See which celebs gave in to alimony and shared their millions, going down in history as the most expensive divorces ever!
1.Tiger Woods & Elin Nordegren – $750 Million
Tiger Wood’s reputation was shattered when his adulterous behavior with dozens of random women was discovered. Woods and his ex-wife Elin Nordegren officially split in 2010 after six years. Tiger was reportedly forced to hand over $750 million in their divorce.
Since Jolie filed for divorce from Pitt, the couple has been working with a private judge. She asked for full physical and joint legal custody of their children. It’s too soon to tell, but rumor has it that the divorce will end up costing $400 million.
Angelina Jolie & Brad Pitt – $400 Million
3. Kevin Costner & Cindy Silva – $80 Million
16 years of marriage and three children later, the Hollywood couple decided to call it quits as a result of Costner’s alleged infidelity. The Hollywood actor ended up having to pay $80 million to Silva in the divorce and later admitted that he had a child on the side with socialite Bridget Rooney.
Kevin Costner & Cindy Silva – $80 Million
4. Alec & Jocelyn Wildenstein – $2.5 Billion
Jocelyn managed to get $2.5 billion out of her ex-husband Alec Wildenstein, French businessman and billionaire. Known for her plastic surgery, which cost her a total of $2 million, Jocelyn thought changing her look would keep her husband around.
Alec & Jocelyn Wildenstein – $2.5 Billion
5. Michael & Diandra Douglas – $45 Million
Michael Douglas married Diandra in 1977, and had a son with her a year later. In 1995, Diane filed for divorce. By the end of their divorce, Diandra received a $45 million settlement, which was half of the actor’s net worth at the time.
Michael & Diandra Douglas – $45 Million
6. Robert & Sheila Johnson – $400 million
After 33 years of marriage to his partner, Sheila Johnson, co-founder of BET Robert Johnson separated in 2002. Two years before their divorce, in 2000, Johnson sold BET to Viacom for $3 billion; of which Sheila ended up getting $400 million.
Robert & Sheila Johnson – $400 million
7. Bernie & Slavica Ecclestone – $1 Billion
Bernie and Slavica Ecclestone made headlines for all the wrong reasons after having a divorce settlement worth an incredible $1 billion! Not wasting any time, Slavica turned this money into $1.6 billion from investments.
Bernie & Slavica Ecclestone – $1 Billion
8. Reba McEntire & Narvel Blackstock – $47.5 Million
Reba McEntire and Narvel Blackstock shocked fans when they announced their split in 2015. Despite this, the two remain friends and support each other. Given that there was no prenuptial agreement was in place, we can assume that the couple divided their assets evenly.
Reba McEntire & Narvel Blackstock – $47.5 Million
9. Michael Strahan & Jean Muggli – $15 Million
Michael Strahan met Muggli in 1994 and they married in 1999. Since saying “I do,” the two have had quite the tumultuous relationship. After filing for divorce, Muggli was awarded $15 million in a settlement and $18,000 in child support each month.
Michael Strahan &Â Jean Muggli – $15 Million
10. Rupert Murdoch & Anna Maria Torv – $1.2 Billion
This couple who lasted 32 years and have three children together split up in 1999. Murdoch ended up amassing a net worth of $8 billion. Torv received $1.2 billion as part of the couple’s divorce settlement.
Rupert Murdoch & Anna Maria Torv – $1.2 Billion
11. Heidi Klum & Seal – $70 Million
Heidi claims that Seal’s temper got so out of control, it scared their children. Heidi left with a broken heart and bank account. Despite their prenup agreement, Klum ended up settling the divorce for $70 million.
Heidi Klum & Seal – $70 Million
12. Mel Gibson & Robyn Moore – $425 Million
After 26 years together, Robyn’s final decision to file for divorce was brought on by Mel’s DUI arrest in 2006. Because the couple didn’t sign a prenup, Robyn ended up getting half of Mel’s fortune in the divorce, which was about $425 million.
