It’s hard to imagine they’d trust him much, either. “I used to drink a lot and party pretty hard, and it wasn’t something that I was particularly good at,” Don Jr. admitted to New York. “I mean, I was good at it. But I couldn’t do it in moderation.”
That his father showed up on campus made the connection even easier. As Scott Melker, another member of Donny’s class at Penn, has publicly written, he was hanging out in a freshman dorm next door to Don Jr.’s room when Donald walked down the hall. He was taking Don Jr. to a basketball game, which, for any other father-son duo, might not have been a particularly memorable exchange. But kids on campus knew who Donny’s dad was, and so when they saw Donald knocking on his son’s door, a few nosy neighbors peeked their heads out of their tiny little rooms to catch a glimpse. What they saw was Don Jr. greeting his dad, all set to go watch the game in a Yankees jersey. As Melker tells it, Donald took one look at his son and slapped him across the face. Jr. flew to the ground as his classmates watched. “Put on a suit,” Donald hissed, “and meet me outside.”
It was a vicious cycle. That Don Jr. so desperately wanted to escape his family name and the trappings of a stereotypical rich kid led him to drink, and that he drank himself silly led everyone around him to believe he was exactly the rich-kid stereotype they’d initially expected from a Trump kid.
That was particularly true in Jamaica on March 11, when Don Jr. and a bunch of other Penn kids on break packed themselves into a bar showing the NCAA games to watch their basketball team take on March Madness. So did students from Florida, the team Penn went up against in that first round. On both sides, there was cheering, a little smack talk, and a lot of liquor going around. It was not a blowout like it could have been, but Penn didn’t pull it off. Florida won 75 to 61, and Penn was eliminated almost as soon as they started. The inebriated fans on both sides erupted. Slaps on the back. Shots to celebrate or numb the pain. Sloppy high fives or consoling pats on the back. But Don Jr. took it a step further. He climbed atop a table in the bar and started a chant that he’d hoped would catch on with the rest of his fellow disgruntled Quakers in the room. “That’s all right! That’s okay! You’re gonna work for us someday,” he jeered at the Florida students.
“These were kids from a state school,” one Penn student who was in the bar that day remembered. “The subtext wasn’t hard for anyone to figure out. And it just came out so easy.”
If that sounds like something that could have come out of Donald Trump’s mouth, that is because Don Jr. has spent his life emulating his father, even when he was running in the other direction. He was both abandoned by his father and given everything by him; angry with Donald to a point where they did not speak for years and obsessed with pleasing with him to a degree that he’d say anything to make his father happy. A mix of nature, nurture, and deep scars left by wounds inflicted by his dad made Don Jr. into a yapping attack puppy, trailing wherever he went the senior attack dog with the much bigger bark.
During the 2016 campaign, when Donald slung an insult, Don Jr. was never far behind with a whiffle bat of his own. He called himself “the brute” to describe his own rhetorical flourish on campaign stops (sometimes, he would include his brother Eric in the name. “The brutes,” they’d call themselves, when they spoke together). “He was absolutely intent on showing that he had the same killer instinct as his father,” one longtime friend of the family noted. “It played well, even though that instinct certainly was not the same, and certainly not as effective.” The intention was so strong that it almost made up for it. So Don Jr. crisscrossed the country in 2015 and 2016 as one his father’s most effective surrogates on the campaign trail. From the 1,300-acre bird habitat on the High Prairie Farms in Iowa before its caucus to the Neshoba Country Fair, billed as Mississippi’s giant house party, to the Fox News studio in Midtown Manhattan, to the dais onstage at the Western Hunting and Conservation Expo, Donny was dispatched. He’d sling on his hunting boots, pointing out to crowds just how well worn they were. He’d still