The Apprentices

14 minute read

The ninth hole of the Ailsa course at Turnberry is one of golf’s glittering jewels, a cliffside par 3 with a tee shot over crashing waves toward a lighthouse built on the remains of a 13th century castle. The strip of Scottish coastline is so pretty, you can almost fathom why Donald Trump is standing here, an ocean away from the nearest gettable voter, at the worst possible time.

Back home, his party is mulling revolt. Here in Scotland, he has blundered into a black-swan moment, arriving this crisp June morning just hours after the U.K. elected to bolt from the European Union–a world-altering gamble he egged on. Red golf balls emblazoned with swastikas are scattered at his feet, courtesy of a prankster. But Trump doesn’t want to talk GOP infighting or geopolitical turmoil. He wants to talk legacy. Turnberry is the 10th Trump property to which he’s dragged the cameras during his presidential campaign cum promotional tour. Only this time he isn’t here simply to plug a golf course. “You know why I’m here?” he tells the cameras for the third time. “Because I support my children.”

They are standing over his left shoulder, a portrait of solidarity. Trump’s three eldest kids–Donald Jr., 38; Ivanka, 34; and Eric, 32–are executive vice presidents at the Trump Organization. All have spent nearly their entire professional lives working for their father, rising to oversee the acquisition, development and operation of luxury hotels, office towers and resorts around the world. But these days, tending the family real estate business isn’t their biggest job.

In the most unorthodox campaign in modern presidential history, three of the most powerful figures are the candidate’s children. They have no formal titles nor any prior political experience among them. But Don Jr., Eric and Ivanka–along with Ivanka’s husband Jared Kushner–have carved out unprecedented roles: strategist and surrogate, cheerleader and confidant, moderating influence and humanizing force. “They are his kitchen cabinet,” says Tom Barrack, a billionaire financier and longtime friend of Trump’s who formed a super PAC to support the campaign. “When you look at the cadre of people he really trusts, it’s very few. And they are certainly at the top of that list.”

Together, they have pushed out a campaign manager, become conduits to top GOP officials and rival factions, wooed donors and delegates, courted skeptical members of Congress and crisscrossed campaign backwaters from New Hampshire to Nevada. They help write speeches and shape Trump’s policies on everything from the Middle East to the Second Amendment to women’s health. All three of them will deliver speeches at the Republican Convention in Cleveland.

Presidential offspring have often played roles as important advisers, but the Trump kids are different. The tasks in their portfolio can be as simple as fielding their father’s calls at 11 p.m. on a Tuesday or as complicated as mastering campaign mechanics the candidate ignores. When it became apparent during the spring that Trump was being outmaneuvered in the scramble to line up convention delegates, Eric spent a day dialing each of Pennsylvania’s 54 unbound delegates. Nearly all signed on, so he repeated the feat in subsequent states. “This is a very long and arduous and lonely process,” Eric says, leaning back in a green leather chair by the bay window in the Turnberry tearoom, the sun sparkling on the sea beyond the emerald lawn. “Everything we’ve done, we’ve done together as a family. We’re learning together.”

Legacy has always been one of Trump’s signal ambitions, right up there with wealth and fame. On the desk in his 26th-floor office, high above Fifth Avenue, a framed portrait of his father sits in the space where a computer should be. Before the family brand adorned the skyscrapers of Manhattan, Fred Trump, a hard-charging son of German immigrants, built a sprawling empire in New York City’s outer boroughs. At his father’s wake, Trump told friends that his own highest goal was to leave the family name a little better than he found it.

The next generation of Trumps are as devoted to their dad as they are different. They’re less bombastic. More polished. On message. They’d prefer to share credit and skirt controversy. In conversation, each is cordial and self-possessed, as outwardly normal as one could reasonably expect from billionaire scions who grew up in a 30,000-sq.-ft. penthouse atop Central Park. “It was not an option,” says Ivanka, “to be arrogant or entitled.”

Privilege can come at a price, and the tab for the Trump kids seemed steeper than most. It cannot be easy seeing your parents’ divorce and salacious rumors about their sex lives splashed across supermarket tabloids. They were being tailed by paparazzi before they could drive. When the Trumps dropped off Don Jr. at boarding school, cameras tagged along on an errand to buy bedsheets at Kmart. The scrutiny could have sparked self-destructive behavior or planted a desire to escape. Instead, it drew the family closer.