Mel Gibson & Robyn Moore – $425 Million
13. Frank & Jamie McCourt – $130 Million
Frank McCourt, known as the owner of Dodgers Stadium and Fox Entertainment Group, was married to wife Jamie McCourt until their messy divorce in 2011. Since Frank is such a successful entrepreneur, the divorce ended up costing him a substantial $130 million!
Frank & Jamie McCourt – $130 Million
14. Ron Perelman & Ellen Barkin – $20 Million
The businessman married Barkin, who became his fourth wife, in June of 2000. Their short-lived marriage ended in 2006, and the divorce was expensive. Ellen reportedly received a settlement of more than $20 million after she sold off jewelry Ron had given her.
Ron Perelman &Â Ellen Barkin – $20 Million
15. Greg Norman & Laura Andrassy – $103 Million
When the golf legend left Laura Andrassy in 2008 after 25 years of marriage, for fellow tennis star Chris Evert, he was forced to pay Andrassy an estimated $103 million! You’d think those big payouts would make couples work harder to keep their relationships together.
Greg Norman & Laura Andrassy – $103 Million
16. Johnny Carson & Joanna Holland – $20 Million
Johnny Carson has been married four times, but his most financially successful wife was model/socialite Joanna Holland, who squeezed $20 million out of their long and ugly divorce. When they divorced, Carson was the highest paid TV personality, raking in $15 million a year.
Johnny Carson & Joanna Holland – $20 Million
17. Adnan Khashoggi & Soraya Khashoggi – $874 Million
Saudi Arabian billionaire, Adnan Khashoggi was once thought to be one of the richest men in the world. He married his partner Soraya Khashoggi when she was just 20 years old, but the marriage in an expensive divorce. Soraya was awarded $874 million.
Adnan Khashoggi &Â Soraya Khashoggi – $874 Million
18. Colin Firth & Livia Giuggioli – Approx. $12.5 Million
After 22 years of marriage, Firth and Giuggioli are in the midst of their divorce. Although we cannot know exactly what settlement they will come to, we are assuming the Italian producer will receive half of the actor’s net worth. The duo decided to call it quits two years after Giuggioli admitted to having an affair with an Italian journalist and childhood friend, Marco Brancaccia. Despite their efforts to work through the affair and raise their two sons together, it seems the infidelity got the best of them, and they have called it quits for good.
Colin Firth & Livia Giuggioli – Approx. $12.5 Million
19. Kelsey & Camille Grammer – $30 Million
When these two wed in 1997, there was no prenuptial agreement. After 14 years of marriage and two children, the couple split up in February 2011. Camille ended up on the Real Housewives of Beverly Hills and $30 million of Grammer’s money.
Kelsey & Camille Grammer – $30 Million
20. John & Beverly Charman -$95 Million
When Charman married his high school sweetheart Beverley, he had no money, but during their 29 years of marriage, he become the eighth richest businessman in London. Beverly gave up her job to raise their children, so when the couple separated, Beverly received $95 million.
John & Beverly Charman -$95 Million
21. Samathur Li-kan & Florence Tsang-Chiu-wing -$154 Million
One of Hong Kong’s most powerful billionaires, Samathur Li-Kan, divorced his wife Florence in 2008 because she wouldn’t get an abortion. A Hong Kong judge ordered the wealthy real estate mogul to pay his ex-wife $154 million.
Samathur Li-kan & Florence Tsang-Chiu-wing -$154 Million
22. Roman & Irina Malandina – $300 Million
From 1991 to 2007 Irina Malandina was married to Russian billionaire Roman Abramovich, who was valued at 8.5 billion. When the couple divorced, Irina ended up getting $300 million which included cash as well as lavish homes in Moscow and London.
Roman & Irina Malandina – $300 Million
23. Jesse Williams & Aryn Drake-Lee – Approx. $4 Million
It has been confirmed that Jesse Williams and his wife Aryn Drake-Lee are divorcing amicably. The Grey’s Anatomy star filed for divorce from Drake-Lee, a real estate broker. No settlement amount was disclosed, but is estimated that it will cost around $4 million.
