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Inside Ivanka and Don Jr.’s Fight to Succeed Their Father

The empire begins with a brothel. It stands, sturdy and square, at the heart of a gold-rush boomtown in northwest British Columbia, a monument to careful branding. The windows of the Arctic Restaurant have no signs offering access to prostitutes—even in a lawless Yukon outpost in 1899, decorum rules out such truth in advertising—but Friedrich Trump knows his clientele.

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Curtained-off “private boxes” line the wall opposite the bar, inside of which are beds, and women, and scales to weigh gold powder, the preferred method of payment for services rendered. Word of the restaurant’s off-menu accommodations spreads fast. “Respectable women” are advised by The Yukon Sun to avoid the place, as they are “liable to hear that which would be repugnant to their feelings.” But among lonely prospectors, the Arctic is a hit. Before long, Friedrich is boasting, with a hereditary penchant for hyperbole, that his establishment serves more than 3,000 meals a day.

It’s true that he has plenty of customers. A hundred thousand men have raced north in search of gold at the twilight of the 19th century, hypnotized by a shimmering mirage that Friedrich himself must have recognized. He was chasing a similar figment when he left his German hometown at 16, crossed the Atlantic in steerage, and disembarked on the shores of Manhattan, poor, dirty, and emanating the signature migrant’s stench—widely known then as “ship”—which would cling to him for days no matter how hard he scrubbed. He made a living for a while as a barber, but a living was not what he’d come for. So when he heard about fortunes being made in the Pacific Northwest, he gathered his savings and boarded a train.

Friedrich sees that he can get rich in the Klondike not by digging for gold but by servicing the gold rushers themselves. This is its own kind of extractive business—“mining the miners,” his biographer, Gwenda Blair, will later call it—and it requires a distinct skill set. Quiet and wiry, with a handlebar mustache, he bounces from boomtown to boomtown, conning his way onto scraps of land by pretending to find gold there. Once a claim is secured, he hustles to make as much cash as he can before the local bubble bursts and the miners move on.

A restaurant in Seattle’s red-light district. A boarding house in Monte Cristo, Washington. A trailside tent hawking horse meat and liquor to the men stampeding up Alaska’s White Pass. Each venture turns a profit, but the brothel is the one that makes him rich enough to return home to Germany and have his pick of pretty, much younger brides.

Friedrich and his wife consider staying in their native country, but he is a draft dodger—or so the government says—and his petition for residency is denied. Indignant, he takes his new family and his new money back to New York City, where he is free to pursue that shape-shifting mirage—is it starting to resemble respectability?—without the weight of a past. By the time the Spanish flu takes him at age 49, he’s amassed a modest fortune—the modern equivalent of half a million dollars—and a small portfolio of outer-borough properties. It isn’t Rockefeller money, but it’s enough, just barely, to launch a dynasty.

To keep the family afloat, Friedrich’s widow, Elizabeth, assigns each of her children a job in their fledgling real-estate business. But it’s Fred, the middle child, who has a knack for building, both houses and empires, and he takes charge shortly after high school.

Fred runs the enterprise in a clock-racing, corner-cutting scramble, selling each new house to cover construction costs for the last. He backslaps his way through Brooklyn’s political machine, cozies up to mobsters. One house in Woodhaven leads to two in Queens Village, then several more in Hollis. When the federal government starts offering loans to Depression-plagued developers, Fred is first in line—and soon he has an army of shovel-wielding workers digging 450 foundations out of the East Flatbush swampland.

As rows of mass-produced “Trump Homes” spread across Brooklyn and Queens, the papers call Fred the Henry Ford of home building. Later, when the scandals start to come out—the charges of profiteering, and fraud, and banning black tenants—the papers find other things to call him. Infamy attends each new triumph. By the 1950s, he has built thousands of houses and apartments, and become the kind of landlord Woody Guthrie writes songs about.

When the time comes to plan his own succession, Fred turns first to his eldest son and namesake. But Fred Jr. has no feel for the business—he’s soft and free-spirited, and wants to fly airplanes. Donald is the one with a taste for combat, and to him the great unconquered frontier lies across the East River. Donald sees more than money in Manhattan. He sees fame, status, entrée into elite society—things the Trumps have never had.

The market on the island is crowded and hostile, but Fred and Donald work closely to plot their invasion. Together, they cook books, fleece investors, and fool one regulator after another. Some of the scion’s schemes pay off. Others prove disastrous. But his signal achievement is forging the Donald Trump persona itself—that high-flying playboy, that self-made man, that larger-than-life titan the tabloids can’t resist. It’s a creation of both father and son, and it will do more for the family business than any casino or skyscraper.

Today a photo of Fred sits in the Oval Office, looking out on an empire much vaster and more powerful than even he could have imagined. And while the president writes his chapter in history, the next generation waits in the wings, jockeying for position, feuding over status, knowing only one of them can be the heir.

Portrait of Donald Trump and his kids
Ryan Melgar

I.

They stood shoulder to shoulder—Don Jr., Ivanka, Jared, and Eric—watching the conquest unfold on TV. Ohio was theirs. Then North Carolina and Florida, too. The vaunted midwestern “blue wall” was crumbling on live TV, as ashen-faced pundits muttered about the electoral map. The scene was surreal, and delicious.

While Don and Eric fielded congratulatory text messages, some in the room noticed Ivanka cut through the thick scrum of campaign aides and attach herself to her father’s side. “Did you hear that, Dad?” she asked whenever the TV delivered good news, expertly guarding his attention just as she had since she was a young girl.

Around midnight, the family realized they would need a victory speech. No one had bothered to write one, because Trump wasn’t supposed to win—at least not electorally. He was supposed to go down in a spectacular blaze of made-for-TV martyrdom that all of them could capitalize on. Ivanka had a book coming out. Don and Eric were working on a line of patriotically themed budget hotels. And preliminary talks were under way to launch a Trump-branded TV network that would turn disgruntled voters into viewers. Now they needed a new plan.

