How Donald Trump Jr. Got Stuck In His Father’s Shadow

It’s always been hard being Donald Trump, Jr. “Every time you check in at an airport, it’s ‘Oh, my god, you’re Donald Trump’s son,’” he told me when I spoke to him for my biography of the Trump family. But in the wake of reports that a year ago he had a secret Trump Tower meeting with a lawyer who promised dirt on Hillary Clinton from Russian government sources, it’s gotten a lot harder.

As with many incidents on the growing list of encounters between Russian operatives and Trump campaign and administration officials, it’s unclear whether this particular meet-up will lead to criminal charges or be written off as what White House chief of staff Reince Priebus has called “a big nothing burger.”

But at the least, it provides an opportunity to see whether Donald Jr., now 39, who once told me, “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,” has finally emerged as his own man; or whether, in wanting too much to please his father, he has been an overeager and incautious servant.

When I interviewed Donald Jr., it was at the groundbreaking for construction of Trump Tower Chicago in October 2004. He was 26, and he said that in the four years he had been working for his father, the Trump Organization had changed from being “very New York-centric” to having projects all over the country, “It’s not entirely my doing,” he said, “but these are things I’ve helped push. It’s such a huge brand, it could be global.”

My recollection of him at the time was of someone happy to be where he was. At that age, his father had been itching to take over the company, but Donald Jr. seemed comfortable waiting his turn, “I’m on my way,” he said, “but right now I’m still learning.” He worked hard, but he wasn’t a 24/7 guy like his father; instead, he was “more grounded” and could “lay back in my personal life.” Although “The Apprentice,” then in its second season, was a smash hit, he had no appetite for being on television himself and said, “You’re unlikely to have ‘The Apprentice Jr.’” (In 2007, however, he would join the show, taking a seat at the conference table alongside his father.)

Nonetheless, over the past five days, Donald Trump Jr., 39, has emerged, for less than ideal reasons, from behind his father’s substantial shadow. What made him agree to the meeting last June, at a moment when his father’s campaign was struggling to consolidate its hold on the GOP nomination? History is littered with examples of first sons and their difficult relationships with their fathers and the Trumps are not so different in this regard. What drove the younger Trump likely lies in a bond that had more than its share of drama and in which both father and son disappointed each other many times before they reached a truce on the 26th floor of Trump Tower.

***

When Donald Jr. was born, on New Year’s Eve, 1977, his father, then 31, had already taken over the family business, bonded with infamous fixer Roy Cohn, sued the federal government for $100 million, wangled an unprecedented tax abatement for his first major construction project in New York, the Grand Hyatt, and launched the brand-building, headline-grabbing M.O. that would eventually net him the presidency. There was little chance that his son would wander through life unnoticed.

Growing up in a palatial super-luxury 53-room triplex penthouse atop Trump Tower and attended by nannies and bodyguards, Donald Jr. and his two siblings, Ivanka and Eric, saw little of their workaholic father, who spent every waking hour at his 26th-floor desk. Instead it was their mother, Ivana, a former model, who organized schedules packed with lessons and sports and the elaborate birthday parties children of the very rich tend to have in Manhattan.

“I brought up the children singlehandedly,” Ivana Trump said in October 2016 at a benefit in New York according to the New York Daily News. “Donald wasn’t really interested in the children until he could talk business with them. When they turned 21, I handed them over to him and said ‘Here’s the finished product, you can take them from here.’ ”

Donald Sr. talked about his somewhat distant relationship with his children in his book The Art of the Deal, which came out in 1987. “I adore [my three children], but I’ve never been great at playing with toy trucks and dolls,” he wrote. “Now, though, Donny is beginning to get interested in buildings and real estate and sports, and that’s great.” His son was not quite 10 years old at the time the book came out, so just how interested he might have been in real estate is open to debate. “I tell Donny I’ll be home as soon as I can, but he insists on a time. Perhaps he’s got my genes: the kid won’t take no for answer.”

During the school year the children attended exclusive private schools—Donald Jr. was at all-boys Buckley—and spent time with their Trump grandparents, who lived in Queens, and with Ivana’s Czech parents, Milos and Maria Zelnicek, who lived in Trump Tower six months of the year. In the summer, according to New York Magazine, they went back with Ivana’s parents to Czechoslovakia, where they polished their Czech— Donald Jr. reportedly speaks the language fluently—and Milos passed on to his grandsons his passion for hunting and fishing. “My father is a very hardworking guy,” Donald Jr. told New York, “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.”

This privileged but predictable routine changed dramatically and, for the children, traumatically in 1990, when the Trump marriage hit the rocks and Donald Sr. moved to a smaller apartment in Trump Tower. The ferocious tabloid coverage of the messy breakup rattled the oldest son. (”Best Sex I Ever Had!” had to be a particularly confusing explanation of the split for a kid who hadn’t even hit his teens.) “It’s not easy at 12 to walk out of school and see the front page of every newspaper talking about your parents’ divorce,” Donald Jr. told me. After being ridiculed by schoolmates and, according to Vanity Fair, reduced to tears by a newspaper report that his father and his mistress, model Marla Maples, were spotted at an Elton John concert, Donald Jr. told his father, “All you love is your money” and refused to speak to him for the next year.

In 1991, Donald Jr. was packed off to the Hill School, a Pennsylvania boarding school that was known for being regimented. It was the kind of place many teens might have resented, but according to New York, Donald Jr. found being there a relief. “There was a time when my parents had a lot of security guards around. Again, one of those things that I probably rebelled against,” he told the magazine. “And then, when I went to boarding school, it all kind of went away—all those inconveniences that I found obtrusive.”