slick back his hair, a style, he would joke, that made him an unlikely hunter and voice for Middle America. He’d talk about how all the county fair food and quick fast food stocks were making it hard for him to fit into the suits he’d donned for years as an executive in his father’s real estate company. Maybe he’d even give them up for good. A life on the trail, in flannel shirts and jeans and, sometimes, orange hunting vests or construction hats, seemed to suit him, which is part of the reason why campaign officials wanted him out on the road. Ivanka, in her tailored sheath dresses and stilettos, appealed to one audience—the coastal crowd and wary women who needed a knowing wink even to consider listening to the kind of brash and bombast her father trumpeted throughout the campaign. Don Jr. assured a base of people for whom the brash and bombast was Donald’s biggest draw that he wouldn’t back down from that sort of rhetoric. He was a city kid bred in boarding school and Palm Beach and triplexes, but he left all of that behind. He instead laid into Hillary Clinton, lashed out about the need to drain the swamp, and served as a loyal pit bull, defending some of this father’s most incendiary language. Sure, his father might tell women that they were fat and shouldn’t be eating candy, but he’d say the same thing to his son. That’s just the kind of guy he was. Was it politically correct to say rapists were coming over to the US from Mexico? No. But it was what the American people wanted and finally, they had someone who spoke like, and to, them when they’d felt forgotten or left out of the conversation. Finally, a politician who spoke the way they spoke, who would fight for them the way they desperately needed.
“Sometimes you have to say it like it is, and when you have the problems like we do in this country, sometimes you have to use the hammer,” Don Jr. said onstage at the Western Hunting and Conservation Expo in 2016. “It’s nice to be soft, when you can, but you can’t be afraid to speak your mind and say things like they are.”
And he said it like he saw it over, and over, and over, in interviews, and in speeches, and most often on his Twitter account. In an interview with a Philadelphia radio station in 2016, he bemoaned that the mainstream media cozied up to Hillary Clinton, giving her a pass while drilling into his father. “They’ve let her slide on every discrepancy,” he said. “If Republicans were doing that, they’d be warming up the gas chamber right now.” Not long after, he tweeted a photo of a bowl of Skittles, comparing them to Syrian refugees. “If I had a bowl of skittles and I told you just three would kill you. Would you take a handful? That’s our Syrian refugee problem.”
All of these instances created a swirl of outrage. Critics called Don Jr. racist, anti-Semitic, dumb, intolerant, a liability. In another campaign, his remarks would have gotten him benched for good, or at the very least temporarily sidelined. But like his father, he appeared to be Teflon Don Jr. Instead of adopting contrition, he came out combative. His actions and words weren’t the problem; the outrage was. The American people wanted fighters like them, who weren’t concerned with being politically correct and were unafraid to speak their minds. This is why Americans needed a leader like his father and a First Son like him. His self-defense reflexes were put to such constant use in those two years on the campaign that he went into something of a withdrawal once his father took office—though of course he continued to attack anyone he deemed in opposition of himself and his family. “I thought I’d be going back to my regular job,” he told a crowd gathered to hear him speak at the Dallas County Republican Party’s Reagan Day Dinner in March 2017. “But once you get a little bit of a taste of that action, it’s hard to leave. You know, listen, deals are still exciting, but when you’re sort of the guy out there 24/7, every day fighting in this thing—it’s like a great fight, the intensity.”
Don Jr. had spent the two dozen years before his father threw his hat into the ring going from one great fight to the next. When Barbara Walters asked Donald who his most challenging kid was, he barely took half a breath before responding, “Don.”
The fact that Don Jr.