One by one, they retreated from the buzzing hive on the 14th floor of Trump Tower and rode the elevator up to their father’s penthouse. Steve Bannon and Stephen Miller—sleep-deprived and pulsing with adrenaline—began punching out a draft for the president-elect to read. But Ivanka took one glance over Miller’s shoulder and concluded that it wouldn’t do. (Someone who read it later summed up the tone as “We won; fuck you.”) The next act of the Trump story was beginning tonight. This was a task for family.

Gathered around the dining-room table with a coterie of aides and allies, Trump’s three oldest children took turns dictating while the speechwriter typed. The final product—a laundry list of thank yous interspersed with patriotic platitudes—was notable only for its un-Trumpian restraint. With his family lined up behind him onstage, Trump intoned, “I pledge to every citizen of our land that I will be president for all Americans.”

The speech was bland and forgettable, but hall-of-fame oratory wasn’t the goal. The remarks were a placeholder, a chance for the family to work out their next moves. “They’re undeniably adaptable,” Kellyanne Conway, a senior adviser to the president, told me of Trump’s children. “When the family business was real estate, they learned contracts and building approvals and architecture. Then it was television, and they learned that industry. Now, a decade later, they’ve turned around and learned politics.”

But this latest reinvention has set off a power struggle within the first family, one that has played out largely away from public view. The president and his children—who declined to be interviewed for this story—have labored to project an image of unity. But over the past several months, I spoke with dozens of people close to the Trumps, including friends, former employees, White House officials, and campaign aides. The succession battle they described is marked by old grievances, petty rivalries—and deceptively high stakes.

In his brief time on the political stage, Donald Trump has commandeered the national conservative movement, remade the Republican Party in his image, and used his office to confer untold value on the Trump brand. Between their business holdings and their political influence, the Trumps could remain a fixture of American life for generations. The question now dividing the president’s children is not just which one of them will get to take up the mantle when he’s gone—but how the family will attempt to shape the country in the years ahead.

For a nation founded in revolt against monarchy, the United States excels at preserving its own royalty. Once a name and fortune are made, the machinery of American power churns into gear. Wealth is passed down through trusts. Important jobs flow to unaccomplished heirs. Famous families get mythologized in the media, celebrated in the culture. The result is a ruling class dominated by dynasties—from the Rockefellers to the Roosevelts, the Mellons to the Murdochs.

Members of these clans tend to justify their privilege by claiming to uphold a tradition of patriotism and public service passed down by their forebears—a refrain that has echoed especially throughout America’s most durable political dynasty.

The Trumps like to invoke the Kennedys in their own mythmaking. The president has called Melania “our own Jackie O.” Ivanka’s husband, Jared Kushner, whose father reportedly sees himself as a “Jewish Joe Kennedy,” had a framed photo of JFK in his Manhattan office. And close Ivanka watchers have noted that her Instagram feed—filled with idyllic photos of family life against the backdrop of the White House—has a certain Camelotian quality.

But if Camelot was always a romantic facade, the Trumps have dropped the ennobling pretense. Like a fun-house-mirror version of the Kennedys, they reel across the national stage swapping the language of duty and sacrifice for that of grievance and quid pro quo. Ask not what your country can do for you, they seem to say; ask what your country can do for the Trumps.

In considering which of his children should carry on his legacy, Trump is now caught between competing visions for the future of the family—one defined by a desire for elite approval, the other by an instinct for stoking populist rage.

But Stephen Hess, a scholar who studies American political dynasties, says succession can be unpredictable in presidential families. Unlike in business, where a patriarch can simply install his chosen heir as CEO, politicians often see their best-laid plans upended by voters: Think of the Bushes anointing brainy, well-behaved Jeb, only to have George W. surprise everyone by beating him to the White House.

For Trump—a distant and domineering father who has long pitted his offspring against one another—the unsettling reality is that the choice of who will succeed him may be out of his control.

II.

The Trump children grew up surrounded by the trappings of dynasty. Their home was an eponymous skyscraper—all glass and gold and capital letters—that doubled as a symbol of their family’s power. Famous surnames can have an enveloping effect on those who carry them, flattening every outside aspiration until the family is all that matters. To young Don, Ivanka, and Eric, the whole world felt as if it could fit within Trump Tower.

From afar, their lives looked like a Richie Rich–style fantasy. They had an entire floor of the triplex penthouse to themselves, with rooms full of toys and big-screen TVs, and nannies and bodyguards attending to their whims. Michael Jackson, their neighbor, stopped by to play video games. Limousines shepherded them around the city.

But within the family their father cultivated a Darwinian dynamic. On ski trips, when they raced down the mountain, Trump would jab at his children with a pole to get ahead of them. His favorite fatherly maxim was “Don’t trust anyone”—and he liked to test his children by asking whether they trusted him. If they said yes, they were reprimanded. Sibling rivalry flourished. “We were sort of bred to be competitive,” Ivanka said in 2004. “Dad encourages it.” (Tiffany and Barron, born later to different mothers, seem to have been spared from this contest.)

For Trump’s three oldest kids, the defining drama of their childhoods came in 1990, when he left their mother for Marla Maples, moving out of the penthouse amid a tabloid feeding frenzy. Eric, then 6, was too young to fully grasp what was happening, but his siblings understood, and they reacted in different ways. Don, who was 12, lashed out at his father—“How can you say you love us?” he reportedly spat during an argument—and refused to talk to him for a year. Eight-year-old Ivanka was afraid of what she might lose in the divorce. “Does it mean I’m not going to be Ivanka Trump anymore?” she asked, tearfully.

