One of the greatest enigmas of 2016, explained.

By Hannah Seligson

September 07, 2016

Not long after her parents’ very public, very mortifying divorce, an adolescent Ivanka Trump sat with her father in the back of his private plane, waiting to leave New York for Palm Beach. The doors were closed and the engines were on, but they were still missing Marla Maples. Donald’s second wife—the woman he had left Ivanka’s mother for—was late. She was always late. This drove Donald crazy.

They were just about to take off when Ivanka spotted a distressed Marla rushing toward the plane. Ivanka tapped Donald to alert him to the figure on the tarmac below. Maybe, she thought, he could tell the pilot to cut the engines. But Donald merely raised his hands. Pretty soon his wife was just a speck on the ground.

“Come on, Dad,” Ivanka said, once they were airborne. “She’s just five minutes late.”

“No, Ivanka,” he replied. “You have to be on time.”

When she was 28 years old, Ivanka wrote about this episode in her autobiography, The Trump Card: Playing to Win in Work and Life. She saw neither cruelty nor petulance in what her father did. She saw a valuable life lesson from a man she spends the rest of the book praising as a visionary. “Of course, my father wouldn't have drawn such a firm line if Marla hadn't been chronically late,” she wrote. “That was just one time too many as far as he was concerned. And it was the last time, too, because she never missed the plane again.”

By now, this pattern should be familiar to anyone who has heard that Donald wants to make America great again. He does or says something appalling, and more often than not, Ivanka will attempt to smooth it over. On some occasions, she will tactfully explain what he really meant to say; on others, she lends credibility merely by appearing Instagram-perfect at his side, her grace in inverse proportion to his mania. More than anyone else in his inner circle, Ivanka is responsible for whatever veneer of decency the Trump operation can claim to possess. As Mike Pence said of Donald at the Republican National Convention: “You can’t fake good kids.” “She’s the daughter everyone wants,” R. Couri Hay, a publicist and longtime friend of the Trump family, told me.

Unlike her father, Ivanka measures every single word. Her public demeanor is almost unnervingly pleasant. She has a supportive husband, the real estate developer and publisher Jared Kushner, and three beautiful children. Not only does she help run the Trump Organization, but she also operates a successful business of her own. She’s a marketing genius—a split between Sheryl Sandberg and Martha Stewart—who has figured out how to use female empowerment to sell lace crop tops and floral printed bags. On her website, she offers career advice to women, along with recipes and fashion tips, and on her highly trafficked social media channels, she favors aspirational quotes like “begin every day with purpose” and “prove smart is sexy.” Her father thinks she should be on the $10 bill, or in his cabinet.

And for most of the campaign—through Donald’s attacks on “rapist” Mexican immigrants and a “biased” Mexican judge (Gonzalo Curiel), through his mockery of a journalist (Serge Kovaleski) with a physical disability and a cable TV host (Megyn Kelly) with “blood coming out of her whatever”—Ivanka’s reputation has remained intact. While it helps that Ivanka, a registered Independent, mostly grants interviews to morning shows and lifestyle publications like Harper’s Bazaar and Town & Country, even the more adversarial press has been kind, regularly characterizing her as “savvy,” “poised” and “intelligent.” “Donald Trump Isn’t Even the Best Presidential Candidate in His Family,” read a headline in The Washington Post this spring.

But since the RNC, there have been signs that even Ivanka’s fiercely guarded personal brand is beginning to suffer. A poll published in Cosmopolitan last month found that only 28 percent of women aged 18 to 34 hold a favorable view of her. An article on Ivanka’s website about “how to make it as an unpaid intern,” which probably would’ve gone unnoticed a year ago, was savaged for being offensively out of touch. More and more, people are growing suspicious of her motives—whether it’s about her $500 donation to Pam Bondi, the attorney general of Florida, around the time complaints against Trump University were being reviewed by the state, or her claim that Donald is “absolutely not a sexist,” in part, because he employs her. In late July, The New Yorker said that Ivanka has learned to deploy “her charm as a kind of weaponized graciousness.” A couple of weeks later, a Vanity Fair headline proclaimed that “Ivanka Has Her Own ‘Woman Problem’ now.”

