But he was kind, polite, handsome, and in the business, a power player with his own paper. His family, flawed as it was, was tight and worth billions of dollars. He, like her, prized familial loyalty above everything else, which, after her parent’s divorce, outweighed intelligence in terms of what she looked for in a mate. “I could never be with someone whose motives I was constantly questioning and I certainly couldn’t stand worrying about whether he’d run off with the first blonde who came along once I got my first wrinkle,” she said in an interview when she was nineteen. She saw that in the man she refers to as a “great New Jersey boy.” Her friends saw how happy he made her and how perfectly suited they were, and all encouraged her not to let him get away. She saw him volunteer to help his friend’s parents and siblings negotiate apartment leases and find office space and appreciated that he would want to stop by the seven parties she had to make an appearance at in one evening, before spending the rest of the night answering emails and waking up the next morning before dawn to work out before heading to the office. He never got frazzled like she did. “He’s unbelievably calm,” she told Redbook. “I think he’s a mutant.”
Even on the campaign, he often tried to keep people around him calm. Katrina Pierson, the Tea Party activist turned national spokesperson for the Trump campaign, remembers that Jared would find people in the office or make phone calls if the media wrote something unflattering about them. “He would go out of his way to say, ‘Don’t worry about that, just let it go,’” she remembers. “He was cognizant that people were putting everything on the line for his father-in-law, and he wanted them to know that their work was appreciated by the family and the higher-ups in the campaign.” That happened to extend to her. Pierson’s fortieth birthday fell smack in the middle of the Republican National Convention in Cleveland at the end of July 2016. “I was so bummed to have to go and be in Cleveland for it,” she said. “Nobody wants to spend their fortieth birthday at a convention in Cleveland.” She vented to Jared, who she knew was distracted by handling a hundred different things at the time. That night’s programming focused on opportunity and prosperity, under the mini theme of “Make America First Again.” The campaign had to wrangle its hodgepodge list of speakers set to take the stage that evening—Jared’s brother-in-law Eric, oil and gas baron Harold Hamm, Newt and Callista Gingrich, conservative radio goddess Laura Ingraham, senators Marco Rubio and Ted Cruz, Florida attorney general Pam Bondi, Wisconsin governor Scott Walker, retired astronaut Eileen Collins, and vice presidential nominee Mike Pence, to name the most notable. Still, when Pierson got back to her hotel room late that night, she had a whole slew of goodies set up for her. There were a dozen mini cupcakes, a mix of chocolate and vanilla, with red, white, and blue sprinkles and a campaign sticker slapped onto the plastic container holding them all. Then there was the black bag with the gold Trump Winery logo on it, stuffed with red, white, and blue tissue paper and some of the family’s finest blends. There was a Trump Pence 2016 bumper sticker, two canvas tote bags, also stuffed with the patriotic paper, one with a Trump Make America Great Again insignia, and another with little red Republican elephants printed in horizontal lines across it, both filled with Trump-branded goodies. There was a handwritten card from Jared, as well, all exclamation points and well-wishes. “Even with all the chaos and the pressure, Jared still made sure I didn’t feel like I was away from everyone on my birthday,” she said.
He was as persistent after the initial lunch with Ivanka. Not long after she sent the email to her friend saying what a good time she had—the same day they met—he sent her an email. He invited her to a party his friends were throwing downtown, and instantly she knew she would say yes. “Oh my god. Oh my god. Oh my god,” one of her best friends, someone she met at Penn and became closer with after she graduated, remembers her saying at the time after she read his message. “She was so clearly smitten with him from the second she met him. That he followed up so quickly, clearly he felt the same way.” So she took him up on the invitation, dragging this friend down to a sweeping loft in SoHo. A band was playing, his friends were hanging around, and they all left together, going out to another bar in the neighborhood so that Ivanka and Jared could keep things going as long as they could that night. “I had seen the way she interacted with other guys she liked or even other guys she dated,” the friend said, “and it was never anything like that. Things got heated and they got heated pretty quickly after that.”