Donald Trump with his three oldest children and his then-wife, Ivana, in 1988
Donald Trump with his three oldest children and his then-wife, Ivana, in 1988 (Norman Parkinson / Iconic Images)

In the years that followed, Don seemed to define himself in opposition to his father. Trump loved golf, so Don stayed off the links. Trump was a teetotaler, so Don drank heavily. In his college fraternity, he developed a reputation for blacking out. “He was drinking himself into a really dark place,” said one former fraternity brother, who recalled Don breaking down in tears at a party as he talked about his father. “He hated what his dad did to his mom. For a while, he didn’t even want people to know his last name.” (A spokesperson for Don said: “This is fiction.”)

Ivanka, meanwhile, worked to stay close with her father. She stopped by his office every day after the divorce, and when she was at boarding school she called home often—seeking his advice, and asking questions about the family business. Later, Ivanka would recall with pride how her dad interrupted important meetings to talk to her: “He’d always take my call.”

On June 16, 2015, Ivanka strode across a dais in the atrium of Trump Tower and beamed out at the crowd. “Welcome, everybody,” she said, a glint of amusement in her voice. “Today, I have the honor of introducing a man who needs no introduction.”

That Donald Trump had chosen Ivanka to feature so prominently at his campaign kickoff seemed natural. He’d been grooming her for years to take over the family empire. She was the golden child—beautiful, telegenic, and in possession of that most important family trait: a compulsive image-consciousness.

According to an aide who helped launch Trump’s presidential bid, Ivanka was the one child for whom he voiced concern while he was deciding whether to run. “I know they’re gonna go after me for the women,” Trump told the aide. “The problem is, they’re gonna go after Ivanka, too, for the ex-boyfriends.” His daughter’s romantic history included a succession of problematic exes—from Lance Armstrong to James “Bingo” Gubelmann, a D‑list film producer who would later be arrested on cocaine charges with Maroon 5’s bassist.

Ivanka had a brand to protect, something Trump understood. She’d been tending to her image since she was a teenager—carefully evolving the Ivanka persona from party-girl socialite to lean-in lifestyle guru. She had her own fashion line and a flagship boutique in SoHo. Alongside Jared—another real-estate scion—she had wedged herself into Upper East Side society, earning invites to exclusive charity functions and a cameo on Gossip Girl.

Ivanka may not have thought her father could win the presidency, but she chose to treat the campaign as a brand-enhancement vehicle. She posed for glossy magazines, and sat for soft-focus interviews on Good Morning America. After speaking at the Republican National Convention, she served her Twitter followers a link to the pink sheath dress she’d worn onstage and encouraged them to “shop Ivanka’s look.” The dress sold out within 24 hours, a sign of the broader strategy’s success: In the first half of 2016, Fast Company reported, net sales at her clothing line were up nearly $12 million.

Navigating the campaign this way required finesse. Ivanka kept her distance from the uncouth rallies in places like Reno, Nevada, and Toledo, Ohio. While Trump riled up the country with Muslim-ban proposals and Mexican-rapist panics, she perched herself on a higher plane, where she just wanted to talk about the issues that really mattered to her, like affordable child care and the gender pay gap. Campaign staffers grumbled that Ivanka’s policy preferences were more closely aligned with Aspen weekenders than Rust Belt voters. “People started to realize this wasn’t about Trump’s vision,” one former aide told me. “It was about Ivanka’s ability to feel comfortable in her New York circle.”

But few were willing to challenge her. Rumors swirled that a state-level staffer had been fired after displeasing Ivanka. True or not—a spokesperson for Ivanka declined to comment—the story reinforced an impression that the candidate’s favorite child was untouchable. “It all felt very Tudor,” said the former aide. “Aside from whispers in the bathroom, nobody would dare say anything bad about Ivanka. It was the kind of thing that would get you tarred and feathered.”

While Ivanka soaked up the spotlight, Don was consigned to the margins of the campaign. The two had long been a study in contrasts. Where she whispered, he shouted; where she was careful, he was reckless. Unlike Ivanka—who couldn’t wait to follow her dad into real estate—Don had taken a more leisurely path to the family business after college, bartending and bumming around Colorado for a year and a half while his father seethed.

[Read: Donald Trump Jr., the troublemaker]

With his slicked-back hair and pin-striped suits, Don had carried a certain fratty energy into adulthood that periodically got him into trouble. (In 2002, Page Six reported that he got a beer stein to the head at a New York comedy club after some patrons thought he was “reacting too enthusiastically to [Chris Rock’s] ethnic humor.”) He spent weekdays working at the Trump Organization, where he developed a millionaire’s belief in low taxes, and weekends in the wilderness with his hunting buddies, where he gained an appreciation for gun rights. As a result, Don came to conservatism years before the rest of his family.

Yet when Don offered to help his father’s campaign, many of the tasks he received had a whiff of condescension. Trump had always been embarrassed by his son’s hunting, especially after photos emerged in 2012 of Don posing with the severed tail of an elephant he’d slain in Zimbabwe. But now that the candidate was wooing rural Republicans, he was happy to let Don put on that goofy orange vest and shoot at stuff for the cameras. “You can finally do something for me,” Trump told Don, according to a former aide.

Don had long ago come to understand that Ivanka was his father’s favorite. “Daddy’s little girl!” he liked to joke. But making peace with her husband’s status in the family was harder. Ever since Ivanka had married Jared, Don had been made to watch as this effete, soft-spoken interloper cozied up to his dad. “The brothers thought Jared was a yes-man,” said a former Trump adviser. “Don, especially, looked at him as very suspect.”

But Ivanka and Jared’s real power was rooted in Trump’s aspirations for the family. The couple stood as avatars for the elite respectability he’d spent his life futilely chasing. They belonged to a world that had long excluded him, dined in penthouses where he’d been derided as a nouveau riche rube. Cultivated and urbane, they embodied the high-class, patrician ideal he so desperately wanted the Trump name to evoke.

