To be sure, Don Jr. still lived a life of privilege and leisure and relative ease. His father helped him buy an apartment. He gave him an executive position within a real estate company bearing his name as soon as he returned from his lost year in Aspen, with a college degree and no other work experience than his years as a dockhand in the Trump Marina and what he’d soaked in trailing his father around job sites as a kid. He did fly commercial when he traveled for business, though, unless he was flying with his father, and he almost always flew coach, though sometimes he’d snag a business seat if it wasn’t much more expensive or the travel schedule was particularly grueling. “We’re too cheap,” he told the New York Times in 2007, “and try to save money where we can. . . . I try to upgrade when I can with frequent flier miles, but that’s been getting increasingly difficult.” He went through security like the rest of the universe—something he’d avoided his childhood on his dad’s plane in private airports, where you walk right on board without so much as a wave to the guys on the tarmac. He told the Times that he’d missed a flight to Boston around the time of the interview because of a mishap with a $20 battery-operated Brookstone alarm clock he’d bought at an airport kiosk a few months earlier. He’d stowed it away in his carry-on, and sent it through the X-ray scanner before he made his way through the metal detector. The TSA agents screening his bag thought the clock looked suspicious, and despite the famous last name on his ticket, and his insistence that it was just a tiny little travel clock, they shut the security lane down and called in the state police. After a few minutes, they determined that it was in fact an alarm clock. Meanwhile, Don Jr. was being held, shoeless, in the security line, watching the minutes tick closer to his flight departure time. “I felt like an idiot,” he told the Times. The plane left without him, since the whole thing took about a half hour. But he did get to keep the alarm clock in the end. “Sometimes it pays to be a Trump,” he joked.
The Trump Tower triplex he grew up in is 33,000 square feet (though, like many things tied to Donald’s material possessions and valuations of his assets, there is some debate over its true size versus Donald’s estimation of its vastness). The first apartment he shared with his wife Vanessa was a little more than 1,500 square feet. It had two bedrooms and parquet floors, one room with sky-blue walls and one painted deep red, a zebra-print rug in the guest room. They didn’t have a housekeeper to tidy up after them, at least in the early years, in contrast to the fully staffed household in which he grew up. They filled the apartment with hand-me-down furniture—an antique canopy bed Vanessa’s mom had used for two decades, brown leather couches Don used in his bachelor pad. There were sentimental objects Ivana and Donald would never have had in their homes, too—oil paintings made by Vanessa’s Danish grandfather, the childhood teddy bear she’d kept since she was six months old, and the “Captain Pickle” doll Don had hung on to from his childhood. In the kitchen, where he spent a great deal of time, he kept an organized fly-fishing collection and a cast-iron skillet in which his grandmother Mary had cooked all the Trumps’ family meals in their Queens home. Don Jr. and Vanessa cooked at home, too. They preferred it to going out. “I learned at a young age . . . in the single digits—8 or 9 years old . . . and was into it,” he recalled of his love for cooking. He studied the chefs at Mar-a-Lago, learning how to make seafood, curries, Italian stuff that he later started whipping up for his wife. They filled their home with family photos and snapshots of their wedding and photo albums, which he said were all he’d take if the building were to go up in a blaze and they had to make a quick exit. “There wouldn’t be [a fire],” he clarified, “because this is a Trump building.” (In early April 2018, a fire on the fiftieth floor of Trump Tower broke out. There were no sprinklers, and one resident died in the blaze.) Their two little yappy Havanese puppies—Fraggle and Faluffa—had the run of the place, and around Christmastime their parents got them a little tree of their own, “because we’re idiots,” Don recalled in 2008. He was stingier when it came to presents to his siblings. “Look, I’ve been re-gifted presents that I’ve given my family,” he admitted that same year. “You know, they’re like, ‘Oh, great, thanks!’ and then you end up getting it back the next year.”
As much as Don Jr.’s confrontational affect and his decision to live a lower-key lifestyle were because of and in reaction to his father, they were also, in part, inherited from him. His father passed down other traits the connection to which are harder to deny. “I think I probably got a lot of my father’s natural security, or ego, or whatever,” Don told New York Magazine. “I can be my own person and not have to live under his shadow. I definitely look up to him in many ways—I’d like to be more like him when it comes to business—but I think I’m such a different person, it’s hard to even compare us. His work persona is kind of what he is. I have a work face, and then there’s my private life.”
