UP GROWING With IVANKA
I met Ivanka Trump at an all-girls school on the Upper East Side, and we were inseparable for more than a decade. Gradually, though, our differences divided us—“Why would you tell me to read a book about fucking poor people?” she once asked—and I watched her blow up her carefully curated image of refined privilege to embrace her father wholesale
By Lysandra Ohrstrom
Ivanka Trump was my best friend growing up. We first met when I joined her seventhgrade class at Chapin, an all-girls school on Manhattan’s Upper East Side that had a reputation for attracting a blueblooded, feminine but ambitious cohort of young girls. After spending the previous four years in social isolation in the suburbs, I was eager to land on the popular side of the classroom, ruled by Ivanka and about five other entitled, precocious preteens. It was the grunge era, so we moshed around the classroom to the dystopian wails of Nirvana, wearing our uniforms of green plaid kilts (tailored shorter the more popular you got) and stacked-heel Steve Madden loafers. By that time most of us were allowed to roam freely around Manhattan above 57th Street before dark, and we rebelled by taking the subway to Patricia Field’s in the Village or dyeing our hair with blue Manic Panic from Ricky’s. Some of us even went to Sheep Meadow to “dye our hair green,” the classroom code for a certain forbidden activity.
Ivanka and I hung out occasionally at first. I got a last-minute invite to her 13th birthday party, where about 15 of us caravanned to Atlantic City in a trio of limos and camped out in the penthouse suite of the Taj Mahal for the weekend, supervised by two wary members of her dad’s security team. She called me to pose in a photo spread for Sassy magazine because none of her usual group was available. I remember swinging by her dad’s office at Trump Tower so she could borrow his credit card to go shopping. Though he never remembered my name, Mr. Trump seemed to have a photographic memory for changes in my body. I’ll never forget the time Ivanka and I were having lunch with her brothers at Mar-a-Lago, and while Mr. Trump was saying hi, Don Jr. swiped half a grilled-cheese sandwich off my plate. Ivanka scolded him, but Mr. Trump chimed in, “Don’t worry. She doesn’t need it. He’s doing her a favor.” Conversely, he’d usually congratulate me if I’d lost weight.
Ivanka and I really bonded one summer when a group of Chapin girls went to Paris for a language program in what would be the first of many trips she and I took together. That July, we delighted in breaking the rules in harmless ways. When we took field trips into the city, we pretended to get lost on the metro and went to the movies on the Champs-Élysées or the Picasso museum instead. Once, we all decided to wake up at dawn, sneak to London on the Eurostar for the day, and make it home in time for the 11 p.m. curfew, but everyone got scared and bailed except for me, Ivanka, and one other girl. After that trip, Ivanka and I were inseparable.
We remained that way for more than a decade, more sisters than best friends. Sure, she loved to talk about herself and was shamelessly vain, but she was also fun, loyal, and let’s face it, pretty exciting. In our late teens and early 20s, it felt like Ivanka and I were always on the same page or up for the same adventure, whether it was leaving Bungalow 8 early to watch a Lifetime movie or horseback riding through a town in Nicaragua because we had never been there before. After college, we started moving on increasingly divergent tracks. I went to Beirut for my first reporting job, and Ivanka experimented with her own form of postcollegiate rebellion: commuting to Brooklyn for a job with real estate developer Forest City Ratner. Still, we remained close. Then in 2009, shortly after I was one of two maids of honor in Ivanka’s wedding, our friendship finally broke under the weight of our differences.
IT WAS EASY Ito ignore the dozens of press inquiries that flooded my inbox when Donald Trump announced his candidacy because I didn’t think he would win. Then, when Ivanka joined her dad’s administration, I was sure she would step in to moderate her father’s most regressive tendencies—not out of moral commitment but because caging children and ripping up climate agreements was a bad look in the halls of Davos. The Ivanka I knew painstakingly developed a polished, intellectual offshoot of the Trump brand, blending the language and look of white millennial feminism with the mythical business acumen she claimed to have inherited. Her objective was always a more refined brand of celebrity than her dad’s bombastic variety—the kind that allowed her to be graciously received by the B&T and Maidstone set and invite Blake Lively over for a girls’ dinner, but also serve as an inspirational example of a “woman who works” to the middle-class housewives to whom she peddled her fashion brand.
