Ivanka Aeternum

After the White House, she probably can’t go back to the city that made her. So she has cannily devised another exit strategy.

Ivanka and Jared, aged with FaceApp. Photo: Source Photograph: Max Mumby/Indigo/Getty Images
Ivanka and Jared, aged with FaceApp. Photo: Source Photograph: Max Mumby/Indigo/Getty Images
Ivanka and Jared, aged with FaceApp. Photo: Source Photograph: Max Mumby/Indigo/Getty Images

The Hamptons season was in full, humid swing when Ivanka Trump went missing at its most important geezer party. Each Fourth of July weekend, Lally Weymouth, the 76-year-old daughter of the Washington Post’s former owners, celebrates her birthday with an event that’s like a “D.C.–New York–glitterati bar mitzvah,” says Anthony Scaramucci, a guest at the seated dinner for hundreds in a striped tent on her estate, where a microphone is set up on a stage for speeches attesting to her grit and longevity. Weymouth’s crowd is the mix of politicos, media personalities, and financiers that drives Americans crazy — they’re supposed to hate each other, not party together — from Commerce Secretary Wilbur Ross to Democratic fund-raiser Alan Patricof to ex-titans like former Goldman Sachs CEO Lloyd Blankfein. It’s also notable for the considerably advanced age of the attendees. “If you’re under 50, you’re under threat of Lally seating you at a kids’ table,” says a friend of Ivanka’s who’d had a fight with her husband earlier that day about accompanying her to the party. “He said he didn’t want to be there when someone had a heart attack on the dance floor.”

This is the scene Ivanka liked before she arrived at the White House, a scene that occasionally tolerated her father but more often excluded him — real power brokers, kingmakers, people who knew the way the world worked instead of simply sliding down the surface of it — though she wasn’t a Hamptons person in particular. When she was young, Donald and her mother, Ivana, rented a cottage on the ocean for a couple of summers; she’d play in the surf while a bodyguard stood next to a limo idling in the driveway, her father stalking around inside talking about how much he had to do in the city and how much the houses out here sucked. One time, when she was a toddler and Ivana was pregnant with baby Eric, they drove through a roller coaster of the beach’s sand dunes (a not-unheard-of practice in the pre-climate-change ’80s), and afterward Ivana almost had a miscarriage, lying on the floor, shaking, her bottom half mottled with blood.

As a teenager, Ivanka came to the Hamptons intermittently as the guest of friends. She did the party-girl thing: chatted up hot Argentine polo players at Saturday-afternoon games, danced at nightclubs in potato fields with models who may not have been able to drink legally — that blasphemous Jeffrey Epstein scene.

Then, over the course of the past decade, Ivanka transformed. Everyone knew she wasn’t rolling in dough, what with Donald’s bankruptcies and general miserly nature — and even Jared Kushner, her dreamboat billionaire husband who once seemed like such a good match, had thrown part of his father’s fortune down the drain. But she craved being in the mix. And in the vortex of inherited wealth swirling around the Hamptons like the Great Pacific Garbage Patch, she and Jared struck the rich octogenarian set as a cut above: polite, Ivy-educated, compulsively groomed, tall as poplars, and more respectful than other ungrateful millennial heirs (beloved grandsons and granddaughters excluded).

But this year Ivanka didn’t go to Lally’s to kiss the ring. Did she think her role as adviser to the president meant she was better than them, this crowd whose members travel here from midtown helipads, own four or five houses, and have their names emblazoned in fine stainless-steel letters on cancer wings? Was she off someplace else with more-significant people, people who move world markets and control armies, some of whom also take endangered animals as pets? At the party, as guests chose their entrées and the Motown band pumped out tunes, there were further questions about Ivanka’s absence: Was it a snub, because she was flying closer to the sun and didn’t need this crowd anymore, or was she simply not here because she was embarrassed to show her face? The latter explanation, in part, would have been the legacy of a few years spent in her father’s never-ending rage war, a mutual excommunication period in which Ivanka and the New York society she’d spent her 20s cozying up to got more and more disgusted with each other, seemingly by the day. Getting Lally Weymouth to proclaim Ivanka the next Jackie O. was always going to be a hard sell, but now that whole fantasy of becoming the city’s most glamorous grande dame just seemed preposterous. Things had only gotten more humiliating, it seemed, in just the past few days, when she became the world’s laughingstock at the G20 in Japan. There she was, trying to drop some knowledge about women and the global economy, when French cameras caught her being dissed by IMF chief Christine Lagarde and leaders of the Western world’s most important countries, all the while flapping her hands around like a baby seal with its flippers.

