When the film premiered at Sundance, reviewers praised Ivanka as “poised,” “well-bred,” and grateful for her position. “I can’t say I know anybody our age who comes from that kind of background who is operating on that level, or anywhere close,” Johnson said of his friend’s ability to work hard and stick to a coherent message.
The problem with this branding is it leaves out one whole side of Ivanka, the realer one. Much of her young life was a tale of two Ivankas—the one she painstakingly narrated to the public to project the image she thought best served her brand, and the true version. The two are sometimes completely at odds. For example, the veneer of Ivanka as a champion for women who work—a defining pillar of her image as a private business owner and throughout her new political life—chips slightly when it comes to light that her eponymous brand had a meager parental leave policy and relied on subcontractors whose policies were worse. Sometimes, though, when she lets herself be herself—and this is something her friends say privately all the time—Ivanka reveals herself as a much more nuanced, relatable, aspirational person than the version of herself she’s crafted, with a delicious rebellious bent.
The truth, for most famous people, is quite a bit closer to earth than the shiny version they want other people to see. That is certainly the case with Ivanka. In reality she was a relatively normal teenager and young adult within the confines of first the prestigious Chapin School on the Upper East Side, and later Choate, the boarding school in Wallingford, Connecticut. Her parents were splashy, and she was modeling while she went to school, which automatically puts her in a different category than most of her rich-kid classmates. As much as she talked about eating at McDonald’s and preferring to hail taxis rather than taking her father’s limousines, she grew up, when she wasn’t shuttling between their Greenwich home and private club in Palm Beach, sleeping in her family’s gilded Manhattan triplex on a pillow embroidered “When a woman is tired of the Plaza, she is tired with life.” (The Plaza, which her father owned in the 1990s and her mother ran, was her own expansive playground.) Her friends at Chapin nicknamed themselves the Funny Pink Bunnies Club, a meaningless, self-formed little clique, not unlike their more studious classmates’ group, the Eraser Club; another clique went by the moniker the Fearsome Five. Later, outsiders referred to Ivanka’s friends as the Lindseys, a name given quite literally: all of them other than Ivanka were named Lindsey.
She did have an uncommonly kind side. There was a homeless man she’d pass on her way to Chapin. He looked as though he couldn’t walk, and he asked passersby for spare change to help him get a bite to eat or take care of his legs. For years, as often as she could, she would give him whatever change or dollar bills she could scrounge up. One night, it was later than usual. The Midtown scrum had already cleared out, and when the man thought no one was looking, he handily got up and walked away. For years, Ivanka would tell friends how disheartening that moment was, to see someone she’d believed needed her help deceive her, deceive everyone. He had just been putting on a show this whole time, and she’d fallen for it.
And she could be as unfailingly polite as she often portrayed. When Ivanka was in college, she visited a Chapin friend who’d gone on to college at Emory. The friend arranged for her to stay in the dorm room of a classmate who was off campus for the weekend. The rooms were so tiny that adding an extra body, let alone a suitcase full of stuff, to the dorm room made it almost uninhabitable, so the extra space was appreciated. As Ivanka packed up her things to leave after her few days in Atlanta, she made sure to leave the girl whose room she’d borrowed a thank-you note.
It is true that Ivanka was no Paris Hilton, as she frequently pointed out, but she was not entirely immune to temptation. She once went missing on a family vacation in Aspen, sending her parents into a frenzy. After the police had been called, she turned up with a ski instructor.
Several people at Chapin recall a “scandale” in her last year as a student there. The all-girls school, founded by a suffragette in 1901, sits on Eighty-Fourth Street and East End Avenue, separated from the East River only by Carl Schurz Park. Its motto is Fortiter et recte, “Bravely and rightly.” The future Jackie Kennedy went there, along with the daughters of other uptown socialites. Girls in the school’s uniform of green pleated skirt and white collared shirt tend to plants in the greenhouse and get placed on one of two teams in elementary school, green or gold, which will compete against each other throughout their time there. This still being Manhattan, a hot-dog vendor, a kind older man, set up his cart outside the park, right across from the school. A few classrooms directly faced him, in one of which Ivanka happened to be one day during eighth grade. That’s where she and a friend decided to flash the hot-dog vendor, out a school window.
