Andy Scott and Carmen RibeccaMarch 16, 2018 3:33 ESTUpdated: Nov. 13, 2018 9:34 am EST
There was a time when Donald Trump Jr., the eldest son of President Donald J. Trump and ex-wife Ivana Trump, could slip under the radar unnoticed, despite a sketchy past filled with partying and personal problems. Those days are over, but the sketchiness remains as Trump Jr. has become a major figure in the congressional investigations into Russian meddling in the 2016 election.
But even before the federal government started poking around into the life of Ivanka Trump's lesser known older brother, the general public has long been curious about him. After all, he is a scion of one of America's wealthiest citizens. So, what was his childhood like? Does he have the same ambitions as his father? Does he speak Czech?
Okay, you probably weren't wondering about that last one, but we answer that question and more as we dig deep into the untold truth of Donald Trump Jr.
Like father, like son
Vanessa Trump Donald Trump Jr. Children
2005 was a big year for both Donald Trump and his son, Donald Trump Jr. In the span of 11 months, they both married former models at Trump's married famous Mar-a-Lago resort in Florida. The senior Trump, of course, took the hand of former model Melania Knavs, in January of that year, while his son would walk down the aisle in November with model-actress Vanessa Haydon. According to a 2017 profile in The New York Times, dad introduced the couple to each other at a fashion show in 2003, although neither of them remembered the encounter until they were reintroduced six weeks later by a mutual friend.
At the time of their nuptials, the couple's wedding announcement said Haydon was studying to receive a bachelor's degree in psychology at Marymount College in Manhattan. She worked for the prestigious Next Model Management and Wilhelmina Models, and at one point dated Oscar-winner Leonardo DiCaprio. She's now reportedly a stay-at-home mom who helps take care of the couple's five children.
On March 15, 2017, the couple announced their separation via a joint statement to Page Six, but before we get to that, let's dig into some of the untold truths of the man who now runs his father's business empire.
He allegedly got his wife's engagement ring for free
Donald Trump Jr. Vanessa Trump
While their nuptials landed a coveted spot in The New York Times' weddings section, their engagement was trashed by rival newspaper the New York Post. In an article titled "Trump Jr is the cheapest gazillionaire," sources alleged the "heirhead" (get it?) snagged a $100,000 engagement ring for free so long as he agreed to make promotional appearances for the jeweler who designed the ring, Bailey, Banks & Biddle. According to sources for the Post, paparazzi and TV camera crews were invited to what it described as a "less-than-romantic" and "taste-deprived" unveiling of the ring at the Short Hills Mall in New Jersey, even though Trump had allegedly popped the question to Haydon about two months prior.
Nope. Romance definitely isn't dead.
He's fluent in Czech
Donald Trump Jr.
According to multiple profiles of the Trump family, Trump Jr. grew especially close to his maternal grandfather, Milos Zelnicek, when he was a young boy. According to New York magazine, junior's maternal grandparents spent six months of every year living with the kids in Trump Tower, and The New York Times reported that Trump Jr. traveled to Prague for six-to-eight weeks every summer, where Zelnicek "schooled him in camping, fishing, hunting and the Czech language."
Trump's relationship with Zelnicek proved valuable for a number of reasons. "He needed a father figure," Ivana told The New York Times in 2017. "Donald was not around that much. They would have to go to his office to say hello to him before going to school." Trump Jr. said spending time in the woods allowed him to escape the often claustrophobic atmosphere of New York City.
According to New York magazine, Zelnicek died in 1990, which was an especially fraught time for Trump Jr. He was trying to process the fallout from his father's corporate bankruptcy filing, as well as his dad's scandalous affair with Marla Maples, which ended his marriage to Ivana. And speaking of that tabloid frenzy…
He didn't speak to his father for a year
Donald Trump Jr. Ivana Trump
According to New York, Trump Jr. was just 12 years old when his parents' messy divorce splashed all over the covers of the New York tabloids. It wreaked havoc on the boy's life.
"You're not quite a man, but you think you are," he recalled. "You think you know everything. Being driven into school every day and you see the front page and it's divorce! THE BEST SEX I EVER HAD! And you don't even know what that means. At that age, kids are naturally cruel. Your private life becomes very public, and I didn't have anything to do with it: My parents did."
Trump Jr. blamed his father for the divorce and did not speak to him for a year, according to New York. He later claimed his silence was fueled partially by his living arrangement. "When you're living with your mother, it's easy to be manipulated. You get a one-sided perspective," he said.