She seemed so out of place, but she was making a place for herself, too — post–White House, post–New York, even post-America, a princess diplomat astride the globe, flying the next day to South Korea to greet service members, accompanying her father to the demilitarized zone to meet Kim Jong-un, and watched by people all around the world for whom the images would be indelible, the proximity much more important than the snootiness. Who cared whether some New Yorkers were cringing with shame. As always, her father was among the audience, though of course he already believed she belonged. This spring, while she was touring the Ivory Coast, she revealed that he’d offered her the job of running the World Bank; he thought it made sense, he said, because she was “good with numbers.”

Illustration: Gluekit/Source Photograph: Rubin Utrecht/EPA-EFE/Shutterstock

Many daughters have made a mark in their fathers’ administrations — Andrew Johnson’s daughter was a hostess for her father, Maureen Reagan traveled to Africa, and Anna Roosevelt influenced FDR, particularly during his last year in office, plus kept her father’s relationship with his mistress a secret from her mother. Earlier in the Trump presidency, Ivanka seemed to fall somewhere on this spectrum: She was the first First Daughter in American history with an official office and a portfolio in the West Wing, but that seemed to be about all she had — a blonde, elegant presence rather opposed to the character of the gangster who had stolen the presidency. Her relative impotence was a media joke, as story after story reported that Jared and Ivanka deeply opposed this or that noxious policy or statement only to lose out. The couple seemed to be incompetent at navigating the White House and equally desperate for the world to regard them as sympathetic forces by having their representatives leak such stories again and again.

Yet, over time, almost everybody in the White House but Jared and Ivanka has disappeared — Steve Bannon, Reince Priebus, Gary Cohn, even four-star Marine general John Kelly, who was expressly meant to rein in the power of Ivanka and others but ultimately became the victim of their machinations. And even if one still couldn’t point to anything “Javanka” had accomplished on major policy issues, aside from the increasingly bipartisan issue of prison reform, one had to reckon with the fact that, in a White House snake pit where power, not policy, was the coin of the realm, they had seemed to … sort of win.

Of course, the point of politics is to actually make change, and while Jared did seem to be actively shifting the balance of power in the Middle East, Ivanka’s game has been harder to parse. She’d made the White House her power base, but it was one with a vacuum at its center. She wasn’t engaging deeply on domestic policy or the 2020 reelection campaign. She flew above the storm, deftly or through sheer luck not jeopardizing her own liberty, while her older brother, father, and husband all faced significant investigations over Russian interference, potentially presenting her with the ultimate Abrahamic test as she picked sides among them — and then they all got away with it, at least for now.

But this summer Ivanka transformed into someone entirely alien and new. She’s a frum Donatella Versace, her platinum hair parted severely down the middle, clad in increasingly conservative floor-length dresses, with an uncanny-valley beauty that’s the inverse of her father’s slack meat sack, and speaking in the ever-huskier whisper of a phone-sex operator who went to boarding school. Five years ago, you might have guessed her future was to be the next generation of the Trump dynasty — more polished, more presentable, speaking in full sentences and declining to serve McDonald’s at dinner parties. Maybe she wouldn’t be selling real estate, but she’d still be the new face of one of New York’s great families, maybe even an aristocrat in her own right. That was what she’d been raised to be, the shiny hood ornament of the Trumps. As her mother once told author Dominick Dunne, “In 50 years, Donald and I will be considered old money like the Vanderbilts.”

These days, in her role as ambassador for Trumpism and relatively silent witness to family separation at the border, Ivanka has instead incinerated everything about her reputation that once insulated her from accusations of complicity with her father. She seems like she may be building a new life for herself with a whole new base — abroad, where cities change their contours for her before a visit, as Hyderabad did by moving the beggars on her motorcade’s path into shelters. Wherever she appears, a media scrum of photographers follows, pushing and shoving like she’s a Kardashian at a Starbucks. At home, as for a reality star, a glam squad arrives in the morning at her D.C. mansion. “If you go to Ivanka’s for breakfast, the whole family is all perfectly dressed, even the kids. I don’t think there’s another family like that in the United States,” says someone who was present.

Long perceived by MAGA die-hards as a shifty liberal, Ivanka is now mostly beloved on the right, where she polls better than her father in the critical states of the industrial Midwest, leading to speculation on mid-tier news sites that she might replace Mike Pence on the 2020 ticket and to fans’ dreams about Ivanka 2024. In the meantime, conservatives of many stripes are bowing at her feet. “There have been many very brilliant women in world history: Angela Merkel, Maggie Thatcher, Hillary Clinton, Elizabeth I, Catherine the Great,” George H.W. Bush adviser Doug Wead explains in an email. “And there have been many very beautiful women. But in my humble opinion, you can only count on one hand those considered by history to be both brilliant and beautiful. Cleopatra? Drusilla, sister of Caligula? Diane de Poitiers? Not many. But Ivanka Trump would be in that mix.”

