He did his fair share of drinking himself, but hunting helped him cut down a bit. “[Hunting has] been a great, great value in my life, and probably kept me out of a lot of other trouble I would have otherwise gotten into,” he told Bowsite. “I think when you’re waking up at 4:00 a.m. in the morning to get into a deer blind or to, you know, get in a stand, or to go waterfowl hunting, whatever it may be, it was a lot harder to be up at three in the morning from the night before, and so I owe the outdoors.” In Colorado, he’d go out with friends he made—former members of the US ski team in far better shape than he was—who were fairly skilled bow hunters. Don knew he was at the end of his rope in Aspen by the time the three guys went out on public land to hunt elk during the month of August. His bank account was running thin, and there would be a time where his father perhaps wouldn’t keep an office open for him in Trump Tower—not if he defied him for too long. As he tells it, his brain was starting to atrophy, and he was ready for something more. But there was time for one last go at it. He and his buddies spent weeks chasing the things with no luck. They had two days left of the season—two days left before Don Jr. decided he was going to pack up and head back to New York and resign himself to being the Trump heir everyone expected him to be—when they saw hoofs through the bushes below them. They were on such a steep slope that they couldn’t move up or down when the elk came into view, rounding a bend of brush seven yards in front of them. “It was just incredible,” Don Jr. told Bowsite. “I mean, there’s not many more intense experiences than that.”
It did get more intense. He and Eric often went on hunting trips together, including for Eric’s bachelor party (“better than a no-win trip to Vegas,” Don Jr. later said, adding that he brought his young son along for the seven-mile hike with a bunch of his friends who’d never hunted before. It was not exactly Mar-a-Lago or the night out doing karaoke at Chelsea Piers that Ivanka chose for her bachelorette party years earlier). They hadn’t told Donald they were going on a week-long hunting trip so far into the bush that it took days to get to the kill spot. Don Jr. had been hunting seriously for more than a decade by this point, but he had a mishap. His scope hit him smack in the head and sliced into his forehead like a hot knife into butter, nearly straight through to the bones in his skull. They were too far away from any kind of civilization for him even to get to a doctor who could stitch him up, even if he wanted to. He couldn’t call Donald, because they were too far out of range. And Donald didn’t know where he was anyhow. So he dug into his kit and pulled out the Krazy Glue that had languished there during his many trips. He glued the pieces of his flesh back together before they continued on, leaving a little line in the middle of his face that plastic surgeons back home would have undoubtedly easily avoided.
It would have been just as easy to avoid the public relations nightmare and blistering backlash Don Jr. and Eric got in 2012, when photos of a hunt they’d gone on in Zimbabwe two years earlier surfaced online. There was a grinning Don Jr. in a loose green jacket, dirt-stained khakis held up by a tactical belt filled with unused ammunition that would eventually end up in other wildlife, mud-caked boots, and a backward camo cap containing his jet-black hair. He leaned up against the lifeless big black buffalo he’d just shot dead, his rifle in his left hand, his right arm resting against the buffalo’s horns. In another shot, Don Jr. held up a knife in one hand and the tail of an elephant he’d just killed—pink and gory at its root, where he’d sliced it off the animal’s body. Don’s own palms were covered in blood, his hair slicked back in the same 1980s Wall Street banker style he favored throughout his father’s presidential campaign. There was another in which he and Eric, in matching khakis and toothy smirks, posed with a giant cheetah, not unlike the enormous, plush FAO Schwarz stuffed animals their little brother Barron posed with soon after he was born for a magazine spread shot in his Fifth Avenue nursery. This cheetah was real, though, and now it was dead, hanging over Eric’s arm after they’d killed it a little while earlier. Eric himself posed for photos with his rifles and the kudu and buffalo he killed. In one photo, taken by the light of a raging fire, he sits on a dead buffalo he’s shot like a chair, shaggy blond hair falling, half smiling like an Abercrombie model. He’s leaned three guns against its body and hung his hat on one of its horns.
