It is fascinating to study how certain women meet their millionaire or billionaire sugar daddies. In this series, we document the relationships women have had with famous millionaires, and this may shed some light on meeting a millionaire and marrying a sugar daddy.

Although Ivana was certainly a success in her own right as an Olympic athlete and Canadian model, she truly hit financial success when she met and married Donald Trump, son of a very wealthy real estate magnate Fred Trump.

How did Ivana chance upon meeting and eventually marrying Donald Trump? After her divorce from her first husband, Ivana happened to be in a swanky New York restaurant the same night Donald was. In fact, Donald Trump gave Ivana and her friend his table because all of the other reservations were completely full. It was from this chance meeting that Ivana became the famous and illustrious Mrs. Trump.

Unfortunately, in 1990, Ivana caught onto rumors regarding her husband’s affair with Marla Maples, leading her to petition for divorce in 1991. With the affair in her back pocket and contributions to the Trump business organization as negotiation tools, Ivana settled for $20 million from Donald Trump, in addition to a $14 million estate.

Though not a typical sugar daddy relationship (Ivana was actually a bit older than Donald), Ivana’s marriage into the Trump family brought her out of skiing obscurity into major financial fame. Interestingly, she is now playing the role of married sugar mommy to an Italian male model who is 23 years her junior.