This is an astounding turn of events for those who knew her in New York, many of whom thought they’d had her number since she threw all in with her father’s business in her 20s, or at least since she married in 2009. She was the flashy shiksa daughter of a celebrity showman in Manhattan, and Jared was the buttoned-down Orthodox Jewish real-estate heir from New Jersey, which sounds like a rom-com plot and seemed, at least at first, like a way for Ivanka to break with tradition; she’d gone with a straight arrow for a mate instead of a wild man. And they knew much more about Ivanka and her family than that, as well as the true nature of her relationship with her father, which hasn’t been as well understood as it should be despite being a constant source of curiosity and horror, and the nature of her upbringing — which is that she was raised on her own.

Like everyone, the Ivanka of the present can be understood only in the context of the person she was in the past. I know, in part, because I was there, growing up in the party world of New York in the 1990s and 2000s too. Ivanka declined to speak with New York other than off the record, which we declined; this story is based on 60 interviews with her friends and colleagues, which also form the basis of a narrative podcast series I have been reporting for six months.

From left: Captured by paparazzi at age 10 with her father in 1991. At a Seventeen fashion show during her modeling period in 1997. Photo: The LIFE Picture Collection via Getty Images; Shutterstock.
From left: Captured by paparazzi at age 10 with her father in 1991. At a Seventeen fashion show during her modeling period in 1997. Photo: The LIFE Pi... From left: Captured by paparazzi at age 10 with her father in 1991. At a Seventeen fashion show during her modeling period in 1997. Photo: The LIFE Picture Collection via Getty Images; Shutterstock.

The Weymouth crowd might have looked down on pre-presidency Donald for a long time, but back when Ivanka was a kid in the Reagan ’80s, the Trumps were a golden family in New York, the epitome of the new nouveau riche even if Donald’s pockets were filled with his father’s money. They were too Kardashian for most, establishing their fiefdom of Trump hotels, the Trump Shuttle airline, Trump casinos, the Trump Princess yacht, but no one I talked to says Ivanka was a brat as a kid. Ivana ran a tight ship (well, she didn’t exactly run it: “Of course she had women for the shopping and the meals and the baths,” a friend says huskily). As a child, Ivanka had painting, singing, swimming, and piano classes. “You have to keep kids busy, busy, busy, busy, busy so that they don’t have time to get in trouble,” says Ivana, calling me from her home in Miami. She says Ivanka “hated piano,” but she doesn’t have much else to say about her daughter that I haven’t heard before, nor anything that might give insight into the depths of her psyche. “You cannot really show the vulnerability,” she tells me, speaking about herself, though it seems she could be speaking about the rest of the family, too. “Because people take advantage of it; the press take advantage of it. So you cannot show the weakness even if you have some.”

From Ivanka’s birth, Donald was absent — never changed a diaper, didn’t do bottles, dishes, naps. In their 66th-through-68th-floor triplex castle in Trump Tower (they actually lived on the 56th, 57th, and 58th floors, but he’d added ten fake floors to the official count to make the building sound taller), he and Ivana lived on an entirely different floor from their children. He left before they arose, waiting for the nannies to transport the kids to his 26th-floor office on their way to school. He was the great Oz behind an oak desk, the golden-haloed god in his Brioni suit — and in Ivanka’s dreams, this may still be the man she sees.

Stories about Ivanka and her brothers’ childhood often seem to pay fealty to her father, like the one Ivanka used to tell about gluing a bunch of Legos together to make a building, after which everyone just knew she was going to go into construction; the same story has been told by Eric and Don Jr. with each as the child Lego-gluer fated to run a real-estate empire. Family lore also tends to reinforce Donald’s belief that Trumps are hardier, better, than New York society aristos. And unlike members of the “Lucky Sperm Club,” as Donald called the beneficiaries of inherited wealth, which includes him, his kids would work for everything they had. Whether in service of this or because he didn’t want to share his wealth with anyone, Donald didn’t spoil Ivanka with presents and wads of cash. She didn’t even have a credit card. She had to ask him for his, an elaborate pantomime that still often ended with the card clasped in her little hot hand.