Much of the credit goes to their mother. Ivana Trump was an immigrant from communist Czechoslovakia and a taskmistress who would not brook dissent. (Donald Trump has two other children: a daughter Tiffany, 22, with his second wife Marla Maples, and a son Barron, 10, with his current wife Melania.) Their dad wasn’t much for changing diapers, but he drilled his kids on a mantra of clean living. “I was strict with them, and their mother was strict with them,” says Trump, who touches nothing stronger than soda. “I would constantly preach to my children: No drugs, no alcohol, no cigarettes.”

Work was always a family activity. Don Jr. recalls going to his grandparents’ house when he was 5 or 6. He went around collecting rent, knocking on doors of middle-income apartments that Fred owned in Queens. The Trump kids rode bulldozers around their father’s construction sites and took jobs at his properties. At 15, Ivanka spent a summer shadowing the foreman who oversaw the construction of Trump World Tower in Manhattan. Eric worked in landscaping, Don as a dock attendant in Atlantic City. “To say we weren’t spoiled would be laughable,” Don says, “but we were spoiled with the right things.”

Trump was keenly aware that children of successful parents are apt to buckle under the attendant pressures. “Secretariat didn’t always produce winners,” he says. He didn’t push his children into real estate. And while each chose to join the company shortly after graduating from college, he was a hands-off mentor, letting them learn the ropes little by little while he gauged how much responsibility they could handle. “If they weren’t good, I would tell them to do something else,” Trump says. “But they turned out to be very good.”

Ivanka recently led the acquisition of Doral, a luxury golf resort in Miami, and is overseeing the hotel conversion of Washington’s Old Post Office building, a landmark a few blocks from the White House. Don is responsible for the development of a new luxury hotel and condo tower in Vancouver and handles the Trump Organization’s commercial leases. Eric spearheads golf and construction projects, like the $290 million renovation of Turnberry. Whatever sibling rivalries may exist, they are careful to mask them. “Family businesses tend to have very binary outcomes,” says Ivanka, who has also built her own women’s lifestyle brand. “We’re lucky.”

And unmistakably their father’s children. Like his, their adjacent glass-encased offices in Manhattan are decorated with magazine covers and photo spreads: Ivanka in Vogue, Don shouldering a crossbow for Esquire. A pair of paintings of the old man sit on Eric’s floor. Campaign swag is everywhere. Politics is a new game, with quirky rules and hidden minefields. But it’s really no different, the Trumps say, from constructing a new golf course or hotel. You study the term sheets. Take on big ventures with untapped value. Then figure out a way to sell your product to the masses. “Whether it’s real estate or anything else,” says Don, “[my father’s] always seen what’s lacking and given that to the market.” When the family felt golf courses were cheap, they bought every course they could get their hands on, Eric adds. “When we had hotel opportunities, we’d go buy hotels.” A Virginia vineyard came on the market for what they judged to be a bargain price: “We learned a lot about wine, and we bought it,” says Eric. “We didn’t know anything about being on TV, but we figured it out pretty quickly, and The Apprentice was on for 15 seasons.”

Which brings us to their biggest show yet. “It’s been insane,” admits Don. He is drinking a Red Bull at Turnberry shortly after stepping off a red-eye to Scotland from an outdoorsmen’s conference in Colorado. The Trump sons are avid hunters and anglers. And their first campaign task was shoring up their father’s Second Amendment bona fides. During the Iowa caucuses, they addressed NRA members and trekked into frigid cornfields to hunt deer and pheasant with local politicos. “Don did so good, they’re still talking about it,” Trump says of one speech to a gun group. “He knew more about rifles than they did.”

Soon they were ubiquitous. They toured VFW events, civic clubs and talk radio to testify about their father’s merits. Out in the states, the Trump operation was a skeletal collection of relative neophytes: for the key role of Iowa co-chair, Trump hired Tana Goertz, a motivational speaker and media personality he once fired on The Apprentice. Campaign manager Corey Lewandowski was an outsider with few party allegiances.

And so Don and Eric, who were willing to go anywhere and talk to anyone on behalf of their father, found themselves filling a vacuum. Don often spends hours a day conferring with a rotating cast of party bigwigs, members of Congress, rivals and allies alike. “They are the eyes and ears of the campaign,” says Roger Stone, a veteran Republican strategist and longtime Trump adviser. “Their most important role is passing along information to him.”

