Ivana Trump’s Chaotic Love Life: Before Donald, After Donald, and the Art of Getting Everything

It is a truth universally acknowledged—at least in the gilded, gossipy canyons of Manhattan—that all that glitters is usually just a very expensive, temporary lease. And no one lived this truth quite like the late, great Ivana Trump. She gave us the greatest three-word manifesto of the 1990s: “Don’t get mad—get everything.” A line, mind you, delivered in an iconic cameo in The First Wives Club that perfectly distilled her public image: the ultimate, stylish, victorious divorcée.

But if you peel back the layers of that fabulous, unapologetic-capitalist persona—past the Trump Tower pink marble she helped design, and the massive divorce settlement she secured—you find a love life that was less a gilded fairy tale and more a spectacular, years-long tabloid scandal that makes today’s celebrity breakups look like a politely worded email exchange. Ivana had four trips down the aisle, and each one, in its own glorious way, proved that the Czech-born socialite didn’t just walk through life; she bulldozed it, leaving a trail of ex-husbands, legal depositions, and screaming headlines in her wake. Forget the $20 million settlement from the second marriage; the real story is the drama that paved the way.

The Passport Marriage: The Ultimate Starter Husband

Before the yachts, the mansions, and the whole “Trump” thing, there was a quiet little arrangement back in 1971 Czechoslovakia. Our girl Ivana, then Ivana Zelníčková, needed to defect from a Communist state without completely burning her bridges back home. Enter Alfred Winklmayr, an Austrian skier and, shall we say, a deeply platonic pal.

The narrative here, as juicy as a Park Avenue social lunch, is that this marriage was purely transactional. A business deal, really, with a wedding ring instead of a handshake. Her own lawyer, Michael Kennedy, later made the stunning revelation that the marriage “was never consummated.” You read that right. We’re talking about an Austrian passport acquisition masked as a wedding—the ultimate example of Ivana’s legendary pragmatism, even at a young age.

They didn’t share a home, but she got her Austrian citizenship and the freedom to travel. Two years later, in 1973, it was a quiet absentee divorce in Los Angeles. This wasn’t heartbreak; this was strategy. It was also the first in a pattern: marry up, get what you need, and move on. The only real heart-stopping tragedy in this period was the death of her genuine love interest, playwright Jiří Staidl, who died in a car crash that same year. A heavy start for a woman whose life would become defined by high-wire spectacle.

The Big One: Donald, Marla, and the Ski Slope Showdown

Fast forward a few years to 1976, New York City. Ivana, a model, meets Donald Trump. A whirlwind courtship, a 1977 wedding, three children—Donald Jr., Ivanka, Eric—and the power couple of the 1980s was born. This wasn’t just a marriage; it was a brand partnership. Ivana, sharp, driven, and impeccably styled, became the executive vice president of interior design for the Trump Organization, managing properties like the Plaza Hotel and Trump’s Castle in Atlantic City.

They were it. The New York society pages practically stamped their faces on the city’s currency. Then came Aspen, Christmas 1989, and a fateful encounter outside a snowy restaurant that blew up their carefully curated empire.

It was Ivana versus the future Mrs. Trump, Marla Maples, in a showdown that would make Dynasty writers weep with envy. As Ivana recounts in her book, Raising Trump, Maples sashayed over and dropped the ultimate verbal grenade: “I’m Marla and I love your husband. Do you?” Ivana’s legendary, unladylike retort? “Get lost. I love my husband.”

The whole messy spectacle hit the tabloids with the force of an actual earthquake. The next day, the New York Post delivered the infamous, screaming headline: “The Best Sex I’ve Ever Had.” Only, it wasn’t Ivana giving the rave review; it was Marla, boasting about Donald. Cue the public humiliation.

