Ivana Trump and Rossano Rubicondi's Former Marriage: The Ups and Downs of Their Romance
Trump, 72, confirmed her ex-husband's death to PEOPLE on Saturday after Rubicondi's friend and Italian TV personality Simona Ventura announced his death on Twitter Friday.
Trump and Rubicondi, who briefly married in April 2008 after six years of dating, divorced less than a year after tying the knot in Palm Beach, Fla., after an often long-distance marriage filled with many ups and downs.
Sources previously told PEOPLE the more than 20-year age gap between the pair did not contribute to their split, but conflicts between Rubicondi and Trump's children put a significant amount of pressure on the short-lived marriage.
Before their wedding, sources said the $3 million Mar-a-Lago nuptials almost didn't happen after a huge disagreement the night before over the prenup.
"Ivana's children as well as Donald were opposed to the marriage for fear that he was using her for her money," a source in the prenup negotiations for Ivana's fourth marriage told PEOPLE at the time.
"Ivana got $21 million when she divorced Donald [Trump] so between that and her successful book sales, etc.," continued the source. "He was a model and bit-part actor but very handsome and charming. They wanted to protect their mother from [Rubicondi] whom she dearly loved."
The couple was able to come to an agreement and moved forward with their marriage. "They resolved their differences, but Ivana's three kids really didn't like Rossano, and it remained an issue in their relationship," the source said at the time.
In 2008, Rubicondi told PEOPLE, "I am very excited about marrying Ivana. It does not bother me that she is older. She is an amazing woman, the whole package for me. She is an athlete, smart, sexy, funny and an astute businesswoman. We have a great time together."
Though the marriage didn't last, Trump and Rubicondi continued to date on and off until 2019.
"They truly loved each other and enjoyed each other's company," a Palm Beach social source told PEOPLE. "They love the jet set life, fine restaurants, hotels, resorts, and they both like work. He was not a freeloader, he held his own but he always spent more than he had. And he had one grandiose idea after the next."
In 2017, he reportedly had plans to open a healthy pizza eatery called "Rossano to Go" but a source told PEOPLE at the time that Rubicondi encountered a slew of financial problems, owed other money and faced a lawsuit.
Despite the multiple setbacks, Rubicondi and Trump continued their relationship until 2019.
A source previously told PEOPLE, "He can be charming, and [Ivana] loves European men."
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Although they never officially made their second-go at their relationship exclusive, The Raising Trump author also had a home in Florida, where the two would often spend time together.
"They both liked Miami and its diverse opportunities," a Palm Beach source told PEOPLE.
Another source close to Ivana described the late Rubicondi as "smart" and a "good person."
"They were friends through it all," the source shared. "He was a playboy and had many other girlfriends. They were often in different parts of the world so the on and off thing was good for both of them."
Details surrounding Rubicondi's death are not yet known.