Portions of Don’s private life are perhaps where he and his father align most, and women seemed to be a place in which they overlap. His sister spent years distancing herself from fellow blond New York heiress Paris Hilton, making her club-rat image a foil to the squeaky clean, hardworking image Ivanka wanted to project, but Don Jr. was far softer to Hilton. In the early 2000s Chris Wilson, a rookie Page Six reporter, turned up to a party on the roof of Playboy headquarters on Fifth Avenue. Hilton was there, in a high-low sartorial mélange of a belly shirt and a diamond choker, and as the evening progressed Don Jr. showed up as well, his standard greasy bob looking extra greasy and bob-like for the occasion. Wilson had never met Don Jr. before, though he had met his father a few times, once in Trump’s house, which he thought looked like a casino designed by Saddam Hussein. Don Jr. was wasted by the time the three of them somehow ended up sharing a cab to go home—Hilton on one side, Don Jr. on the other, Wilson as a buffer smack in the middle of them. Paris needed one, because Jr. continually arched himself over Wilson to paw at the heiress, trying to rub her exposed belly like a genie who would grant his late-night drunken wish. Paris had no interest, clinging to Wilson and radiating a not-so-subtle “help me” signal from all angles of her spray-tanned face. Somehow, the three of them managed to take a photo together, which Page Six was going to run under the caption “The Art of the Feel.” It ultimately got scrapped.
Don Jr. had more success with another model, though it took a bit of time. He’d tagged along with his father to a fashion show in 2003 in New York—not exactly his scene, but he obliged. This was a more palatable parental request for the single twenty-six-year-old, who’d settled into an executive role at his father’s company by then. It was Donald who spotted a leggy, long-haired blonde walking in the show. He approached Vanessa Haydon, a fellow Upper East Side–raised, private-school-bred girl coming into the limelight. Donald introduced himself and said he would like her to meet his son, Donald Trump Jr. Before the show began, Don and Vanessa made the uncomfortable small talk that would come from two young people being thrust together with one’s father tagging along and prying eyes all around. At intermission, Donald approached Vanessa again, as if the first conversation had never happened at all. Again he introduced himself and told her that she should meet his son, Donald Trump Jr. “Yeah, we just met,” she told him, looking toward Don Jr. as if his dad had lost his mind.
Fate—or the intensely small circle that is the twentysomething scene on the Upper East Side, depending on your subscription to romantic fantasies—brought the two back together again less than two months later, at a birthday party at Butter, a downtown restaurant-cum-club that was the place for a New York minute. They found each other and talked for what felt like most of the night before she realized who he was, that she had met him weeks earlier at the fashion show. “Wait,” she later recalled saying. “You’re the one with the retarded dad!”
The way the media wrote about Vanessa—the story they created around her—was not unlike the way they described Melania when she first started dating Donald—all sunshine, success, good breeding, and no drama. The whole
truth of both women’s pasts was initially entirely left out. Just as Melania was described as a college graduate with two degrees, who grew up with a fashion-designer mother and thrived in an impressive modeling career, Vanessa was introduced to the world by the Times and other publications as a woman who grew up in a townhouse and blossomed into a tennis star at the Dwight School, “who with her athletic build, buttery tan, blond hair and sunny smile seems like a Brian Wilson fantasy.” She joked and wore jeans and avoided social climbing and signed with the impressive Wilhelmina agency, even though her mother ran a modeling agency of her own. Vanessa Haydon, the Times wrote, was “born for the role” of becoming a newly minted Trump.
