Ivana Trump and Rossano Rubicondi, 23 Years
Donald Trump’s first wife, skier/model/businesswoman Ivana, divorced him in 1992. Two husbands later, Ivana Trump married actor Rossano Rubicondi in 2008. At the time, Ivana was 59 and Rubicondi was 36, making her 23 years his senior. While the couple divorced a year later, they appeared on the Italian version of “Dancing With the Stars” in 2018.