Her experience was completely different when she visited Georgetown, where she knew a few friends from Chapin, Choate, and the city more generally. The friends, who were a couple of years older, loved it there, and they offered to let her come visit for a weekend after her less-than-appealing few days with her brother at Penn. She had a much better time there. She loved Washington, too, since it was still close enough to New York. Ultimately she decided that was the school for her, and it was. She started dating Greg Hersch, a city boy who went to Buckley and Horace Mann before heading down to Georgetown. He had an apartment off campus, and the two of them got a dog, a yellow lab named Tyler who slept like a little human, all stretched out on his back. Hersch and Ivanka’s older friends started to graduate while she was still an underclassman, and she realized she had done little to make friends her own age. She decided to transfer, and, at her father’s urging, turned her sights back to Penn. She wanted to go into business anyway, not politics; Wharton wouldn’t be so bad.
Unsurprisingly, the rumors continued after high school, all the way through college, and after she moved back to New York postgraduation. By that point, they were less about little parties and admissions scandals than Ivanka’s dating life and alleged dalliances with cocaine. “It was New York City, she was doing modeling or did modeling and hanging out with a very rich, very social crew,” recalls one friend who says he “partook” with her. “The idea is not totally revolutionary.” Ivanka has vehemently denied ever doing cocaine, but has said she was at parties where people around her were doing it.
Those rumors did not stop once she met Jared, even after they were married, and even if the idea was not totally revolutionary. They were palling around with famous, well-heeled friends, and people gossip about celebrities hanging out with one another, doing things that they would not necessarily want splashed across headlines. There is a bit of deliciousness in hearing about stars behaving just like us, even if that behavior is mundane. It is a truth so unanimous that even Us Weekly devotes pages of each issue to the subject, showing celebrities hoisting their groceries into the trunks of their cars or spilling lunch on their sweaters. The delight comes not necessarily from salaciousness, though that does not hurt, but from the idea that it is both a joy and somewhat of a relief to see celebrities who seem perfect get knocked down a peg to our level.
Natalie Portman’s wedding to the dancer and choreographer Benjamin Millepied late in the summer of 2012 is the perfect example. It had all the trappings of a Hollywood fairy tale: an award-winning actress met the love of her life while he choreographed her as a twisted ballerina in Black Swan, a role for which she nabbed an Oscar. He proposed, and then the couple had a baby boy, and later they invited their closest family members and friends to a weekend at a private home off the Pacific Coast Highway in California. Diane Sawyer and Mike Nichols were on hand, as were Macaulay Culkin and Ivanka and Jared. Ivanka and Culkin had known each other for years. As eleven-year-olds, the two went on a kiddie date. Culkin was filming Home Alone II at the Plaza Hotel in New York for about a month and a half, and at the time, Donald owned the joint. Ivanka turned up in a red dress and roamed the halls, taking photos and dipping into the shops set up in the hotel. As a token, Culkin gave her a signed VHS tape of his classic Home Alone. More recently, Jared and Portman had gone to Harvard together, and she came to their Bedminster wedding as a guest. There no shortage of gossip for their Harvard friends to talk about when it came to the wedding years later. But what their pals talk about years later, particularly when it comes to Jared and Ivanka’s presence that evening, is the fact that she smoked weed with the rest of the young people in that Harvard–meets–New York crew. A cause for celebration, and fuel for the rumor mill, indeed.
The other sort of chatter around Ivanka had less to do with her and more to do with her father. Parents at both schools famously talked about how cheap he was. At Chapin, many parents were generous with donations—time, wine, hors d’oeuvres—to the school’s annual book sale. People recall Donald balking at the suggestion. “I already pay enough tuition for this place. I’m not giving more,” he said. Of course, there are murmurs on the Upper East Side that Donald didn’t even make good on his tuition for all the years Ivanka went there, and that she left with an outstanding balance, though there is no public record that this is so. Some Choate classmates remembered the same. Carl Icahn gave a tremendous amount to the school—a science center, a scholar’s program, buildings bearing his name. When the development center called recent graduates in her class, some would joke that Trump had really done nothing.