Jared and Ivanka’s courtship, which began in earnest in the spring of 2007, was quite public. They were spotted stealing kisses at Bowlmor Lanes; she toured the Observer newsroom, where, once they settled into his office, they kept the door open so that prying eyes could see them together; they holidayed in St. Barth, and tipsters sent Gawker details of them flying home to JFK airport from Nice after a trip together, with Ivanka in business class and Jared reading The Observer and a Michael Chabon book in coach. They met up in baggage claim once they landed.
Jared’s family, observant Modern Orthodox Jews, wasn’t thrilled with the match. Ivanka, though hardly raised religiously aside from the nightly prayers she said with her Irish nanny, was Presbyterian. She had worn that little silver cross around her neck when she taped the interview for Born Rich, after all. Seryl, Jared’s mother, had a particularly hard time with the idea, and urged her son to cool his heels. The breakup in 2008 devastated Ivanka. Though the couple now insists to friends that they hadn’t split because of religion, Ivana Trump wrote in her recent book that her daughter told her his family would not let Jared marry her because she wasn’t Jewish.
Ivanka sobbed to a business associate on a helicopter ride to Atlantic City for a meeting at her father’s casino soon after. “I told her that I knew they were going to get back together, and that I’d bet her $100 he’d come crawling back in a few months.” (The associate never got her to pay up. She is like her father.) Many of her friends thought the breakup wouldn’t last long; they were effortless together. But she was pragmatic and compartmentalized, as she always was. She was heartbroken, yes, but she had work to get on with, and she didn’t say no when other guys asked her out on dates.
It took the highest-end, most harebrained matchmaking scheme to bring the two back together. Wendi Murdoch, then still married to Rupert Murdoch, called Jared, inviting him on their 184-foot sailing yacht, the Rosehearty, for a weekend. He was working too hard, Wendi said, and could stand a weekend at sea with them. He agreed, and arrived to find Wendi had invited Ivanka too, under the same guise. (Ivanka and Jared have paid back this billionaire matchmaking in the years since. They have set up seven couples who went on to get married. Ivanka has referred to it as her “secret talent,” though some friends have joked that it’s a way to make sure she and Jared have a built-in circle of friends who will always be, if not loyal, grateful to them.)
Ivanka agreed to convert, though she claimed that she didn’t have that far to go: “I’m a New Yorker. I’m in real estate. I’m as close to Jewish with an ‘i-s-h’ naturally as anyone can start off.” She started working with Rabbi Haskel Lookstein of the Congregation Kehillath Jeshurun, a Modern Orthodox shul on Eighty-Fifth Street, though friends of the Kushner family said they remained unconvinced. The process is long and grueling, and hers was especially tough, since Charlie made a point to involve himself in the matter. She studied the Torah, agreed to observe Shabbat with Jared’s family, and committed to learning Jewish laws and traditions. In the thick of the process, she and Jared attended the annual, and dreaded, Inner Circle dinner—a black-tie schmooze-fest at the Sheraton where New York politicos and reporters reluctantly make the rounds. An acquaintance who barely knew her at the time remembers Ivanka making small talk about how she was learning to cook. The acquaintance was, too, at the time, and asked her if she’d come across any helpful cookbooks. “Yes! I have a great one,” she shared. “It’s called Kosher Cooking.” She urged her to check it out.
“That’s the thing about Ivanka,” an associate said of
Ivanka’s ability to take something like conversion on. “She’s such a perfectionist and takes everything, and herself, very seriously. So when she says she’s converting, she will read every book and learn every recipe and start participating with his family to do all the holidays.” To her longtime friends, particularly those she cooked for or those who were Jewish, this came as a surprise. “She just could not cook. She really could not,” one remembered. “And once she was going through the conversion, she always made fun of how little we knew about the religious and traditions. I was so impressed by how much she enjoyed learning about it.” That was just the way Ivanka did things, the friend noted. Plus, she was presented with a leopard-print Swarovski-crystal-encrusted mezuzah for her troubles.