Don—the screwup, the blowhard, the hunter—didn’t stand a chance.

Trump with Ivanka in 1991
Trump with Ivanka in 1991 (Life Picture Collection / Getty)

Tensions between Don and Jared sharpened in the spring of 2016, as it became clear that Trump was going to fire his campaign manager. With Corey Lewandowski on the way out, Don and Jared each began vying for larger roles in the campaign, according to two Republican operatives who worked for Trump.

People close to the candidate knew he would never entrust his campaign to his son—Don’s chances of taking the reins were “less than zero,” a former adviser told me. But Don seemed like the last one to realize it. He hustled to prove that he was up to the task, swapping texts and emails with anyone who said they could help his dad’s candidacy. It was during this period that Don set up a meeting with a Russian lawyer who claimed to have dirt on Hillary Clinton. “The Trump Tower meeting was Don’s move to take over the campaign,” a former aide told me. “He was trying to show his father he was competent.” (The spokesperson for Don said: “More fiction.”)

The full extent of the mess Don was making wouldn’t be clear for another year. But even in the moment, the meeting was a bust. The Russians rambled about adoption policy, Jared emailed his assistant looking for an excuse to leave, and no useful intel was produced. Don had wasted everybody’s time.

Jared and Ivanka took a savvier approach to consolidating power, cultivating the new campaign chairman, Paul Manafort, as an ally. By the fall, Jared was traveling virtually full-time with Trump on his private plane, while Don was sent to stump in far-flung states no one else had time for. “I just wake up in the morning and go to whatever city they tell me to,” Don complained during one trip, according to a travel companion. “Jared’s the smart one. He has it all figured out.”

But Don discovered that he had a knack for campaigning. Bounding into county fairs and hunting expos in boots and blue jeans, he dazzled crowds with his knowledge of duck blinds and fly-fishing—sounding more like a Trump voter than a Trump. He thrived in the shouty, testosterone-soaked realm of #MAGA Twitter, where his provocations routinely went viral. Don’s habit of amplifying memes from the right-wing fever swamps generated controversy. (One infamous tweet compared Syrian refugees to poisonous Skittles; another featured the alt-right mascot Pepe the Frog.) But it also helped turn him into a kind of Breitbartian folk hero. “He’s one of the bros,” Mike Cernovich, a popular far-right social-media personality, told me. “He has a classically masculine personality, and you don’t feel like he’s a snob. He really likes the meme culture—it’s not fake for him.”

Don may have lost the inside game to Jared and Ivanka, but he was building a grassroots base of his own. When fans began calling on him to run for mayor of New York City—and Don responded with a bit too much enthusiasm—his father quickly shut it down. “Don’s not going to run for mayor,” he said in an interview with Sean Hannity. But Trump couldn’t put an end to his son’s political career that easily. By the end of the election, Don’s budding #MAGA stardom was undeniable—and he had no intention of walking away. “Going back to doing deals is boring,” he reportedly told a gathering of gun enthusiasts. “The politics bug bit me.”

III.

With the election over and the presidency in hand, the Trumps got to work doing what they did with any new asset: figuring out how to sell it. Their initial cash grabs were clumsy and relatively small-scale. When the soon-to-be first family was profiled by 60 Minutes, Ivanka’s jewelry line blasted out a “Style Alert” advertising the $10,800 bracelet she’d worn on air. When Trump met with the prime minister of Japan, Ivanka—who was pursuing a licensing deal with a Japanese apparel conglomerate—sat in on the meeting. As ProPublica would later reveal, she also helped ensure that a portion of her father’s inauguration budget was spent at the Trump International Hotel in Washington.

Eric and Don—tasked with running the Trump Organization while their father was away—looked for their own angles. They doubled the membership fee at Mar-a-Lago, which was already being described as the “winter White House,” and pushed forward on the development of their down-market hotel chain, American Idea. Working with a pair of Mississippi businessmen they’d met on the campaign trail, the Trumps planned a series of red-state budget hotels stuffed with star-spangled tchotchkes and decorative Americana, such as vintage Coca-Cola machines in the lobbies.

Eric in particular welcomed the challenge of running the family business. He’d always been the one most interested in construction and architecture, and many in the company assumed that he would take over day-to-day operations when his father retired. Now that he had a chance to prove himself, Eric planned to exploit every opportunity. “The stars have aligned,” he proclaimed. “Our brand is the hottest it has ever been.”

Jared, meanwhile, was busy attending to his own brand. When the December 20, 2016, issue of Forbes hit newsstands, the cover featured Trump’s favored son-in-law—his arms folded, his lapels peaked, his hair a perfect coif—grinning triumphantly above a headline that seemed tailored to torment Don and Eric: “this guy got trump elected.” Inside, readers were introduced to a heretofore unfamiliar version of Jared: the visionary strategist who had run the Trump campaign like a “stealth Silicon Valley startup.”

The brazen credit-grabbing rankled people who’d worked on the campaign. “He never sacrificed or risked a thing,” a former staffer complained. “Then, after the win, he came in to grab the spoils and anoint himself grand pooh-bah. It was gross.” Don and Eric were similarly vexed, according to people close to the family.

Jared had wasted little time in wielding his influence. Just days after the election, he’d persuaded Trump to fire Chris Christie as the head of the transition team. Christie had been the federal prosecutor responsible for putting Jared’s father behind bars a decade earlier, and the dismissal was widely interpreted as an act of vengeance. But the shake-up also gave Jared a strategic advantage, allowing him to exert control over hiring for the new administration.