Jesse Williams & Aryn Drake-Lee – Approx. $4 Million
24. Eddie Murphy & Nicole Mitchell Murphy – $15 Million
Although the marriage seemed a happy one, the couple divorced in 2006 after nearly twenty years together. Following their split, Eddie Murphy dated and had a child with former Spice Girl Mel B. Nicole went onto date Michael Strahan. Currently Eddie is dating Paige Butcher and the couple have a child together.
Eddie Murphy & Nicole Mitchell Murphy
25. Ted Dansen & Casey Coates – $30 Million
Ted Danson met Casey Coates in 1976 and the pair were inseparable for 15 years. Things went south after Danson and Whoopi Goldberg began having a secret affair. In one of Hollywood’s most expensive divorce settlements at the time, Danson paid Coates $30 million.
Ted Dansen & Casey Coates – $30 Million
26. Harrison Ford & Melissa Mathison – $118 Million
17 years of marriage and having two children couldn’t save this doomed Hollywood couple. Ford and Mathison divorced in 2001, and with no prenuptial agreement, she ended up getting away with $118 million of the actor’s cash.
Harrison Ford & Melissa Mathison – $118 Million
27. Johnny Depp & Amber Heard – $6.8 Million
Amber accused Depp of being abusive, and eventually a settlement of over $6 million was decided on. Amber vowed to donate the money to charities. Although the couple never had children together, Depp has two, including model Lily-Rose Depp.
Johnny Depp & Amber Heard – $6.8 Million
28. Rupert Murdoch & Wendi Deng – $1.8 Million
The News Corporation CEO didn’t waste any time as he married Deng 17 days after his previous divorce was finalized. In June 2013, Murdoch decided Deng wasn’t doing it for him anymore and divorced her too, settling for $1.8 million.
Rupert Murdoch & Wendi Deng – $1.8 Million
29. James Cameron & Linda Hamilton – $50 Million
This relationship came to an end after Cameron was unfaithful while on the set of Titanic. Within days of Cameron winning an Oscar for the movie, the couple announced their separation and Linda’s $50 million settlement.
James Cameron & Linda Hamilton – $50 Million
30. Michael & Juanita Jordan – $168 Million
After years of trying to make the marriage work, Michael and Juanita Jordan mutually agreed on a divorce. As part of the settlement, Juanita received $168 million, on top of the couple’s seven acre Chicago mansion and custody of their children Jeffrey, Marcus, and Jasmine.
Michael & Juanita Jordan – $168 Million
31. Alex Baldwin & Kim Bassinger – Approx. $3 Million
Kim Bassinger and Alec Baldwin were married for 9 years and had a daughter together before splitting. The divorce was tough, with Kim blocking Alec’s visitation rights to their daughter. It is reported that they settled for around $3 million.
Alex Baldwin & Kim Bassinger – Approx. $3 Million
32. Steve & Elaine Wynn – $741 million
Steve Wynn managed to strike out twice, with the same woman! Wynn divorced Elaine Wynn, for the second time in 2010, costing the billionaire $741 million!
Steve & Elaine Wynn – $741 million
33. Paul McCartney & Heather Mills – $48.6 Million
Paul McCartney and Heather Mills celebrated their marriage with a $3.2 million wedding in Ireland, he probably wasn’t thinking that he’d be spending a whole lot more than that dissolving it. McCartney had to pay her $48.6 million settlement.
Paul McCartney & Heather Mills – $48.6 Million
34. Vladimir Potanin & Natalia Potanina – $7 Billion
Vladimir Potanin is reported to be one of the richest men in Russia, worth an estimated $14 billion. He was married to Natalia Potanina for 30 years before calling it quits in 2013. The divorce was extremely complicated, and Natalia received around $7 billion.
Vladimir Potanin & Natalia Potanina – $7 Billion
35. Michael Polsky & Maya Polsky – $184 Million
Michael Polsky is one of the most famous businessmen in the world, formerly the owner of SkyGen, it was only natural that his divorce was going to cost him! He split from his wife Maya in 2003 and it cost him an astonishing $184 million.
