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Did Their Father Really Know Best?

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Donald and Don Jr. with their fiancées Melania Knauss and Vanessa Haydon.  

A nasty divorce, workaholic parents, boarding school, piles of money—it’s often a recipe for trouble. And those same ingredients did turn some of Don’s peers into dissolute malcontents. I bring up Born Rich, the documentary about children of incalculable wealth and privilege directed by Jamie Johnson, a Johnson & Johnson heir. It’s a rather depressing film, one that leaves you with the sense that all of the subjects, which include a Newhouse, a Bloomberg, and a Vanderbilt-Whitney heir, harbor a deep resentment toward their parents. Except, that is, for Don’s sister, Ivanka. She comes across as uniquely well-adjusted, articulate, poised, respectful, and of-this-planet.

Don launches into a good-natured semi-rant about the rest of the film’s subjects, most of whom he knows. “I couldn’t believe it,” he says, his voice rising an octave. “I was like, ‘Do you hear the words that are coming out of your mouth? Are you out of your mind?’ Their parents gave them anything they could have ever wanted. And they hate their parents! I’m not close with any of them, but it’s very one-degree-of-separation.”

How did the Trumps escape this fate? The most important thing his parents did, says Don, was to make the kids work as teenagers. Donny’s first job, at the age of 13, was as a dock attendant at the marina at Trump Castle, making minimum wage plus tips tying up boats. “We were spoiled in many ways, but we were always taught to understand the value of the dollar. If there was something we wanted, we had to earn it. Even in college, we were very fiscally responsible. I had 300 bucks a month; anything I wanted beyond that, I had to work for.”

Not that Don never had his problems. It was during college, at the University of Pennsylvania, where he was enrolled in the Wharton undergrad program, when the repressed anger surfaced and the rebellion began. He had a reputation for getting into drunken, do-you-have-any-idea-who-I-am? fights. “To be fairly candid,” he says, “I used to drink a lot and party pretty hard, and it wasn’t something that I was particularly good at.” He laughs. “I mean, I was good at it, but I couldn’t do it in moderation. About two years ago, I quit drinking entirely. I have too much of an opportunity to make something of myself, be successful in my own right. Why blow it?”

When Don graduated, he decided to take a year off and live in notoriously boozy Aspen, Colorado—something his parents did not like one bit. (They know as well as anybody that Aspen spells trouble.) “I had a great time,” he says, “but your brain starts to atrophy. It just wasn’t enough for me.”

No one in his family believed Don would ever come around to work with his father. “But I knew that it was something I wanted. I was following my dad around from a young age. I don’t know if it’s genetic, or just because I was surrounded by it, but I was always fascinated with building and construction and development. I guess I just wanted to make sure that I was making the right decision.”

Just then, an older gentleman peeks his head into the conference room to tell Don that he has a meeting scheduled and needs us to move. For a second, I think he’s going to pull Trump family rank, but then, very politely, he asks, “Is someone in the large conference room?”

Indeed, there are people in that room. “Okay,” says Don with a bit of macho swagger, “we’ll slide over there and kick them out.” In the end, he does not make anyone move but asks to borrow someone’s office. When we settle down again, I notice that there’s a Donald Trump doll sitting on a shelf above our heads.

One of the most appealing things about Donald Trump Jr. is that he does not seem the least bit tormented about the fact that his father is Donald Trump Sr., though he does concede that the universal reaction he gets at airline check-in counters or whenever he uses his credit card— >I?“Donald Trump?! You don’t look like Donald Trump!”—has grown tedious.

“I think I probably got a lot of my father’s natural security, or ego, or whatever,” he says. “I can be my own person and not have to live under his shadow. I definitely look up to him in many ways—I’d like to be more like him when it comes to business—but I think I’m such a different person, it’s hard to even compare us. His work persona is kind of what he is. I have a work face, and then there’s my private life.”

Today, his work for the company is mostly in acquisitions and development, focusing on the redevelopment of the old Delmonico Hotel at 502 Park Avenue and the Chicago project seen on The Apprentice. He works closely with his father, talking to him about business at least once a day. “He’s a very fair boss,” says Don. “At the same time, you have to be on top of everything, because there’s no one who works harder than he does. He’s a machine.” He laughs. “I’ll check myself, in the sense that I’m not going to do anything in a disrespectful manner in front of other people, but there’s a point where I’ll go into his office and close the door and it’s like, ‘Listen, this is crazy.’ But he can ride me harder than he can ride the other people because . . . he’s my dad.”

The transformation from angry Donny to self-possessed Don has surprised a lot of people. “I used to really think that Donny would one day just get on a boat and sail away and leave this world. Those periods when there was the drinking were his way of escaping,” says one person who knows the family. “I was pretty shocked when I realized how deep some of his problems have gone. I’m so happy he turned a corner.”

It helped that he was able to screw up without the world watching. Thanks to his parents, he’s kept a remarkably low profile over the years. “When I was younger,” he says, “I went out of my way to avoid any kind of media attention. To this day, I meet people and they’re like, ‘I didn’t know he had a son! You mean Ivanka’s not the only one?’ She did her modeling thing, she was out there a little bit more. But if there was a reporter within 100 miles, I was in the background somewhere, trying not to be seen.”

But there is, I suspect, another reason Don stopped fighting his birthright and learned to love being a Trump: Despite his protests to the contrary, he is his father’s son. One woman who went to the University of Pennsylvania with Don tells me, “He was almost disappointingly normal.” To the chagrin of the fraternities for rich, well-connected kids—and despite their clamoring for his membership—Don chose FIJI, a frat known for attracting “regular guys.” His girlfriend, on the other hand, was widely considered to be the hottest girl in his class. This, of course, sounds an awful lot like his boss, a man who cares very little about running with the in-crowd but who plainly enjoys the company of a foxy lady.


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