Ivanka became a real-life Eloise when Donald bought the Plaza, the grand hotel on Central Park, and Ivana managed it as the equal to her man — even if her man had publicly announced he was paying her only “one dollar a year and all the dresses she can buy” for her services. Remaking herself as Zsa Zsa in a power suit, Ivana went to balls each night, performing her ablutions while Ivanka, idolizing her professional mother, watched intently from her seat on the lip of the tub — the daubing of perfume, the red lipstick, the hair brushed to the ceiling. But behind the scenes, Donald was a cheater. One-night stands with brassy showgirls and spokesmodels were his thing, according to an old friend, and he was none too discreet. On the annual Trump-family vacation to Aspen in 1989, he surreptitiously flew in Marla Maples, Miss Hawaiian Tropic 1985, stashing her in a penthouse. This was a brash maneuver even for him, and it backfired spectacularly. One day on the slopes, as Ivana waited for lunch in a powder-pink onesie, Ivanka and her brothers trailing behind, Maples appeared. “I’m Marla, and I love your husband — do you?” she asked. Ivana shrieked, “Get lost!” and the sound traveled from Aspen to the gossip pages in New York faster than the Concorde.

The “divorce of the decade” was big business. A tale “bigger than Dynasty, badder than Dallas, and spicier than General Hospital,” said Geraldo Rivera on one TV special, squealing, “She busted him on the slopes!” This crucible formed Ivanka’s personality, leading her to be on guard with the press at all times and to cover up her private life and thoughts from all but an innermost circle. Though Ivanka has in recent years said her parents told her about the divorce on her own, she said in a rare unguarded interview that she’d learned about it in the papers: “I was going to school one day and I saw in one of the news boxes a huge picture of, um, both of my parents. And there was a rip down the center of the picture. And this was before I had officially been told that they were getting a divorce.”

For a girl raised around aristocratic families, this was quite an education in tabloid values. The divorce also gave Ivanka a complicated perspective on being a professional woman. Donald said Ivana had to go because of her corporate aspirations: “Putting a wife to work is a very dangerous thing,” he remarked at the time. “There was a great softness to Ivana, and she still has that softness, but during this period of time she became an executive, not a wife.” He fought her over every penny, and the big reveal was that he had to — the golden empire was leveraged beyond anyone’s dreams. And though the city’s sympathies were with Ivana, the other big reveal was that, over time, Ivanka took her father’s side. A friend compares this to the way Zoë Kravitz spent her teenage years hanging out with her dad, Lenny, instead of her mom, Lisa Bonet. It’s much more fun to run with a celebrity father than a complicated mother; or perhaps, as in many families with patriarchal narcissists, Ivanka’s father drove a wedge between daughter and mother. The other thing Ivanka learned from this period of time, with her father’s fortune dwindling, was that she would need to work to make her own.

From left: With her mother, Ivana, at the 25th-anniversary party for Studio 54 in 2004. With Paris Hilton at the release party for Hilton’s single “Stars Are Blind” in 2006. Photo: Ron Galella Collection via Getty Images; Foc Kan/WireImage/Getty Images.
From left: With her mother, Ivana, at the 25th-anniversary party for Studio 54 in 2004. With Paris Hilton at the release party for Hilton’s single “St... From left: With her mother, Ivana, at the 25th-anniversary party for Studio 54 in 2004. With Paris Hilton at the release party for Hilton’s single “Stars Are Blind” in 2006. Photo: Ron Galella Collection via Getty Images; Foc Kan/WireImage/Getty Images.

Donald barely paid attention to his daughter after the divorce. “She was ‘poor little rich girl’ and very neglected,” says a friend, describing Ivanka constantly asking to sleep over. “Her childhood friends became her family because her real family wasn’t fucking there for her,” says another. Even surrounded by these confidants, however, Ivanka rarely spoke of her feelings about the divorce. She said what truly affected her, the trauma she carried, was her Irish nanny Bridget Carroll’s sudden death in the basement of her parents’ country home. Her friends were flummoxed by this and thought it was a smoke screen of some kind. But perhaps if Ivanka thought too hard about her parents’ divorce, she would have to blame her father for the split, and that was not a path she was willing to tread.

Ivanka was always a good student, but she was no kind of good girl. For her birthday party in junior high, she invited about 20 girls from Chapin, her Upper East Side all-girls school, to the Taj Mahal in Atlantic City, all of them crammed into stretch limos without chaperones, which other parents would never have allowed had Donald actually told them about this plan. The girls acted crazy: flashing people out the windows, whipping off bras and putting them on the limos’ antennae. In the hotel suite, they rented porn and ran around naked. Classmates who remained at home heard about the trip in excruciating detail and felt horribly left out. But Ivanka wasn’t trying to hurt anyone. There was simply a natural order to things, and in that order she was at the top and others were at the bottom, and she felt no need to exert herself to make anyone more aware of this fact. They knew.

