Donald Trump Jr.'s Conflicted World: How His Parents' Divorce Drama and His Relationship With Dad Shaped His Life

The real estate scion was exposed to a lot of tabloid headlines at a very early age and spent a significant amount of time being mad at his father

By Natalie Finn Mar 22, 2018 1:00 PMTags
Donald Trump, Donald Trump, Jr., The ApprenticeNBC

For the most part, Donald Trump's children have had nary a negative thing to say about what it's like having Donald Trump for a father.

Sure, he was always working, but when you called him at the office he just patched you into his meeting. Sure, he spent a lot of spare time golfing, but then you just learned how to golf too. You never wanted for anything, but at the same time, you inherited a fierce work ethic. And at the end of the yellow brick road, after Wharton or Georgetown, there was a job waiting for you at the Trump Organization. 

"It's definitely not always easy," Donald Trump Jr. said during a sit-down with his dad and sister Ivanka Trump for Forbes magazine in 2006, when the kids were just getting involved with The Apprentice and Trump asked his son if it was easy or difficult having a famous father. "There's definitely advantages to it. We've got to be spoiled, hopefully in all the right ways, getting great educations, getting to travel the world—but I think you've done an amazing job, and Mom's done an amazing job, really getting us to work for everything we ever really wanted in our lives, and I think that's why we're successful at what we do today."

"It's tough because you're tough—but in a good way," added Ivanka with a million-dollar smile.

Twelve years ago that was all viewed through a promotional, pop culture lens, no follow-up questions needed. But the son who shares a name with the real estate tycoon and reality-TV star turned president of the United States remains a walking example of just how "not always easy" it could be growing up Trump.

Don Jr., whose wife Vanessa Trump filed for divorce last week after 12 years of marriage, was 12 years old when his own parents divorced in legendarily acrimonious fashion.

Czech model and Olympic skier Ivana Trump had married Donald Trump on April 7, 1977, and their eldest son was born that New Year's Eve. They'd go on to have two more children together, Ivanka and Eric Trump, and become the toast of New York society in the 1980s. The Trump name became synonymous with over-the-top luxury, buoyed by "The Donald's" affinity for gold, his bravado and his boundless enthusiasm for self-promotion. Together Donald and Ivana were the power couple, the real-life Carringtons of the commercial real estate scene.

In his 1987 book The Art of the Deal, Trump said (via ghost writer Tony Schwartz), "I adore [my kids], but I've never been great at playing with toy trucks and dolls. I tell Donny I'll be home as soon as I can, but he insists on a time. Perhaps he's got my genes: the kid won't take no for an answer."

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In 1990, Ivana was overseeing the renovation of the Plaza Hotel, which Trump had bought for $400 million. Noting that they were restoring the hotel to its original luxurious glory, not adding glitz that would be more suitable for an Atlantic City casino, Trump told Playboy that year, "So I don't use glitz in all cases. And in my residential buildings I sometimes use flash, which is a level below glitz." Asked what all of the real estate and toys he had amassed meant to him, he quipped, "Props for the show."

Pressed to explain, he said, "The show is 'Trump' and it is sold-out performances everywhere. I've had fun doing it and will continue to have fun, and I think most people enjoy it."

(Incidentally, when the subject of running for president came up, he twice said he didn't want the presidency, but expanding on the subject of politics he added, "Well, if I ever ran for office, I'd do better as a Democrat than as a Republican–and that's not because I'd be more liberal, because I'm conservative. But the working guy would elect me. He likes me. When I walk down the street, those cabbies start yelling out their windows.")

Trump told interviewer Glenn Plaskin that his marriage was "just fine. Ivana is a very kind and good woman. I also think she has the instincts and drive of a good manager. She's focused and she's a perfectionist." Asked about her as a wife, versus as a manager, Trump replied, "I never comment on romance…. She's a great mother, a good woman who does a good job."