The school didn’t kick her out for that. That same year, she traveled to Mar-a-Lago to put together her modeling portfolio and lied to administrators about why she was missing school, which irked them far more than the scandale du hot dog. At Chapin, the school uses the period between eighth and ninth grades to pull students who, for various reasons, they don’t want at the school aside. “I’m sure you’d be happier somewhere else” is the standard line.
Ivanka enrolled for high school at Choate, where she was immediately recognizable but seemingly normal. Some of what people remember about her in school is so distinctly normal teenage behavior that it’s easy to imagine Ivanka and a few girls gathered in a friend’s dorm room during her sophomore year so that one of them could teach her how to give a blow job, using a banana. She invited other girls in her dorm into her room to watch 90210 episodes.
Her class had its typical cliques—the exchange students, the day students who didn’t board in the dorms, the jocks—which meant that there were only about thirty or forty kids in her more social circle on campus, in which Trump wasn’t the only notable last name. Ivanka would strut down the path between buildings, linked arm in arm with other girls. “That was kind of her runway,” one former classmate told me. Because she was so tall, taller than most boys on campus, and her legs were so long, she propelled herself at a rather brisk pace as she walked from building to building and class to class. “Maybe that contributed to the perception of her being out of reach to people who didn’t really know her as well,” another classmate remembered. “It wasn’t that she was dodging them. She was just long-limbed. But people maybe saw her as sort of out of their world and kind of untouchable.”
At least some of this untouchable aura had to do with the fact that she built her modeling career primarily while she was at Choate. She would get permission to leave campus to go on photo shoots. Ivanka said it was a way to quell her endless boredom; her classmates have said it was a special perk, extended to her only because of her famous last name. What most students did not know was that when she was out of town, she would keep up with her homework and do assignments on the road. She faxed homework to the school on time for teachers to review. If she missed a class, she still did all the required reading, which is more than most students not working jobs at the same time did. She had made a pact with her parents: they would let her model and skip out on some classes in order to do so, as long as she kept her grades up. The deal was that she needed to hold onto a 3.9 grade-point average. If it slipped from there, her modeling privileges would immediately be revoked.
When she wasn’t out of town, modeling, she was going back to New York most weekends, sometimes taking Choate friends with her. Sometimes they would take the train. It was a quick trip through Grand Central, not far from Trump Tower, but sometimes her father would send her an SUV with a member of his security team to drive her home.
One of her classmates who took a few trips back to New York with her remembered walking into Ivana’s house to see the dining room table covered in jewels. “Oh, Tiffany’s must have brought stuff by for my mom to try on,” she told her friends. They’d pop in at her father’s office to say hi, and he’d sometimes comment on the way she looked. “She had dyed her hair brown fo
r a modeling shoot, and he told her she needed to bleach it back,” one friend remembered. “It was the first time I’d ever heard a parent so pointedly comment on their kid’s appearance like that.” In fairness to Donald, she’d caused a stir on campus, too, when she came back as a brunette. Blond was her thing, and she gave no one any warning or real explanation for the change.
She would go to dinner with her New York friends, where they’d talk about not eating fruit because it had too much sugar, and take limousines to nightclubs where, despite the fact that they were fifteen, they got plucked out of line and ushered right in. One friend, after seeing the way she interacted with her parents’ staff, told her that she was like Eloise, the naughty little blond children’s book heroine who lived and wreaked havoc in the Plaza, with her absentee parents and doting nanny. “When she’d go home, we would go into normal family life, which wasn’t normal family like the way I knew it,” the friend remembered. Ivanka would run errands for her modeling and get her hair cut or nails done, sure. But she always made time to say hi to all of the people who worked around her parents, whom she was obviously very, very close to—the elevator man, the cleaning people, her nanny. “With them, it was always a very warm, loving relationship.” Was it as warm and loving with her parents? “I wouldn’t call it loving in the traditional sense,” the friend recalled. “They’d talk a lot. They’d tell her she needed to get a better grade in this class, pick at her for something else or advise her how to handle something else. Her mother had her own life, as a very unique woman, and her dad worked a lot.”