The process wrapped up when Ivanka appeared before the traditional beth din, a three-person religious panel, and had a dip in a mikvah, a ritual bath used to cleanse oneself before major milestones and life events. She chose the Hebrew name Yael, which technically means “mountain goat.” Other translations put it closer to “to ascend.” It is also the name of a biblical hero who saved the Jewish people by using her feminine charms to woo an enemy general into their tent before killing him by smashing a tentpole into his temple.
Jared proposed with a 5.22-carat cushion-cut diamond ring, set in platinum, from Ivanka’s signature jewelry line, which he helped design before the style was named after her in the Ivanka Trump Fine Jewelry collection. “I got engaged last night—truly the happiest day of my life!!!” she tweeted in July 2009. So started a whirlwind, and very public, few months of planning. She hired celebrity wedding planner Preston Bailey to coordinate the events, and Brian Marcus, whose family had shot over fifty family events over the years for the Kushners—as well as one of Donald’s weddings, and the Murdochs’, too—to do the photos. Ivana wasn’t much involved with the planning, but Ivanka told friends that her mother was a nightmare throughout, sending her a new guest list and list of requests every week.
They sent out Tiffany invitations (her “something blue”) to five hundred people for a traditional Jewish ceremony in October at her father’s 525-acre golf club in the rolling hills of Bedminster, New Jersey (her “something borrowed”). Guests found a promotional flyer for a round of golf at one of the family properties tucked inside the envelope (her “something distinctly Trump”), though Ivanka denies slipping in marketing material. She decided on a Vera Wang gown in the style of Grace Kelly (her “something old”) and turned down offers to sell the wedding photos. She wanted to do the same thing John Kennedy and Caroline Bessette had done for their wedding a decade earlier, releasing one photo after their wedding.
The couple registered for seventy-five items at Williams-Sonoma, Crate & Barrel, and Tiffany’s, though their china came from elsewhere. The items were minimal—mostly sterling and glass—and reflected what they thought would be a normal young married life, with long afternoons spent in the kitchen and meals enjoyed at home together in the evening. Guests snatched up the four $10 spatulas and a set of matching lapis cotton place mats and napkins for $4.95 and $3.95 each, respectively. Sheet pans, a rolling pin, a Bundt cake pan for $34. At Tiffany’s, they listed $175 bottle stoppers and $325 cake servers and sauce ladles and carving knives for about $100 less, and sterling silver picture frames for $200 more. The much-coveted registry mainstay, a KitchenAid stand mixer, made the list, but the most expensive item was a $1,350 footed bowl in sterling silver from Tiffany’s; they initially asked for two of these, but scaled it back to one.
The bachelorette party consisted of a blindfolded bride on a Hudson River boat ride and late-night karaoke with champagne. The day before the wedding, the weather cleared—Ivanka thought that was a good omen—and she went for a hike on the morning of the wedding. Family photos started promptly at three in the afternoon, with the ceremony an hour later.
They erected clear-sided tents in a remote area on the expansive property’s green lawn. Through them, guests could see the trees, leaves on fire at their mid-autumn peak. The auburns and yellows and reds would be a grand enough background for any couple’s exchange of vows. But the Trump-Kushners went further. For the ceremony, hundreds of gilded chairs were set up for guests like Corey Booker, Russell Crowe, Andrew Cuomo, Rudy Giuliani, Jamie Johnson, Jim McGreevey, Natalie Portman, Ed Rendell, Emmy Rossum and Adam Duritz, Barbara Walters, and Anna Wintour, between imported trees standing throughout the tent. The couple met under a thicket of greens and thousands of willowy white buds dangling to create a traditional—if ornate—chuppah. Bridesmaids Tiffany and Vanessa Trump, Don Jr.’s wife, wore dusty lavender gowns designed by Carolina Herrera; their mothers were dressed in peach. Melania, in a low-cut purple satin number, rescued Barron, the ring-bearer, when he lost his way. Chloe and Grace Murdoch sprinkled petals down the aisle as flower girls. Ivanka’s Vera Wang covered her shoulders, as is customary for Orthodox women. It still managed to show a bit of her bust, as is customary for the ladies Trump. It cascaded into layer upon layer of Chantilly and Lyon lace. Ivanka had taken a group of her closest friends to try on dresses at a few bridal ateliers and shops in the city, but settled on Vera. Her friends came along to each fitting, and to the final one she invited her bridal party and a Vogue editor to inspect every detail. After the ceremony, a friend of Ivanka’s who was gown shopping for her own wedding at Vera Wang’s atelier noticed a dress hanging on a rack called “the Esther” that was startlingly similar to her own. The friend excitedly reported the news back. “You know, Vera had asked, and asked, and asked to do my wedding dress, and I paid for the dress and everything,” Ivanka said, adding that she had been given a steep discount. The dress would be given a lot of publicity, after all, and the young Trump was never one to pass up a deal. Plus, all celebrities, whatever degree of stardom they possess, know that the more money you have, the less of it you actually have to use, anyway.