Her central role within the campaign also seems increasingly hard to reconcile with the presence of accused serial sexual harasser Roger Ailes, who is helping Donald with debate preparation, and new campaign manager Steve Bannon, whose ex-wife accused him in court of saying he didn’t want his girls going to school with Jews. (Ivanka converted to Judaism when she married; a spokesman for Bannon has denied that he ever made the comment.) As a former classmate of Ivanka’s recently asked me, “Is Ivanka and Jared’s complicity worse than Donald’s acting out because they have enough sense of what’s normal and decent?”

Ivanka's true feelings about the race and her father have become one of the great mysteries of this election. And while those feelings are the subject of increasingly intense discussion, very few people who know her are willing to go on the record, with many citing fears of legal retribution or social pain. Still, over the last three months, I’ve spoken with dozens of people, a mix of family friends, former schoolmates, business associates, political professionals and members of her social circle who are more than just passing acquaintances. The woman these sources described, mostly under the cover of anonymity, is an Ivanka who has never been seen in public, someone who is altogether more complex than the polished televised version—and a lot more apt to stomach the worst of her father’s transgressions.

All photos/Getty

By most accounts, Ivanka’s childhood wasn’t an unhappy one, just turbulent and isolating. Her earliest years were filled with maids and cooks and bodyguards. There were regular charity events and gallery openings to attend; paparazzi flashes were never far away.

Her mother Ivana worked a lot. She managed the Trump Castle Hotel and Casino in Atlantic City and then oversaw the renovation of the Plaza Hotel, as a sort of decorator-in-chief. But on most days, Ivana had breakfast with the kids and helped with their homework after school, said R. Couri Hay.

Donald, on the other hand, was more of a spectral presence around the house. This July, Tony Schwartz, the ghostwriter who worked on The Art of the Deal, tweeted that in the year and a half he spent shadowing Donald, “I never once saw Ivanka Trump in his office and I never heard him once mention her name.” Christina Lewis Halpern, a former staff writer for the Wall Street Journal who now runs a nonprofit called All Star Code that fosters entrepreneurial talent in young men of color, formed a similar impression when she spoke with Donald for an unpublished profile of Ivanka around the time Trump Card came out. “I remember asking him what Ivanka’s favorite food was,” she said. “He told me, ‘She likes lots of foods.’ What parent doesn’t know what their kid’s favorite food is? I remembered from spending time with Ivanka that her favorite food was pasta. I found this to be revealing about the kind of dynamic they have.”

In true Ivanka fashion, she tried to put a positive spin on her parents’ busy schedules. “They were always available to me and my brothers,” she wrote in her book. “Maybe not in the most typical ways, but in what ways they could be.” She said she appreciated how her father found time to teach her business lessons and how her mom taught her proper etiquette, almost as if she were a student at a European finishing school. Ivana insisted that her daughter greet every single guest at the cocktail parties she and Donald hosted in their Trump Tower apartment. "I learned to keep everyone's name straight and to remember little snippets of our past conversations and layer them onto our current ones,” Ivanka wrote. “I learned to be a good and gracious host, collecting people's coats and taking their drink orders.”

Ivana and Donald with the kids in happier times
Ivana and Donald with the kids in happier times. NORMAN PARKINSON ARCHIVE/GETTY

Around the time of her 9th birthday, her parents’ marriage started to disintegrate. Every detail of their divorce got blasted in the tabloids. Before Ivanka had even met the woman who would become her stepmother, she read in The New York Post that her father had given Marla Maples “the best sex [she] ever had.” There were also front-page stories about her parents’ prenuptial agreement and the exact moment that her mother decided to visit a psychiatrist.

The press coverage grew so fevered that the headmistress of Ivanka’s elementary school told students at a weekly assembly to protect her as best as they could, recalls someone who was there. Photographers started lurking outside the Chapin School, and Vanity Fair reported that Ivanka was seen crying on campus. Ultimately, the attention got to be too much, and Ivana airlifted Ivanka and her two brothers out of Manhattan. For three months, the children lived at the Trump family estate in Palm Beach, where tutors made sure they stayed up on their schoolwork, according to New York magazine.