And just as it later came to light that Melania had not in fact graduated with architecture and design degrees but instead dropped out after a year, and that her mother had actually been a textile factory worker, Vanessa’s fuller past didn’t stay in the past for long. For as much as Vanessa might look like a Beach Boys muse, she may have actually been more of a Scorsese chick at her core. Haydon first came into the public consciousness in 1998, when she was spotted lip locked with Leonardo DiCaprio, who, at the time, was white hot in a post-Titanic universe, at a party in Soho. The pair dated only a few weeks, long enough for gossips to pick up on her saying how the star found dating a “down to earth” girl like her and her agents to jump on her fifteen minutes of famous flingdom by selling modeling photos of Haydon to foreign newspapers. Her romantic dalliances beyond DiCaprio captured headlines and the sharp tongues of those who knew her at Dwight, as well. For years, on and off, she dated a man who went by the name Vallantine, whom she met as a teenager. Legend had it that Vallantine, a member of the Latin Kings who lived in Astoria, was not every Upper East Side mother’s dream suitor for her aspiring model daughter. But the topic was catnip for Vanessa’s classmates and contemporaries and all of their parents who found out about the relationship. Rumors swirled about her briefly moving into his apartment, about her wearing starter jackets in yellow—a show of support for the Latin Kings color—and maybe stopping by a meeting for the Latin Queens. She visited Vallantine in Rikers once he was locked up on drugs and weapons charges, though the frequency of her prison visits was a subject of some debate. Her spokesman at the time told the New York Post, which gamely reported on all the rumors after she started dating Don Jr., that she visited Rikers only once, after she and Vallantine had already broken up, to translate for his mother, who spoke no English. Her rep also denied that she was involved with the Latin Queens or wore yellow in solidarity. “She used to be this hard-rock in leather and baggy jeans,” one teenage friend said of Haydon to New York magazine, in a story about DiCaprio. “She was a total gangster bitch.” Another friend referred to her “an ill thug.” New York also pointed out that in her high school yearbook, her classmates voted her Most Likely to Wind Up on Ricki Lake.
Don Jr. took a page out of his father’s playbook when it came to his proposal. Donald had accepted a hefty discount from Graff Diamonds on Melania’s thirteen-carat sparkler when he proposed in 2004. The jeweler, which also appeared on an episode of The Apprentice, noted an uptick in sales after it ingratiated itself with the Trumps, and Donald bragged to the press about how he’d knocked some money off the price of the rock. And so when it came time for Don Jr. to pop the question—only six months after his dad had asked his third wife to marry him—there was a jeweler willing to foot the bill, and a Trump willing to take advantage of it.
The difference, of course, was that Donald proposed with the discounted ring in private, before the couple walked the red carpet at the annual Met Gala. It was different for Don Jr. After a year and a half of dating, he took his girlfriend to New Jersey. The couple arrived at the Short Hills mall, where TV crews and paparazzi were waiting. They’d been invited by the real estate heir as part of an agreement made with the jeweler Bailey Banks & Biddle. If Don Jr. proposed in front of flashbulbs, and agreed to additional promotional appearances on behalf of the jewelry store, then the $100,000 four-carat emerald-cut diamond, set in platinum and surrounded by two smaller trapezoid diamonds and fifty-six others around the ring, would be his for free. So, in November 2004, right in the middle of the suburban Jersey mall, with television cameras rolling, Don Jr. got down on one knee and asked Vanessa to marry him. Yes, yes, yes, she said gamely for the cameras, though she would later admit that Don Jr. had proposed to her a couple months earlier in their apartment. Perhaps the Times was right when it said she was born to be a Trump.
The day after the proposal, the Post headlined its story “Trump Jr. Is the Cheapest Gazillionaire—Heirhead Proposes with Free 100G Ring,” calling it “what has to be one of the cheesiest wedding proposals on record.” Donald was not happy with the reviews. A few weeks later, he told Larry King on CNN that he “wasn’t thrilled” with the way his son went about it. “I certainly don’t like it with respect to a wedding ring,” he said, without mentioning his own most recent wedding ring discount. “I said, ‘You have a big obligation. You have a name that’s hot as a pistol. You have to be very careful with things like this.’”
