The 30 Ugliest and Most Expensive Celeb Divorces Ever

Divorces often end up ugly and that is no different for celebrities. Millions of dollars are usually on the line. Maybe they should think twice before tying the knot. Prenup! With all the drama that ensues, we’re taking a look at some of the ugliest celebrity divorces of all time.

1. Garth Brooks & Sandy Mahl – $125 Million

 

The famous country crooner and his college sweetheart Sandy Mahl sadly parted ways due to difficult times in their relationship and divorced in 1999 after 15 years of marriage. Mahl was awarded a whopping $125 million in the divorce settlement.

2. Donald and Ivana Trump: Other Half Awarded 20 Million

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Trump and Ivana separated in 1990. Donald was rumored to be having an affair with Marla Maples. Even though Donald's real estate empire was on the verge of bankruptcy at the time, Ivana ended up winning an unexpected $20 million divorce settlement.

3. Chris Rock and Malaak Compton-Rock, in December: 35 million Is At Stake.

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The couple married in 1996 and apparently had a prenuptial agreement which is no longer valid due to a "sunset clause". This means the contract became void after the couple is married for a certain number of years. Yikes!


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4. Michael Jordan and Juanita Vanoy: Other Half Awarded $168 million

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The greatest basketball player of all time and his wife were divorced in 2006 after 17 years of marriage. Juanita received custody of their children and saw a sweet $168 million settlement. Let's not forget she also received their seven-acre Chicago mansion.

5. Neil Diamond and Marcia Murphey: Other Half Awarded $150 million

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The singer married Marcia Murphey in 1969, and split in 1994. Even though she was left with half, Diamond said “she’s worth every penny.”

6. Arnold Schwarzenegger and Maria Shriver: Estimated to be between $250 and $375 million

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This one isn't fully finalized, but after a 25-year marriage Maria Shriver did file for divorce in 2011 because of any affair he had with a housekeeper, whom he also had a son with. The estimated damage is between $250-$375 million.

7. Brad Pitt and Angelina Jolie: TBD

Since they been married, since 2014, Brad Pitt has made far more than Angelina Jolie," Forbes' Robehmed tells E! News. Pitt "has made close to $80 million, $76.5 is the exact amount. Angelina has made closer to $40 million so he has made nearly double what she has earned since 2014.

8. Paul McCartney and Heather Mills: Other Half Awarded $48.6 million

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The infamous Beatles front man and ended the marriage with Heather in 2008.


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9. Amy Irving and Steven Spielberg: Other Half Awarded $100 Million

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The couple married in 1984 and divorced in 1989. They had one child together.

10. Michael Douglas and Diandra Douglas: Other Half Awarded $45 million

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The couple was married in 1988. They split in 2000.

11. Mel Gibson and and Robyn Moore: Other Half Awarded $425 million (2006)

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This is the largest settlement in Hollywood history. Mel Gibson married the former dental nurse Robyn Moore in 1980, and they separated in 2006.


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12. Madonna’s divorce from Guy Ritchie: Other Half Awarded Between $76 million and $92 million

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Guy Ritchie was Madonna's second husband. They married in 2000 and split eight years later in 2008. Ritchie won out having been awarded between $76 million and $92 million.

13. Melissa Mathison and Harrison Ford: Other Half Awarded $85 million

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The couple split in 2004. The couple had two children together and Melissa, a screen writer, cited 'irreconcilable differences' as the reason for the dissolution.

14. Michael Douglas and Diandra Douglas: Other Half Received $45 Million

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15. Robert Johnson and Sheila Crump: Other Half Awarded $400 million

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Robert and Sheila Johnson are co-founders of BET, and stayed married for 33 years before divorcing in 2003. This is a fun fact, Robert was the first African American billionaire, so that means a large chunk of the fortune for Sheila.

16. Boris Berezovsky and Galina Besharova: Other Half Awarded $160 million

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Boris Berezovsky is one of Russia’s most elite. This after originally being a teacher and only earning £60 a month.He married Galina Besharova in 1991, but divorced in 2010.

17. Charles Edgar Fipke and Marlene Fipke: Other Half Awarded $200 million

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If you don't know Charles Fipke, he is only the first person to discover diamonds in Canada’s Northwest Territories. He married Marlene Fipke in 2000. When they divorced Marlene received 1/5th of Charles’ company, valued at $123 million, amongst other things, bringing the total to about $200 million.