Michael Polsky & Maya Polsky – $184 Million
36. Charles Fipke & Marlene Fipke – $200 Million
Charles Fipke discovered the first diamonds in Canada’s Northwest Territories, which in turn made him a very rich man. Charles divorced Marlene after being married for a number of years, and the divorce cost him close to $200 million, making it one of the biggest divorce settlements in Canada.
Charles Fipke & Marlene Fipke – $200 Million
37. Gwen Stefani & Gavin Rossdale – $2.5 Million
Gwen and Gavin were considered a happy successful couple, however like most matches in Hollywood their marriage came to an end after 13 years and a total 20 years together. Their settlement estimated to cost around $25 million. Since the split, Gwen has gone on to date Blake Shelton.
Gwen Stefani & Gavin Rossdale – $2.5 Million
38. Steven Spielberg & Amy Irving – $100 Million
Three and a half years into their marriage, the couple agreed to divorce. In the end, Amy Irving got $100 million for the divorce which might seem like a lot, but it was just a drop in the bucket for Spielberg, who’s worth more than $5 billion.
Steven Spielberg & Amy Irving – $100 Million
39. Hilary Duff & Mike Comrie – $2.5 Million
Hilary Duff was considered one of America’s teenage sweethearts throughout the 2000’s. The world was thrilled for her when she married Mike Comrie, however, the marriage didn’t last. What followed was a messy divorce and a settlement which cost around $2.5 million.
Hilary Duff & Mike Comrie – $2.5 Million
40. Demi Moore & Bruce Willis – $90 Million
Demi and Bruce were married for 11 years and have three daughters. They divorced in 2000, and Bruce said that he felt like “he had failed as a father and husband.” Demi moved on with a younger man, Ashton Kutcher, as well as a $90 million settlement.
Demi Moore & Bruce Willis – $90 Million
41. Arnold Schwarzenegger & Maria Shriver – $375 Million
Arnold Schwarzenegger and Maria Shriver had a difficult split after 25 years of marriage. Shriver filed for divorce following the news of his affair with their housekeeper. Since they never had a prenup agreement, Shriver ended up getting $375 million and custody of their children.
Arnold Schwarzenegger & Maria Shriver – $375 Million
42. Harold Hamm & Sue Ann Arnall – $974.8 Million
Harold Hamm, one of the biggest entrepreneurs in the gas and oil industry, divorced his wife Sue Ann Arnall in 2012 after 24 years of marriage. The legal battle ended when Sue accepted Mann’s settlement check of $974.8 million!
Harold Hamm & Sue Ann Arnall – $974.8 Million
43. Teddy Landau & Michelle Branch – Approx. $300 000
Grammy Award winner Michelle Branch married her bass player Teddy Landau and the marriage lasted nearly 11 years. However, it didn’t last and the couple decided to separate, which was then followed by a divorce. The settlement cost close to $300,000.
Teddy Landau & Michelle Branch – Approx. $300 000
44. Allen And Tawanna Iverson – $32 Million
After being married for 24 years and having five children with a man who mounted a hefty $150 million debt, Tawanna decided to file for divorce. While in the divorce court, Allen shouted to his wife, “I don’t even have money for a cheeseburger!” to which Tawanna responded by handing him $61. After pleading for her back, Tawanna withdrew the papers but it was not long until she backtracked. She re-filed for divorce in 2013 and was awarded everything in the post-nuptial agreement, a staggering $32 million.
Allen And Tawanna Iverson – $32 Million
45. Madonna & Guy Ritchie – $92 Million
The marriage between the Madonna and Guy Ritchie lasted only seven years. Luckily for Guy, the couple didn’t have a prenuptial agreement, and he made out like a bandit getting somewhere between $76 and $92 million as part of the divorce settlement.
Madonna & Guy Ritchie – $92 Million
46. Dmitry & Elena Rybolovlevi – $4.5 Billion
After 26 years of marriage, Dmitry and Elena called it quits. Dmitry ended up coughing up half of his money in a six-year legal battle that saw the Russian billionaire handing over $4.5 billion to Elena.