“It was evident from the word go that these two amazing young men are everything but the ‘city slickers’ you would expect!” their tour guide wrote of the two men when the photos went public. The vast majority of reactions were decidedly more negative. It was a code red for PETA and wildlife advocates. The Apprentice almost immediately lost one of its advertisers. The chief executive of Camping World told TMZ that its ad had already aired on NBC during an episode of that season of Donald’s reality show, but he “wouldn’t spend another nickel with them” after the photos came to light. Even some of their friends who were well aware of their hunting couldn’t believe the tastelessness of the photos. That they would kill these animals was perhaps callous, but it was part of who they were; that they would pose with them so gleefully seemed less defensible; and that they’d do so knowing the possible press these photos could receive—coming from the Trump family media genes—was inexcusable. Donald did try to defend the photos and his sons. “They’re hunters and they’ve become good at it,” he told TMZ at the time. “I am not a believer in hunting and I’m surprised they like it.” (Donald banned Don and Eric from doing interviews about their hunting until the campaign, when advisers repeatedly told him that they were in a perfect moment in which surrogates who could actually speak with authority on the Second Amendment would really help him in the race. “In the early days of the campaign, the base was terrified that Obama was going to take away all their guns, so we thought it was the perfect time for Don to do outreach,” one adviser remembered.)
Don Jr. didn’t need his dad’s tepid response when the photos surfaced. He attacked the critics far harder this time on his own. “I am not going to apologize because some eco nuts want me 2,” he wrote in one tweet. “I’m not going to run and hide because the PETA crazies don’t like me,” he tweeted to a critic. “I HUNT & EAT GAME,” he responded to someone else. He also assured another person on Twitter offended by the photos that “it was not wasteful” because “the villagers were so happy for the meat which they don’t often get to eat. Very grateful.” He further defended himself against people who called him and his brother “bloodthirsty morons” in an interview with Forbes around the same time. Those people did not truly understand hunting, he said—and certainly they did not, and could not, understand what hunting meant to Don Jr. “If you wait through long, cold hours in the November woods with a bow in your hands hoping a buck will show or if you spend days walking in the African bush trailing Cape buffalo while listening to lions roar, you’re sure to learn hunting isn’t about killing,” he explained. “Hunting forces a person to endure, to master themselves, even to truly get to know the wild environment. Actually, along the way, hunting and fishing makes you fall in love with the natural world.”
For all the spoils and privileges and riches and comforts and opportunities and open, gilded doors dealt to Don Jr., he’d gotten some pretty rotten cards too. He was a poor little rich boy in the most classic sense. In some ways, particularly in his childhood and early adolescence, life had beaten him down. It makes sense, then, that he would grow up feeling as though he needed to always be swinging back.
Hunting gave him an outlet in which to do that. Don Jr. had so many abnormal things, but he lacked the normal securities and unconditional support systems normal children grow up without even knowing they have. Those things he lacked, he found in the sport. First, it let him be anonymous, which was something life alongside his famous parents never afforded him, as desperately as he wanted it. “When I was younger, I was very ardent about being anonymous,” he told the New York Post in 2002. “I stayed in the background and let my parents do their thing, and didn’t have a problem with it. I didn’t want to get sucke
d in to it.” He often talks about how there are men he’s hunted with for years who have no idea what his last name is, and when they do find out, they already know him well enough as a normal guy in a hunting vest who knows his way around a rifle that the Trump doesn’t much matter. It also was one area in his life in which he felt in control. From elementary to boarding school to Penn, his parents had decided where he would go to school. “I had the complete Ivy League résumé coming out of high school,” he told Esquire. “I had the grades. I had the boards. I played varsity sports. I was the editor of our school newspaper, the yearbook, the literary magazine. But I thought, maybe I should go to the University of Colorado out in Boulder or to the University of Vermont and ski.” But his dad thought otherwise when Don Jr. suggested that maybe Donald’s alma mater was not the right place for him. “Listen, don’t be a schmuck,” he said. So Don Jr. went, majoring in finance and marketing in Wharton, as his dad had before him. His parents decided it was a bad decision to move to Aspen after college. They decided where it would be appropriate for him to work, how to work, where to vacation, and later, whom to marry. Out in the middle of nowhere, he called the shots—quite literally. It was an area his father had no expertise or interest in, so it belonged to him. For the first time in his life, he’d found a place where he was the boss, and without a dad who everyone thought knew better breathing down his neck.