was the only one of his kids who was both old and strong-willed enough to confront his father after the Marla incident played out in Aspen and he moved out of the triplex undoubtedly factored into Donald’s answer. It was Donny who shouted at him that he didn’t care about his kids, and that the only thing that mattered to him was money. But Don Jr. had a sixth sense for sniffing out when someone was spoiling for a fight, and he would jump right in their path once he found them. He’d pester his father to find out when he was coming home from work, Donald wrote in The Art of the Deal. “I tell Donny I’ll be home as soon as I can, but he insists on a time,” Donald wrote. “Perhaps he’s got my genes: the kid won’t take no for an answer.” In the height of the mayhem surrounding his parents’ divorce, when paparazzi were following him to school, he beat up two boys in his Buckley class when they snickered about the headlines about his father’s affair and his sex life with Marla. He rarely shied away from drunken skirmishes and pissing contests at Penn, and that urge didn’t lessen with age. A few days shy of his twenty-fifth birthday, Don Jr. sat at a table with two women close to the stage at the Comedy Cellar, a little club on McDougal Street in Greenwich Village. On weekends, a line snakes around the block, past the holes in the wall just off NYU’s campus selling falafel and bongs and booze, with people waiting to head down the few stairs and inside to watch stand-up. It was nearing two in the morning when other people around Don Jr. had had enough. He’d been loud and obnoxious and distracting for hours. Three couples had told him to pipe down, according to a New York Post account at the time, but he brushed them off. “People at a neighboring table thought Trump was reacting too enthusiastically to a comic’s ethnic humor,” the Post reported. It escalated from an eye-rolling annoyance to a full-on throwdown once Don Jr. raised his glass and splashed some beer on a woman at a nearby table. It is not clear if it was intentional or an accident—a malicious retaliation or a drunken mistake in the heat of the moment. It didn’t much matter to the two men who watched the beer fly out of his glass and onto the woman. “You think that’s funny?” one guy bellowed. Before he knew it, the man and another guy he was with had tossed their beer steins at him, which whacked him square in the head, smashing and sliding out of that slicked-back hair. Someone called the police, who turned up and took Don Jr. to St. Vincent’s Hospital, where doctors closed the gash on his head with twenty-eight stitches. No charges were filed against him. But the two men who hit him with their glasses—twenty-three-year-olds from Staten Island and Brooklyn—were arrested and charged with assault before they were released on $5,000 bail.
One of the guy’s family members told the Post that their relative was hardly hot-tempered. “He had to have been provoked,” he said. “You’d have to push his buttons hard . . . for him to fight back.” A longtime friend of the Trump family, who’s known Don Jr. since before Donald and Ivana got divorced, always comes back to this story when asked about Don Jr. “I’ve seen a lot of rough stuff in my life, and I have to tell you, I’ve never once seen someone break glass over a person’s head,” he said. “Punching a guy in the nose? Pushing him to the ground? Okay. Breaking a chair, even. Do you know what kind of a jerk you have to be get a beer stein broken over your head? That tells you everything you need to know about a kid.”
Publicly, Donald defended his son. “He was blindsided,” he said of Don Jr. to the Post. “I’m going to sue their ass off. I’m also going to sue the club for allowing this to happen.” The club’s owner at the time did not sweat the threat too much. “Maybe I’ll countersue Don Jr. for disrupting the club.”
It wasn’t the first time Don Jr. brushed with the law. Less than a year earlier, he traveled to New Orleans for a few days celebrating Mardi Gras. He reveled a bit too hard, perhaps, and on February 25, 2001, police rounded him up and arrested him on a charge of public drunkenness. The real estate heir, whose parents boasted about telling all of their children every morning before they went to school that they were never allowed to drink or do drugs or get in trouble, and who have repeatedly bragged that their kids actually listened, spent eleven hours behind bars before he was released.