At around the same time, one of Ivanka’s nannies died. "She'd been like a second mother to me, my closest confidant, and now it felt as if I needed her warmth and wisdom all the more," Ivanka wrote in Trump Card. There are few passages about her parents that are quite so loving.

Somehow, Ivanka emerged from this tumultuous period not as a sullen, rebellious teenager, but as the most responsible member of her family. As Hay told me, “Because she is used to being watched, she doesn’t do or say the wrong things.” At a photo shoot for a teen magazine in 1995, a couple of years after the tabloids moved on to other, non-Trumpian targets, some of her girlfriends from summer camp asked her about a boy she had been seen with. “They kept trying to get it out of her whether she had kissed him and she wouldn’t say anything,” recalls the manicurist hired for the photo shoot. Finally, 14-year-old Ivanka had had enough. She turned to the girls and said, as calmly as she could, “I don’t discuss those things in public.”

Ivanka was starting to build a strong sense of obligation toward the Trump name. In her book, she told the story of the day in high school she went to get her belly button pierced. Right before it was about to happen, her father called—just a coincidence, she says—and when she hung up, she decided to leave the parlor. Piercing her belly button, she felt, wouldn’t reflect well on her parents and everything they had built. “[I had] to preserve and protect the family name and reputation,” she concluded, “which, after all, were now my name and reputation, too.”

All photos/Getty

Earlier this summer, a friend of Jared and Ivanka's made an interesting point about the dates of some of Donald’s worst tweets of the campaign. Notice how they came while the couple was off the grid observing the Sabbath or another Jewish holiday, he told me.

On the day of the Orlando nightclub massacre, while Ivanka would be celebrating Shavuot, the anniversary of the day Jews received the Torah from God, her father badly undermined his argument that he would be a responsible leader during a crisis by tweeting, “Appreciate the congrats for being right on Islamic terrorism.” A few weeks later, on the morning of Saturday, July 2, he tweeted the now-famous six-pointed star atop an image that also included Hillary Clinton, a pile of cash and the words “most corrupt candidate ever.” Several Sabbaths after that, Trump retweeted another meme (tangentially related to a character named Pepe the Frog) that tickled the white supremacists who support his campaign. And a few more Sabbaths after that, he used the horrific gun death of Dwyane Wade’s cousin to boast that black Americans will “VOTE TRUMP!”

“It could be a big problem if the people who make our president not crazy aren’t available one day a week,” this friend told me.

Their father-daughter dynamic—certainly sui generis in modern American politics—has elements of a role reversal. Ivanka acts like the parent with her inexhaustible patience for cleaning up messes, while Donald acts like a rebellious child constantly testing the limits of how far he can go. "If we could clone Ivanka and have one at the RNC, one at the headquarters and one traveling with him, we'd be much further along than we are today,” said Matt Mackowiak, a Texas-based Republican consultant.

“She is always trying to calm him down and say, ‘I don’t know if this is good for business,’” a close associate of Donald’s told me. In 2012, when Donald was beginning to question whether President Obama was really an American citizen, Ivanka asked him to stop, this source said. As she put it to her father, it was a bad idea to attack the president politically at a time when the Trump Organization was seeking permission from the federal government to develop the landmarked Old Post Office in Washington, D.C. (Donald kept shouting about birth certificates anyway.)

Even if she’s not always successful, people around the Trump operation know she’s their best shot at preventing him from going off on some irreversible tangent. Also during the the birther controversy, Donald was scheduled to appear on the “Today” show, something he did often as one of NBC’s biggest stars. But on this occasion, the “Today” producers wanted him to discuss politics in addition to “The Apprentice.” Donald’s showrunners “suddenly told us that Ivanka would be joining him,” one “Today” producer recalled. The implication was that if Ivanka simply sat next to him on camera, she would help to dial him back.

“She is up there talking about women in the workplace while the crowd is basically chanting ‘lock up the bitch,’” a classmate remarked.

“Here's an early example of Ivanka being used to keep her dad from saying inappropriate things about politics and stay on message,” the producer said.