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Asked what marriage meant to him, whether it specifically meant "monogamy," he said, "I don't have to answer that. I never speak about my wife—which is one of the advantages of not being a politician. My marriage is and should be a personal thing." Trump continued, "I think any man enjoys flirtations, and if he said he didn't, he'd be lying or he'd be a politician trying to get the extra four votes. I think everybody likes knowing he's well responded to. Especially as you get into certain strata where there is an ego involved and a high level of success, it's important. People really like the idea that other people respond well to them."

That interview appeared in the March 1990 issue of Playboy, so it was conducted—reportedly over the course of 16 weeks—some months beforehand. Because by February 1990, the Trumps' marriage had imploded. Their separation was announced Feb. 11.

According to the Chicago Tribune, it all came to a head when the Trumps went to Aspen in December 1989 for their holiday ski vacation and Donald split his time between his wife and 26-year-old model Marla Maples—and then the three of them all ended up at the same party and none of them left. Ivana had words with Maples at the most popular restaurant in town and proceeded to have an argument with her husband at the edge of the slopes in front of a growing crowd of intrigued onlookers.

"I feel for her," Maples said of Ivana, recalling the Aspen confrontation in Vanity Fair's November 1990 issue. "I think she must have known in her heart it wasn't about me. There would never have been any discussion of my and Donald's friendship if things had been good... I was his friend for so long and I constantly said to him, 'Stay and make it work. Don't give up the marriage—you've got your kids.'"

At the time, funny enough, op-ed writers and society columnists welcomed the juicy respite from all the heated political news of the day.

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''He likes Ivana very much, but it just wasn't working out,'' a Trump spokesman told The New York Times a few days after the separation announcement in February 1990. ''So for the good of all, he decided to leave."

Also per the Times, the Trumps had a prenuptial agreement that his legal team said had been amended several times over the years, with the most recent deal stipulating that Ivana would get $20 million, their 47-room country estate in Greenwich, Conn., and custody of the kids.

Trump's reported estimated net worth at the time was between $1.5 billion and $4 billion.

Ivana's lawyer called the prenup "unconscionable and fraudulent," while a PR spokesman for Trump called it "100 percent enforceable in a court of law."

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At one point, Ivana, who was vice president of the Trump Organization and president of the Plaza Hotel, was briefly barred from entering the Plaza until her lawyers "negotiated and won her admittance," her rep told the Times, calling the whole situation "quite unseemly."

Trump had also reportedly denied being more than friends with Maples (whom he'd go on to marry in 1993) or Catherine Oxenberg, another woman he was rumored to have romanced.

Ivana then made headlines by lunching with Trump's mother and sister on Valentine's Day at a celebrity-friendly NYC hot spot. According to the Washington Post, she countered the prenup with a demand for $150 million, the Plaza Hotel, and a private jet—as well as custody of Don Jr., Ivanka and Eric.

The final dissolution of their assets had yet to be decided, but the Trumps' divorce was granted on Dec. 11, 1990, on the grounds of "cruel and inhuman treatment" on Donald's part, the New York Times reported.

"I wish Ivana the best," Trump said at the time. "I have no doubt that she will do very well in the years to come." Ivana reportedly agreed to not publicly discuss the particulars of the marriage—though she had automatically become one of the world's most famous divorcées. 

Trump attorney Jay Goldberg told the Times that the "cruelty" cited by the judge was Ivana having to see her future ex-husband squire Maples around in recent months. "That's the cruelty, that it caused Mrs. Trump to have anxiety and sleeplessness," Goldberg said. "The claim was that media attention to the relationship supposedly between himself and Miss Maples in 1990—that's important, 1990—caused Mrs. Trump to endure pain and suffering that amounts to cruel and inhuman treatment."

Meanwhile, Don Jr. was old enough to be aware that the breakdown of his parents' marriage had become a tabloid sensation. Eric later remembered that the divorce brought him and his siblings closer together, telling New York that his older brother "kept tabs on everything that my grandfather taught him over the years and that I was too young to appreciate. And I'm definitely closer to Ivanka because of it. She took me under her wing and raised me, took me shopping, tried to make me cool." And Ivanka even said that she felt the divorce brought them closer to their father.