Dmitry & Elena Rybolovlevi – $4.5 Billion
47. Lionel Richie & Diane Richie – $25 Million
After seven years, the singer and his second wife, Diane Alexander, called it quits. After a dragged out legal dispute, Diana was awarded the couple’s $5 million mansion and a lump sum of $20 million, burning a huge hole in the artist’s fortune.
Lionel Richie & Diane Richie – $25 Million
48. Jeff Bezos And MacKenzie Bezos – $66 Billion
Being married to the world’s richest man has its perks, but divorcing them isn’t too bad either. Amazon CEO, Jeff Bezos, who is worth an estimated $137 billion, has just announced his divorce to wife, MacKenzie, on Twitter. Since he founded the company after their marriage, MacKenzie could be entitled to half his Amazon-based fortune, a whopping $66 billion! Bad news for Bezos, as he will need to sell or pledge shares to fund a settlement that huge, reducing his control of the company.
Jeff Bezos And MacKenzie Bezos – $66 Billion
49. 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.
Garth Brooks & Sandy Mahl – $125 Million
50. Dr. Phil McGraw & Debbie Higgins – Approx. $1 Million
Dr. Phil had a failed marriage with his high school sweetheart Debbie Higgins, who McGraw divorced after three years. The split cost around $1 million as at that point he didn’t have much. Higgins calls herself the “secret first wife of Dr. Phil.”
Dr. Phil McGraw & Debbie Higgins – Approx. $1 Million
51. Bill Gates and Melinda French Gates – $80 Billion (Estimated)
This ultra-wealthy couple has been together for over 27 years but decided to call it quits in 2021. Their reason for the split was that they felt they couldn’t “grow together” anymore as a couple.
Bill Gates and Melinda French Gates – $80 Billion (Estimated)
We’re not sure what growth they felt still needed to be done, given the enormous success they achieved together, it seems that even the greatest achievements weren’t enough to keep this relationship going. While their exact settlement remains confidential, it’s estimated to be around $80 billion.
52. Mike Tyson and Robin Givens – $10 Million
Mike Tyson and Robin Givens’s divorce cost more millions than the time that they stayed together. The couple only lasted eight months but the split earned Robin a whopping $10 million.
Mike Tyson and Robin Givens – $10 Million
Apparently, she could have gotten even more but she stresses that she was never interested in Mike’s money and she married him out of love. While we appreciate the sentiment, that’s a pretty interesting claim from someone who just made $10 million from an eight-month marriage.
53. Adele and Simon Konecki – $90 Million (Estimated)
Adele and Simon were together for seven years and all seemed to be going well but their marriage only lasted two years, implying that the switch to becoming husband and wife didn’t work out for them.
Adele and Simon Konecki – $90 Million (Estimated)
Although they never disclosed the details of their divorce, they didn’t have a prenuptial agreement, meaning that Simon would be entitled to half of Adele’s $182 million fortune. Given Adele’s significantly happier energy since the split, it’s clear that money truly can’t buy happiness.
54. Phil Collins and Orianne Cevey – $47 Million
This former couple had an extremely messy divorce in which Orianne refused to leave Phil’s $40 million mansion. Phil had to take legal action to remove his ex-wife, and her new husband, from the property. The house in question has since been sold for $39 million.
Phil Collins and Orianne Cevey – $47 Million
This isn’t Phil’s first expensive divorce, though. He also paid a whopping $34 million to Jill Tavelman when they split. Hopefully, this singer’s next relationship will be built to last – or at the very least end amicably.
55. Janet Jackson and Rene Elizondo – $10 Million
Janet Jackson has had a lot of unfair things happen to her and, unfortunately, her divorce settlement with Rene Elizondo can be added to that list. Despite their prenuptial agreement, Janet still had to shell out spousal support as Rene claimed that he signed the prenup “under duress.”
Janet Jackson and Rene Elizondo – $10 Million
Given what Janet went through after her Superbowl wardrobe malfunction with Justin Timberlake, she seems pretty used to men blaming her for the consequences of their actions.