Don was not happy with this arrangement. More than once, according to aides familiar with the process, he would recommend someone for a job only to have Jared intervene and insist that personnel decisions be run through him. Worse, Jared seemed intent on staffing the Trump White House like it was a charter jet to Davos. He recruited Gary Cohn, a Goldman Sachs executive and registered Democrat, to serve as the president’s chief economic adviser. He lobbied for Steven Mnuchin, a hedge-funder cum Hollywood producer, to be named Treasury secretary. Don managed to usher a handful of loyalists into his father’s administration—but Jared and Ivanka ended up with many more.

People close to Trump speculated about what Jared was hoping to get out of all this. Some thought he was simply seizing the chance to fill his Rolodex with world leaders and Wall Street titans. Others would later point to a sweetheart deal his family cut with a Qatari investment firm as evidence that Jared’s involvement in foreign policy had a profit motive. (A spokesman for Jared denied this.)

Whatever the reason, the couple’s headlong dive into politics proved difficult to reconcile with Ivanka’s brand. As the inauguration approached, she found herself under siege on the Upper East Side. A horde of New York artists—including some whose work she personally collected—gathered outside a downtown building where she kept an apartment to protest her role in Trump’s “fascist” agenda. Activists launched a viral Instagram campaign juxtaposing her glamour shots with appeals from frightened constituents: “Dear Ivanka, I’ve been raped and I need to have an abortion”; “Dear Ivanka, I’m afraid of the swastikas spray painted on my park.”

This struck Ivanka as profoundly unfair. She—the author of a forthcoming book on women in the workplace and frequent participant in female-empowerment luncheons—was a misogynist? She—a convert to orthodox Judaism and supporter of numerous respected Jewish charities—was an anti-Semite? What did these people expect her to do, disown her father?

But as much as the attacks bothered Ivanka, they also made something clear: The White House wasn’t going to boost her lifestyle business—if anything, the coming years would politicize it beyond repair. To take advantage of this moment, she would need to think bigger. Fortunately for Ivanka, A‑list celebrities and thought leaders were now flocking to her. Leonardo DiCaprio, Sheryl Sandberg, Anne-Marie Slaughter—all of them wanted a spot on her calendar. She didn’t need to sell handbags or luxury condos to command the attention of America’s elite. Her proximity to the Oval Office was enough.

The week before Trump entered the White House, Ivanka announced that she was taking a leave of absence from the Trump Organization and her fashion line. The seat of the family empire wasn’t in Manhattan anymore. It was in Washington—and that’s where she and Jared would be.

IV.

The American presidency has always been shaped, for better or worse, by unelected family members. Hillary Clinton was the architect of her husband’s health-care plan. Bobby Kennedy served as his brother’s attorney general. Eleanor Roosevelt traveled the country on behalf of her wheelchair-bound husband to survey New Deal programs, and Edith Wilson is said to have effectively run the White House after Woodrow suffered a stroke.

Still, modern presidents do not, as a rule, hire their children to work in the West Wing. So when, in March 2017, Trump made Ivanka an assistant to the president, and Jared a senior adviser, the appointments attracted more than a few critics. Some compared Trump to a third-world autocrat stacking his regime with relatives. But Ivanka was certain the naysayers would thank her in the end.

Her confidence was not unreasonable. People close to the Trump family had long marveled at how Ivanka handled her father. The playful Aw, Dad eye rolls, the giggles at his jokes, the strategically deployed fawning followed by subtly asked-for favors—these little performances, honed over a lifetime, had taken on an almost mythical quality among Trump’s friends and employees, who say no one’s better at getting what they want from him.

The presidential agenda Ivanka envisioned was one her former Manhattan neighbors would approve of. With her help, Trump would enact a paid-family-leave program and reform the criminal-justice system. He would update the nation’s infrastructure, and preserve LGBTQ rights. Republican, Democrat, these were just labels. Once fair-minded people saw what her father had accomplished—what the Trumps had accomplished—the family’s legacy would be secure.

The first test of Ivanka’s persuasive powers came when White House officials began drafting an executive order focused on expanding protections for religious conservatives. Ivanka, who knew the order would be seen as anti-LGBTQ, enlisted Tim Cook—the gay Apple CEO, whose respect her father craved—to lobby Trump against signing it, according to a former White House aide. She also privately reminded her father that Vice President Mike Pence had faced nasty political blowback when he’d stumbled into a religious-freedom culture war as governor of Indiana.

Ivanka’s crusade culminated one night in the president’s private study, where Trump was discussing the issue with a small group of advisers. A former aide who was present at the meeting recalled Pence launching into an impassioned defense of the executive order, only to have Trump cut him off. “Mike, isn’t this the shit that got you in trouble in Indiana?” he snapped. Pence quickly retreated as blood rushed to his face. It was clear to all in the room that Ivanka—standing quietly in the corner—had won. When Trump did eventually sign the order, it had been dramatically watered down.

But as time went on, Trump began to tire of Ivanka and Jared’s incessant lobbying. Every time he turned around, they were nagging him about something new—refugees one day, education the next. It never stopped. Their efforts to change his mind about the Paris climate accord exasperated the president, who took to mocking their arguments when they weren’t around. “They’re New York liberals,” he would say, according to a former White House aide. “Of course that’s what they think.”

When the president withdrew from the Paris Agreement in June 2017, the illusion of Ivanka the Trump whisperer collapsed. “Look, It’s Time to Collectively and Officially Give Up on Ivanka Trump,” Vogue declared. “Ivanka Trump is never going to come through,” a New York Times op-ed announced. Vanity Fair published a savage story about her and Jared’s early adventures in elite Washington, where they were widely regarded as dilettantes. “What is off-putting about them,” one politico told the magazine, “is they do not grasp their essential irrelevance. They think they are special.”

