Donald Trump Jr. is the Trump who has not always seemed at ease with being a Trump. He grew up in the penthouse of Trump Tower but was happy to escape the gilded trappings of his Manhattan childhood to spend parts of the summers hunting and fishing with his maternal grandfather in the woods of what was then Czechoslovakia.
After graduating from his father’s alma mater, the Wharton School at the University of Pennsylvania, he tended bar in Aspen, Colorado, rather than immediately join the family business. Several months later, on Feb. 25, 2001, during a Mardi Gras celebration in New Orleans, he was arrested on charges of public drunkenness and spent 11 hours in jail.
“I think, like anyone else, I made my mistakes,” Trump said of his arrest. “We have to be honest with ourselves. I’m not good at it, moderation. You have to have the conversation, be a realist, and say, ‘I guess I’m not doing myself any favors.’”
In 2001, Trump, the eldest of the five children from Donald Trump’s three marriages, went to work for the Trump Organization in the same building where he had grown up. He rose to executive vice president, and his status as a family member in good standing was on display when he appeared as a boardroom adviser on “The Apprentice,” the NBC reality show that re-established his father as a celebrity mogul nearly two decades after he had captured the public’s attention with his first best-seller, “The Art of the Deal.”
Now Donald Jr., 39, has completed his own apprenticeship.
Since his father was sworn in as president, he and his brother Eric, 33, have taken over management of the Trump Organization, with Donald Jr. overseeing commercial licensing and much of the international business and Eric managing the golf courses, among other duties. Donald Jr. is also a rising figure in Republican politics and a robust defender of the family name. As a public speaker who brings in an estimated $50,000 per speech, he has impressed conservatives with a rough, straightforward manner that belies his cushy upbringing.
Like his father, he uses Twitter to thrash liberals and lend support to those who are friendly to the president’s populist agenda. Given that he is a skilled outdoorsman and a member of the National Rifle Association who owns dozens of firearms, among them a Benelli Super Black Eagle II (for hunting waterfowl) and an AR-platform semi-automatic rifle (for marksmanship competitions), Trump also connects with heartland voters in a way that his more refined sister Ivanka may not.
While Ivanka and her husband, Jared Kushner, have lately elevated their social profile in Washington and Palm Beach, Florida, while keeping close contact with the president, her oldest brother has largely avoided the balls and benefits, preferring to hunker down in Midtown during the workweek and spend weekends in the Catskills with his wife, Vanessa, and their five children.
“Don is the more chill version of any of the kids,” said Dee Dee Sides, who has known him since the early 2000s.
He came into his own as a public figure during the presidential campaign. On the stump he was equally at ease before crowds in both Mississippi and Michigan, and television pundits gushed about his political future after his bluntly effective speech at the Republican National Convention, with some mentioning him as a potential mayoral candidate in New York City.
“I don’t know if I could go all-in at that,” Trump said of a political career. “There is a part that is incredibly enticing. But it’s not human most of the time.”
Even as he embraces his new status in business and politics, Trump sounds, at times, as if it is some kind of anomaly.
“If I could miracle myself away,” he said, “I would live out West.”
Into the woods
Trump’s friendships are rooted, for the most part, in hunting and fishing, sports that do not appeal to the golf-loving patriarch of the Trump family. He said he decided early on not to measure himself against his father.
“I think people are often surprised, but I never defined myself as, ‘I’m the business guy who has to supersede what my father has done,’” he said. “He’s a totally unique individual. Somehow having to top his accomplishments is never the way I perceived things.”
He developed a distaste for living in public at an early age. In 1990, his father separated from his mother, Ivana Zelnickova, a Czech model and skier, after having an affair with model and sometime actress Marla Maples. Donald Jr. was 12 at a time when gossip columnists, some encouraged by his father, chronicled the family soap opera. During this time, Donald Jr. did not speak to his father for a year, New York magazine reported in 2004 in an article about the Trump children.
Before the divorce, Donald Jr. found a role model in someone quite different from his father: his maternal grandfather, Milos Zelnicek, an electrician who was an avid outdoorsman. In the summers, he stayed at the Zelniceks’ home in a town near Prague for six to eight weeks at a time, and his grandfather schooled him in camping, fishing, hunting and the Czech language.
“He needed a father figure,” his mother said in a telephone interview. “Donald was not around that much. They would have to go to his office to say hello to him before going to school.”
Zelnicek, who died in 1990, allowed his grandson a freedom not readily available to a child of Fifth Avenue. As Donald Jr. put it: “He said: ‘There is the woods. See you at dark.’ I think I felt a little trapped in New York City.”
Despite the advantages of wealth, Trump said his life at home was not always easy. “In our family, if you weren’t competitive you didn’t eat,” he said. “You had to fight for what you wanted.”
His mother recalled walking into the breakfast room one morning and noticing that the chandelier was broken: “Ivanka said it was Don Jr. So I put him over my knee and spanked him. He said, ‘Mom, it wasn’t me!’”
