Don Jr. and Eric, along with their sister Ivanka, are stepping out from their father’s shadow and taking ever-greater responsibility of the family business. But how do they cope with the pressure of being sons and heirs to one of the most controversial figures in the world?

Don Jr.

It’s a dollar bill. But a dollar bill with a difference. “I’m looking at it pinned up above my desk now,” says Donald Trump Jr. – talking via a transatlantic phone call between London and New York.

This one, he explains, was signed and handed over to him by his father and namesake, the property magnate, TV personality, presidential critic-in-chief and owner of one of the most talked about hairstyles in the world. This Donald is reckoned to have about 4 billion more where that one-buck note came from, so it’s no great financial loss, but Trump the Younger is in no doubt about its significance. “It was a bet about a certain job; he was down on it, and I said it was going to be ok [which it eventually was]. It’s the ultimate bet within the family – a signed dollar bill as an acknowledgement of the handover. But he’s taken plenty from me as well.”

Whatever the running tally in their father-and-son wagers, Don Jr, now 37, is trusted enough by his father to have risen to executive vice president of development and acquisition, a title that he shares with his brother and sister, Eric (31) and Ivanka (33). (He also has a half-brother and a half-sister from his father’s two subsequent marriages.)

Don Jr. admits that there may be some people who think that he and his siblings have been elevated to positions of power and responsibility within The Trump Organisation because of their surname, but he doesn’t lose sleep over it. “I don’t care what these people think,” he says. “I’m pretty secure in myself. I’m happy being underestimated.”

He first started working for his fathers’ company aged 14, beginning on “the bottom rung” as a dock attendant at a casino in Atlantic City before progressing to working with landscaping crews on development sites. “While I’m the son of a very rich guy,” he says, “I could still drive a D10 Caterpillar bulldozer if I needed to.”

After college at the University of Pennsylvania, Don Jr. Worked in a bar and as a fly-fishing guide for a year – “to get stuff out of my system before I entered the real world and make sure that I never had any regrets” – but he has been committed to the family firm since 2001. Leasing is his main focus, with recent and ongoing projects including new towers and hotels across Vancouver, Rio and Mumbai.

It’s not that his father is stepping back or thinking of retirement any time soon. Instead, he, Ivanka and Eric are stepping up. “As an organisation we’re now able to handle a greater bandwidth than we would have been able to in the past. And there are certainly more international jobs; it’s an organisation that’s much less New York-centric and US-centric than it used to be.”

But when, eventually, his father is no longer at the helm of the company, is he, as the eldest son and heir, the best-placed candidate for the top job? “It’ll likely be shared responsibility,” he says, diplomatically. “And anyway, my father’s thing, and his father’s thing before him, was that ‘to retire is to expire’. So I don’t think it’s going to happen anytime soon.

Eric

It’s little over half-way through the month and, already, Eric Trump has racked up close to 30,000 miles of air travel. “Obviously I spend an inordinate amount of time on flights,” he deadpans. Not that he’s complaining.

“We all wear so many different hats. One day we’re at Turnberry, the next day we’re acquiring a another new golf course [last year the company snapped up Doonbeg golf course, on the Atlantic coast of Ireland], later that day we’re doing The Apprentice – which is the number one show on TV – then the following day we’re buying a winery in Charlottesville, Virginia. We’re doing a lot of great things; doing them as a family and having a lot of fun.”

It doesn’t always happen, but their different specialisms mean that Eric often finds himself working alongside his older brother and sister on the same project. He takes care of construction, leasing is down to Don, while Ivanka has responsibility for interior design.

“It’s all very pragmatic and works nicely,” says Eric. “We always joke that three of us will respond by email in exact same way to a question. I think we all see things the same way, and much of that comes from my father.”

From his mother, the Czech former model Ivanka Trump, Eric says he and his siblings got a sense of worldliness – he places a high value on travelling at a young age and the perspective that came from spending school holidays in the country of her birth. “Doing international real estate, it’s a real leg-up.”

But his childhood wasn’t all easy. He and Don Jr. both admit that the very public breakdown of his parents’ marriage in 1992 – played out for all to see in the international press at the time – was difficult to bear. “Divorce is always messy,” says Eric. “It’s never a nice thing. But I give them credit that they were able to insulate us.”

Like his older siblings, Eric says a strong work ethic was ingrained in him from a young age. “We never had a minute of free time. My parents were both believers in that. I was wiring houses at 13 years old and laying marble. It teaches you the value of a dollar, and it teaches the trades of the industry that we’re in now. I think contractors were shocked by how much we knew about building and how things are built. If you’ve pulled the wires through the wall yourself, it’s a lot harder for those guys to rip you off.”

“You have to earn your stripes. Even today, there’s no one who spends more time on an airplane or gets to the office earlier or knows more about the projects than us. So I think actions have to speak louder than words.”

Eric married Lara Yunaska, an associate producer at television network CBS, at the end of last year, and says that children are likely to come along at some stage in the near future. Although he has no plans to match his brother’s brood – Don Jr. and his wife, the model Vanessa Haydon, have just welcomed their fifth.

And while he insists that all his father’s grandchildren will be free to make up their minds about the careers they follow, there’s no hiding the fact that Eric likes the idea of extending the Trump dynasty.

“There’s no question,” he says. “We’ll never be a public company. I hope that in 20 years time, when the company’s triple the size it is now, we’ve built more incredible hotels, we’re still laughing together and having a great time and our kids our coming into the business – then we can do it all over again.”

The Donald: Like father, like sons?

What is the most significant character trait that Don Jr shares with you?

Don has great determination. No matter what he’s doing, he will keep at it until it’s finished – a great trait to have in this business. I am the same way.

What is the most significant character trait that Eric shares with you?

Eric can visualise very readily. He also has vision. I have the capacity to be a visionary and will sometimes step out of my usual endeavors into something new – and to great success.

What is the most valuable attribute that Don has that you don’t see in yourself?

Don is very focused. I’m focused too, but Don can really be single-minded and plough straight ahead.

What is the most valuable attribute that Eric has that you don’t see in yourself?

Eric has an easy-going nature. Easy-going is not an adjective that would apply to me.

If you could have only passed on one business lesson to your children, what would it have been?

To keep your focus.

If you could have only passed on one life lesson to your children, what would it have been?

Know your priorities. Family is very important to all of us. We work as a unit. I’m happy I’ve passed that on to them. They have a big responsibility, and having family behind them will give them support and resilience.

This article was published in print in our Spring Issue, 2015