Instead, I’ve watched as Ivanka has laid waste to the image she worked so hard to build. In private, I’ve had countless conversations with our childhood friends about how appalled we are that she didn’t publicly oppose Brett Kavanaugh’s Supreme Court nomination or most of her dad’s especially repugnant policies. But in public, we’ve stayed silent because that’s what we are taught to do. I told myself my account wouldn’t make a difference because people had grown inured to the run-of-the-mill instances of misogyny, elitism, and poor character that I could recollect. In reality, I was afraid I’d lose friends and get skewered as a hypocritical elitist looking to capitalize on her Trump connection. My disgust with the Trumps was outweighed by my fear of being dragged through the mud. Even now, as self-proclaimed former friends vow that Ivanka can never show her face in Manhattan again, few of these detractors are quoted by name.
A few months ago, after I voted early against her dad, I began to write about my friendship with Ivanka with no eye toward publication. But the more I wrote, the surer I became that I did not owe her my silence. I think it’s past time that one of the many critics from Ivanka’s childhood comes forward—if only to ensure that she really will never recover from the decision to tie her fate to her father’s.
As she’s touted the achievements the Trump administration has made for the middle class while not-so-covertly pursuing a massive wealth transfer to corporate America, I’ve been reminded of a phone call we had in our mid-20s. Ivanka always solicited book suggestions from me, and I had recently recommended Empire Falls, Richard Russo’s 2001 Pulitzer Prize–winning novel about the life of a diner manager in working-class Maine. “Ly, why would you tell me to read a book about fucking poor people?” I remember Ivanka saying. “What part of you thinks I would be interested in this?”
Another memory that often occurs to me is of Mr. Trump delivering a toast to a room full of diners at Mar-a-Lago, who watched him as devotedly then as his red-capped followers do today. They laughed when he addressed them as the richest Jews in the world, complimented their luxury sports cars in the parking lot, and gleefully recounted the fight he was waging against the Waspy club across the street, which he dismissed as a dump. Beneath the taunting, it was obvious that Mr. Trump was insecure; back then, Palm Beach’s old-guard communities were among the few not seduced by his wealth.
In contrast, it took no time for old money to embrace Ivanka. During summers in high school she would usually come visit me in Newport, where I grew up in a Waspy beach community frequented by many of the same sort of people who patronized the club across from Mar-a-Lago. This set used to deride people like the Trumps, but Ivanka won everyone over. She was refined and fun to be around. She subscribed to The Atlantic and spoke about her lifelong dream of leaving her mark on the Manhattan skyline. After every conversation, strangers marveled at how she had turned out so unlike her parents.
But in private, rougher, more Trumpian edges poked out. Ivanka regularly relayed stories of teachers or observers who commented that she had the most innate talent they’d ever seen for whatever new pursuit she was taking up. She never wore a Halloween costume that wasn’t flattering, which means she usually showed up to costume parties looking beautiful and boring. She always stopped at Mcdonald’s for cheeseburgers. She cursed. And of course, she had the Trump radar for status, money, and power, and her dad’s instinct to throw others under the bus.
One of the earliest memories I have of Ivanka from before we were friends is when she blamed a fart on a classmate. Some time later, she goaded me and a few other girls into flashing our breasts out the window of our classroom in what was labeled the “flashing the hot dog man” incident. Ivanka had basically been the ringleader, but she pleaded her innocence to the headmistress and got off scot-free. The rest of us were suspended.