In her rebellious phase, she dyed her hair blue, listened to grunge and country music, and cried over Kurt Cobain’s death, none of which her parents were excited about. She also developed another habit that friends say her father did not like — she became a prodigious reader of great novels, burying her nose in Fitzgerald, Hemingway, Austen, Morrison. In her 20s, she said her favorite book was Ayn Rand’s Atlas Shrugged and she had modeled herself on its capitalist heroine, Dagny Taggart.

“Her father hated that Ivanka was a major reader; she’ll never admit this, but I think it threatened him,” says an old friend. In truth, father and daughter kept to themselves. Ivanka mostly grabbed her father’s attention either by flattering him or by appearing at the moment he had someone important on speakerphone, when he’d let loose a series of weird rhetorical questions for the VIP: “Isn’t my daughter Ivanka the best? Isn’t she the greatest?” When she began modeling at 15 in the late 1990s, blossoming into a gorgeous girl with the oversize features and blonde hair of ’60s Italian film star Monica Vitti, muse of director Michelangelo Antonioni, he amped up another question: “Isn’t she the most beautiful girl you’ve ever seen?” When asked about the president complimenting Ivanka, Stephanie Grisham, the White House press secretary, says, “The president makes no secret of the fact that he is proud of his daughter.” She adds, “To say her father was threatened by her in any way — much less for reading — is not only false but laughable.”

Though Ivana drank, Donald had been living clean after his older brother died of alcoholism in 1981; that death is “absolutely” the reason Donald became so fixated on success, on overturning the failures of the past, says Nikki Haskell, an old family friend. So when Ivanka started smoking, drinking, taking drugs, hanging out at bars and nightclubs, and making out with guys on pool tables at pre–voting age, she had to keep all of that secret from her father, and it does not seem he has ever known about it or wanted to know. Even a decade ago, she was telling Oprah, “I’ve never been very interested in being sort of a wild party girl — an ‘It’ girl. My father is very strict … No drugs, no drinking, no smoking.” Though she was occasionally photographed smoking, friends say Ivanka never developed a drinking problem, and when Don Jr. did, she covered up for him as best she could.

She’s always “the same consistent friend,” says Maggie Cordish, a friend and former adviser. “She hopped on a train to Baltimore when I had a family issue. She was there four hours later.” She was the protector of her brothers, and they remain close to this day. She wasn’t a tomboy back then, but she was a girl’s girl — she was into loyalty, she had her friends’ backs, she didn’t try to steal their boyfriends even if she could. The issue, others say, was she thought only about … herself. That’s the No. 1 thing friends from her past say about her: She isn’t a “mean person” or a “bad person” but is simply afflicted with the same disease of narcissism as her father. She is the movie projector and the screen.

But not when her father was involved. She operated in fear around him, says a friend. Sometimes she would tell a taxi to drive around the block if she saw him getting out of a car in front of her. When Ivanka would receive a call with his number on the caller ID, she’d become very anxious. She’d have a momentary panic about what he was going to say about her life and whether she was about to be blindsided by his disapproval. “I think she knew,” the friend says, “and at times resented, that she was a prisoner to the condition of seeking his approval at all times.” When they’d talk, “she was very careful. It was like listening to a person talking to her boss.”

But in her father’s presence, Ivanka never talked back or even rolled her eyes. Friends I spoke with have not seen them fight. She played the dutiful daughter on flights to Mar-a-Lago with her friends when her father would do cringey things like put a VHS tape of his recent media clips on the TV or ask them which female stars they considered hot. Among the members of New York society in the ’90s and early aughts, he was seen as a credit clown, a joke, but never to Ivanka. His chauvinism frustrated her, however, and she was repelled by the way he talked about women’s bodies — who was fat, who was not. In 2003, when Paris Hilton’s sex tape was leaked on the internet, Donald wouldn’t stop talking about it, saying, “Paris is laughing all the way to the bank, she’s got the last laugh, she’s marvelous.” Ivanka could not believe her father was not only idolizing an airhead heiress caught blowing a guy on a night-vision video but encouraging her to follow Paris’s lead. (Speaking from the White House, Grisham says, “This is untrue and is disgusting.”)

“The thing with Paris hurt Ivanka a lot,” says a friend. “He was heartbreaking to her at times.” But as with so much of her father’s behavior, she buried her feelings and moved on. She told herself that the story of her father’s attitude toward women was, simply, complicated, according to friends. Donald hired many women at the Trump Organization, she knew, and these women weren’t universally pretty; he wanted to employ women with traditionally masculine attitudes and almost enjoyed feeling discomfited by them, having them boss him around. Her father may have had issues with women, she felt, but he did not meet the textbook definition of a misogynist — a belief she seems to hold to the present day.