He was arrested for public drunkenness
Donald Trump Jr.
According to a 2004 profile piece in New York magazine, Trump Jr. developed a reputation for being a heavy drinker at his father's alma mater, the University of Pennsylvania. "To be fairly candid, I used to drink a lot and party pretty hard, and it wasn't something that I was particularly good at," he said. "I mean, I was good at it, but I couldn't do it in moderation."
After graduating from college, Trump Jr. took a year off and moved to Aspen, Colo. where he tended bar and continued to drink. In 2001, he was arrested for public drunkenness and spent 11 hours in jail while celebrating Mardis Gras in New Orleans.
"I think, like anyone else, I made my mistakes," he told The New York Times in 2017. "We have to be honest with ourselves. I'm not good at it, moderation. You have to have the conversation, be a realist, and say, 'I guess I'm not doing myself any favors.'"
He has reportedly remained sober since 2002.
Some people thought he'd never turn it around
Donald Trump Jr.
Because of his wild partying days, some weren't so sure the eldest Trump son would become the businessman he is today. "I used to really think that Donny would one day just get on a boat and sail away and leave this world. Those periods when there was the drinking were his way of escaping," a person who knew the Trumps told New York. "I was pretty shocked when I realized how deep some of his problems have gone. I'm so happy he turned a corner." The magazine reported that even some family members didn't think Trump Jr. was destined to work with his father's real-estate business.
Trump Jr. says he had no doubts. "I knew that it was something I wanted," he told New York. "I was following my dad around from a young age. I don't know if it's genetic, or just because I was surrounded by it, but I was always fascinated with building and construction and development. I guess I just wanted to make sure that I was making the right decision."
He used to maintain a low profile
Donald Trump Jr. Donald Trump Ivanka Trump
For reasons positive and, uh, not so much, Trump Jr. now has to fight hard to avoid the national spotlight, but there was a time when he was actually able to stay out of the press. "When I was younger, I went out of my way to avoid any kind of media attention," he told New York in 2004. "To this day, I meet people and they're like, 'I didn't know he had a son! You mean Ivanka's not the only one?'" He continued, "She did her modeling thing, she was out there a little bit more. But if there was a reporter within 100 miles, I was in the background somewhere, trying not to be seen."
Something tells us he wishes he could go back to those days right about now.
A hunting trip to Africa sparked global outrage
Eric Trump Donald Trump Jr.
Trump Jr. came under fire in 2012 after TMZ obtained photos of a hunting trip he and his brother, Eric Trump, took to Zimbabwe the previous year. A photograph depicting Trump Jr. holding the tail of an elephant they'd killed sparked outrage from animal rights groups. Even the boys' father seemed a bit dumbfounded by the foray, telling TMZ, "My sons love hunting. They're hunters and they've become good at it. I am not a believer in hunting and I'm surprised they like it."
Despite the backlash, Trump Jr. says publicity from the controversy yielded some benefits. "There were people who I didn't know who were hunters. And, from that perspective, I get invited [to hunt] a lot," he told The New York Times. He added, "Too much of hunting has turned into the notion of the kill. It's a component, the meat. But so much is experiential, so much is relationships. It is sitting in a duck blind with seven people, cooking breakfast. For me, it's been a great way to see the world. The least interesting part is the three seconds it takes to pull the trigger."
He's highly controversial on Twitter
Donald Trump Jr.
Remember when we said, "Like father, like son?"
Well, during his dad's presidential campaign, junior got into a heap of trouble for posting controversial messages and memes on Twitter. Perhaps his biggest oops occurred in September 2016, when he posted an image comparing Syrian refugees to a bowl of Skittles. The image said, "If I had a bowl of Skittles and I told you just three would kill you, would you take a handful? That's our Syrian refugee problem." Alongside the since-deleted post, Trump Jr. tweeted, "This image says it all. Let's end the politically correct agenda that doesn't put America first."
The tweet created an uproar, but Trump Jr. defended his actions, claiming (via ABC News), "To me it was a simple metaphor. You know people will today make what they want of anything, and they see the worst in everything and they look for subtext that doesn't exist."
He has continued to ignite controversy on Twitter. There was the time he live-tweeted fired FBI Director James Comey's testimony before the Senate Intelligence Committee in June 2017; and the time he shared the full contents of an e-mail exchange that reportedly contained evidence that he had met with a Russian lawyer who allegedly had damaging information about Democratic presidential candidate Hillary Clinton.
