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 America's elite boarding schools, upper-class offspring gain independence from high-achieving parents, prepare for the Ivy League, and learn how to be outstanding members of high society. But for the older Trump children, being sent away to boarding school provided some much-needed distance from their parents. Eric Trump and Donald Trump Jr. were whisked away to boarding school in the wake of Donald Trump's extramarital affair with Marla Maples. They attended The Hill School in Pottstown, Penn. Don Jr. found it a relief from the usual tabloid headlines and constant security guards. "When I went to boarding school, it all kind of went away," he told New York magazine. "All those inconveniences that I found obtrusive." He reportedly didn't speak to his father for a year or attend his 1993 wedding to Maples.

A few years later, 15-year-old Ivanka Trump followed a similar path out of her parents' hair and into Choate Rosemary Hall, an elite private boarding school in Connecticut. "I think my mom threatened to put me up for adoption a few times," she told Marie Claire in 2007. "[Then] I was all of a sudden in the prison of boarding-school life, and all my friends in New York were having fun."

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." 

On Father's Day 2020, Donald Trump Jr. interviewed his father and jokingly asked, "Which is your favorite child, and why is it Ivanka?" The POTUS diplomatically answered, "All the same, hundred percent." Don Jr. previously stated that Ivanka Trump is their father's favorite child in a 2015 interview with Barbara Walters, as siblings Eric Trump and Tiffany Trump seemingly laughed in agreement. Donald Sr. confirmed it himself in a 2004 profile for New York magazine: When the journalist asked Donald Trump "if there was any favorite-playing" among his children, Trump answered, "Come on! Daddy's little girl!" Though Tiffany was 11 years old at the time, Donald was referring to his oldest daughter. "Let me tell you one thing: Ivanka is a great, great beauty," he said, adding, "Every guy in the country wants to go out with my daughter."

Donald's remarks about his eldest daughter have raised eyebrows for years. Wwhen she was 16 years old and hosting the 1997 Miss Teen USA beauty pageant, Donald reportedly asked Brook Antoinette Mahealani Lee, who was Miss Universe at the time, "She's hot, right?" in reference to his own daughter, according to The New York Times. He also told Howard Stern (via CNN), "She's actually always been very voluptuous." Stern then called Ivanka "a piece of a**," to which Trump replied, "Yeah." In a 2006 appearance on The View, he also famously said, "If Ivanka weren't my daughter, perhaps I'd be dating her." Yikes!

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.

Like Ivanka Trump, Tiffany Trump tried on multiple hats outside of the family's traditional real estate path and its new political path. In 2011, at the age of 17, Tiffany released a pop song called "Like a Bird." The heavily-Autotuned song includes lyrics about "crawling through the liquid love." At the time, she expressed an interest in pursuing a professional music career and was working towards a full album in collaboration with German EDM producer Torsten Stenzel, according to Yello's "The secret history of Tiffany Trump's lost album." The fledgling songstress reportedly had eight additional track in the works, but "Like a Bird" never... took flight. 

Clearly, her debut single didn't turn her into Beyoncé overnight, and Tiffany eventually abandoned her dreams of pop stardom in favor of pursuing a more traditional Trump path: attending the University of Pennsylvania's Wharton School of Business — as Donald Trump, Donald Trump Jr., and Ivanka had — to pursue a BA in Sociology. While at Penn, she landed an internship with Vogue with a little help from big sis Ivanka, and made her runway debut during New York Fashion Week in 2016. In May 2020, Tiffany graduated with a JD from the Georgetown University Law Center in Washington, D.C.

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." 

Donald Trump Jr. made headlines by appearing in marketing materials for Desert Tech, a gun company operated by an extremist, polygamous religious sect. Starting on July 24, 2020, the company posted multiple social media posts and a promotional video which featured the first son shooting rifles in Utah. "Awesome time guys. Can't wait to do it again soon," Don Jr. commented on one of the Instagram posts. "Great being with you guys. Awesome stuff," he wrote under another.

One of the photos featured Donald, Jr. posing in a Desert Tech hat alongside the company's founder, Nicholas Young. According to CBS News, Young holds an influential position in religious sect The Order, which "has been deemed a hate group by the Southern Poverty Law Center" for its anti-Black and anti-LGBT teachings. Since Spring 2020, the U.S. government had been trying to seize Desert Tech's headquarters in the wake of an alleged billion-dollar fraud scheme perpetrated by several other high-ranking members of the sect. Although neither Young nor Desert Tech were directly implicated in any crimes related to that ongoing federal investigation, many criticized Don, Jr.'s association with the company.

In response to the backlash, Don Jr.'s representative released a statement, which read, in part, "Don routinely gets offers from 2nd amendment enthusiasts from around the country ... He had never met the owner of Desert Tech prior to going shooting with him, has no personal relationship with him, only spoke to him about shooting..." 

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."

Shortly after Donald Trump won the 2016 election, his wife Melania Trump and their son Barron Trump made headlines for choosing to stay at Trump Tower in New York while Donald moved into the White House. Melania and Barron stayed in Manhattan for nearly five months so that nine-year-old Barron could finish his school year at Columbia Preparatory and Grammar School, before moving to the White House in June 2017.

It's no surprise Barron would be reluctant to leave the Trump Tower, where he reportedly had "a whole floor to himself," as Town & Country claimed, while describing the New York to D.C. transition as "a downgrade." Of the move, Donald Trump confirmed his son's lack of enthusiasm about the downgrade. "He does love New York and he loves his school," he told People in 2016. "He does like what he's got right now. That would be a whole change of life." And while swapping a whole floor for a single bedroom probably didn't appeal to a kid who is accustomed to the high life, the coronavirus pandemic of 2020 seemed to make things even worse.

Asked by reporters in April 2020 how his son was dealing with shelter-in-place orders, Donald told reporters (via News 18), "[Barron] is like everyone else. I mean everything is shut down. He's in his room he's happy but he's not as happy as he could be."