Ivanka seemed consumed by her coverage. Omarosa Manigault Newman, who worked in the White House for the first year of the administration, recalled Ivanka derailing a senior staff meeting to complain about a Saturday Night Live sketch that portrayed her as the face of a perfume named “Complicit.” “Ivanka was thin-skinned,” Newman wrote in her memoir, “and could not seem to take a joke.”

Ivanka’s favorite-child status had long been tied to the good press she generated for her dad. “For Trump, everything comes back to optics,” Cliff Sims, a former White House aide, told me. “She is the archetype of what he wants—the most beautiful face, the most buttoned-up message, everything just exactly the way it should be.” But as Ivanka became a less attractive surrogate, Trump’s patience with her and her husband waned. A news story about Jared using a private email server to conduct government business prompted a presidential meltdown in the Oval Office. “How could he be so stupid?” Trump fumed, according to a White House official who was present. “That’s what Hillary did!”

Trump reportedly began telling allies, “Jared hasn’t been so good for me,” and lamenting—in jest, perhaps, though no one could say for sure—that Ivanka could have married Tom Brady instead. More than once, the president wished aloud that the couple would move back to New York.

Ivanka reacted to her sudden loss of influence by affecting an airy, just-a-daughter pose. “I try to stay out of politics,” she said in an interview with Fox News—a puzzling claim for a White House official. To those who knew her, it was clear she was disoriented. For the first time since she was a girl, her privileged place in the family seemed uncertain.

So when, in July of 2017, Don’s ill-conceived Trump Tower meeting with the Russians became public—putting Jared in jeopardy—the couple did what they had to do. Jared released an 11-page statement effectively blaming the radioactive meeting on his brother-in-law while absolving himself. In a gratuitous bit of knife-twisting, he recounted emailing an assistant, “Can u pls call me on my cell? Need excuse to get out of meeting.”

The statement infuriated Don, according to family friends—not just for the way it threw him under the bus, but for the way it belittled him. But Jared’s maneuver worked on the audience that mattered most.

Watching cable-news coverage of the fiasco from the West Wing, Trump shook his head wearily. “He wasn’t angry at Don,” a former White House official recalled. “It was more like he was resigned to his son’s idiocy.”

“He’s not the sharpest knife in the drawer,” Trump said with a sigh.

V.

Saturday Night Live has a running bit in which Trump’s two eldest sons appear in tandem, with Don portrayed as the smart, responsible big brother and Eric as a kind of bumbling man-child. In an episode last year, Don answered questions about the Russia investigation while Eric ate Play-Doh. Real-life Don seems to delight in these sketches, and has even publicly volunteered to come on the show to play himself. But within the Trump family, associates say, the brothers’ roles are exactly reversed.

Sequestered in Trump Tower, Don spent the first year of his father’s presidency as a kind of armchair pundit, watching the news on TV and firing off tweets. He showed little interest in running the Trump Organization with Eric and longed instead for the political arena. But he rarely called his dad at the White House—“I feel ridiculous bothering him,” he told a reporter—and his dad called him even less. In fact, no one in the first family took Don’s political ideas seriously, least of all Jared and Ivanka. “You never heard them say, ‘We’ve got to get Don Jr.’s opinion on this,’ ” a former White House official told me.

In private, Don complained that the West Wing had been overrun by Democrats, and griped that even the true believers were too passive. Having immersed himself in the online meme wars, Don seemed to believe the White House’s woes could be solved with the kind of aggressive lib-owning that came so naturally to him. Instead, his father had put his faith in a timid preppy. When photos were released of Jared in Iraq in the spring of 2017, sporting a flak jacket over his oxford shirt and blazer, Don spent the afternoon trading gleeful text messages with friends about the Martha’s Vineyard–meets–Mosul getup.

But beneath all Don’s carping was a more personal grievance: While Jared and Ivanka moved freely through the West Wing, he was stuck on the outside, his face pressed up against the glass.

Everybody who works for Trump learns sooner or later that imitating him will only draw his contempt. The tragedy of Don Jr. is that he seems never to have learned this lesson. As his mother has recalled, Trump resisted when she wanted to name their first son after him: “You can’t do that!” he protested. “What if he’s a loser?” That Don went on to confirm his father’s fear largely by trying to mimic him—in temperament, style, speech, and career—points to the unique difficulties of being the president’s namesake.

In March 2018, Page Six reported that Don’s wife, Vanessa, was filing for divorce after 12 years of marriage. The echoes from his childhood were hard to ignore. The couple had five kids—including a daughter who was about the same age he’d been when his parents split up—and the tabloids were circling.

Hoping to spare their children from the media circus Don had experienced, he and Vanessa committed to keep their no-contest proceedings quiet. He told his publicist he didn’t care what reporters wrote about him, but requested that they respect his kids’ privacy and keep in mind that some of them were old enough to read.

Trump had been ambivalent about Don’s wife. (Some traced his doubts back to her teenage romance with a member of the Latin Kings gang; others pointed to an oft-retold story about Vanessa meeting Don’s dad at a fashion show and later joking that he was “retarded.”) But the president was even less enthusiastic when his son started dating Kimberly Guilfoyle.

The Fox News host had lobbied to become White House press secretary early in the administration, but Trump had shown little interest, according to two former aides. “Even he can tell the difference between the attractive women on Fox who have a little bit of substance, and those who will be derided as airheads,” one aide said. Now she was gallivanting across the gossip pages with his son, and posing for photos on the South Lawn.

The family was friendly to Guilfoyle in person, but there were signs of disapproval. One source told me that after her attendance at a White House Fourth of July party sparked a round of fawning press coverage—upstaging Jared and Ivanka—Don was contacted by an official informing him that he would need to clear his guests the next time he visited. And as Thanksgiving approached, the president made it known that Guilfoyle wasn’t welcome to join the family at Mar-a-Lago, two Trump associates told me. (Spokespeople for the White House and Don denied this.)

