Born in the former Czechoslovakia where she was an alternate on the Czech Olympic ski team in the late 1960s, Ivana first met The Donald in 1976 when she was working as a model in New York. That Ivana was married at the time didn't seem to be an issue: She divorced her husband and tied the knot with Trump a year later. Ivana spent the 1980s living atop the Trump Tower and "working" alongside her husband as his Vice President of interior design, helping craft the signature gaudiness that his properties are now famous for. But their relationship eventually dissolved amid a tabloid frenzy in 1990 after it was revealed that Donald was cheating on her with a younger model, Marla Maples. After a messy legal battle, the couple divorced in 1991, and Ivana walked away with a reported $25 million.
Ivana seems to have picked up some lessons in self-promotion from her ex-hubby. Since the split, she's used her image to endorse products like Coors Light, Pizza Hut, and Kentucky Fried Chicken. Ivana has stamped her name on a handful of products, including a tacky line of jewelry, perfume and clothing called "Ivana Haute Couture." On top of the endorsements, she has also written a book. In 2005 she gloriously tried to replicate her husband's success on TV with a reality show of her own, Ivana Young Man. which was originally slated for Fox but ended up airing very briefly on Oxygen.
Ivana's first husband was professional skier George Syrovatka, whom she married in the late '60s. Following her divorce from the Donald, Ivana was somehow optimistic enough about romance to marry for a third time in 1995. Alas, her marriage to Italian businessman Riccardo Mazzucchelli lasted just 20 months. Still, hope springs eternal, and in April '08 she married Italian "actor"/playboy Rossano Rubicondi, who's more than 20 years her junior, but their relationship was dubbed "on and off" later in ‘08. [Image via Getty]