The 33 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! Here are 33 of the ugliest and most expensive celeb divorces!

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

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.

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

In the end the couple did not fight over their children's custody nor spousal support.

Not a bad ending.

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

The couple married in 1996 and apparently had a prenuptial agreement which is no longer valid due to a "sunset clause".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!

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

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.

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

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

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.

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

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.

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

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.

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

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.

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

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.

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

This is the largest settlement in Hollywood history.

Mel Gibson married the former dental nurse Robyn Moore in 1980, and they separated in 2006.

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

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.

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

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.

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

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.

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

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.

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

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.

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

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.

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

The couple was married in 1988.

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

They split in 2000.

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

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

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

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

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.

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

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.

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

The 16-year marriage ended in 1994.

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


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

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

The settlement was handled divorce privately, buy rumor has it cost Costner $80 million.

The couple split in 2004.

26. Kelsey Camille Grammer: $30 million.

The couple married in 1984 and divorced in 1989. 

They had one child together.

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

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.

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

Former Nanny and Model Elin had two children with Woods.

They separated after numerous rumors of infidelity.

19. Garth Brooks and Sandy Mahl: Other Half Awarded $125 million.

The couple were college sweethearts.

They separated in 2001.

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

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.

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

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.

32. 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.

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

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

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