Funnily enough, Ivanka was awarded a few superlatives in the Choate yearbook during her senior year on campus. One of them was Most Likely to Succeed, the universal common calling card every Type A overachiever brags about for decades to come, and certainly the superlative that sounds most Trumpian in its braggadocio. Classmates now say she also took Most Likely to Donate a Million Dollars to Choate—which, given the family history, now and then made classmates chuckle.
There was also talk among Ivanka’s friends that her heralded performance in Born Rich was more than a disciplined message and good breeding. At the time, Ivanka was dating James “Bingo” Gubelmann, a square-jawed, raven-haired socialite whose family fell on the same New York–Palm Beach axis, and who happened to be the film’s producer. After seeing the film, her fellow castmates were less than subtle in suggesting that at least part of her positive treatment in the film had to do with the fact that she was influential in the editing process.
While he may have spared her in the film, Gubelmann was part of one of Ivanka’s most public breaks from the perfect image she crafted. In the summer of 2004, she stormed out of the Stephen Talkhouse, an East End institution where sweaty, overserved house-sharers in button-downs come to hear cover bands and do bumps in the bathroom off Route 27 in Amagansett, on Long Island. She had apparently gotten into it with Gubbelmann inside, and locals saw her dash across the street and tuck inside a nearby Mobil station, where Gubelmann chased after her. They exchanged words, and she unceremoniously slapped him across the face before they made amends and went back into the bar, where they stayed until about 2:30 in the morning.
The reality of Ivanka’s modeling career was slightly different, too. Donald wanted it for her, bad, to the point where he suggested to friends that breast implants might help her along. One friend recalled getting a frantic call from Maryanne Trump, Donald’s sister, urging him to talk Donald out of letting her get plastic surgery that young. “It’ll ruin her,” she said into the phone. When his friend confronted him about it, he denied that she was getting implants. At the end of the call, he asked, “Why not, though?”
On shoots, she was abidingly well-mannered and punctual and grateful for the opportunities. But when a photographer asked her, at sixteen, to pose using a vacuum cleaner, she had no idea how to use it. On another shoot for a Saks Fifth Avenue catalog, with about forty other models on set at Chelsea Pier 59 on the Hudson River, famed photographer Patrick DeMarchelier had to reverse course on his vision. DeMarchelier had wanted a shot of the men without shirts and the women without pants. Ivanka, however, wasn’t wearing any underwear—a fact she had to reveal to handlers on the set.
Chapter 7
“Bashert”
“It’s bashert.” “They’re bashert.” “Bashert.” Their friends and colleagues and associates separately repeated the same Hebrew word when asked why Ivanka and Jared Kushner settle into one another. The word roughly translates into something being preordained, fated, inevitable, and in the case of a romantic match, a soul mate. And it makes sense that the word came up as often as it did when describing Javanka: of course this match was inevitable, fated, and preordained, particularly for two people as single-mindedly striving and media-savvy.
In some ways, all matches between especially moneyed young men and women are inevitable—good matches, anyway. There are, after all, only so many people who swim in this silver spoon of a dating p
ool, within this hyperspecific socioeconomic bracket, appropriate age range, metropolitan area, and post–Ivy League social set and career choices. It’s a tried-and-true real-world algorithm that rarely produces happy, lasting true love, but so often creates a true arrangement. For many of these people, whose lives revolve around closing deals, and marriage—a first one, at least—is indistinguishable from the rest. On its face, Javanka’s relationship was the gold standard of this sort of deal. Both are heirs to impressive real estate thrones, though, by the numbers, his far more than hers. They are the same age; both are tall and dimpled, Ivy League–educated, and work-obsessed. They are blindly loyal to their families and hell-bent on expanding their empires.