With Donald Trump, it’s always about Donald Trump. “He has never had anyone confront him about anything in his life,” said Nikki Haskell, a former talk show host who has known Donald for decades and is volunteering for his campaign. “That’s why he went off on Megyn Kelly. It happens.” Jared Kushner, who has assumed a powerful role within the campaign and has been married to Ivanka for almost seven years, is also deferential to his father-in-law, addressing him as “Mr. Trump.” Why? “Because that’s what Donald wants,” according to a Trump adviser. (A representative for Kushner Companies rejects this characterization of Jared's relationship with Donald.) The same Trump advisor told me that even though Ivanka is widely known to be his favorite child, “she is extremely scared of her father, like everyone else. She knows you can’t push him. She knows once he goes off on these things, he won’t back down.”

Someone who has spent time with Ivanka and Donald individually observed that “Ivanka has been shaped by having a narcissistic parent and always having to be attuned to Donald’s emotional state.” Some psychologists believe that if a child grows up feeling as though it’s difficult to receive the love and attention of an egocentric parent, one unconscious response can be learning to prioritize a parent’s needs over one’s own. This behavior is described as “pathological accommodation,” a term coined by the late psychiatrist Dr. Bernard Brandchaft. Brandchaft suggested that this dynamic often leads to a loss of freedom, as the child—even into adulthood—is faced with a terrible choice: either provide what you think your parent wants, or risk conflict or abandonment. Or, in Donald’s world: risk being left on the tarmac.

It’s clear which of these two paths Ivanka has chosen for herself. In Trump Card, Ivanka wrote about how deeply she internalized her father’s lesson about punctuality after the tarmac incident. As proof, she recounted the story of her first day working at a real estate company many years later. She cut short a trip to the Hamptons so that she could practice her commute over the weekend, and woke up from an anxiety dream at dawn. She arrived at the office two hours before anyone else and sat alone in the hallway the whole time, waiting for a coworker to unlock the front door.

Ivanka and Donald at the groundbreaking
“She is always trying to calm him down and say, ‘I don’t know if this is good for business,’” a close associate of Donald’s said. GETTY

Obsessive punctuality is just one of many traits she has absorbed from her father. When Lewis Halpern was reporting on Ivanka in 2009, she called the University of Pennsylvania's registrar’s office to fact-check the claim on the back of Ivanka’s book (since repeated by many media outlets and also on the paperback released a year later) that she graduated summa cum laude. It’s a distinction that requires a 3.8 cumulative grade point average.

Lewis Halpern said that an employee at the registrar's office told her that Ivanka had graduated cum laude, two notches below summa, with a 3.4 grade point average. This employee appears to have overlooked two university protocols: releasing grade point averages and having the registrar's office confirm information to a journalist. (“I talked the person into it,” Lewis Halpern told me.)

When presented with this information last week, Ivanka’s team acknowledged the error and noted that other bios of hers (including on the Trump Organization website) reflect her actual degree distinction. “Any instance of confusion surrounding the specific level of honors she earned will certainly be clarified,” said Abigail Klem, her chief brand officer. This exaggeration of her academic record brings Ivanka into similar territory as other members of the Trump family. For decades now, Donald has allowed the media to report that he graduated number one in his class from the Wharton School, although there’s plenty of evidence indicating otherwise. And Melania Trump’s website (since taken down) claimed that she graduated with a college degree that she hasn’t been able to prove exists.

Several people who know Ivanka well told me that she holds herself in high regard. She writes unironically about how proud she was to have taken the subway to Brooklyn in her twenties—on a holiday schedule, no less. She also applauds herself in her book for not turning out like a lot of affluent peers who “tapped their toes and tapped their kegs and tapped their parents' patience and best intentions waiting for some far-off day when they might gain control of their pot of gold.”

And she has reason to be proud. As the Executive Vice President of Development and Acquisitions at the Trump Organization, she oversees dozens of big-money projects. She has negotiated some prime deals, like the ones for the Old Post Office building in Washington and the Doral Hotel & Spa in Miami. (She traveled to Florida mere days after giving birth to her first child to secure that sale.) At the same time, she has built an eponymous clothing and jewelry line that is sold by major department stores. Her next book, due in the spring, will almost certainly join her first on the bestseller list. She’s not yet 35.

