kosher and observes the Sabbath. (The pair have contributed extensively in the past to Democratic candidates.) "Jared and Ivanka are centered in a more low-key, contemporary, family way," said Don Jr. in February, when asked to compare the Kushner-Trumps to his parents.
But she's still her father's daughter. According to Vogue, the pair were set up by friends who thought they could do deals together. Ivanka says now, "Whenever we see them, we're like, 'The best deal we ever made!'"
A GOOD NAME As for their father's campaign, the boys seem to dig it. They joined their dad for his campaign kickoff speech in the atrium of Manhattan’s Trump Tower on June 16. They flew with their father to Cleveland aboard Trump’s Boeing 757 to watch their father debate the nine men trailing him in the Republican field. Ivanka, while present for the announcement and the debate, is reportedly a little less enthusiastic. A report on New York's website said that she had drafted a statement in which her father would walk back some of his comments about immigration but he had declined to release it.
While the usual concern for a presidential candidate's family is how greater fame and scrutiny might shake up their lives, that's probably not what vexes the Trump family. One wonders instead whether an unscripted and sour remark from the patriarch could make his properties less palatable to those in the market for luxury. Already this summer, a number of companies have backed away from the Trump brand. Every week Trump stays high in the polls is another chance for him to upset a different constituency and blemish the name that will someday just belong to his children.
Then again, maybe the family can survive anything. In a statement to Travel and Leisure, Donald Jr. said that the hotels were having a good year. As their father once said about the name Trump, "It's German in derivation. Nobody really knows where it came from. It's very unusual, but it just is a good name to have."