That’s just the crunchy shell. Crack it slightly, and you’ll see that their gooey innards have been pulverized exactly the same way, too. Both fell victim to their father’s bad, selfish behaviors. Donald publicly cheated on Ivanka’s mother and, in the aftermath, played their divorce out in the press. Jared’s father, Charles Kushner, was convicted of eighteen counts of tax evasion, witness tampering, and illegal campaign donations and sentenced to two years in prison when Jared was twenty-four. Both Ivanka and Jared had to pick up the pieces and cover for their fathers. Jared took over the family business while his father was in federal prison, decades before most real estate scions would get to make even one major deal without holding Daddy’s hand. Ever since she was a teenager, doing press for her modeling career, Ivanka had gone on public offensive for her dad and his businesses, from defending his remarks on The View about how he would date her had she not been his daughter to stumping about his respect for women throughout the presidential campaign—even after the Access Hollywood tape came out. Donald used his daughter as a human shield in private, too. Once, when he had just started dating Melania, he told a friend that he might get into some more public hot water. He had been fooling around in the Trump Tower triplex with model Kara Young earlier that day—leaving what he described as a mess of twisted sheets in the bedroom and towels smeared with her makeup in the bathroom, forgetting that Melania already had access to the apartment. When Melania confronted him about the foundation rubbed into the towels, he told her that Ivanka had come over that day after a modeling shoot. The makeup, he said, was hers. Just ask her.
In the summer of 2006 Jared canceled a trip he’d planned to Germany to watch the World Cup so he could make a $10 million offer to buy the New York Observer, the salmon-tinged weekly that covered the ins and outs of Manhattan movers and shakers. After years of having their name tarnished in the press, the Kushners bought back some control and an entrée into an elite world in which Jared wanted to play. Ivanka made a less fraught brand play by joining The Apprentice to help bolster her family’s properties.
Perhaps the deepest similarity, though, is their ability to compartmentalize. Both know the truth about their fathers—a blowhard philanderer on one side and a brutalizing convicted felon on the other—and have spent their lives trying to prove themselves and pledge their loyalty to those fathers anyway. Ivanka and Jared watched their dads tear apart their families and turn their backs on everyone. They vowed never to do that to each other or back to their fathers or to the family they would create together.
As much as Jared and Ivanka are the publicly polished, more tolerable versions of their parents, in private the roots show through. Those who have worked for or with both often have the same advice for others taking them on as clients or bosses: be aware of who they can turn into on a dime. “These people eat their young, so just understand that,” one former associate recalled being advised before working with the couple. “They had internships at Goldman Sachs when they were fifteen years old. That’s not a thing you and I can understand. That’s just how they were raised.”
If one upper-crust truism is that you unescapably marry your own mirror, the other is that you often marry your father. “Well, he’s a decent, caring, hardworking man,” Ivanka told an interviewer in 2006, a few years before she met Jared, when asked if she’d end up with a guy like Dad. “And since they’re all desirable traits in a human being, I probably would be drawn to someone very similar.”
In Jared, there are certainly shades of Donald, who was also raised by an impossible, ghoulish patriarch who wielded money like a string that kept his children inextricably tangled to him forever, despite his unambiguous brutality. They both grew up as outsiders looking into Manhattan—Donald from Queens, and Jared from New Jersey. Led by that special blend of inexperience and consequence that only true wannabes with Daddy’s wallet possess, they were both initially drawn to buildings that made a splash rather than ones that made good sense.
Where Donald and Jared differed was with the press. Donald relished seeing his name in print and his face on the cover of magazines—even fake ones, like the faux Time covers hung at various Trump-owned golf courses. In the days before TiVo, he’d often tell dinner companions that he would be late or have to scoot early so he could watch an interview he’d taped earlier that day (in the White House, he has what he calls a “super TiVo” so he can spend much of his day speeding through cable news coverage of his presidency). Kushner, on the other hand, is keener on controlling the industry than being covered by it. For him, it has been about glad-handing its moguls, and trying to become one of them, rather than one of their subjects.