The need that hunting filled most was the gaping opening left by Donald. His father, much like Donald’s father before him, had spent time with Don Jr. as a child only on his terms. Donald’s children would come to his office and play on his floor while he worked, until he shooed them off up the private elevator from Trump Tower’s twenty-sixth floor to the triplex forty floors up. If they wanted to see him on the weekends, they’d tour construction sites with him—though they did come to love that part for themselves. If they went on trips, they were to properties their dad owned, which meant they weren’t actually vacations so much as extended business meetings. A longtime associate of Donald’s remembers joining Donald and a reporter from the New York Times’ Los Angeles bureau who was working on a story about the Trump Organization and its press-courting boss for a dinner at the Atlantic City casino he owned. It was the mid-1990s, not too long after the divorce between Donald and Ivana had been settled, and Don Jr. was down there working at the Trump Marina to make spare cash. His dad insisted he come for the meal, meaning he had to sit through the tedious show his father put on for the reporter—the same braggadocio he’d likely heard a million times. He was still angry with his dad over the divorce, and he was a teenager. It was the last place Don Jr. could ever want to be on a weekend evening. He sat sullen and silent throughout the meal, rarely engaging, mostly because his father rarely acknowledged that he was even at the table, the associate remembered. Donald turned on the charm when another thirteen-year-old boy approached their table. It was his birthday, and his parents had given him the option of doing anything to celebrate—a trip to Disney World, a meal at any restaurant he could dream up—but he wanted to go to the Taj Mahal, just in case Donald Trump was in town. Donald was delighted, and warned the boy and his family not to go to the casino. “The only person who makes money in the casino is the person who owns it”—him, he told them—“so if I were you, I wouldn’t go down there.” The family smiled sheepishly, got a photo, and slunk away. After the meal, Donald insisted on walking through the casino floor with the reporter and his associate, knowing Don Jr. wasn’t old enough to go along with them. So he sent his son down a separate staircase. “We never saw him again the rest of the night,” the associate remembered. “I had to ask Donald if he wanted to make sure he got back okay. ‘Eh, he’ll be fine,’ he told me.”
Don Jr.’s grandfather, Dedo, stepped in to fill the empty space first. By the time Don Jr. was in kindergarten, Dedo would send him off into the woods for hours on end. The boy would go alone, or with Eric once he was old enough, but he knew that his grandfather was doing it for his own good, and would be there, at the wood’s edge, waiting for him to return. He also knew that he would meet other boys his age playing outside, boys who grew up a world away from the mansions and private schools and jets with his last name boldly printed on their wings, kids who instead lived in then-Communist Czechoslovakia who couldn’t even imagine the wealth Don Jr. took for granted. “I really learned what it was like to see the other side,” Don Jr. told an audience at the Western Hunting and Conservation Expo decades later, during his father’s presidential campaign. “The more and more I went back and had friends there, I learned that everything in life didn’t have to do with material goods. It was about relationships.”
One of those relationships was forged years later, once he arrived in Pottstown, Pennsylvania, to attend the Hill School. The dean of students on campus, who happened to be an expert shot, took a liking to Don Jr., who, he soon found out rather unexpectedly, had spent as much time as he had with his grandfather learning how to shoot a bow and handle a gun and survive for hours in the outdoors without security or maids or limos catering to him. He’d rouse him at six in the morning and bring him to meet his hunting buddies in town. “From that point on, I just fell in love with the hunting lifestyle,” Don Jr. said at the expo. “I fell in love with it. There’s been so many guys along the way that have been mentors.”