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18. Roman Abramovich and Irina Malandina: Other Half Awarded $300 million

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Irina Malandina filed for divorce against Roman Abramovich in 2006. Roman is a known Russian business tycoon. The reason is a supposed affair. Although Malandina tried to get the full half of Abramovich’s fortune ($6 billion), she was only awarded $300 million.

19. Craig McCaw and Wendy Petrak: Other Half Awarded $460 million

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Craig McCaw is the founder of McCaw Cellular, which AT&T acquired for $11.5 billion in the 90s. Wendy Petrak and McCaw married in 1974 and split in 1997.

20. Steve Wynn and Elaine Pascal: Other Half Awarded $740 million

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Steve Wynn is chief executive of Wynn Resorts. He married Elaine Pascal in 1963, divorced in 1986 and remarried again in 1991 before finally splitting in 2010. Elaine received 11 million shares of the Wynn stock when they divorced which equals a hefty $741 million.

21. Bernie Ecclestone and Slavica Ecclestone: Other Half Awarded $1.2 billion

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Bernie Ecclestone is the president and CEO of Formula One racing. He married former model Slavica Ecclestone and they divorced in 2009 after two children together.

22. Rupert Murdoch and Anna Maria Torv: Other Half Awarded $1.7 billion

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Ruport Murdoch and Anna Maria Tory had three children and were married for 32-year. They divorced in 1998-1999. Torv was awarded over $1.2 billion.

23. Rupert Murdoch and Wendi Deng: Other Half Awarded $1.8 billion

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This one is a shocker. Murdoch married Wendi Deng only after 17 days from when his second divorce was finalized. They divorced in 2013. Murdoch was 82 and Deng 44 years of age.

24. Alec Wildenstein and Jocelyn Perisse: Other Half Awarded $2.5 billion

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Alec Wildenstein's family became wealthy in the art dealing business. Alec inherited billions from his family. He married Jocelyn Wildenstein, but after he got caught with his 19-year old lover Jocelyn was able to land an insane settlement of $2.5 billion plus $100 million every year for 13 years after.


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25. Phil Collins and Orianne Cevey: Other Half Awarded: $47 million

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The 5 year marriage which ended in 2008 cost Collins a big chunk of change at almost $47 million.

26. James Cameron and Linda Hamilton: Other Half Awarded $50 Million

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Having held 11 Oscars with Tatanic in 1998, it was no surprise what kind of money was at stake. The couple split and Linda took $50 million to the bank in 1999.

27. Cindy Silva and Kevin Coster in 1992: Other Half Awarded $80 Million

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The 16-year marriage ended in 1994. The settlement was handled divorce privately, buy rumor has it cost Costner $80 million.


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After 18 years of marriage and bitter battle the couple split in 2000.

28. Kelsey Camille Grammer: $30 million.

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They have two children together and split after 14 years of marriage.

29. Kenny Rogers and Marianne Gordon: Other Half Awarded $60 million.

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Roger's fourth wife, Marianne Gordon was the most expensive out of his five. They divorced in 1993 after 16 years of marriage and one child.

30. Tiger Woods and Elin Nordegren: Other Half Awarded $100 million

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Former Nanny and Model Elin had two children with Woods. They separated after numerous rumors of infidelity.

31. Heidi Klum and Seal: Heidi's $70 Million at Stake

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According to Klum, she demanded a divorce because she was worried about the effect Seal’s 'inability to control his temper' was having on their children.  But in the end, the couple didn't fight over their children's custody nor spousal support. Not a bad ending to a seemingly ugly split.

32. Adnan Khashoggi and Soraya Khashoggi: Other Half Awarded $850 million

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Adnan Khashoggi, is Saudi Arabian businessman who married a 20-year-old Soraya Khashoggi in 1961. They divorced in 1982 and the settlement ended in an over $2 billion sum.

33. Samathur Li Kin-Kan and Florence Tsang-Chiu-wing: Other Half Awarded $157 million

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Samathur Li Kin-Kan is a Hong Kong billionaire who divorced his wife in 2011 because she did not want an abortion. This divorce was recorded as the largest in Asian history.

34. Michael Polsky and Maya Polsky: Other Half Awarded $184 million

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Michael and Maya Polsky divorced in 2007. They were married 31 years. They have an interesting back story having moved to the US with only $500 in their pockets. Michael is the founder of Invenergy LLC.