Donald didn’t call Ivanka much while she was at school, but he did send her mail a few times a week. Almost always, they were newspaper clippings—about him, or her, mostly—with notes scribbled in Sharpie on them. Rarely did he put any note or message in the envelopes, but the frequency with which they came stood out to other students on campus.
When she did stay in Wallingford, she’d head into town with her classmates to a café where the owners would let kids buy cigarettes and smoke them inside. (Once she got to Wharton, she would use the fifteen-minute break in her 9:00 a.m. statistics class to step outside Huntsman Hall and suck down two cigarettes. She wore a full face of makeup, flat-front khakis, and a Burberry trench coat all the time.) Her father turned heads at graduation for bringing not only a bodyguard, but also his new wife, Melania, whom many of Ivanka’s male classmates (and their fathers) couldn’t stop looking at during the ceremony. “I just remember all of our heads slowly turning as we walked by her,” one male member of the class recalled. “My dad had a good chuckle at that.”
Donald and Ivana did not make many trips up to Choate, though they made a few, eating in the dining hall with other visiting parents with little fanfare. This was at least in part because Ivanka went home so often. For a time, her parents kept both of her bedrooms—at Ivana’s and in Donald’s triplex—like mini–time capsules: the same Madonna poster tacked to her walls, the same frilly canopy bed and floral prints on all the furniture.
Classmates don’t remember Ivanka as politically active, but she opted to take a bunch of classes in political history and one in constitutional law. She was opinionated in class, as Choate students are encouraged to be. One year she went with her classmates on a trip to Washington, DC. They met with lawmakers and toured all the monuments, and she participated in Model Congress, proposing legislation in model congress that would give free AZT to all people with HIV on welfare. Many remember her as unfailingly polite and uncommonly kind, particularly for someone from her background. “A lot of the kids there were raised by wolves, and I knew a lot of rich kids who were messed up as a result,” one classmate remembers. “That wasn’t her.”
That she’d been raised by intensely competitive parents, however, certainly brushed off on her. Ivana was a near-professional skier, after all, and Donald was self-obsessed and possessed to make himself a name in the New York real estate world. Ivanka had her own streak of competitiveness, though less masochistically. “She herself was a really good skier, and really hated to lose or share that kind of spotlight,” one friend since kindergarten said. Another longtime friend noted that she loved going to the movies as she got older, commissioning friends and later Jared, before they had kids, to join her at a theater every Sunday in New York. Invariably, she would order popcorn to chomp on, but she never wanted her companions to steal her bounty. So she developed the tactic of oversalting the popcorn so that no one would want to stick a hand her bag. “You can’t even imagine what it tastes like after she’s done with it,” one movie companion of hers remembers.
Another of Ivanka’s classmates at Choate had a condition called prosopagnosia, or facial blindness, meaning he had trouble recognizing faces. He would memorize a specific feature, like someone’s hair color or the shape of their lips, and look out for that to figure out who he was interacting with. High school, and Choate, in particular, is hard enough, but with about 220 people in their class, most of them dressing in much the same way and speaking with the same East Coast rich-kid lilt, the disorder was debilitating. He felt socially awkward and isolated, and his grades slumped as he grew more frustrated.
He had a few classes with Ivanka, who made him feel like a nobody by comparison, especially in their mandatory tennis class. They both got put in the class for those who were not necessarily the most gifted of athletes, and one afternoon were assigned to play each other. She wiped the floor with him, partly because she had been playing in Palm Beach and Greenwich for years, but also because he was so intimidated by her. He walked off the court embarrassed, expecting a long, silent solo trudge back to another part of the campus. Ivanka hung back, though, made small talk about how nice the breeze felt, and asked him questions about himself. From that day on she said hello to him when nobody else did, every time she saw him in class and in the halls.
She was also polite enough to not chew out her date to Choate’s version of the senior prom, called “the Last Hurrah.” A Canadian jock, he was as big and handsome and clunky and heavy on his feet as one would assume of the star of the school’s hockey team. The two danced much of the night, as most of the students did, with some good old-fashioned ballroom thrown in for good measure. He stepped on her feet so many times throughout the evening that she limped all the way back to her dorm, which, fortuitously, also housed the school nurse’s office, where she paid a late-night postdance visit.