He claims he doesn't talk to his father about business
Donald Trump Melania Trump Barron Trump Donald Trump Jr. Ivanka Trump
In January 2017, amid a flurry of questions regarding conflicts of interest, then-President-Elect Trump agreed to hand over his business dealings to his two sons and to Trump Organization Chief Financial Officer Allen Weisselberg.
Although the move raised a few eyebrows to those on the left, his eldest son has insisted on multiple occasions that he barely speaks to his father now that he's president of the United States. "I basically have zero contact with him at this point," he said in March 2017, according to NBC News.
He reiterated this stance to The New York Times in July 2017. "I haven't spoken to him. Maybe just to say hello. It feels trite. I feel ridiculous bothering him." He added, "Where is the breaking point? If I see him once a month, is that too much? Once a year? My point is, it's a no-win scenario. But, in the end, we both fully recognize that what he is doing now is far more important than absolutely anything going on in the business. And we will conduct ourselves accordingly."
His half baked partnership with WikiLeaks didn't go well
Donald Trump Jr.
As a member of his father's presidential campaign, Trump Jr. was caught in the dragnet of the FBI's investigation into possible Russian collusion. In December 2017, he testified before both the House and Senate Intelligence Committees, which are also conducting their own parallel investigations. Prior to those testimonies, however, The Atlantic broke the story of secret correspondence between Trump Jr. and the hacktivist organization, WikiLeaks, which seemed to show that Trump Jr. was once again "eager to obtain damaging information about Hillary Clinton, despite its provenance." (He previously came under scrutiny after a meeting with a Russian operative who claimed she had incriminating information on Clinton.)
Trump Jr. responded by publishing his full correspondence with WikiLeaks on Twitter, a move that also lead to the revelation that he'd spoken with other high-level campaign staffers about the secretive messages. According to Vox, this not only further damaged the embattled campaign, but also served to prove that Trump Jr.'s possible attempt at collusion was not only bumbling, but ineffective to boot. Whoops.
Did we mention he really likes Twitter?
Donald Trump Jr.
In February 2018, Trump Jr. used Twitter to achieve the impossible: He turned a meme about memes into another meme. Thanks to a typo he made while attempting to mock The Washington Post's motto "Democracy Dies in Darkness," the internet's face subsequently melted off after Trump Jr. tweeted the phrase "democracy dies in dankness."
But as we've already mentioned, Trump Jr.'s been a busy boy on social media long before #danknessgate. For example, just a week earlier, he made it a point to drag Hillary Clinton's viral Grammy appearance in which she read a passage from Fire and Fury, the scathing expose of his father's first year in office. A few months before that, Trump Jr. thought he'd posted a clever Halloween tweet featuring his 3-year-old daughter, Chloe, in which he wrote, "I'm going to take half of Chloe's candy tonight & give it to some kid who sat at home. It's never to [sic] early to teach her about socialism."
It didn't go over well, leaving him on the defensive against "blue checkmark SJWs," and "PC lib crap." But none of Trump Jr.'s Twitter controversies have ever slowed down his limited-character rantings, which is perhaps the way in which he is most like his old man.
He's literally a housewarming gift for the wealthy
Ivanka Trump Donald Trump Jr.
A January 2018 report from The Guardian revealed an unusual — and possibly unethical — marketing tactic being used by Trump Towers' newest build in India: "Buy a flat, meet Trump junior" — That's the slogan used by M3M Tribeca Developers, an Indian franchisee of the Trump Organization that is building the "ultra luxury residential project" near Delhi, and whose director was quoted saying, "About an initial 100 buyers will fly to the US where Donald Trump Jr will host them."
Aside from that being an odd perk to plunking down serious cash for a swanky flat, it could be problematic for the White House, according to Citizens for Responsibility and Ethics in Washington Chairman Norman L. Eisen, who called the practice "an ethics atrocity." Eisen added, "Access to the first family should not be for sale. It's particularly inappropriate because we know he is in constant communication with his father, so it does create a conduit to attempt to influence the president and one of his closest confidants and family members." Yikes. That sounds bad. Maybe he could just send them one of those greeting cards that records your voice instead.
His childhood was kind of sad
Donald Trump Donald Trump Jr.
With the publishing of her memoir, Raising Trump, Trump Jr.'s mom, Ivana, pulled the curtain back on a few seemingly painful memories from her eldest son's upbringing. During a promotional interview for the book with ABC News, Ivana told the story of how she was the one to name all of the children, including Don Jr. even though his father initially protested, citing his worry over the fact that the boy might turn out to be "a loser."