“We designed it exactly how I wanted it to look. I chose every detail with her. It was perfect,” the friend recalled her saying. “And then after the wedding, Vera went and tweaked the dress to make a cheaper version of it, a copy with some less expensive details.” The friend remembers hanging up the phone, worried that she had annoyed Ivanka about the dress all over again.
Predictably, her jewelry bore her name as well. She wore more than a quarter of a million dollars in jewelry—all of it from her own collection—including a $45,000 diamond hairpiece, a 26-carat art deco platinum and diamond estate bracelet, and 9.67-carat mixed-cut diamond cluster earrings worth $130,000, behind which her softly waved old-Hollywood hair was tucked. Jared wore a custom black tuxedo and traditional bow tie, his hair parted and swept to the left and pinned down slightly by his yarmulke.
“It was stunning. And grandiose, even by New York standards,” one guest remembered. “The only weird thing was the rabbi started talking about all the Jews suffering around the world at the start of the ceremony, which did not exactly scream romance.”
Their faith was at the center of much of the evening. In the reception tent, long chandeliers hung around the room over the all-white tables. As the room erupted into the traditional hora, this being an Orthodox wedding, the men were separate from the women. Later, the men did another traditional dance, and the women were asked to leave the dance floor, which confused a number of the New York society guests who had not been to a wedding quite so Orthodox. Nicole Kushner, Jared’s sister, took a few of Ivanka’s friends aside and explained the tradition, the roots of it, and why it was important to them. “I thought it was very kind of her to do, until she asked us to leave, and I realized she had been dispatched by the bride and groom to make sure people weren’t uncomfortable and didn’t scoot out early while the men were dancing about the tent.”
Ivanka did not flinch at any of it. “She acted as if she was a chosen one all night,” one guest remembered. “It wasn’t as if she was a Jewish American Princess, even. It was as if she’d been made the Jewish American Queen.”
The couple crowd sourc
ed their wedding song on Twitter because they had trouble coming up with one on their own, and eventually landed on David Gray’s weepy “This Year’s Love.” It’s a melancholy ballad that some guests noted was fitting for the couple. “Aren’t the words something about being hurt by someone lying and hurting and needing to feel safe before losing control?” one attendee chuckled. “It was perfect for them.” The cake was a hulking Sylvia Weinstock confection: seventy inches and thirteen layers of lisianthus, roses, peonies, lilies of the valley, and baby’s breath, crafted in sugar, encircling each tier, in whites, pinks, ivories, creams, and flesh tones.
Donald gave what guests remember as a short, sweet toast, during which he acknowledged Ivana and made a few jokes. “Be happy and enjoy your life,” he offered.
“Her parents kept mostly quiet and did not speak much,” one guest recalled. “Charlie’s toast was the one everyone talked about.” Guests recall Charlie’s toast mentioning his initial hesitation to see his son marrying someone who was not Jewish, which, he said, was so important to their family. But he saw how she treated his son, and how she devoted herself to her conversion, and how in love they were, and he came around to feeling right about it.
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