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, Colo., 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,” Mr. 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, Mr. Trump, the eldest of the five children from Donald J. 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 semiautomatic rifle (for marksmanship competitions), Mr. Trump also connects with heartland voters in a way that his more refined sister Ivanka may not.
While Ms. Trump and her husband, Jared Kushner, have lately elevated their social profile in Washington and Palm Beach, Fla., 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,” Mr. 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, Mr. 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
Mr. 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 the 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, Mr. Trump 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.”
Mr. Zelnicek, who died in 1990, allowed his grandson a freedom not readily available to a child of Fifth Avenue. As Mr. Trump 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, Mr. 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, the former Mrs. Trump said.
The divorce was made final in 1992, and Mr. Trump’s father married Ms. Maples the next year. Donald Jr. went to boarding school, the Hill School in Pottstown, Pa., 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 Mr. Trump’s college friends. “He was trying to escape it.”
The young Mr. 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 fund-raising 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, N.Y., where he ran into Gentry Beach, an acquaintance from college who was working at a Manhattan investment firm.
“We loved being outdoors,” said Mr. Beach, who grew up in Dallas.
Mr. Beach, 41, introduced Mr. 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,” Mr. 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. Ms. 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 Mr. 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, Mr. Trump accepted a ring from the Bailey Banks & Biddle jewelry store in Short Hills, N.J., 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.”
Business and Politics
Although Mr. 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 Senator Ted Cruz of Texas at the annual Reagan Day fund-raising dinner, where he delivered a speech.
He told the crowd that he had 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, Mr. 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.
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.”