WHILE IVANKA LAID the foundation for her conquest of Manhattan, I was experiencing a new reality in Lebanon as it was rocked by a string of political assassinations and a decimating war with Israel. The gulf between us became increasingly apparent. During my first two-year stint in Beirut, Ivanka emailed me messages like, “When are you getting your ass back to NYC? You’re going to be replaced.” I remember her being the only person who didn’t ask what the war was like. By the time I did return home, she had started dating Jared Kushner, whose family has personal and business ties to Israel, and my pro-Palestinian stance began to chafe. Since 2007, I’ve worn a necklace with my name written in Arabic, and Ivanka grew increasingly irritated by it. One night in the middle of dinner, she glanced at the necklace and said, “How does your Jewish boyfriend feel when you are having sex and that necklace hits him in the face? How can you wear that thing? It just screams ‘terrorist.’” But Ivanka was skilled at blunting her more Trumpian comments with equally typical acts of generosity. Once, she lent me her apartment for about six hours during a trip home from Lebanon so I could rendezvous with my boyfriend. She connected me with Peter Kaplan, the late editor of the New York Observer, who hired me as a freelance writer between 2007 and 2009. If I was single, she and Jared often tried to set me up with a roster of eligible bachelors in what I always felt was an effort to elevate me to the ranks of people they wanted to socialize with. When I was an intern at Al Jazeera English, I ended up on an awkward date with a close associate of Rupert Murdoch’s; I sat through a group dinner while Jared, Wendi Murdoch, and the New York Post higher-up they had their eyes on for me discussed the expendability of journalists in the digital age and ignored me.
Still, Ivanka asked me to be in her wedding party in 2009. The months between her engagement and wedding were a flurry of activity in which I was honored to participate. When I started a new job in a different field the day after their wedding, however, I expected my best friend to ask how it was going. After what could have been days or weeks, I sent her a text that said something like, “Hey, I started a new job the day after your wedding, and you haven’t asked a single question about it.”
Her reply was along the lines of, “Ly, I’m too busy for this shit.”
THAT WAS MORE or less the end. She still sent presents on my birthday and invited me to her Halloween birthday parties at Trump Soho, and there were a couple more group dinners. When my son was born, she sent me a gold-plated bracelet engraved with his name. We were both polite, but we no longer belonged to each other’s inner circles.
For the past four years I have tried to tune out the conversation that dominated international media, but it is nearly impossible to ignore when the person who used to pluck ingrown hairs from your bikini line suddenly appoints herself an unelected public official and begins to torch democracy. When Ivanka posted a photo of herself onstage with her children at a Trump rally, I wondered aloud to another friend from the Manhattan private school world what her endgame might be. Ivanka deigned to dress Middle American housewives when I knew her, but she did not pretend to want to hobnob with them. Predictably, as she began moving with the real power brokers of the world, Ivanka became increasingly certain that she and the rest of the capitalist elite had better solutions to the plight of America’s struggling working class than elected officials. But aligning herself with her dad’s banana republic–style administration made no sense to me until my friend suggested that Ivanka took her kids to the rally to show them that they are American royalty. This seemed most plausible. What is more royal than presiding over subjects that you disdain?
I’ve been a good WASP and kept quiet until now, even as I’ve grown increasingly repulsed by Ivanka’s ability to aid and abet her father. I’ve been comforted by the certainty that the backlash from those whose respect she craves most must sting. Still, I miss my old friend. I miss going to Green Kitchen on First Avenue at 1 a.m. for “mozzarazza,” hailing down a boat in Amsterdam for a tour, belting out “Anna Begins” and songs from Les Mis on road trips. But most of all, I miss the time when the Trump family quest for power was not dangerous to the country.
A day before Joe Biden declared victory, Ivanka issued a tepid statement about how “every legally cast vote should be counted,” still clearly hoping that she could be enriched and adored by the public she exploits even as she’s embraced on the slopes of Aspen. “Goodbye @Ivankatrump,” read one reply. “You will be loved by the people you disdain and disdained by the people you want to be loved by. There will never be a Met Ball for you again. You are fated to live out your years as an aging, corrupt, villainous Barbie; paying the price for what you did.”
Though I hope that fantasy comes true— the damage the Trump family has done is unforgivable—I expect Ivanka will find a soft landing in Palm Beach instead, where casual white supremacy is de rigueur and most misdeeds are forgiven if you have enough money. It’s the perfect spot for her to lie low, shielded from the consequences of policies she pursued for four years, and from having to interact with her MAGA following. Surely Ivanka will still market whatever branded products she can sell them, and many whisper that she will harness their loyalty in a future run for president.
Whether she’s able to rehab her image or not, I hope she couldn’t drown out the applause of the city she once aspired to rule, cheering her political downfall. I was with them, crying with relief, matched only by the regret and shame I feel for not holding my former friend to account sooner.