Unlike Don Jr. — who enrolled at Donald’s alma mater, the University of Pennsylvania, after Donald had reportedly smoothed the path — Ivanka went to Georgetown, a university without a connection to the Trump family, but transferred to Penn her junior year. After graduating with a degree in finance and art history, she signed up at real-estate developer Forest City Ratner but went to work for her father a year later, like many heirs to the city’s real-estate fortunes. What was behind these decisions? “Ivanka always has to prove to herself that she’s gotten ahead on her own without her father,” says a friend. “She really has no idea she’s privileged. She genuinely thinks she’s earned everything she has. She goes on and on all the time about how hard she works.” Did she work hard? “Sure, but she works hard the same way everyone works in New York — she still goes to the gym and meets friends for dinner.”

In New York in her early 20s, Ivanka ran with a cool after-hours crowd even though she was transforming her look in a way that was very not Chapin; she was posing boobs-out on the cover of Stuff magazine, turning herself into the leggy, busty, blonde Barbie type Donald had chased his entire life. At the Trump Organization offices, she took on the role of executive with gusto — she’d be just like her mother, the professional woman, but her professional life would be entirely in service to her father. According to a friend, she was hesitant at times about his business, of licensing his name to Third World oligarchs perhaps seeking to launder funds, as in the Trump Soho or the Trump hotel in Azerbaijan, to name two projects she shepherded. But she justified it to herself as part of the way the world works, and only a moron would not take every advantage offered to her. Working for her father wasn’t a financial bonanza, and she had no trust fund to prop her up. In the mid-aughts, when New York’s socialites began becoming as famous as Paris Hilton — the “celebutantes” — Ivanka wanted to secure the high-profile beauty and fashion deals they were receiving, but she also saw them as beneath her, a bunch of girls with fake jobs as jewelry designers. For her own fine-jewelry line, she would make a serious play, taking as her partner a diamond heir from the Bronx, who has since been accused of fraud and extortion.

Ivanka and her father started spending more time together; two people never showing vulnerability were now national stars on The Apprentice. Some people started to notice that they shared another affliction, the Manhattan disease of constantly discussing who was up and who was down in the power structure. “Did you ever hear them talk about politics?” I ask someone close to both. “No, they talked about other people’s money.” They did not share their own money, of course. Like her father, never a charitable type, Ivanka does not donate to Chapin, says a source close to the school’s board.

With husband Jared and Mayor Mike in 2015. Photo: Dimitrios Kambouris/VF15/WireImage

Among Ivanka’s friends, her relationship with Jared is perceived as a lit match. Without him, they don’t think she would have climbed the particular greasy pole of Weymouth’s birthday party. She had previously preferred party-boy boyfriends whose big extended families impressed her but not her father, who’d wanted her to marry a celebrity. She often became enmeshed in their families, taking on the preppy style of chatter and the Lilly Pulitzer fashion of her Palm Beach boyfriend Bingo Gubelmann. Kushner, to whom she was introduced by her diamond dealer, was no sort of blue blood, but his family was large and outwardly appeared kind, though privately so diabolical a former colleague described the Kushner patriarch’s anger as akin to “an animal foaming at the mouth.”

In her 20s, she said her ideal man, the one she had fantasies about, was Christian Bale in American Psycho playing Patrick Bateman, who is, of course, an ’80s scenester just like her father was back then — suspenders, slicked-back hair, chops up women for a hobby. Jared is handsome when you first look at him, but upon contemplation, his face is a Cubist construction. The eyes seem to refract rather than reflect light, and he has an unpleasant cast to his mouth; what he’s turning over in his mind seems to be expressed less through words than through the railroad-straight set of his lips. His words have always been charming, so charming that some in New York found him unbearably polite, with his constant affirmations of how interesting he found the conversation he was having with you. And as a kid from New Jersey trying to make it in New York, he’d do whatever it took to raise his profile. With Jared by her side, Ivanka left her hard-partying crowd for tamer friends like Ralph Lauren’s kids, married tech bros, and Wendi Murdoch, the wife of elderly mogul Rupert Murdoch, with whom Jared became close.

As always, Ivanka took her image in the press seriously, particularly the one in the New York Post, which she read each morning, just like her father. A female reporter there who met Jared for lunch or coffee about once a month for a couple years says, “He did the ‘Aw shucks, I’m naïve’ thing, and it was hard to piece out if it was an act because he came off so deer-in-headlights.” Jared told her, baldly, that he was interested in picking her brain about how power and media players worked. The reporter found Ivanka to be much more normal, a friendly person who would nevertheless make coy statements like, “ ‘I saw Wendi recently and told her how great you are’ — like, ‘Hey, remember, I’m friends with your boss’s wife.’ ” Jared and Ivanka seemed to want to be in the Post all the time; Ivanka knew her father loved it when she was mentioned in the paper. But after the couple married, the reporter received a different message from Jared. “Suddenly he didn’t want me to write about the two of them at parties anymore,” she says. “We’d have to make it seem like they were really serious people.”