The Divorce Settlement: Get Everything

What followed was the most explosive, high-stakes, headline-grabbing divorce of the decade. The legal battle lasted well into 1990, becoming a circus that kept gossip columnist Liz Smith employed for months. Ivana was fighting for her due, pointing to her immense contributions to building the Trump empire. She wasn’t just a wife; she was a C-suite executive who managed to run a casino and a hotel while raising three future moguls.

And then, the bombshell deposition. Ivana alleged that Donald sexually assaulted her in 1989. She later “toned down” the claims in a statement, saying, “As a woman, I felt violated, as the love and tenderness that he normally exhibited towards me were absent. I referred to this as a ‘r—,’ but I do not want my words to be interpreted in a literal or criminal sense.” It was a painful, public retreat from a truly shocking claim, but it underscored the sheer brutality of the battle.

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She signed a non-disclosure agreement—naturally—but she did manage to walk away with a $14 million settlement, a 45-room mansion in Connecticut, an apartment in Trump Plaza, and the use of Mar-a-Lago for one month a year. The “get everything” philosophy was cemented.

The Post-Trump Whirlwind: Short-Term Italian Flings

With $14 million in her pocket and a whole new, independent brand to build, Ivana didn’t exactly retreat to a quiet life of solitude. She launched clothing lines, wrote self-help books, and was back on the market, darling.

In 1995, she married Italian businessman Riccardo Mazzucchelli. This one was blink-and-you-miss-it, lasting just two years before they divorced in 1997. The split wasn’t exactly quiet, either, involving lawsuits, a broken promise of a $10 million house, and a public exchange of insults, because of course it did. Ivana was a creature of chaos, and her relationships seemed destined to follow that high-octane pattern.

Then came Rossano Rubicondi, a younger Italian actor and model who was two decades her junior. The six-year courtship led to a lavish 2008 wedding at Mar-a-Lago, hosted by none other than ex-husband Donald Trump. Only in Ivana’s world can an ex-husband host your fourth wedding to a handsome playboy.

The marriage itself barely made it out of the honeymoon phase. It lasted about 20 months. The official reason? The classic “long-distance” lament. “Rossano wants to live in Miami and work in Milan. But I am a New Yorker and my family, friends, and businesses are here,” she told the press. The unofficial, more spicy rumors involved the inevitable conflicts with her children, who were apparently concerned their mother was being used for her considerable fortune. The drama simply never stopped.

Though they divorced in 2009, Ivana and Rubicondi remained an on-again, off-again item for years, frequently popping up in the social columns together until 2019. It was a bizarre, co-dependent relationship that seemed to prove that for Ivana, a little bit of romantic drama was just part of the furniture, like pink marble or a massive prenuptial agreement. When Rubicondi tragically died in 2021, Ivana was reportedly devastated, confirming that even the most chaotic relationships can hold deep, genuine feeling.

The Ivana Archetype: Getting the Settlement and the Last Word

Ivana’s life trajectory is a classic Hollywood scandal pattern, only played out in real life: the glamorous immigrant chasing the American dream, securing wealth and power through marriage and business acumen, and then facing a spectacular, public downfall only to rise again. She was the originator of the “divorcée as brand” long before it became a commonplace career move.

Her great contribution to pop culture wasn’t her interior design (though that pink marble is certainly a choice) but her unwavering commitment to getting paid—emotionally, financially, and culturally—for all the public hell she endured. She took the trauma of a massive divorce and turned it into an advice book that told women to “take his wallet to the cleaners.”

This pattern—marry for gain, divorce for a fortune, and then sell the story—is one we see repeated. Think of the entire genre of reality star divorcées, from the Real Housewives cashing in on their splits to the celebrity who manages to leverage a high-profile breakup into a massive career boost. Ivana wrote the playbook. She was the original reality TV star who weaponized her social status, her wit, and her sheer, unapologetic hunger for luxury.

In the end, Ivana Trump had everything she wanted: the independence, the millions, the children, and most importantly, the last, incredibly witty word. She may have been a “first wife,” but she made sure she was always the main event.