He still blamed his father for the divorce, and in 1993 he refused to attend his father’s wedding to Marla, an over-the-top affair at the Plaza Hotel that featured a 7-foot-tall cake, giant bowls of caviar, and a celebrity guest list that included O.J. Simpson, Rosie O’Donnell and Howard Stern. But he didn’t completely break free of his father’s orbit: He spent summers working as a dock attendant in Atlantic City and at Trump Organization construction sites, and he attended his father’s alma mater, the Wharton School at the University of Pennsylvania.

But, unlike his famously teetotaling father, when the younger Trump was at Wharton he earned a reputation as a belligerent boozer. “I used to drink a lot and party pretty hard,” he told New York, “and it wasn’t something I was particularly good at. I mean, I was good at it, but I couldn’t do it in moderation.”

Although his father had seen him as drawn to real estate, Donald Jr. raced in the other direction after college—heading to Aspen to keep the party going. His parents didn’t approve and the speculation was that Donald Jr.’s job tending boats in Atlantic City would be the last time he worked for his dad. But after a year he grew tired of the mindless high life in Aspen and returned to the fold in New York. “I knew that [working for my father] was something that I wanted,” he told New York. “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 I was making the right decision.” In 2000, he began working at the Trump Organization as executive vice president for development and acquisitions, and five years later, again following his father’s example, he married a model, Vanessa Haydon, with whom he would have five children.

Like his sister Ivanka, Donald Jr. likes to present himself as someone with his own opinions. “I’m the one person who can stand up to my father,” he told me. “I’m the only one who’s not afraid to pull him aside and say, ‘Here, take a look at the larger picture.’”

But again like Ivanka, the public has seen no evidence of him having any such forthright talks with his father, much less any suggestion that his father changed course as a result. Perhaps he saw what happened to his mother, who pushed to have a major role in the business. After doing better as head of one of the Trump-owned casinos in Atlantic City than Donald Sr.’s own team, she was rewarded with the top job at the Plaza Hotel, then owned by Donald Sr., and his public taunt that her salary would be a dollar a year and all the dresses she wanted.

***

So is there a chance that Donald Jr. is different from his father? Or is he perhaps more similar, and more devoted, than he would care to acknowledge?

His father is known for being a remarkable cheapskate, and so is he. In 2004, following his father’s lead in getting a hefty discount on Melania’s engagement and wedding rings in exchange for a mention of Graff, the seller, on “The Apprentice,” Donald Jr. invited the news media to his own bended-knee proposal to Vanessa at a New Jersey strip-mall jewelry store in exchange for a $100,000 engagement ring.

During the campaign and now during the Trump administration, he has followed in his father’s rhetorical footsteps, retweeting white nationalist memes and giving a radio interview (he says unwittingly) to a white supremacist. On another occasion, he compared Syrian refugees to a bowl full of Skittles candies and said “a couple of these will kill you.” At other times, he has even acted as his father’s attack dog. During James Comey’s testimony in June before the Senate Intelligence Committee, while Donald Sr. maintained an uncharacteristic silence, Donald Jr. kept up a steady stream of combative tweets.

Similarly, during the current controversy over the 30-minute chat with the Russian lawyer, Natalia Veselnitskaya, at which his brother-in-law Jared Kushner and then-Trump campaign chairman Paul Manafort were also present, Donald Jr. has provided Donald Sr.-style contradictory responses. After Kushner was forced to acknowledge that such a conversation had occurred, Donald Jr. suddenly recalled that he was also there, came up with two different explanations for why, and posted tweets about the incident that were, not unlike his father, long on sarcasm and short on facts.

After these responses didn’t calm the waters, Donald Jr. hired a prominent white-collar defense lawyer, Alan Futerfas, whose Fifth Avenue office is a short walk from Trump Tower and who has represented defendants linked to organized crime.

At this point, Donald Sr., as per his practice of distancing himself from anyone who poses a threat, proceeded to do just that. During the first three days after the story of Donald Jr.’s meeting broke in the New York Times, Donald Sr. fiercely defended Ivanka’s having sat in for him at the G-20 meetings in Hamburg the previous week but remained silent about his son’s apparent efforts to help him.

On the fourth day, Donald Jr. released what he said was his entire email exchange about arrangements for the meeting, A few hours later, White House spokeswoman Sarah Huckabee Sanders read the president’s first response to the matter in what is becoming the administration’s signature style, an off-camera briefing. In its 12-word entirety, the statement read, “My son is a high-quality person and I applaud his transparency.”

The next day, Donald Sr. tapped out two more tweets, calling Donald Jr. “innocent,” labeling the ever-louder coverage “the greatest Witch Hunt in political history." That afternoon he told Reuters, "I think many people would have held that meeting." But, as he had since returning from the G-20 summit, the man who never turns down a chance to stand in front of a camera remained behind closed doors until he boarded Air Force One for a state visit to France.

Back in 2015, when Trump was still duking it out with the other Republican candidates for the presidential nomination, Barbara Walters asked him to name the most challenging of his children. Without hesitation, albeit with just a hint of humor, Trump had responded, “Don.” Since that time, Trump had won not only the GOP nomination but the presidential election, and he was now the most powerful man in the world. But the answer, it seemed, was still the same.

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