Some suspected that the president was simply fed up with the distraction the relationship posed. But according to one longtime Trump adviser, there may have been another reason for his displeasure. Over the years, Trump had frequently made suggestive comments about Guilfoyle’s attractiveness, the adviser told me, and more than once inquired about whom she was dating.

But while Trump may have been less than thrilled about the relationship, among rank-and-file right-wingers “Donberly”—as the couple nicknamed themselves—was a hit. Appearing side by side at Republican rallies, they bantered about each other’s pet names—she was “Pooh Bear,” he was “Junior Mint”—and railed against Democrats. They went on hunting trips and posted selfies with rifles on social media. Fans on Twitter began referring to Guilfoyle as the “future first lady,” and she made little effort to tamp down the speculation.

When an interviewer on Breitbart News’s radio show made a comment about Don’s political potential, Guilfoyle didn’t hesitate: “I think he’s the No. 1 up-and-coming political figure, for sure, on the right.”

VI.

As the 2018 midterm elections approached, Don decided to get serious about politics. He hired the Republican strategist Andrew Surabian to help shape his press coverage, and began fielding requests to join candidates on the campaign trail.

Crisscrossing the country with Guilfoyle in the year that followed, Don emerged as a veritable right-wing phenom. At the University of Georgia, more than 2,000 young Republicans lined up to hear him speak. At the Conservative Political Action Conference in Maryland, he was swarmed by fans clamoring for selfies and autographs. Charlie Kirk, the founder of the student organization Turning Point USA, recalled a summit in West Palm Beach that featured conservative A-listers such as Tucker Carlson, Greg Gutfeld, and Jordan Peterson. Don drew a bigger crowd than any of them.

To the surprise of many in elite GOP circles, he also excelled at schmoozing wealthy donors, raising millions of dollars for conservatives in closed-door fundraisers. “He’s as good in a room of six people as he is in a room of 6,000,” says Tommy Hicks Jr., a co-chair of the Republican National Committee and a friend of Don’s.

But the stump was where Don really shined. Taking the stage to wild applause from riled-up MAGA-heads, he riffed and ranted and cracked jokes about gender identity. To watch Don in these settings was to see a man morphing into his father—the vocal inflection, the puckered half-smirk, the staccato “Who knows?” punctuating key sentences. It was as though he had studied his dad’s delivery, practicing each tic in the mirror.

By November 2018, Don had appeared at more than 70 campaign events across 17 states—and powerful Republicans were abuzz. “I could very easily see him entering politics,” Senator Kevin Cramer told me. “I think his future is bright,” said House Minority Leader Kevin McCarthy. Newsmax’s CEO, Chris Ruddy, told me he’d personally encouraged Don to run for office; Sean Hannity called him “a born natural leader.” Senator Rand Paul went so far as to say that Don was one of the best Republican campaigners in the country. “If you can’t get the president,” Paul told me, “he’s a close second.”

Notably, many of these Republicans seemed less enthusiastic about his sister. Cramer, for example, spent 15 minutes in a phone interview gushing to me about Don’s “accessibility” and “irreverence” and gift for “connecting” with voters. But when I asked him about Ivanka, he paused. “She’s a little bit harder to get,” he replied, politely. “Her faith prevents her from traveling on the Sabbath.” Charlie Kirk was similarly careful when we spoke. While all of Trump’s adult children were helpful to the cause, he told me, “I can honestly say that outside of his father, Don is the No. 1 most requested speaker, and he brings the most energy to the conservative base.”

None of this newfound excitement about Don seemed to rub off on the president, however. People close to Trump told me he remained enchanted by the idea of Ivanka as the inheritor of his political legacy. During trips to Mar-a-Lago, he was often heard rhapsodizing about her potential to be the first female president. Don’s political prospects, if they came up at all, were treated as an afterthought. If there was any doubt about which child Trump favored, his Twitter feed told the story: In the first two years of his presidency, he tweeted about Ivanka 16 times, while Don received just four mentions—all of them about the Trump Tower scandal.

[Read: Inside Ivanka’s dreamworld]

Trump floated Ivanka for various prestigious jobs, including United Nations ambassador and head of the World Bank. When Washington snickered, she settled for a more amorphous role that let her travel the world to speak on pet issues. She appeared onstage with Angela Merkel in Berlin, and addressed a conference on women’s empowerment in Tokyo. On a trip to Africa, she wore flowy dresses as she laughed and danced (and posed for photos) with Ethiopian women. She even began to claw her way out of Upper East Side exile, thanks to her high-profile advocacy for the Republican tax bill—which slashed rates for the rich, and the corporations they owned. “As people got richer, [Ivanka and Jared] started getting welcomed back in by their old friends,” says Emily Jane Fox, a Vanity Fair reporter who wrote a book about the Trumps.

But as Don’s visibility grew, the cold war between him and Ivanka intensified. Now that each had their own teams of allies and advisers, they had grown paranoid that the other’s henchmen were planting damaging stories about them in the press. A few days before the midterms, McClatchy published a story under the headline “Trump Kids on the Campaign Trail: Don Jr. Wows, Ivanka Disappoints.” Ivanka’s camp was enraged, and suspected that Don was behind the story. Later, Don confronted Ivanka over rumors that her team was undermining him in off-the-record conversations with reporters. “Tell your people to stop trashing me to the media,” he said, according to someone familiar with the conversation. (Spokespeople for Don and Ivanka disputed this account and denied that there is a rift between them.)

Trump and Don Jr. with Fred Trump (standing) in the Plaza Hotel in 1988
Trump and Don Jr. with Fred Trump (standing) in the Plaza Hotel in 1988 (Time Life Pictures / DMI / Life Picture Collection / Getty)

While his siblings jockeyed for political position, Eric spent most of his days at Trump Tower. Don was still technically on the company’s payroll, but between hunting trips and campaign stops, his presence in the office was irregular at best.