On top of that, Ivana also revealed to The New York Post that during her ugly divorce from Donald, he once informed her that he was "keeping Don Jr.," but after about a half hour, the boy was promptly returned to his mother. "I knew Donald would not know what to do with him," Ivana told The Post. Sad, right?
One of Donald Jr.'s college dorm neighbors, Scott Melker, posted a story to Facebook (via The Concourse) back in 2016 that echoes this same tense father-son relationship. According to Melker, many onlookers watched as Donald arrived to pick up Donald Jr. to attend a Yankee game, only to be shocked when Donald allegedly "slapped [Don Jr.] across the face" for the apparent sin of wearing a jersey. "Put on a suit and meet me outside," the elder Trump allegedly said before walking out of the dorm. Not surprisingly, the Trumps have denied the story, but when put into context of Ivana's icy childhood anecdotes, is it really that hard to believe?
Unhappily ever after
Donald Trump Jr. Vanessa Trump
On March 14th, 2018, Page Six delivered the dirt that Donald Trump Jr. and his wife of more than a decade, Vanessa Trump, were separating. In a statement published by the tab, the Trumps said they "decided to go [their] separate ways" and still "have tremendous respect for each other" and would like "privacy during this time." One interesting tidbit about the filing, which Vanessa initiated, is that she sought "an uncontested proceeding." That's according to TMZ, who suggested the reason for that may be that the power couple has a strong prenuptial agreement. However, Vanessa later reversed that filing status and went ahead and hired a famed criminal defense attorney to represent her in the divorce, so questions remain.
As for why this is all happening? The truth is still untold, but anonymous sources abound and those insiders have all kinds of theories: Don Jr. is away hunting too much; Vanessa doesn't like the political spotlight; Don Jr.'s public grandstanding and Twitter trolling have changed him as a person.
While the "why" is purely speculative at this point, one thing is clear: Don Jr. didn't wait long to move on. By early May, Page Six reported that he'd already been dating Kimberly Guilfoyle "for a few weeks." At the time, Guilfoyle was a co-host Fox News' The Five. She's since left the network, and the pair have gone so awkwardly public with their relationship, that we now know they refer to each other as "Pooh Bear" and "Junior Mint." All of the cringe.
Is Aubrey O'Day trying to tell us something?
Donald Trump Jr. Aubrey O'Day There's More!
After news of Donald Trump Jr.'s pending divorce broke, the rumor mill lurched to life with the sordid tale of his alleged affair from "late 2011" to early 2012 with singer and Celebrity Apprentice contestant Aubrey O'Day. According to Us Weekly, Trump Jr. met O'Day during season five of the reality TV competition, and they quickly fell so in love that they were even "trying for [a baby]," according to an insider.
Their flame was apparently snuffed out when Trump Jr.'s wife "found email exchanges" between the two, and they went their separate ways. Trump Jr. pieced his marriage back together for the next six years, and O'Day went on to a high profile romance with Jersey Shore star Pauly D.
Trump Jr. and O'Day haven't publicly commented on their rumored romance, although O'Day has apparently dropped some hints (via The Daily Beast) in the form of surreptitious social media messages, a song boldly titled "DJT," and the following lyrics on another track: "You said that was the reason for your pain / But you were scared to ruin your family's name / Your wife's the only one glad we are over." Hmm…
Did he fall on the sword for the family's political dreams?
Donald Trump Jr. continues to be a successful fundraiser and political hype man for right wing candidates. However, according to a June 2018 GQ profile of the eldest Trump child, his political career is something no one would have predicted.
"I don't remember him having political views," one of Trump Jr.'s college friends told the mag. "I didn't see anything emerge until the campaign." Another former classmate agreed, saying, "What's surprising is that the tone and the rhetoric are so … Fox News-ish. The anger is surprising. None of us would've guessed that he would've been so outspoken in either direction." Another Trump campaign staffer, Charlie Kirk, even went a step further, alleging that Trump Jr. perhaps wasn't thrilled about joining the political fray. "He got dragged into this fight out of loyalty," Kirk said.
The irony in all of this, of course, is that Trump Jr. has become one of the main targets of special counsel Robert Mueller's investigation into possible collusion between Russia and the Trump campaign. And as of this writing, it's looking more and more like Trump Jr. could face some very serious legal penalties for his alleged communications with Russian actors who attempted to interfere with the 2016 U.S. Presidential Election. Ruh-ro.