Random Most Egregious Male Gold Diggers (13 items)

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  (#1) Frédéric Prinz von Anhalt

  • 75

  Prinz von Anhalt, born Hans Robert Lichtenberg in Germany, rose to economic prominence when he was the subject of an adult adoption by Princess Marie-August of Anhalt, of which she conducted thirty-five in total. Following the adoption, Prinz von Anhalt was royalty by surname alone, though this distinction meant little in the context of his successful entrepreneurial career. In 2018, he came clean about his past, admitting that he swindled his way to a fancy title.

  At 39 years old, Prinz von Anhalt met actress Zsa Zsa Gabor, who was 26 years his senior. The pair married four years later, although Prinz von Anhalt later admitted to marrying Gabor not for love but for "friendship"—a friendship that allowed numerous and shameless extramarital affairs.
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  (#2) Alfonso Diez

  The Duchess of Alba made international headlines in October, 2011, when she married Alfonso Diez, a civil servant 24 years her junior, at the age of eighty-five. The Duchess, who has an estimated net worth ranging from $800 million to $4.7 billion, has repeatedly claimed that she was "alone in [the] project [of her marriage]," and that their marriage was out of love, despite what her six children might contend. The quirky, twice-widowed Duchess even signed over much of her estate to her children prior to the marriage, while Diez renounced any claim to the Alba estate.
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  (#6) Kris Humphries

  • 34

  Although Kris Humphries is a successful pro basketball player in his own right, he is perhaps even more widely known for his 72-day marriage to pop culture superstar Kim Kardashian.

  The young NBA player dove into a whirlwind romance with the reality TV star that included countless media appearances, tabloid covers, and an outlandish fairy-tale wedding that allegedly made the high-profile couple $18 million. Although the Kardashians forced Humphries to sign a prenup prior to the televised matrimonial ceremony, he may have profited off of the union regardless thanks to numerous tabloid and E! deals.
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  (#4) Dean McDermott

  • 52

  When McDermott met actress Tori Spelling on the set of Mind Over Murder, he was a struggling actor who was married and in the process of adopting a child. After meeting Spelling, however, he left his wife of over ten years and married Spelling in a private Fiji ceremony in 2006. While the Spelling inheritance is approximately $500 million, Tori's share is only $800,000––a fact that only partially quelled rumors of McDermott's perceived ill intentions. 
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  (#13) Guy Ritchie

  • 50

  Though Guy Ritchie is known as a filmmaker, his ex-wife, singer and international superstar Madonna, made him a much wealthier and more widely known celebrity than he may have ever been on his own. Ritchie and Madonna––who have a ten-year age gap in her favor––were married for almost eight years and had two children together. The couple finally split in 2008, and Ritchie received between $10 million and $92 million in the resulting settlement. 
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  (#7) Kevin Federline

  • 40

  Kevin Federline has been a back-up dancer, rapper, model, and reality star over the course of his career. One of his most famous titles, however, is that of pop star Britney Spears's former lover.

  After splitting with longtime beau Justin Timberlake, Spears's decision to start a relationship with Federline was a game changer in the pop star's wildly successful career. While their marriage and divorce––all of which took place over two years––might have been Spears's mental tipping point, Federline emerged from their split unscathed and with custody of their two children. He also received $20,000 a month in child support and a spot on the new Australian reality show, Excess Baggage.

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