Then there is Ivanka. “She is, without question, one of her father’s most trusted advisers,” Stone says. In her third trimester of pregnancy, Ivanka joined her father on the campaign trail before early primary contests and taped get-out-the-vote robocalls and video messages, which she posted for millions of followers on social media. It was easy to spot her influence when Trump praised Planned Parenthood for providing vital health services to millions of women–a broadly popular position that broke with conservative orthodoxy. “We bring unique perspectives to the table. Obviously I am a millennial woman,” she says. “He raised me to be opinionated. When he asks my opinion, I give it. Sometimes I give it unsolicited. And one of the amazing things about my father is he is very receptive to feedback.”

In nearly every bid for the White House, the candidate’s spouse plays the role of chief family surrogate. Melania Trump, a former model who retains the thick accent of her native Slovenia, has made the rounds, even speaking occasionally at rallies, but she spends much of her time raising the couple’s young son and does not weigh in on many campaign decisions. That has freed the spotlight for Ivanka, a poised and disciplined speaker, as a counterpoint and character witness who can vouch for his personal qualities, including the ones you may not see when the cameras are rolling. In interviews, Ivanka casts Dad as a feminist who hired and promoted women to senior positions long before his peers did. Ivanka, not Melania, will introduce Trump when he takes the stage to accept the GOP nomination in Cleveland on July 21.

Of all the advisers to the presumptive Republican nominee, perhaps the most influential is a longtime Democratic donor. Ivanka’s husband Kushner, the son of a prominent New Jersey developer, has his fingerprints on almost every facet of the campaign. He punches up Trump’s speeches, represents the campaign at high-level meetings and rebooted a digital operation stuck in the dial-up era. “A brilliant guy,” Trump says of his son-in-law.

Kushner runs as cool as Trump does hot, and one of his jobs has been putting out fires. When Trump said he’d be “neutral” in the territorial conflict between Israelis and Palestinians, Kushner–an Orthodox Jew–scrambled to soothe raw feelings in the GOP. After Trump came under fire in July for a tweet widely criticized as anti-Semitic–an image of Hillary Clinton against a backdrop of $100 bills and a six-pointed star, like the Star of David–Kushner leaped to his defense. “My father-in-law is an incredibly loving and tolerant person who has embraced my family and our Judaism since I began dating my wife,” he wrote in a rare open letter for the Observer, the New York broadsheet he owns. His impact is immeasurable, says a Republican ally with close ties to the campaign. “Whenever [Trump] thinks, I’ve got to get this right–that’s when he gets Jared on the line.” Part of the bond is a sense of kinship: like Trump, Kushner inherited a family real estate company and carried it to greater heights. “He’s done great in real estate,” Trump says. “But I will say, he loves politics.”

The apprentices finally grabbed the reins of the campaign last month. When they heard reports that Lewandowski had peddled negative stories about Kushner to reporters, the kids confronted Trump over a Father’s Day gathering at his Bedminster, N.J., golf club. (Lewandowski denies the allegation.) Campaign chairman Paul Manafort, a veteran Republican strategist, was given the helm. But as Trump weighed his options for a running mate, he leaned on the advice of his three eldest children and his son-in-law as heavily as anyone else’s. “It’s a family decision,” says a senior campaign official.

“Working with him for as long as we have,” Eric explains, “I think he has developed a level of trust in us that would be very hard for most people who came into a campaign seven months ago to replicate.”

The 2016 campaign was billed as a clash of political clans, but family has often been more burden than blessing. Jeb Bush never overcame dynastic fatigue. Bill Clinton’s tarmac summit with Attorney General Loretta Lynch made his wife’s campaign cringe. The Trump kids have made rookie mistakes as well. Don unwittingly sat for an interview with a white-supremacist radio host. Eric compared waterboarding to a fraternity hazing rite.

But as the campaign rolls on, their clout is only growing. And it will extend into the White House if Trump wins. Don, for one, has been entertaining dreams of becoming Secretary of the Interior. “Looking at other deals,” he admits, “it just doesn’t have the gravitas of everything that’s going on right now.” His father is not yet sold. “Anything’s possible,” says Trump, who still expects his children to run the company when he leaves. “They’re turning out to be very good at politics,” he adds. “Right up there with people who have been doing it all their lives.”

Back in Scotland, Trump stood among Turnberry’s rugged dunes, beaming in his blazer and boasting about his family’s resort renovation. A reporter interrupted, pointing out that running a country was not the same as running a golf course. “You’d be amazed how similar it is,” Trump replied. “It’s a place that has to be fixed.” The work ahead was nothing new. But first the family needs to close its biggest deal yet. Together, as always.

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