It turned out that Ivanka lied, his mother said.
The divorce was made final in 1992, and Trump’s father married Maples the next year. Donald Jr. went to boarding school, the Hill School in Pottstown, Pennsylvania, where he practiced skeet shooting, and then it was on to Wharton, where he rowed crew and joined the Phi Gamma Delta fraternity. People who knew him then saw him as distinct from his parents.
“He wasn’t into the gold,” said Jennifer Ireland Kubis, a New York real estate agent who dated one of Trump’s college friends. “He was trying to escape it.”
The young Trump also earned a reputation for hard partying, which seems to have continued until the Mardi Gras arrest. He no longer drinks, and he has suggested that the discipline of the sporting life kept him from going over the edge: “I know that the benefits I got from being in the woods, from being in a duck blind, from being in a tree stand at 5 o’clock in the morning, kept me out of so much other trouble I would have gotten into in my life,” he said in a speech at a fundraising banquet for the 2016 Western Hunting and Conservation Expo in Salt Lake City.
During his first year in the family business, he spent weekends at the Mashomack Preserve Club in Pine Plains, New York, where he ran into Gentry Beach, an acquaintance from college who was working at a Manhattan investment firm.
“We loved being outdoors,” said Beach, who grew up in Dallas.
Beach, 41, introduced Trump to Thomas Hicks Jr., 39, a Dallas friend whose father, an equity investor, once owned the Texas Rangers. Through the years, the three have hunted white-tailed deer in Texas, birds in Scotland and pheasant in Hungary.
“For some people – you see that in New York a lot – they go hunting once every other year and they talk about it at a cocktail party for the next two years until they do it again,” Trump said in an interview. “For me, it is the way I choose to live my life.”
Being friends with Donny, as his closest friends call him, can be tricky, given the divisiveness of his father’s politics. Sides, for one, said she did not discuss politics with her friend. “Our views are different,” she said. “Don has never asked me, and he would not ask.”
It was his father who introduced Trump to Vanessa Haydon, the woman who would become his wife, at a fashion show in 2003. A onetime model with the Wilhelmina agency who once dated Leonardo DiCaprio, she had grown up on the Upper East Side.
At the time of their engagement, Trump accepted a ring from the Bailey Banks & Biddle jewelry store in Short Hills, New Jersey, in exchange for publicity, recreating his proposal at its Short Hills Mall location in New Jersey. Soon afterward came an unflattering headline in The New York Post: “Trump Jr. Is the Cheapest Gazillionaire: Heirhead Proposes With Free 100G Ring.” Even his father joined in the criticism, saying on the CNN talk show “Larry King Live,” “You have a name that is hot as a pistol, you have to be very careful with things like this.”
Donald Jr. and Vanessa were married at the Mar-a-Lago club in Palm Beach on Nov. 12, 2005, 10 months after his father married former model Melania Knauss.
These days Vanessa Trump’s Twitter account, with the handle @MrsVanessaTrump, frequently retweets her husband’s posts pertaining to family life, many of which include photographs of their weekends in the Catskills, where they fish and shoot, and ride all-terrain vehicles and snowmobiles.
Business and politics
Although Trump has been charged with holding down the family business without input from his father – who resigned his position in the company without relinquishing his financial stake – he took advantage of his new standing within the Republican Party to dine last Saturday with a group of political heavyweights that included Sen. Ted Cruz of Texas at the annual Reagan Day fundraising dinner, where he delivered a speech.
He told the crowd that he had virtually “zero contact” with the president since the election, but added that he had found it difficult to resist the pull of politics. “I thought I was out of politics after Election Day,” he said, adding that he had thought he would “get back to my regular life and my family.
“But I couldn’t,” he said.
Two weeks before the Dallas speech, Trump found himself in the role of real estate tycoon during a stop in Vancouver, British Columbia, for the opening of a Trump International Hotel and Tower. Although the building unveiled that day was, at 63 stories, the city’s second highest, the city’s mayor, Gregor Robertson, skipped the event after demanding for two years that the Trump name be stripped from the building’s facade.
The president’s son began his talk with a poke at the news media: “I’d like to thank the press,” he said. “Just kidding.” Outside, about 100 protesters waved signs and shouted “Love Trumps Hate.”
To a large degree, his public image has been shaped by photographs that surfaced online in 2012 and re-emerged last year. They were taken during a hunting trip in 2010 arranged by Hunting Legends International, a safari company based in Pretoria, South Africa. A licensed guide accompanied Donald Jr. and Eric, along with a ranger from the Zimbabwe national parks department, who monitored the hunt.
One photograph shows the Trump brothers taking a helicopter to the Matetsi, a region of Zimbabwe abundant with elephants and endangered leopards. Another shows Eric with his arms wrapped around the limp body of a dead leopard. Perhaps most disturbing to nonhunters and to those who do not hunt endangered or vulnerable species was the picture of Donald Jr., knife in one hand, the bloody tail of an elephant in the other.