Ivanka was hardly the only daughter of a well-known and wealthy family on campus. Carl Icahn’s daughter Michelle was in her class. Publishing heiress Amanda Hearst also attended Choate, just a few years behind her. But classmates remember that there were never any persistent rumors about any of them other than Ivanka. There was the famous one about a party at a faculty member’s house. The teacher, Charles “Chuck” Timlin, was a beloved longtime member of the staff who taught Ivanka English and coached a few teams before becoming the school’s athletic director and a form dean and house adviser. Timlin’s son was in Ivanka’s class, though he was heavy into sports, and he and Ivanka were not particularly friendly. She was far closer to the elder Timlin, as many students were at the time. So when he invited a group of students, Ivanka included, to his house, she went. The party, as these things tend to do, got busted. Call it luck or intuition, but Ivanka left before that happened. Still, her classmates were quick to tattle that she had been there, and like the others who had been at the Timlins’ gathering, she was drug-tested. She passed, and walked away with Choate’s version of a slap on the wrist, put on restriction (something like detention) for a few weeks. As a Choate student, you are supposed to hold yourself to a higher standard of conduct. Even if you yourself are not doing something wrong, simply being around bad things is a violation of that standard.
Other students walked away with far worse. Some were suspended. Others, expelled. Now, of course, this could have been explained by the fact that Ivanka had not, in fact, done anything wrong other than show up to a party. She’d passed the drug test. She
’d left before the party was busted. But some of her classmates saw it differently. Magically, the model daughter of a loudmouthed rich New York developer walked away from something they’d been chained to. Rumor had it that her father had called in, made a stink, and got her out of the whole mess. The truth rarely matters in the reputational meat grinder that is a secluded Connecticut boarding school; perception is the only reality. (Years later, in 2013, when two former students shared with school officials accounts of sexual misconduct they’d experienced as students, Choate’s board of trustees hired an investigator to look into allegations of a pattern of sexual abuse at the school dating back to the 1960s. In 2016, the Boston Globe’s Spotlight team published an exposé detailing the alleged abuse, prompting an independent investigation by a law firm. The report found that at least twelve former teachers had sexually molested and, in one case, raped students. One of the teachers named in the report was Timlin, the teacher who threw the party, the one Ivanka had been close to as a student. Two students had come forward; he had invited one to his home, where he kissed and groped her, and the other he had visited at the campus health center, kissing her, caressing her hand, and telling her “I wish I could make love to you right now,” and “I always thought you were really sexy . . . sexiest girl in the class.” He was let go in 2010.)
The rumors about Ivanka persisted beyond the one party. One had her father hiring a limo to bring her take-out from restaurants in New York City—about a two-hour drive—so that she could have her favorite meals on campus. One that came up year after year was that Donald had continually tried to get the administration let him build a helipad on campus so Ivanka could fly home to New York on weekends. Another was about her decision not to go to the University of Pennsylvania, from which her father graduated, as did her brother Don Jr. Some classmates were convinced it was because she was rejected by the school; others thought it was because she had a boyfriend elsewhere. The truth, it turns out, had to do with Don Jr. He hosted his sister on campus for a weekend to show her around before she decided where she would apply. Donny was a partier; his buddies were preppy frat boys straight out of central casting, who relished taking part in hazing rituals long after they had been initiated into Greek life, and they drank themselves into stupors. The whole weekend left a bad taste in her mouth. It did not help that Ivanka arrived on campus worn out and already in something of a sour mood. She and a longtime friend from Chapin, whose older sister had also gone to Penn with Donny, came down for the weekend together. Ivanka drove, and they decided to make a quick detour at a rest stop somewhere along the way. Someone had to use the bathroom; they wanted a snack. They got back on the road and immediately resumed their teenage gossip. They didn’t go to school together anymore, and teenage minutiae pile up quickly into mountains over which every inch must be combed, so there was a lot to catch up on. They didn’t stop talking until they both saw the Twin Towers appear over the dashboard. Only then did it dawn on them that after their pit stop, Ivanka had gotten back on the highway going in the wrong direction, and that by that point, they were nearly back where they’d started in Manhattan. What should have been less than two hours in the car door-to-door ended up taking the entire day. By the time they finally arrived on campus in Philadelphia, they were hardly in the mood.
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