Inside The Secret Lives Of The Trump Children

Even before Donald Trump took the nation's top job, the Trump family was one of the most famous families in the United States. Built on a multigenerational luxury real estate empire and tied together by a string of tabloid-fodder marriages, the family has been well-acquainted with publicity and controversy for decades.

Donald's three oldest children with ex-wife Ivanka Trump — Donald Trump Jr., Ivanka Trump, and Eric Trump — have drawn criticism and mentions of the word "nepotism" for their active roles in their father's political administration and business dealings. Tiffany Trump, Donald's only daughter with his second wife Marla Maples, also speaks in support of her father but often falls under the radar in the Trump clan. And Barron Trump, the youngest, and only son with current wife and Melania Trump, is Donald's only child to reside in the White House.

Despite their silver spoons and silver platters, has money bought happiness for the famous family? From the Trump Tower to the White House, let's observe some of the lesser-known stories of the Trump brood.

In Ivana Trump's memoir Raising Trump, she claimed it was her decision to name Donald Trump Jr. after his father. At the time, the older Donald reportedly protested, "You can't do that! What if he's a loser?" The very start of Don Jr.'s life, according to GQ, was similarly fraught. The mag reported that shortly after he was born on New Year's Eve 1977, his father went home to ring in the new year and his mother "put a boa and a mink over her hospital gown" and went to visit a friend on another hospital floor. Then, under the watch of his first nanny, Don Jr. "broke his leg and nearly drowned."

Ivana wrote in her book that an adolescent Don, Jr. "expressed his pain with anger, and he was really angry." During college, he had a reputation for getting into drunken fights. In 2010, the younger Donald told a journalist he felt pressure to live up to his father's name. "You want to please someone like that, and he's a perfectionist," he said (via GQ), adding, "There's definitely always that shadow that follows you around, like how is this guy — the son of someone so good at what he does — going to act?"

In his own 2019 memoir Triggered: How the Left Thrives on Hate and Wants to Silence Us, Don Jr. wrote that he eventually "[gave] up drinking for good," after realizing that given his family's history with destructive alcoholism, his partying was "a recipe for disaster." 

Over the years, Ivanka Trump has drawn attention not only as Donald Trump's daughter, but also as a model, fashion designer, judge on The Apprentice, and an active participant in her dad's presidential administration. But his other daughter, Tiffany Trump, hasn't been exposed to nearly as much limelight. Because of their 12-year age difference and the fact that Tiffany was born as a result of Ivanka's father cheating on her mother, outsiders may assume there's some bad blood between the half-sisters. But based on Ivanka's first book, The Trump Card: Playing to Win in Work and Life, Ivanka seemed to take her big sister role in stride.

When a 15-year-old Tiffany told Ivanka about her anxiety over asking their father for an allowance, Ivanka took matters into her own hands. "Big Sis did an end-around to save Tiffany the trouble," she wrote in her book, adding, "I didn't tell her, of course, but I went to our father and suggested he think about surprising Tiffany with a credit card for Christmas, with a small monthly allowance on it." The plan worked and, according to Ivanka, the gesture built Tiffany's gratitude for and trust in her big-sis confidant.

Over the years — and particularly since she's been a member of the first family — Ivanka Trump has committed some fashion faux pas that have less to do with style and more to do with politics. Following Donald Trump's election in November 2016, Ivanka appeared with the Trump family on 60 Minutes, wearing a $10,800 bracelet from her own line, which was later highlighted in a promotional email from the same line. Of the backlash, which, according to CBS News included questions "about whether it's appropriate for her to use news interviews to promote her business," President Trump said, "Who cares?"

This was the first of many instances in which Ivanka and other family members were criticized for blurring the line between politics and private business interests. Then, during his first address to Congress in 2017, Donald focused on American jobs and American-made products. His catchphrase for the address was "Buy American and hire American." For her own appearance at the event, Ivanka was deemed hypocritical for wearing a $3000 dress by French designer Roland Mouret (shown above). Ivanka now-shuttered fashion line was further criticized by outlets including The Washington Post, which pointed out that "all of its dresses, shoes and handbags were produced in other countries, such as China and Indonesia." 

The Donald J. Trump Foundation was a private organization that dissolved in 2019 as the result of a court order. In 2017, the foundation was criticized for funneling $100,000 of donations for child cancer patients through the Eric Trump Foundation into Donald J. Trump Foundation revenue. According to Forbes, More than $500,000 in donations for sick children were re-donated to charities, including organizations that were directly tied to Trump family business interests and those who paid to host golf tournaments on Trump properties. Eric started the Eric Trump Foundation in 2007 to raise money for the St. Jude's Children's Research Hospital, and stopped fundraising once his father was elected president.

In 2018, the Donald J. Trump Foundation agreed to shut down in the wake of its controversies, which included the above misuse of funds, as well as other instances where charitable contributions were allegedly used for business purposes at other Trump enterprises. "The Trump Foundation [functioned] as little more than a checkbook to serve Mr. Trump's business and political interests," then-U.S. Attorney General Barbara Underwood said at the time (via AP News). In November 2019, New York Attorney General Letitia James issued a statement detailing the court order against Trump and his three eldest children, Donald Trump Jr., Eric Trump, and Ivanka Trump, who all served as Trump Foundation directors, which stipulated, among other restrictions that they "undergo compulsory training to ensure this type of illegal activity never takes place again."