Ron Galella/WireImage

But Don Jr. was barely 12 when rumors of his dad's infidelity started taking up newspaper real estate and, siding with his mom in the war of words—fueled by what Ivana told New York Daily News columnist Liz Smith and what Donald was telling Cindy Adams of the rival New York Post—he didn't speak to his father for a year. He was also very close to his maternal grandfather, Milos Zelnicek, who along with wife Maria lived half the year at Trump Tower. Don Jr. and Eric also made regular summer trips to the Czech Republic (then Czechoslovakia) to spend time hunting and fishing at the family's home outside of Prague, and Milos died while his daughter was going through divorce proceedings.

"Listen, it's tough to be a 12-year-old," Don Jr. told New York magazine in 2004. "You're not quite a man, but you think you are. 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."

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He admittedly blamed his father, who had moved out of the family's Trump Tower triplex and onto a lower floor, for the divorce.

"And that's, perhaps, not actually what it was," he acknowledged. "But when you're living with your mother, it's easy to be manipulated. You get a one-sided perspective."

It was also a tender age to realize, as he told the Times in 2006, "Sometimes being a Trump, everyone kind of wants to see you fail."

Ivana Trump recalled putting on a brave face for her kids. "When we did the separation, one thing I made sure of, I never, ever show any panic," she told New York. "I never cry in front of them, I never scream in front of them. Because if they would see that I'm in a panic, they panic, too. Sometimes I just wanted to [she made two fists] kill or scream. But I did not do it. That was No. 1. No. 2: I never, ever spoke one bad word against Donald. It's the only father they have and they will have. So they were my two rules."

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Conceivably to get them out of the fray, Ivana, who had been awarded full custody, decided on private boarding schools for the kids—Choate for Ivanka, The Hill School in Pennsylvania for Eric and Don Jr, after which Don Jr. attended his dad's alma mater, Penn's Wharton School, and partied like your average frat boy. After he graduated, Don Jr. did something that truly separates him from his siblings: he left the fold for awhile. He moved to Aspen to tend bar and ski, and get into a little trouble. Or a little more trouble, that is.

"To be fairly candid," Don Jr. told New York Magazine in 2004, "I used to drink a lot and party pretty hard, and it wasn't something that I was particularly good at. I mean, I was good at it, but I couldn't do it in moderation. About two years ago, I quit drinking entirely. I have too much of an opportunity to make something of myself, be successful in my own right. Why blow it?"

He reflected to The New York Times in March 2017, "I think, like anyone else, I made my mistakes. 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."

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In February 2001 he was arrested for public drunkenness in New Orleans during a Mardi Gras celebration and spent 11 hours in jail. In December 2002 he needed stitches after a fellow patron at a comedy club, apparently annoyed by Don Jr.'s boisterousness (and because his beer had splashed on a woman at a nearby table), smashed him in the head with a beer stein.

"I'm going to get those motherf--kers for sure," Trump Sr., fired up by the possibility of litigation, told the New York Daily News about the two men who hurt his son. (They had been charged with assault.) "I'm going to sue their ass off." Told that his son was supposedly being very rowdy and needed escorting out of the club, Trump fired back, "It's not his style. He's very soft-spoken. A guy laughs at a comic and you hit him on the head?"

In 2001 Don Jr. went to work for the Trump Organization, eventually becoming executive vice president for development and acquisitions. (Since his father became president, he and Eric have been tasked with running the family business, with Don Jr. heading up most international ventures and commercial licensing. He told the Times two months after his dad took office that, despite his fervent public defense of his father and his tendency to lash out at their critics on Twitter, he hadn't talked to Donald Sr. except "maybe just to say hello. It feels trite. I feel ridiculous bothering him.")

He explained his sojourn to Aspen as a brief break, not as a meaningful move to distance himself from the family.

