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Home » Ivana Trump’s post-Donald loves — from businessmen to boy toys

Ivana Trump’s post-Donald loves — from businessmen to boy toys

by Staff
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Ivana Trump is best known as the colorful ex-wife of Donald Trump.

But the mother of three, who passed away Thursday at the age of 73, was married once before Trump, whom she divorced in 1992, and twice after their union ended.

The Czech-born businesswoman was first married to Australian Alfred Winklmayr. Little is known about their two-year union, which ended in 1973, but the pair did not have children.

She married “the Donald” in 1977, a union that produced three children — Donald Trump Jr., Ivanka and Eric — plus countless tabloid headlines.

After their relationship crumbled, Ivana then moved on to a string of spouses and partners who were all globe-trotting Italians.

From 1995 to 1997, she was hitched to Italian businessman Riccardo Mazzucchelli, who started wooing her in 1991 after her high-profile split from Donald. He initially proposed with a 10-carat diamond, according to People magazine, but she declined and only accepted three years later when he offered her a Burmese sapphire.

But a mere 20 months into their marriage, the headstrong pair reportedly split because they fell out over business. In true Trump form, the dramatic divorce played out in the tabloids with a war of words.

Ivana Trump with her third husband, Italian Riccardo Mazzucchelli.
Getty Images

“I’m very sad, I cry. I love Riccardo. This is a tremendously hard time for me. It’s very painful to go through six years of relationship with a person and to be disappointed or filing for divorce or whatever,” she told the magazine.

Meanwhile, the monied businessman proclaimed to have “loved Ivana a lot, and I think I did my very best. I did for her more than Donald ever did,” he said, before adding that he was sabotaged by her previous spouse.

“I’ve been crucified by the press. He’s done nothing but knife me in the back,” Mazzucchelli proclaimed. “Maybe he’s jealous.”

The then-real estate tycoon reportedly told a friend, “Everybody knows that Ivana’s in love with me. This guy tried to compete with me from the start, and Ivana used him to get to me. She’s disappointed that it didn’t work out on any level.”

Mazzucchelli died in 2017 at the age of 74.

Ivana Trump and Roffredo Gaetani in front of the red Ferrari he gifted her for her birthday
Ivana Trump and Roffredo Gaetani d’Aragona in front of the red Ferrari he gifted her for her birthday.
Ron Galella Collection via Getty

In 1997, she started dating Italian aristocrat Roffredo Gaetani d’Aragona in 1997, and the pair were frequently seen at society parties around New York City. According to a New York Times profile, the pair met in Monte Carlo.

Unlike her third husband, Trump had kind words for Gaetani.

“Roffredo, I think he’s a very high-quality guy,” he told the paper.

A racing aficionado who was the president of Ferrari of Long Island and reportedly once challenged Mickey Rourke to a fight, Gaetani d’Aragona bought Ivana a red Ferrari for her birthday. They remained together until he was killed in a car accident in 2005.

When it came to her next spouse, she emulated her husband by going for a much younger lover. She tied the knot with “boy toy” Rossano Rubicondi, an Italian actor who was 23 years her junior.

The pair celebrated their union in a lavish affair at Mar-a-Lago in 2008, where publicist R. Coury Hay told The Post that an excited Rubicondi “trotted down the staircase” and pumped his fist to the “Rocky” theme.

Ivana and Rossano Rubicondi married in 2008.
Ivana and Rossano Rubicondi married in 2008.
SplashNews.com
Ivana Trump with Rossano Rubicondi attending a party in 2007 in Porto Cervo, Italy
Ivana Trump with Rossano Rubicondi attending a party in 2007 in Porto Cervo, Italy.
WireImage

“Usually the bride enters from there and gets all the attention. But Rossano was such a proud peacock that he couldn’t help himself,” Hay said. “Some of [the] guests were appalled.”

Though their marriage was over by 2009, they remained on and off again for about a decade and even competed together on the Italian version of “Dancing With the Stars” in 2018.

“The relationship just ran its course,” she told Page Six in 2019. “Rossano spends a lot of time in Italy and I spend a lot of time in New York, Miami and St-Tropez, and he has to work,” she said. “The long-distance relationship really doesn’t work. We had a good time and are friends. The split was amicable.”

Rubicondi died in October 2021 due to complications from melanoma.

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