When he was 12, his storybook New York childhood insulated by wealth and privilege was shattered by his parents' divorce. But he went on to study at Wharton, and eventually returned to the family business.
He and his wife, a former model, are a poster couple on Manhattan's young and wealthy social circuit. They have five bright children. They have been ambassadors for Operation Smile, the charity that treats children with cleft palates.
He has also shot an elephant, cut its tail off and held it up for a photograph.
Mr Donald Trump Jr is now 39 and executive vice-president of the Trump Organisation, which had revenues of US$9.5 billion (S$13 billion) last year. He splits the management with his brother Eric, 33.
In adulthood, Mr Trump Jr has emerged as a combative advocate for his father, United States President Donald Trump. He has maintained a steady stream of tweets defending his father and lashing out at the "fake news" media.
But the liberal media, which regularly disparages the Trump family, has focused on him anew after he released a chain of e-mails that led to a controversial meeting in June last year with a Russian lawyer to purportedly obtain damaging information on his father's Democratic rival for the presidency Hillary Clinton.
He appeared to have gone into the meeting despite being informed almost as an aside by the middleman - a music producer for a Russian pop star - of "Russia and its government's support for Mr Trump".
"If it's what you say, I love it," Mr Trump Jr said in reply to Mr Rob Goldstone, the middleman.
Mr Trump Jr has insisted the meeting came to nothing. His father has dismissed the controversy, saying it was quite natural for him to go to the meeting. Many analysts have put it down to political naivete.
Mr Trump Jr is likely to have to testify under oath before the Senate intelligence committee - something he has said he is quite willing to do.
While he has been provocative on behalf of his father, he is not one to normally court the media. But now the name-calling has reached fever pitch. The New York Post on July 11 called him an "idiot".
However, the episode offers some insight into the man.
Mr Trump Jr differs from his father in some respects. Where the father is close to the stereotype of the baseball-cap wearing, hamburger- and-fries-eating conservative American, the son is more like the modern suburban dad-next-door, not as proudly workaholic as his father, and not as focused on money.
In family portraits, he does not hog the picture; he is normally off to the side, while his sister Ivanka takes centre stage. Unlike his sister, he has not started his own brand.
What he has had to endure as the son of an alpha male celebrity father, however, is not usual.
"Every time you check in at an airport, it's 'Oh, my god, you're Donald Trump's son'," he told the writer Gwenda Blair, when she met him for her 2000 family biography, The Trumps: Three Generations That Built An Empire.
"It would be nice not to have people prejudge you because they see your father a certain way and there's no chance you might actually be different," he said. He was 26 at the time. Ms Blair said the impression she had of him was one of modesty - which was in stark contrast to his father.
From the popular media, the picture is of an entitled rich scion in his father's shadow. Some of that is, of course, true. African safaris, for example, are by definition for the wealthy - a five-day jaunt to shoot a Cape Buffalo costs upwards of US$10,000. But the media's view of the Trump children, with their father never quite accepted in snooty Manhattan, has often been oversimplified.
"It is always more complicated," says Ms Blair, who teaches at Columbia University's Graduate School of Journalism. "I think growing up in what seems like a completely surreal yet, nevertheless, sort of regular childhood in Trump Tower, and then having it blown apart, would have had a heavy impact on him at the age of 12."
His parents' break-up came in 1990. His father was often not present. There were daily headlines; one of them had senior Mr Trump's new love, Ms Marla Maples, reportedly gushing: "Best sex I've ever had." His mother, Ivana, was distressed, his classmates made fun of him, and the paparazzi camped outside his school.
The young boy was packed off to boarding school and refused to attend the wedding when his father married Ms Maples in 1993.
He was close to his Czech grandparents. It was through his grandfather that he developed a love of the outdoors. And despite all the loathing liberals aim at him over his hunting pictures, these likely appeal to the gun ownership demographic which is heavily pro-Trump.
But years later, "he seems to have gone from a resentful and somewhat rebellious teen, turned the corner into young adulthood, and (is now) homing in on the family business; (he has) stopped his drinking and become not only loyal, but extremely loyal," noted Ms Blair.
"When you read that e-mail chain, he seems to be almost pathetically eager to... deliver to his dad this nuclear weapon," she told The Straits Times. "He seemed to have zero grasp that this was anything but a routine business move. There was no hint of any caution," she said.
"It was the same exact mentality that his father has had throughout his career - the only thing that matters is that you win or you lose... There is no other compass, ever."