That he quickly found out these were guys he could trust played a huge factor in his affinity for the hobby. So many people wanted something from him—his money, his family’s fame and access, his business—and his parents had taught him from a young age that, because of that, there was no one whose intentions he could rely on, not even his own family. He told host Donny Deutsch in a 2008 episode of CNBC’s The Big Idea that his father would repeat the same maxims when he’d go down at seven in the morning before school to give his dad a kiss good morning and a quick hello and goodbye before he started his day. “No smoking, no drinking, no drugs,” his dad would tell him. “But then he followed up with: ‘Don’t. Trust. Anyone. Ever.’ And, you know, he’d follow it up two seconds later with, ‘So, do you trust me?’ And I’d say, ‘Of course, you’re my dad.’ He’d say, ‘What did I just—.’ You know, he thought I was a total failure. He goes, ‘My son’s a loser, I guess,’ because I couldn’t even understand what he meant at the time. I mean, it’s not something you tell a four-year-old, right? But it really means something to him. He knows so many people who have been taken advantage of, whether it’s by colleagues, but even by families.” But when you’re in a duck blind in the middle of nowhere, or you hear hoof steps after a month of no luck finding elk two days before you have to move back to New York but you’re on a slope so steep you can’t move, or a scope splits the skin of your forehead when you’re too far away from any medical professional to call for help, well, you have to trust who’s around you. And mostly, he could. They didn’t want anything from him. Something sent them all out there, on a mission, fleeing the day-to-day, seeking camaraderie, searching for peace. Their reasons were all different, and Don’s were certainly more unusual than most. Most of the people he hunted with weren’t out there escaping anything like what he was escaping. They might not have any window into what led a rich heir who’d grown up in a glass tower covered in marble and gold deep into the bush in muddy hunting boots and ill-fitting khakis. For the most part, many of them didn’t even know his last name. “I think it’s the distinction between those two lives that gives me the relaxation I need,” he told Bowsite. “I can step into the woods and out of the office and it’s exactly the opposite of what I’ve done all week. That’s my form of meditation, so to speak.”
Don Jr.’s form of meditation did come to serve someone other than himself. During the campaign, then Iowa governor Terry Branstad invited Donald to his state for a hunting trip. There was no world in which Donald would have agreed to that, no matter how politically expedient it would be. So he called his son and asked him to take the trip in his place. “Don, you can finally do something useful fo
r me,” he told his son.
In other ways, Don Jr. distanced himself—however slightly—from the narrow world his father occupied. Donald had his sights set on a particular vision of success—a flashy one—in his twenties and thirties. He wanted to be on Fifth Avenue, on the water in Palm Beach, first in the Hamptons and then in Greenwich. He and Ivana went out most nights with people who also lived on Fifth or thereabouts, who wintered in Palm Beach and summered in the Hamptons or in Greenwich and took private jets or chauffeured cars to get there. Everything was the biggest, the most expensive, the goldest with the most marble, and certainly everything made its way to the press somehow. He was the cartoon version of a rich man in Manhattan, and he’d illustrated the whole thing to make sure his image fit the type to a T. Once he had all these things, he’d know he’d arrived, and thanks to the hungry press he aggressively courted, so would everyone else. That Don Jr. drew his own life in his twenties and thirties in a far less flashy fashion is a function of the fact that he’d grown up among it all. He didn’t need to prove anything to anyone. He knew Palm Beach, he knew gold and marble, he knew jets and chauffeurs. Don Jr. arrived simply by being born, and so all these things weren’t exciting or novel or symbols of his success. That is not atypical for a second- or third-generation rich kid, but it was even more pronounced for Don Jr., who had a bit of disdain for the choices his father made in service of his personal wealth and celebrity. So in some ways, Don’s young adulthood sent him in a different direction.
“I definitely don’t have his flamboyance,” he said in 2005. “I am very different in my personal life. I mean, I like fly-fishing and being outdoors. He likes parties and playing golf, and he doesn’t turn the work button off—ever.” As for the public attention, he said, “I don’t want that. That’s his thing and he’s really good at it.”
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