Running the Trump Organization during the Trump presidency had turned out to be more difficult than Eric had imagined. After an initial burst of postelection activity, many of the family’s most ambitious plans collapsed. They were forced to scrap their American Idea hotel chain after ethics concerns were raised. International building projects were delayed amid outcry from watchdog groups. Valuable retail space in Trump Tower sat empty month after month, and socially conscious condo owners called for the Trump name to be scraped off their buildings.

Meanwhile, at Mar-a-Lago, patrons whispered that “the boys” were draining the club of its class with cost-cutting measures after numerous charities canceled functions there. When a rumor went forth that Eric had ordered lower-quality steaks to be served at the restaurant, members erupted in outrage: His father never would have allowed this.

Eric blamed the Trump Organization’s setbacks on partisan politics. “We live in a climate where everything will be used against us,” he told The Washington Post. But within the president’s orbit, there was a growing sense that his sons were driving the company into the ground.

Trump, who’d pledged to recuse himself from business decisions, relied on golf buddies to update him on the company during his weekend trips to Florida. Their reviews seemed to confirm his worst fears. Before launching his campaign, he’d fretted that his kids weren’t ready to take over the business. Now, with Don MIA and Eric flailing, he became preoccupied with what would be left of his company when he returned to it. According to a former White House aide, Trump talked about the issue so often that administration officials worried he would get himself in trouble trying to run the Trump Organization from the Oval Office.

But as the 2020 campaign season entered its early stages, even Eric turned his attention toward politics. His wife, Lara—a conservative activist from North Carolina—was an outspoken surrogate for Trump. Eric had been holding back, worried that his father would disapprove; after all, someone needed to mind the shop. But the president encouraged Eric to join his siblings in the fray. There would be plenty of ways to cash in later. This was the family business now.

VII.

Watching Trump’s children appear on Fox News, one gets the sense that they’re still auditioning for their father’s affection. Ivanka speaks in dulcet tones about how proud, so proud, she is of her dad. Don bashes the “fake-news media” with performative force. Eric, the least camera-ready of the three, clings to talking points, lavishing praise on Trump whenever he gets stuck. (In an interview earlier this year, Eric repeated variations of “He’s the greatest guy in the world” in such reverential tones that even Sean Hannity seemed uncomfortable with the obsequiousness.)

Trump watches these segments from the West Wing and offers a running commentary to whoever is around, according to a former aide. His attitude toward each of his adult children on any given day is shaped by how they are playing on cable news. Ivanka tends to draw rave reviews, while Don’s are more mixed, with the president muttering things like “Why did he say that?” and “He doesn’t know what he’s doing.” Recently, though, his perspective on his two oldest children seems to have shifted.

In June, Ivanka accompanied her father to Osaka, Japan, for the G20 summit. After the meetings, the French government posted a video clip that showed the president’s daughter standing amid a gaggle of side-eyeing world leaders as she tried awkwardly to force her way into the conversation. The clip went viral, spawning a hashtag—#UnwantedIvanka—and a wave of parody Photoshops inserting her into great moments in history: mugging for the camera at the March on Washington, grinning next to Winston Churchill at Yalta. News outlets around the world covered the snub. Pundits called it a damning indictment of Trump’s nepotism, while foreign-policy experts argued that Ivanka’s lack of credibility could harm U.S. diplomacy. A quote from an anonymous Indian diplomat recirculated in the media: “We regard Ivanka Trump the way we do half-wit Saudi princes.”

The episode laid bare the depth of Ivanka’s miscalculation. She had thought when her father took office that the surest path to power and status was to plant herself in the West Wing and mingle with the global elite. But after two and a half years of trying to burnish her credentials as a geopolitical player, Ivanka had become an international punch line. There was, it turned out, no market for a genteel brand of Trumpism.

Don, meanwhile, threw himself into his father’s reelection campaign, while quietly plotting his own future. According to Republicans familiar with the discussions, he considered running for office somewhere in the Mountain West, where his love of guns and hunting could help woo voters. A privately commissioned poll in Montana—passed around enthusiastically among Don’s inner circle—showed that 75 percent of the state’s Republicans viewed him favorably. In April, it was announced that Guilfoyle would join the Trump campaign as a senior adviser.

While Don mulled his options, some allies talked him up as a potential chairman of the Republican National Committee. Others suggested he launch a right-wing political outfit that would allow him to hold rallies and bestow endorsements. The word kingmaker started getting tossed around.

Even the president began to appreciate his son’s political value. During a family gathering at the White House, Trump was overheard questioning Don about whether he’d been using the company plane while shirking his day job. A Republican senator in the room intervened to say that without Don’s work on the campaign trail, the party might not have kept its Senate majority. Trump seemed pleased: “I believe it.”

On a steamy June evening, Trump officially launched his bid for reelection with a raucous rally in Orlando. This time, Ivanka and Jared sat in the audience, while Don—the president’s most skilled warm-up act—strutted across the stage to fervid applause. Bellowing into the microphone until his voice went ragged, he crowed about “crushing the bastards of ISIS” and made fun of Joe Biden for “groping” women. As he neared the end of his speech, Don lifted his arms in the air as if conducting an orchestra, and the arena erupted in chants of “Four more years!”

In that moment, there was little question what the future of the Trump family would look like. After a century and a half of striving, they had money, and fame, and unparalleled power. But respectability would remain as distant a mirage as it was when Friedrich was chasing it across the Yukon. While no one knew when Donald Trump would exit the White House, it was clear what he would leave behind when he did: an angry, paranoid scrap of the country eager to buy what he was hawking—and an heir who knew how to keep the con alive.


This article appears in the October 2019 print edition with the headline “Succession.”

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Author: McKay Coppins

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