Ivanka may have thought Jared was devoted to her and would never cheat on her, which would allow her to think less about her personal life than her professional life as she tried to climb ever-higher heights with a new clothing line and a website promoting working mothers and “Lean In” feminism. Friends say Ivanka did truly buy the Chapin line that women can do everything men can; with her narcissistic tendencies, she simply thought this primarily about women who looked like her and were relatively close on the economic spectrum. Like her husband, she seemed to consider discretion almost a moral good and made sure her outer reputation was one of elegance: thank-you notes, baby presents, cool-cucumber attitude, promotion of others’ projects. “She extends generous gestures,” says Phaidon editor Billy Norwich, the recipient of a lovely tweet from Ivanka about his novel, though they’d never met.

Some people in New York bought what she was selling, and some found it fake. “She’s so polite it’s actually uncomfortable — her whole thing is ‘My father may be tacky and horrible, but I am elegant and refined,’ ” says a fashion editor who dined with her several years ago. And here and there, she has been caught acting less than perfect. “My place card was next to Ivanka’s at a small dinner, and during cocktails I looked over and saw her switch mine with someone else’s,” says architect James Ramsey. “I guess I wasn’t important enough.”

When Donald announced that he was going to run for president, Jared got to work on his own agenda: He wanted to dig himself out of the debt he’d acquired buying the massive office tower at 666 Fifth Avenue and figured a higher profile with government ties might do the trick. With the Qatari government, it eventually did, and he also wanted to strengthen America’s ties to Israel. Ivanka was not sure what she wanted, and she was also not sure what she was getting from this presidency deal at all; she was hoping to finally make a fortune from her clothing line. Before her father was elected, heavily pregnant, Ivanka was stopped at an elevator by Elizabeth McLaughlin, a feminist entrepreneur consulting for Ivanka, who asked how she was feeling. The words spilled out of her: “I’m exhausted. If I had my way, I would throw my television out the window, cancel my newspaper subscription, and turn off my phone, but they won’t let me.”

After her father’s election, Ivanka, although excited by the win, told friends she wanted to stay in New York. Jared argued for D.C., saying they needed to protect her father, and, by the way, now anything — everything! — was theirs for the taking. At their synagogue, at least a few people began referring to Ivanka, the first Jewish member of an American First Family, by a new nickname, that of a savior. Grisham confirms that they called her Esther, after the beautiful Jewish wife of a Persian king who convinced him to cancel an order to annihilate the Jews.

At the G20, incongruously, in June 2019. Photo: The Asahi Shimbun via Getty Images

In D.C., “Hollywood for ugly people,” Ivanka impressed some at the outset with her star power. Senators stopped her in the hall to take selfies, and, once she took on a political portfolio, Republicans clamored for her to bring attention to their pet issues. Those around her felt the public vitriol immediately directed her way was unfair: “If you had a weak leader in a Democratic administration and a 35-year-old mother of three in there trying to make a difference, it would be seen as incredible, but because she’s Donald’s daughter, everyone says it’s disgusting,” says a former colleague. Several people I talked to who are close to her argued it’s anti-feminist to blame a daughter for the sins of the father, as though Ivanka weren’t in the White House only because of her father. “Ivanka Trump didn’t pick Donald Trump to be her father,” says Scaramucci. “On her own, she’s an extremely gifted person — smart, great energy, a great sense of style and taste.” How is she on policy? “Is she a policy wonk? No, but the president’s more of a commonsense person than a policy wonk himself. And you’ve had 40 years of policy wonks who basically destroyed the country.”

New York liberals may have turned against her first, but the anger has just ramped up from there, much of it over the shock that she has not folded up shop as her father careens out of control. Since he didn’t listen to her on issues like climate change and abortion, she stopped trying, telling friends behind the scenes, “I have no control over him” or “I can’t believe people think I can control him” or, sometimes, “My father has never listened to me about — anything!” The day-to-day cognitive dissonance for her in this new role is extreme: She was in the White House, but her father, ever the chauvinist, still called her “Baby” in meetings. And while she tries to remain in a narcissistic cocoon — on Instagram, she follows not one, not two, but 35 fan accounts, flooding her feed with love — she must also have regrets. “She has a bitterness she never had before,” says a friend. “You see it in her eyes and in her brow. She has a sense of spite.”

