The major difference between Don Trump Jr. and Vanessa's divorce and Donald's split with Ivana

Suzy Byrne
Editor, Yahoo Entertainment
Are Donald Jr. and Vanessa following in Donald Sr. and Ivana’s footsteps? (Photo: Getty Images)

In the days following Donald Trump Jr.’s divorce announcement, amid reports of his infidelity with Aubrey O’Day, we started having flashbacks — of father Donald Trump’s notorious 1990 divorce from Don Jr.’s mother, Ivana.

The similarities are there: Both men are real estate moguls who got their start thanks to dad. Same politics and apparently political aspirations. Their beautiful, blond wives were models. There are allegedly other women. The divorces are super high-profile. They were both married for more than a decade. There are a bunch of kids involved. And, of course, money, money, money, money is a major factor for both.

A friendlier turn

During the past weekend, things took a turn, though, when TMZ posted photos of Don and estranged wife Vanessa on vacation with their kids at Mar-a-Lago. While they showed “zero PDA,” they “seemed to be in relatively good moods” at the pool with their brood. The story even brought up the term “conscious uncoupling” — popularized by Gwyneth Paltrow and her amicable ex Chris Martin — though adding “at least for now.” Just the fact that they could sit side by side says something different about their split. After all, the Donald and Ivana were at each other’s throats for years after they uncoupled.

Other signs pointing to the fact that it’s more amicable include Vanessa’s liking some of Don’s social media posts about their children. She’s still letting a Trump spokesperson address rumors related to her.

Perhaps this seemingly friendlier path comes down to what Don went through with his own parents’ spliy. He was 12 years old during the so-called Divorce of the Century, and it led to his not speaking to his father for an entire year.

“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.” That led to him blaming his father for the split, he said, whether it was right or wrong. “And that’s, perhaps, not actually what it was. But when you’re living with your mother, it’s easy to be manipulated. You get a one-sided perspective.”

Donald Trump Jr. with his father at the U.S. Open in 1988. (Photo: Ron Galella, Ltd./WireImage)
The ‘Divorce of the Century’

The divorce battle between Donald and Ivana was epic. To paint the scene, this is the start of the People magazine story reporting the NYC power couple’s breakup in February 1990.

“In a decade of glitz, they were the glitziest; in a decade of greed, they were the greediest: He the scrappy investor who made a fortune wheeling and dealing real estate, she the gregarious, Czech-born outsider who charmed and clawed her way into New York’s most refined social circles. As they fashioned an empire in their own image — and plastered their moniker on nearly every piece of steel, brick and glass they owned — they became, as New York Newsday columnist James Revson quipped, ‘larger than Dynasty.’ They had it, and they flaunted it in a brash, bold, brazen way that seemed to typify their times. So when, only six weeks into 1990, Donald and Ivana Trump announced they were calling off their 12-year marriage, it seemed the perfectly scripted end to a decade of flash and cash.”

The headline Don Jr. referred to related to the divorce — “The Best Sex I Ever Had” — was a quote attributed to his dad’s mistress, Marla Maples. As Donald and Ivana’s marriage unraveled, Ivana and Marla had a catfight on the Aspen ski slopes over Donald amid the very public affair. Of course, that was Trump’s own fault for bringing his mistress on a family vacation. (True story.)

The divorce really exploded because both Donald and Ivana were feeding information to the New York gossip columns. The late gossip maven Liz Smith recalled breaking the news, saying Ivana — who was largely responsible for making Donald into the Donald, someone the press cared about, and had a large role in her husband’s company — called her to the Plaza Hotel, threw her arms around her, while crying, and said, “‘Donald has a girlfriend.'” When Smith reached out to Donald, who had been linked to many women in addition to Maples, he told her, “‘I like Ivana; I might get back with her.’ I couldn’t believe it,” Smith said. “‘I like Ivana.’ Everyone had misjudged Donald. People thought he would be alarmed if it was revealed that he was having an affair. But it turned out he didn’t give a s*** if people knew.” (This gives some insight into his present-day drama with Stormy Daniels and Karen McDougal.)


The 1990 Trump divorce was all over the news. (Photo: New York Daily News)

With Ivana dubbing Donald “cruel and inhuman,” they went on to divorce. That part was just as crazy — no surprise considering he was worth a reported $1.7 billion. Although portions of the divorce documents were sealed, Newsday reported on the financial breakdown, stating that Ivana received a $10 million certified check immediately and $4 million within the next year. She also received the Greenwich, Conn., mansion, an apartment at Trump Plaza in Manhattan, use of Mar-a-Lago for one month a year, a 1987 Mercedes, $300,000 annually in child support, and $350,000 a year in alimony. She also received custody of the three children, including Ivanka and Eric. 

As for Donald, he got Marla. Well, briefly. They had a child, Tiffany, and then married, and then divorced. He married Melania Knauss in 2005. Meanwhile, Ivana also later remarried twice, bringing her total to four. (The exes are now friendly despite their “insane” divorce, Ivana said last year.)

Like father, like son?

As mentioned, Don Jr. didn’t speak to his father for a year after his parents divorced. He and his sibs were shipped off to boarding school, and he spent time with his maternal grandfather in Prague. “He needed a father figure,” Ivana told the New York Times. “Donald was not around that much.” Ivana takes credit for raising their children, saying, “When [my children] turned 21, I handed them over to him and said, ‘Here’s the finished product.'” (She has also said that Donald was worried Donald Jr. would turn out to be a “loser.”)

After frat-boy antics at college and some lost years as a bartender in Colorado, Don Jr. returned to New York and joined the family business, the Trump Organization. Soon after, his dad was his matchmaker when he introduced Vanessa at a fashion show. Vanessa later told Don Jr. that she thought his dad was “retarded” when they were introduced.

Donald Trump Jr. campaigned for his father in 2016. He’s since said he wants to run for office himself. (Photo: Ethan Miller/Getty Images)

When Donald decided to run for office, Don Jr. did some serious stumping for him — and possibly more. We’ll see what an investigation turns out. The younger Trump, who is running the family biz with Eric while his father is in Washington, has also expressed interest in running for office himself, a reported point of contention with Vanessa. She reportedly doesn’t like all the attention the family receives with her father-in-law in the Oval Office. (Death threats don’t help.) But there seem to be bigger issues with the pair, including his alleged affair with Celebrity Apprentice contestant Aubrey O’Day.

It’s too early in Don and Vanessa’s divorce process to tell if they will, in fact, consciously uncouple, as TMZ suggests, depending on the new photos. A lot of it probably depends on the settlement Vanessa gets — and if it’s to her liking. But the new photos are a good sign that they’re at least headed in a more positive direction than Donald and Ivana. And that is a good thing.

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