When it came to the wedding, Don and Vanessa again stuck close to the model Donald and Melania set for them. They chose Mar-a-Lago, where his father and stepmother had had their reception that January, setting a date in November 2005. As they registered at Bloomingdale’s, and Barneys, and of course Tiffany, they began to quietly shop around the exclusive rights to photos and footage of their big day, just as Donald had with Getty and Melania with Vogue. Vanessa didn’t hire a wedding planner, telling OK! Magazine that she’d spent thousands of dollars on bridal magazines, as her soon-to-be stepmother had months earlier. She threw her bachelorette party in Miami, for which Ivanka flew down to join her at the it-club Mansion in South Beach. A week before the nuptials, Hurricane Rita hit Florida, knocking out Mar-a-Lago’s power for days. There was no water, either. The estate’s front lawn, where the ceremony was set to take place, was ravaged by the storm. “We were going to have to have the wedding by candlelight,” Donald told the Post. But the power came back on, as did the water, just in time for the rehearsal dinner on the Friday evening before. The couple hosted their guests for a luau, complete with a roast pig, martini bar, and a DJ Vanessa had heard at her cousin’s wedding in New Jersey. On Saturday, November 12, 370 guests gathered at Mar-a-Lago to watch the eldest Trump heir say “I do.”
The crowd was hardly the litany of celebrities who’d gathered for Donald and Melania’s ceremony earlier that year. Joan Collins, songwriter Denise Rich, and reality TV starlet Brittny Gastineau took their seats poolside, where the couple decided to move the ceremony after Rita tore up the lawn. Donald, in a tuxedo, walked down the aisle with Melania, in a champagne strapless gown flowing out from an empire waist that barely concealed her growing baby bump (Barron would be born four months later). Ivana, in a peach satin off-the-shoulder gown that showed off a diamond necklace with honking pastel stones and fell into bell sleeves covered in ornate silk flowers, left a seat between herself and her ex-husband after depositing her son at his place by the altar, underneath an arch of white and violet flowers. Her mother, Babi, in a bubble-gum-pink dress of her own, filled the spot between them. Don Jr.’s hair was nearly long enough to reach his honking silver bow tie. He slicked it back on top and tucked his locks behind his ears—a mix of California surfer boy and Rachel Green from Friends. His brother Eric, in a darker gray yet equally wide bow tie, stood by his side as, one by one, all ten of Vanessa’s bridesmaids, including Ivanka, made their way down the aisle in their silk pale orchid gowns, cut into deep V-necks. Several flower girls in fluffy white confections followed. Tiffany was not in the wedding party.
Vanessa’s mother walked her down the aisle, as her father had passed away years earlier. The bride worked with Reem Acra to design her gown—bright white and skintight and heavily beaded on its straps and bodice. For the ceremony, a veil puffed out from the bedazzled tiara she wore atop her flowing loose curls, disguising
just how low the back of her dress was cut. She carried a white bouquet filled with calla lilies and little roses, and around her neck she wore a diamond cross. The New Jersey DJ from the night earlier was also a bandleader, who’d set up a ten-piece orchestra for the ceremony and a sixteen-piece band for the reception (he charged the couple $20,000 for the evening, more than double what he typically commanded). They played a cover of Bryan Adams’s “Heaven” for the couple’s first dance inside the grand ballroom, where guests were served filet and a towering cake by Sylvia Weinstock, the same famed baker who’d created the masterpieces for Donald’s weddings; this one was covered in red and pink flowers handcrafted from sugar and fondant. Vanessa surprised Don Jr. with a groom’s cake in the shape of a fish—an outdoorsman’s delight. The groom teared up when he toasted his bride, recalling that it was his father who’d set him up in the first place. “‘That’s the kind of girl you should be with,’” he told his guests his father urged him. The guests noted among themselves that she was exactly the kind of girl Donald himself would have been with, had Melania not been in the picture at the time. Donald toasted the couple as well, as did Ivana, who joked that the couple’s future children would have to refer to her as “Glam-ma.”
Ivana did not have to wait long to get her wish. Two days after their first wedding anniversary, Don and Vanessa invited a group of their closest friends and some family to their apartment. They made another round of toasts, to celebrate not just their first year of marital bliss but also the next milestone. That spring, the couple would become parents for the first time. They shared the news publicly a night later, at a party at the 460 Degrees Gallery on Fifth Avenue at which Vanessa was feted for appearing on the cover of Hamptons Magazine, despite the fact that the couple preferred not to go to the Hamptons, especially in season (Don Jr. would sometimes go out to Montauk to fish once the rest of Manhattan had left their second homes on Long Island in the fall). Barron Trump, Don Jr.’s littlest brother, was eight months old. By that spring, he’d be his baby’s uncle. “They’ll be more like brothers—or brother and sister,” Vanessa joked to the press.
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