Nowhere is this plainer than in Jared’s relationship with Rupert Murdoch. After buying the Observer, he cold-called the News Corp executive, who is fifty years his senior, and asked him to dinner. Murdoch agreed, and at Nobu in Midtown Manhattan, Jared fawned and flattered. “I want to be you,” he told Murdoch, who slurped it up, and they began talking by phone several times a week.
The two grew closer after Jared started dating Ivanka. Murdoch and his third wife, Wendi, playing billionaire versions of Cupid, intervened when the couple briefly broke up in 2008. In return, the Murdochs’ two daughters, Chloe and Grace, walked down the aisle as flower girls at the Trump-Kushner wedding in 2009. A year later Jared and Ivanka were part of a small group of attendees invited to Chloe and Grace’s baptism in the Jordan River, where Jesus himself is said to have undergone the ceremony. The guests—among them Tony Blair, Nicole Kidman and Keith Urban, Larry Page, Hugh Jackman, Queen Rania of Jordan, Kathy and Tom Freston, and Burt Sugarman—all wore white for the ceremony. Wendi, who is described as a “very reserved and quiet person” on the twelfth page of a nineteen-page spread about the events in Hello magazine, a weekly British tabloid confection, arranged the remainder of the trip, which included a tour through the ancient city of Petra, a stay in a Bedouin tent, and a dip in the Dead Sea. “Went swimming in the Dead Sea with my husband and our buoyancy was even greater than expected!” Ivanka tweeted afterward.
At home, Wendi and Ivanka grew closer. For a time, the Murdochs moved into the Trump Park Avenue building where Javanka lived while their own triplex on Fifth Avenue was undergoing renovations. With an address and taste for striving in common, the two started spending more and more time together. In the run-up to the 2008 presidential election, MySpace, which Rupert then owned, at his suggestion considered having Ivanka host a series of discussions with candidates on college campuses across the country. It didn’t pan out, but Ivanka watched the election returns come in with the couple from their screening room. Ivanka stepped out on the eve of her due date with her first child to attend the premier Snow Flower and Secret Fan, a movie Wendi produced. The two collaborated on a bracelet inspired by the film for Ivanka’s fine jewelry line—a cuff available in black resin with white diamonds or pearl resin with black diamonds, engraved with the Chinese character for friendship. They marketed it as a symbol of friendship and sisterhood, priced at $650. Wendi recommended the interior decorator for the Trump-Kushner apartment; reciprocally, after Rupert and Wendi divorced, Kushner hooked his friend up with an architect for his bachelor pad.
Wendi and Ivanka related as mothers, too. Grace and Chloe spoke Mandarin to Ivanka’s children, who, wi
th the help of their neighbors, a Chinese nanny, and tutors, began learning the language almost as early as they were taught English. Arabella Kushner’s Mandarin was a particular point of pride for Wendi, who taught the girl to speak some words in front of social audiences so readily that people sometimes mistook her for one of her own daughters. Wendi and her girls would come over for Shabbat dinner all the time, as Wendi had grown particularly fond of the challah Ivanka served. “She calls it ‘that bread,’” Ivanka told the New York Times. On one Saturday morning, Ivanka turned up at Ivana’s home with her two eldest children. Since it was Shabbat, and she couldn’t, as an observant Jew, exchange money, she needed her mother’s help. Chloe and Grace were selling cupcakes on Fifth Avenue to raise money for a new locker room at their school for a buck apiece, so she dragged her mom outside to fork over a few dollars. They ate them standing in a circle on the street. Until she moved to Washington alongside her husband and father, Ivanka was one of five trustees for a chunk of shares belonging to Chloe and Grace in 21st Century Fox and News Corps and additional interest in Murdoch companies, worth north of $2 billion. She stepped down on December 28, 2016, as she worked with lawyers to remove himself from financial interests and positions that could be perceived as a conflict of interest.
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