Like her father, though, she has a tendency to self-mythologize. Donald likes to talk about himself as a self-made man, a scrappy business genius who left the squalor of Queens to conquer Manhattan. (Never mind that his father gave him, at the very least, $1 million in inheritance and a Rolodex of connections that was probably worth even more.) Similarly, around the time Ivanka was doling out business advice in her first book, Lewis Halpern made a reporting note about how tone deaf Ivanka could be when talking about her quick professional ascent. “In the real world, no one gets hired as a vice president in a multinational real-estate firm at the age of 24,” Lewis Halpern mused.

An entrepreneur from whom Ivanka once sought business advice told me that she asked smart questions. He respected that she was trying to make a name for herself. But it wasn’t lost on him that Ivanka’s own company was headquartered “in Trump Tower, using Trump's resources.

Donald’s feeling was: Why should my daughter have to convert to marry Jared? He should have to convert to marry her.

She was not going out and raising money and doing it alone.” And Ivanka may also have adopted some of her father’s borderline business practices. The Trump Organization and its offshoots have a long history of paying its contractors late, insufficiently or not at all. Over the last 30 years, according to an analysis done by USA Today, Donald has been involved in around 3,500 lawsuits, many of which concern his tendency not to pay people for the work they’ve done. When asked about this record this June, both Donald and Ivanka “shrugged off the lawsuits and others claims of non-payment,” according to USA Today. The newspaper summed up their response like so: “If a company or worker [Donald] hires isn’t paid fully … it’s because the Trump Organization was unhappy with the work.”

Ivanka seems to have made use of this approach with one of her own brands, Ivanka Trump Fine Jewelry. Much like the Kardashians (and her father), Ivanka is in the licensing business. That means she sells her name to manufacturers who then put it on clothes, shoes, bags and the like.

With Ivanka Trump Fine Jewelry, her first major entrepreneurial endeavor outside of the Trump Organization, she sees herself as a principal. In her book, Ivanka recounted being involved in many of the small, early details at the company, like picking out the color scheme for the brand or the exact type of packaging for the jewelry. According to a lawsuit filed in the New York Supreme Court, a company her brand partnered with, Madison Avenue Diamonds, currently owes a jewelry manufacturer named KGK $2.4 million, plus interest.

The problems started in February 2010, when a moonstone from the necklace Ivanka was wearing—a necklace from her personal collection—fell off during what she would later call “a very important meeting.” “I am embarrassed to think that we are selling pieces with such flagrant disregard to quality concern,” Ivanka wrote in an email to two executives at her jewelry line. This triggered Madison Avenue Diamonds to look more closely at the inventory overall. The company said it found that a particular part of the line, the white agate, was substandard and should be recalled. KGK replaced the defective inventory, but Madison Avenue Diamonds still decided to sever ties. It also failed to make good on its seven-figure invoice.

The issue of nonpayment was ostensibly resolved in June 2012, when KGK and Madison Avenue Diamonds entered into a settlement agreement for $3 million. KGK agreed to return computer files of the jewelry designs within 45 days. Madison Avenue Diamonds made its first payment of $625,000 to KGK. Everything seemed like it was going just fine, until there was an issue with the computer files. Madison said it couldn’t open them, and by the time KGK sent them in a new format, it was one day past the 45-day deadline. Madison claimed breach of contract and refused to pay a penny more. So, KGK sued.

Last August, a New York Supreme Court judge ruled in KGK’s favor, saying that the computer file incident didn’t void the original settlement. Madison Avenue Diamonds has appealed the ruling and will be heard in court later this month. Abigail Klem, Ivanka's chief brand officer, has also denied any impropriety on her boss's part: “This litigation involves the actions of a third party licensee and all financial obligations to suppliers rest with them.” Still, four years after the original settlement, KGK hasn’t been paid the bulk of what it is owed.

This summer, Pushpendra Khicha, the chief financial officer of KGK, told me that he had never heard of an issue like this in the company’s 110-year history. Madison Avenue Diamond’s behavior "is completely non-ethical,” he said. “I would hold Ivanka, who was in the loop for many of the business dealings, responsible because ultimately it's her licensing company and she has to make sure it runs on a proper code of conduct. We only came into the business because of her name.”