Animal rights advocates, including People for the Ethical Treatment of Animals, cried foul after Hunting Legends posted the photos, and a sponsor dropped the show “The Celebrity Apprentice,” which Donald Jr., Ivanka and Eric appeared on as advisers, along with their father. Donald Jr. took to Twitter to defend himself, writing to one detractor, “I’m not going to run and hide because the PETA crazies don’t like me.”
He argues that the economic benefit of such safaris to African communities is often overlooked. Further, he said, the controversy allowed him to connect with other sportsmen. “There were people who I didn’t know who were hunters,” he said. “And, from that perspective, I get invited a lot.”
What is lost on nonhunters, he said, is the sense of community that is part of hunting trips. “Too much of hunting has turned into the notion of the kill,” he said. “It’s a component, the meat. But so much is experiential, so much is relationships. It is sitting in a duck blind with seven people, cooking breakfast. For me, it’s been a great way to see the world. The least interesting part is the three seconds it takes to pull the trigger.”
Near the window of Trump’s 25th-floor office is a framed U.S. flag signed by members of SEAL Team 6, the elite Navy unit that brought down Osama bin Laden. On his desk he displays a bronze statue of Theodore Roosevelt, the Republican president and hunter, and a bobblehead doll depicting his father.
If he does not have his father’s gift for theatrics, he does share the president’s unwillingness to back down from comments and Twitter posts that roil liberals.
“I’m not a curated kind of guy,” Trump said. “I don’t sit there and try to massage every possible word. I’m probably a little more like my father in that sense. You know, I say what I’m thinking. Most logical people will interpret it right. But if you are looking to create a story, you can probably come up with something. I learned about that the hard way, in terms of politics.”
Without much of a campaign apparatus last year, the younger Trump traveled in the company of his Dallas friends Beach and Hicks. “They did everything from help me raise money, to get in front of the right people, to carry my bags, to handling schedules,” he said.
At the Republican convention in Cleveland last summer, he made use of a trope that served his father well: targeting the elite, despite his own privilege. “We’ve produced the thickest network of patronage and influence of any country at any time in world history,” he said from the stage. “It’s composed of a self-satisfied people at the top, our new aristocrats.”
Critics said his views were influenced by white nationalists. After an interview with a Philadelphia radio station, he was accused of making a Holocaust reference when he warned that the media would be “warming up the gas chamber” for Republicans who behaved like Hillary Clinton. The Trump campaign later said he had been talking about “capital punishment.”
Trump was also interviewed on a radio show hosted by James Edwards, who has described himself as a “European-American advocate” and whom some have called a white supremacist. Trump was criticized, too, for earning an estimated $50,000 for delivering a speech at an October event at the Ritz Paris hosted by the Center of Political and Foreign Affairs, a French think tank whose organizers have promoted Russian interests in Syria and elsewhere. He declined to comment on his speech.
On Twitter he has reposted false reports and passed along memes favored by white nationalists. An example of this occurred during the campaign, when he compared Syrian refugees to a bowl of Skittles candies sprinkled with a few that “would kill you.” He also retweeted a post by @voxday, who claimed that a woman making a Nazi salute at a Trump rally was a supporter of Bernie Sanders. The claim was false. (Further, @voxday is a pseudonym for writer Theodore Beale, an advocate for the alt-right movement.)
Trump said he did not know who Beale was. “It just popped up in my timeline when someone retweeted it,” he said.
Recently he reposted a Twitter message that said CNN tried to silence guests who went against its supposed liberal agenda. It was also untrue and was later deleted.
While he mainly uses Twitter to defend the president, with frequent attacks on liberals thrown in, Trump also uses it for posts about his family, with many including photos of his wife and children. There is Vanessa Trump, bowling in the basement bowling alley at the White House on inaugural weekend. There is his son Tristan, snuggling with his parents in bed.
On Feb. 10, opening day for the erotic thriller “Fifty Shades Darker,” Trump tweeted, “@MrsVanessaTrump took/dragged me to see the new 50 shades movie and I am the only guy in an otherwise packed theater.”
“It’s two hours of my life I'll never get back,” he said.
As Trump balances home life and work life in a hot political environment centered on his father, he maintains that he does not discuss business with the new president.
“I haven’t spoken to him,” he said. “Maybe just to say hello. It feels trite. I feel ridiculous bothering him.”
Still, critics continue to point out occasions when business and politics seem in danger of mixing, as they did on Jan. 31, when Trump had a front-row seat at his father’s announcement of the Supreme Court nominee Judge Neil M. Gorsuch.
“Where is the break point?” Trump said. “If I see him once a month, is that too much? Once a year? My point is, it’s a no-win scenario. But, in the end, we both fully recognize that what he is doing now is far more important than absolutely anything going on in the business. And we will conduct ourselves accordingly.”
Even the annual Easter Egg Roll at the White House, which is described as a race, could prove a political minefield, he said.
“God forbid one of my kids wins. People will say it was rigged.”
Kitty Bennett contributed research.