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Ivanka Trump was my best friend growing up. We first met when I joined her seventh-grade class at Chapin, an all-girls school on Manhattan's Upper East Side that had a reputation for attracting a blue blood, feminine, but ambitious cohort of young girls, not unlike its most famous alumnus, Jackie O. 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 over by Ivanka and about five other wild, entitled, precocious preteens. It was the grunge era, so we moshed around the classroom in performative angst, wearing our uniforms of green plaid kilts (tailored shorter the more popular you got) and stacked-heel Steve Madden loafers as the dystopian wails of Nirvana blared from a boom box. By that time most of us were allowed to roam freely around Manhattan above 57th Street by bus or taxi 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," which was the code used by the entire classroom in reference to a certain forbidden activity.

Of course, the scene was anything but grungy, especially among Ivanka's cohort, most of whom not only lived in palatial townhouses or duplexes scattered between 60th and 64th streets between Fifth and Park, but retired to equally palatial country houses for the weekend, usually with a friend or two in tow. Below Ivanka's group in the Chapin pecking order were about a dozen other slightly less cool girls, most of whom lived further uptown in Carnegie Hill and the 10028 zip code.

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 under the supervision of 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. When we were not in our uniforms, the look was baby tees and Carpenters from Urban Outfitters; floral, boudoir numbers from Betsey Johnson for the interschool Goddard Gaieties dances, or the sixth floor of Barneys if we were splurging.

Mr. Trump always handed over the credit card after a little feigned outrage about how much money he was giving her mother. He would barely acknowledge me except to ask if Ivanka was the prettiest or the most popular girl in our grade. Before I learned that the Trumps have no sense of humor about themselves, I remember answering honestly that she was probably in the top five. "Who's prettier than Ivanka?" I recall him asking once with genuine confusion, before correctly naming the two girls I'd had in mind. He described one as a young Cindy Crawford, while the other he said had a great figure.

Though he never remembered my name, he 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 one day, 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 summer, 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-Elysées 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 post-collegiate 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 to ignore the dozens of press inquiries that flooded my inbox when Donald Trump announced his candidacy because I didn't think he had any chance of winning. Then, when Ivanka joined her dad's administration, I was sure she would step in to moderate her father's most regressive, racist tendencies—not out of any moral commitment, but because caging young children and ripping up global climate agreements was not a good look in the halls of Davos. The Ivanka I knew spent her career developing and embodying a more polished and intellectual offshoot of the Trump brand, which blended the language and look of white millennial feminism with the mythical narrative of the business acumen and entrepreneurial spirit she claimed to have inherited from her dad. Her objective was always a more refined brand of celebrity than the bombastic, nouveau riche variety her dad had perfected—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 friends who also grew up with Ivanka about how appalled we are that she didn't publicly oppose Brett Kavanaugh's Supreme Court nomination, or any 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 it wouldn't make a difference if I shared my bird's-eye view of the first family because the public had long ago 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 from all sides as a hypocritical, privileged elitist looking to capitalize on her Trump connection. My disgust with the Trumps was outweighed by my fear of being dragged through the mud, dismissed by the family as a nasty loser. 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 in the many takes about her future.

A few weeks ago, after I voted early against her dad, I sat down at my computer and 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. Although friends and family have warned that this article won't be received the way I want, 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 a working-class community in 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?"

When Eric Trump posted a photo on Twitter of a mansion supposedly belonging to Joe Biden and wondered how a politician could afford such a house, I thought about how Ivanka used to point out inconsistencies between a character's profession and their lifestyle when we went to the movies. "Since when can a teacher afford a BMW?" she would ask, munching on her usual small popcorn, coated in what would be an unpalatable amount of salt to a normal person. Or, "Why is a police officer living in a house like that?"

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 the array of 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 Ivanka to be embraced by old money. 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 also used to deride people like the Trumps, but Ivanka won everyone over. She was polite, refined, and fun to be around. She subscribed to The Atlantic and spoke ambitiously about her lifelong dream of leaving her mark on the Manhattan skyline. After every conversation, strangers would marvel at how she had turned out so unlike her parents. There was a moment at the end of college or just after when it seemed like this more understated life of wealth and privilege might appeal to Ivanka—like she might actually veer off the track her dad had laid for her.

But in private, rougher, more Trumpian edges still occasionally poked out. Ivanka would regularly relay stories of teachers or observers who had commented that she had the most innate talent they had 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 at 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 to save herself.

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 has since been labelled the "flashing the hot dog man" incident in Chapin lore. 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 was laying 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 bombings and a decimating war with Israel. The gulf between us became increasingly apparent. During my first two-year stint in Beirut, Ivanka regularly 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 I knew who didn't ask me 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. Sometimes, she would randomly say, "I hate that thing." Then 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 during one of his layovers. 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. When 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 completely.

One time, we were driving to Manhattan from Bedminster, and I think we were having some sort of disagreement about affordable housing in Manhattan. I distinctly remember Ivanka saying something along the lines of, "Ly, I can't talk about this stuff with you anymore because you've really turned into a Marxist."

Still, Ivanka asked me and one other friend to be in her wedding party in 2009. The months between her engagement and wedding to Jared 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 a few days or weeks, I remember sending her a text that said something like, "Hey, I started a new job the day after your wedding, and you haven't asked me a single question about it."

I don't remember her exact reply, but it was something along the lines of, "Ly, I'm too busy for this shit."

A photo of the author and Ivanka in Sassy magazine's December 1996 issue.

Photograph by Scott Teitler. Courtesy of the author.

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. When my son was born, she sent me a gold-plated bracelet engraved with his name. She was never impolite, 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 to the role of unelected public official and begins to torch democracy. When Ivanka recently posted a photo of herself on stage with her children at a Trump rally, I wondered to another friend from the Manhattan private school world what her endgame might be. Ivanka had deigned to dress Middle American housewives when I knew her, but 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 and the creaky bureaucracies they presided over. 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 explanation 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 gondola in Amsterdam for a tour, belting out "Anna Begins" and songs from Les Mis on a road trip. But most of all, I miss the time when the Trump family quest for power was not dangerous to the country.

A day before Biden finally declared victory, I saw Ivanka issue a tepid statement about how "Every legally cast vote should be counted," presumably at her father's behest, still clearly hoping that she can be enriched and adored by the public she exploits even as she's embraced on the slopes of Aspen. "Goodbye @IvankaTrump," reads one reply to her tweet. "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 do hope that fantasy comes true—the damage the Trump family has done is unforgivable, even if perpetrated by my childhood best friend—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 economic and social consequences of the policies she pursued for the past four years, the backlash against them, 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 Ivanka is able to rehab her stained image or not, I hope she wasn't able to drown out the applause of the city she once aspired to rule, cheering and celebrating 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.

Lysandra Ohrstrom ( @LysandraO ) is a Brooklyn-based freelance journalist who covers the U.S. and the Middle East.

This article has been updated.

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Source: https://www.vanityfair.com/news/2020/11/ivanka-trump-was-my-best-friend-now-shes-maga-royalty

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