"...I knew that [working for the family business] 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."

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Despite his loyalty to his father (which has become fairly all-consuming lately), it sounded important to Don Jr. that he maintain his own identity, separate from the brand.

"I think I probably got a lot of my father's natural security, or ego, or whatever," he told New York. "I can be my own person and not have to live under his shadow. I definitely look up to him in many ways—I'd like to be more like him when it comes to business—but I think I'm such a different person, it's hard to even compare us. His work persona is kind of what he is. I have a work face, and then there's my private life."

At the same time, he was firmly back in the fold. Marveling at the entitlement on display in the 2003 documentary Born Rich, in which Ivanka comes off as the least affected of the bunch, Don Jr. exclaimed, "I couldn't believe it. I was like, 'Do you hear the words that are coming out of your mouth? Are you out of your mind?' Their parents gave them anything they could have ever wanted. And they hate their parents! I'm not close with any of them, but it's very one-degree-of-separation." 

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For that same New York profile, the elder Trump practically called Ivanka his favorite, but of course he'd no sooner say anything negative about one of them than they would about him.

"I'll tell you what I've learned: Children are tough. Much tougher than people think," Trump mused. "I think this: I'm a really good father, but not a really good husband. You've probably figured out my children really like me—love me—a lot. It's hard when somebody walks into the living room of Mar-a-Lago in Palm Beach and this is supposed to be, like, a normal life. But they're very grounded and very solid.

"The hardest thing for me about raising kids has been finding the time. I know friends who leave their business so they can spend more time with their children, and I say, 'Gimme a break!' My children could not love me more if I spent fifteen times more time with them."

"Donald wasn't really interested in the children until he could talk business with them," Ivana Trump said at a benefit dinner in October 2016, per the NY Daily News. She says she raised the kids, and "when they turned 21, I handed them over to him and said, 'Here's the finished product. You can take them from here."

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So, they went to work for dad, built-in quality time, answering what Ivanka called "the siren's call" to work on the best projects in the world. (Tiffany Trump, his daughter with Maples, just started law school last year. Son Barron Trump, with third wife and first lady Melania Trump, just turned 12 and is the first first son since John F. Kennedy Jr. to live in the White House.)

"My father's not the type of person that teaches you by saying, 'Come here, son. I'm going to tell you about real estate,'" Trump Jr. explained to the New York Times in 2010. "You learn by watching it. If you don't pick it up, it's your problem." Asked if he felt his dad was harder on him than on other employees, he said, "I think so because he expects a lot from us. He holds us to a very high standard because he doesn't like poor reflections on himself. He's very tough, but also fair."

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Like father, like son, Don Jr. made his own tabloid headlines when he proposed to Vanessa, a model and actress he'd met at a fashion show in 2003. He had accepted a $100,000 diamond ring for free from New Jersey jeweler Bailey, Banks & Biddle in exchange for doing a public proposal at the shop in the Short Hills Mall—and people had some opinions about it.

Trump took his son to task on Larry King Live, reminding him, "You have a name that is hot as a pistol, you have to be very careful with things like that."

In January 2005, Trump married Melania at his Mar-a-Lago estate and that November, Don Jr. and Vanessa followed suit. The couple welcomed their first child together, daughter Kai Madison Trump, in 2007. 

The end of Don Jr.'s marriage was followed by Page Six's bombshell report this week that the real estate scion had an affair with former Danity Kane singer Aubrey O'Day, whom he met when she was a contestant on Celebrity Apprentice in 2011. (That in turn prompted a revisit of her 2013 song "DJT" to dissect for clues.)

On Monday, amid the flurry of cheating headlines, O'Day posted a photo of herself in her underwear on Instagram with the caption, "I'm only interested in the things money can't buy." Perhaps she meant the truth, or it was a reference to Apprentice's "For the Love of Money" theme song—or both. (Otherwise, neither she nor Don Jr. have commented publicly.)