Instead, she seems to have become more aggressive about taking what she may believe is rightfully hers, from a security clearance to using personal email to Chinese trademarks for her businesses to renting her mansion in D.C. from a Chilean businessman who then received permission to mine near a previously protected area of Minnesota. The power of her office is so massive no one can stop her. “Ethics rules are intended to be prophylactic — when all of them were being written after Watergate, people thought that no one would just come in and say, ‘Make me,’ ” says Arthur Lopez, a former federal-government ethics official. We don’t know how many deals she has made for herself abroad, though reports come in from time to time that Israeli intelligence, Chinese intelligence, Saudi intelligence, and who knows who else are targeting Ivanka and Jared, trying to figure out what they’d want in exchange for favoring their countries.

The U.S. government, in Donald’s hands, is still a family business, and he’s going to run it as he likes, which means that everyone is disposable except the family. And Ivanka, more than anyone else, knows how to handle him: flatter him, tell him what he wants to hear. He’s as moody and nonsensically theatrical as a 6-year-old, but the mood will always pass. She’s playing the long game. “The jury’s still out” on how she’ll be perceived historically, says Anita McBride, chief of staff for Laura Bush. “The rules are being rewritten by the Trump administration. We’re not used to family members with all the benefits of being members of the White House staff. Plus they have what every member of a staff wants: access.”

So — what’s next? In the coming months, Ivanka will continue her global trips and attempt to secure wins on her policy concerns, like parental leave, but she will really be looking ahead. With little understanding of social justice and her lifelong aversion to those with less money than she has (always seeking to align herself with those who have more), domestic policy may not be her bag. In addition to the World Bank, the vice-presidency, and the presidency, her name has been floated for U.N. ambassador, the position Nikki Haley vacated and a job friends say would interest her. She spent many years cultivating a polished place for herself in the New York social elite — imagining herself on the right boards and at the right parties with the right friends, the problematic Trump family reputation laundered through the usual parade of heiress tastefulness. But if there wasn’t really any audience for that kind of performance anymore — from her old friends and those right ones — well, fuck ’em. Becoming an American princess projecting her elegance abroad wasn’t that different, and besides, there was probably more money in it now anyway. The Trumps may have kneecapped the American republic and its reputation abroad, but they have somehow managed along the way to achieve an even more improbable-seeming goal: to become royalty, bending the whole image of a nation in their likeness and forcing their way onto the world stage.

Of course, even royalty has to live somewhere, and Ivanka’s friends in New York are fewer and fewer. She breaks bread with New York’s groovy tech Jews, like WeWork’s Adam Neumann, and old people, like Stephen Schwarzman; among the Hollywood yachting set, David Geffen still accepts her. After she leaves D.C., her life could be about swanning around with these few folks, Kim and Kanye, and the Saudis — managing, say, a $100 billion real-estate portfolio for Mohammed bin Salman. Or, like most people when they have lost something they really wanted, she may start a scrappy climb back to respectability. The Kennedy School will take her in a hot minute; maybe her course will be called “Ethics and Decision-Making.” Memories are short, and money talks. She’ll surely get a sinecure somewhere if she wants it, whether it’s her money or someone else’s. “If Ivanka and Jared get the Saudis to donate $50 million to the Met, they’ll put Jared on the board,” says society arbiter Bob Colacello.

But friends seem to think Ivanka won’t come home to New York after Washington — she’s too thin-skinned for that, too likely to be hurt by slights. And she probably wouldn’t want to. She could live in Israel, though that would likely feel like small potatoes, but the clearest move for her is probably Florida, where she could run as a Republican if she wanted to take political office, a snowbird making trips up to Manhattan for the Met Ball and other events. She’d be surrounded by her family and friends in the glamour of Palm Beach, nary an underprivileged person in sight.

Some of these choices, they say, will be determined by just how real the threat of indictments seems — it might push her permanently abroad. And there’s the question of what will happen when Donald passes away. The tragedy of Ivanka, friends say, is her inability to resolve her relationship with her father, and once the relationship is gone, an entirely new person may emerge. “Ivanka never got to an independent adult sense of consciousness,” one says, “where she’s separate from him and ‘I don’t need it.’ It has always been ‘I need it.’ ” To change this state of things would be radical. “All it would take is Donald going to Ivanka and saying, ‘Whatever you do, I admire you and I love you.’ Except he would never come to her saying that. And she would have to believe him.”

Introducing Tabloid

A ten-part narrative podcast series, Tabloid, produced by New York and hosted by Vanessa Grigoriadis, premieres today on Luminary. New York subscribers are eligible for a free three-month Luminary Premium trial. (Existing subscribers will be emailed a link for access. Not yet subscribed to New YorkSign up here.)

*This article appears in the August 5, 2019, issue of New York Magazine. Subscribe Now!

Ivanka’s Eternal Ambitions