When I told this story to someone who knows Ivanka in a professional context, he told me he wasn’t surprised: “She’s been trained in the Donald School of Business.”

ABOVE/INSTAGRAM. REMAINING PHOTOS/GETTY.

During the Republican National Convention, NBC’s Savannah Guthrie asked Ivanka about the behavior of certain delegates on the floor—particularly those who were hurling crass language at Hillary Clinton. “Sometimes you hear chants like ‘lock her up’ or ‘guilty,’” Guthrie noted. “Are you comfortable with all that?”

Ivanka smiled widely at Guthrie and replied, “It is certainly exciting. And it is a major production.”

Someone who speaks to Ivanka often articulated one explanation for these sort of cheerful deflections: “She loves her father and she is going to be aligned with him,” he told me. “What is she supposed to do? Disavow everything he says? That’s an unrealistic standard to apply to the child of any political candidate.”

In fact, Ivanka has acted against her father’s wishes on only a handful of occasions. One of them, a few sources told me, came when she decided to convert to Judaism. The Trumps are nominally Presbyterian, but have never been particularly religious. Still, Donald didn’t like the idea of Ivanka switching faiths, according to one of his close associates. The power dynamic made him uncomfortable. His feeling, the source said, was: Why should my daughter have to convert to marry Jared? He should have to convert to marry her.

The social mores of Ivanka’s world—Upper East Side, wealthy and white—also discourage airing familial or personal gripes in public. Many of the people I contacted within her social set expressed concerns about speaking ill of one of their own, especially someone they might need a favor from down the line or run into at a charity event. “Because of their cultural capital here in New York City, Jared and Ivanka inspire a certain deference, even among the privileged Upper East Siders who would not vote for Trump and likely find many of his views offensive,” said Wednesday Martin, author of Primates of Park Avenue.

Ivanka’s Instagram @ivankatrump
Two recent Instagrams from Ivanka that got about 50,000 likes. (Left, clockwise) Jared Kushner, Ivanka, Theodore Kushner, Arabelle Kushner and Joseph Kushner. (Right) Ivanka with baby Theodore at a Harper’s Bazaar shoot.

One of the few people who would go on the record, Lewis Halpern, told me that race played a large role in her decision. Her late father Reginald Lewis was the country’s richest black man in the ’80s, and she had a similar upbringing to Ivanka on the Upper East Side. “Mine and my family’s work is about economic and social justice for African- Americans and other historically oppressed people,” she said. “Donald Trump and now Ivanka, as his surrogate, are building a movement that fights against everything that I believe in, everything that I was raised to believe is true about America.”

It’s also unlikely that Ivanka would hear many qualms about Donald’s tactics from her husband. According to news reports, Jared is thrilled about the prospect of making it to the White House or perhaps starting a media company with Donald after the election is over. He also seems to be unfazed by his father-in-law’s racially insensitive positions. Esquire reported that he told some Jewish friends who disliked Donald’s anti-Muslim rhetoric that they “don’t understand what America is or what American people think.” Somebody who has spent significant time with Ivanka and Jared said they genuinely seem to love each other and have a strong marriage. But he also observed how insular their world can be. Their birthday parties, he said, are assemblages of high-society and power types like Hugh Jackman and Eric Schmidt, not of close friends. Another person who went to Jared’s 35th birthday party at the Gramercy Park Hotel told Esquire that the median age of the attendees was close to 70.

I asked someone else who has known both Ivanka and Jared for years why they had thrown their lot in with Donald so whole-heartedly. "Power, power, power, power,” he speculated. “Jared's got plenty of money, but the only way he can separate himself from his family is power. They’re a great match because that's also what Ivanka is after.”

Ivanka
Ivanka will likely lead the Trump Organization after Donald. GETTY

[UPDATE: This piece now includes a comment from Jared Kushner's representative regarding Jared's relationship with Donald Trump.]

Credits

Story - Hannah Seligson
Hannah is a New York City-based journalist. Her work has appeared in The New York Times, The Wall Street Journal and The Atlantic.
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Sandra is the creative director of Highline.
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