Page Six has sources saying that the Trump Jr. marriage was in trouble before O'Day came along, and that Don Jr.'s dad told him to get it together and stick with his wife, who was pregnant with their third child. Vanessa and Don Jr. are now parents of five, with their youngest, Chloe, having been born in June 2014.

But if normal, relatable issues hadn't hastened the end of their marriage before, the strains of the 2016 presidential campaign—and Trump's surprise win—didn't help anything. While the Trump kids' skin had grown increasingly thicker over the years as their brand expanded, Vanessa Trump's time in the spotlight was more about charity galas and photo shoots for Hamptons magazine. Whatever she had dealt with behind the scenes, it wasn't public.

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"It's not wonderful when you're being trolled on Twitter, with people saying really bad things and you have five kids. It's horrible," a friend of the family told the New York Post in December 2016. Both New York City natives, Vanessa and Don Jr. found themselves in sometimes hostile territory right outside their front door.

"They're living their lives as they always have," Trump campaign manager Kellyanne Conway assured the paper about the Trump kids. "They're classic New Yorkers. They love the city, they soak it in—the culture, the cuisine, the friendships."

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"Barron is 10 years old. It's so new for him," Ivana Trump also told the NY Post at the time. "I think [my kids] are around cameras all their lives and are prepared for it." (The first ex-Mrs. Trump would certainly make a splash when, while out promoting her 2017 memoir, she referred to herself as the first lady, "because I'm basically first Trump wife, OK?" She also opined that it "must be terrible" for Melania, being in Washington. Melania was not amused—and Ivana said she'd just have to get over it.)

Eric Trump's wife, Lara Trump, seems to enjoy engaging in a little political grandstanding on behalf of the family, but Vanessa has seemingly tried to remain out of the fray from the beginning, focusing on family and making public appearances—such as at the inaugural ball and the White House Christmas Tree Lighting ceremony—when it was important.  

"They were having problems before they even got married. People were telling her not to marry him before the wedding," a source told Page Six this week. "She was interviewing divorce lawyers before [Trump was elected]. No one thought he'd win. He won and she decided to stay until his term is over. But she just couldn't stand it anymore."

Rather like the family she married into, however, you'd never know it to look at her.

"My sister-in-law Vanessa is a machine," Ivanka told People in July 2016 during the campaign. "She can take all of [my children] and not even notice. She has five children and she's Wonder Woman to me." The mother of three, who along with husband Jared Kushner uprooted their Manhattan life to work in her father's administration, added, "[Vanessa] can be taking care of them all simultaneously, each pulling on her and have direct meaningful connections with each of them at one time. It's remarkable."

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All the while, the pictures of Don Jr. on Instagram sharing tender moments with his kids or otherwise acting like a regular family man continued to diverge from his increasingly brash public image.

Last month, the online animosity turned up-close-and-personal when Vanessa opened an envelope addressed to her husband at their home in Manhattan and it contained a white powdery substance. Feeling nauseous and starting to cough, she called 911 and was taken to the hospital. The powder turned out to be harmless, but a Massachusetts man has since been charged with mailing threatening communications for allegedly sending numerous similar envelopes to public figures. Both Vanessa and Don Jr. took to Twitter to thank first responders, police, the Secret Service and the FBI for taking action.

And while Don Jr. has joined in his father's summation of the Russia investigation as a "witch hunt," it's apparently been bringing him down all the same, along with the increased scrutiny of him, his business and every little thing he or his father says or tweets.

"Don Jr.'s become isolated, distant and just plain angry," a source told People after the split news, adding, "He has not been easy to be around." 

At least as Don Jr. was becoming increasingly entangled in the accusations of collusion against the Trump presidential campaign, his father defended him the best he knew how. "My son is a wonderful young man," Trump told reporters last summer when his son was under fire for meeting with a Russian lawyer who had supposedly offered the campaign dirt on Hillary Clinton. Insisting it was a short meeting, the president said that most people would've taken it.

Glowing praise, coming from Donald Trump Sr.