The Comedy Cellar incident wasn’t the first time Don Jr. had found himself worse for the wear after a scuffle. He told Esquire in 2012 that he’s “broken probably every major bone in my body. I currently have, in my body, fifteen pins and a plate. I’ve broken my femur, both wrists, both ankles—my left ankle twice. My tibia. Tore my rotator cuff. And that doesn’t include knuckles, noses, and don’t get me started.” And it wouldn’t be the last. A few years later, things blew up between a twenty-eight-year-old Don Jr. and a forty-four-year-old woman who lived at 220 Riverside Boulevard, in a 420-unit high-rise on the West Side of Manhattan. In the fall of 2006, Eugenia Kaye sent a letter to other residents living in the building, alleging that the building’s board had misappropriated or misspent $500,000, stemming from a gas bill the building had not paid for six months in a row, even though gas was included in the common charges condo owners already paid each month. Her letter also alleged that the building sponsor had yet to pay back a quarter of a million dollars borrowed from building money without having gotten a green light from the board first. Kaye’s letter successfully roused her neighbors to vote out seven board members, including Don Jr. At the time, Don Jr. stayed quiet about the coup, but his father stuck up for him once the Post caught wind of the story. As he did when news of the bar fight went public, he said that his son had been “blindsided,” this time not by guys with beer steins but by “a woman with extraordinary ambition to be on a board.” This go-around, instead of simply threatening legal action, Don Jr. actually filed a $50 million defamation suit against Kaye, and sought to regain his seat on the condo board. “He’s a good kid and a hard worker. He did a very good job on that board,” Donald added. Everything came to a head at the building’s holiday party by year’s end. There are two sides to how the evening unfolded. The way Kaye told it at the time, Don Jr. came in steaming mad. He found her, got in her face, and shouted at her, cursing and calling her names. Don Jr. claims it was Kaye who lost control, punching the property manager in the face in front of her neighbors. “Welcome to real estate in New York City,” Donald told the Post in response.
Don Jr.’s attack-dog instincts manifested themselves more literally. Friends have nicknamed him “the Fifth Avenue redneck” because of his proclivity toward spending weekends and vacations fly-fishing in Alaska, moose hunting in the Canadian bush, and prairie-dog shooting in Montana. He started hunting with his grandfather during the summers he spent in Slovenia, away from his parents and the trappings of the triplex on Fifth, and picked it up again once he moved to central Pennsylvania after Donald and Ivana’s split to board at the Hill School. He started small—clay shooting at a rifle range on campus—and then began meeting other guys around town to fly-fish, venturing out into the cold, all bundled up, to meet guys at six o’clock in parking lots near campus. “I just got hooked, and then I basically read everything there was to read about all of the different forms of hunting, I just got so into it, I read every book available, I spoke to whoever would listen to me, I went with whoever would take me,” he said in an interview with the online hunting publication Bowsite during the campaign.
That was part of the reason why Don Jr. picked up and moved to Colorado after he graduated from Wharton. “I was probably the first graduate of the Wharton School of Finance to go be a bartender,” he told Bowsite of his decision to live in Aspen for a year after he graduated. Donald and Ivana fumed once he made the choice. His father offered him a job in the Trump Organization; Ivana told him she would give him no money if he wasted his life away as a ski bum boozehound in the middle of the woods. He turned his dad down and turned his chin up at his mom and defied them both anyway. He wanted to make sure he knew what he was getting into before entering the family business and the craziness associated there with it, he told people. He didn’t want any regrets, he’d say, before settling into a life the beats of which he could
plot out with his eyes closed. Plus, he was still chilly with his father, who’d just settled his divorce with Marla and a year earlier and started dating Melania, and he had a lot of drinking left to do before going to work fifteen-hour days with his teetotaling, hot-tempered, impossible-to-please old man. So he left it all behind for a while, and rented a little place in Aspen on Roaring Fork Drive from a local family. It was just a mile away from the Little Nell, the hotel where he and his siblings had stayed with his parents on holidays when he was growing up, but a world away in most respects. He tended bar at the Tippler, an après-ski bar at the base of Aspen Mountain that they opened at the western edge of the Little Nell’s ski run. Locals called it “the Crippler,” the kind of place where vacationers and locals alike soaked their altitude-sick livers in booze and picked up equally-as-wasted singles for the night. People could come in in full snowsuits and spill out onto the enclosed sundeck, or they could come by dressed up, cozying into the maroon upholstered couches or around the built-in backgammon tables. Certainly, the crowd orbited around the oval-shaped bar, where for a year Don Jr. helped them all get drunk.
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