56. Kelly Clarkson and Brandon Blackstock – $1.3 Million
Kelly Clarkson’s $1.3 million payment to Brandon Blackstock may not seem like that much but she also has to pay monthly child support to the tune of $45,601. Furthermore, Kelly was paying $150,000 a month for spousal support, which has since been lowered to $115,000 monthly.
Kelly Clarkson and Brandon Blackstock – $1.3 Million
Brandon will also get some of the couple’s cars, expensive household items, and farm animals. The couple has split custody of their two children, River and Remington.
57. Slash and Perla Ferrar – $6.6 Million
This divorce battle lasted over three years and resulted in some pretty hefty payouts. The Guns N’ Roses guitarist had to pay Perla $6.6 million, plus $100,000 a month in spousal support and $39,000 in child support.
Slash and Perla Ferrar – $6.6 Million
Since their split, Slash has banned Perla from all of Guns N’ Roses’ shows. However, she’s been attending the band’s performances anyway. To be fair, Perla insists that she went to the shows for her son (who was also performing) not for Slash.
58. Kim Kardashian and Kanye West – $1.4 Billion (Estimated)
Kim Kardashian’s relatively low divorce settlement is due to a prenuptial agreement that she signed prior to marrying Kanye West. Although Kimye can’t seem to agree on anything at the moment, neither of them is debating their prenup. Kim’s net worth is $780 million, while Kanye is currently worth $1.3 billion.
Kim Kardashian and Kanye West – $1.4 Billion (Estimated)
That being said, unfortunately, there seems to be no legal contract in the world that can stop the rapper from constantly harassing Kim and her new boyfriend, Pete Davidson. If there were a payout that could save Kim from Kanye’s antics, we have no doubt that she’d go for it – at any price.
59. Russell Brand and Katy Perry – $20 Million
Russell Brand was entitled to $20 million of Katy Perry’s fortune, however, sources claim that he didn’t take a single penny. Russell insists that he doesn’t want Katy’s money and he’s happy with his own earnings, despite the fact that they’re significantly less.
Russell Brand and Katy Perry – $20 Million
The comedian says that he wanted to end his marriage to the pop star amicably, even if that meant skipping out on a huge payday. The couple appears to be true class acts in their split. Maybe they can give Kanye some lessons?
60. Katie Holmes and Tom Cruise – $9.8 Million
Katie Holmes and Tom Cruise’s divorce was already in the public eye due to both of them being celebrities, but it became even more highlighted by Tom’s involvement in Scientology.
Katie Holmes and Tom Cruise – $9.8 Million
Katie’s time with Tom, and the Church of Scientology, earned her $5 million for herself and $4.8 million in child support. Given what we know about both Scientology and Tom, we think that Katie deserved a whole lot more.
61. Gwyneth Paltrow and Chris Martin – $100 Million
Chris Martin and Gwyneth Paltrow had no interest in fighting over anything in their divorce. As the creators of “conscious uncoupling”, they simply wanted to part ways amicably and without any messiness involved.
Gwyneth Paltrow and Chris Martin – $100 Million
To make matters even more ideal, Chris and Gwyneth have similar net worths, so there really wasn’t much to argue about. They each got $100 million and shared custody of their children. That’s not a bad start to conscious uncoupling…
62. Elon Musk and Grimes – $20 Million (Estimated)
Although Grimes and Elon Musk are not yet officially divorced, they have an existing prenuptial agreement that determines how much Grimes would get. Grimes is guaranteed $20 million but she wants a bit more.
Elon Musk and Grimes – $20 Million (Estimated)
The singer is requesting an additional $6 million, $80,000 in monthly alimony, a 5% stake in Space X, and a 10% stake in Tesla. Given Elon’s influence in the world, we’re pretty sure he’ll be able to fight Grimes’s requests.
63. Ben Affleck and Jennifer Garner – $47 Million
This couple’s relationship ended with a lot of assumptions and guesses by the public. From Ben’s “marriage is work” speech, to rumors of cheating, to issues with drinking, it’s a miracle that their marriage lasted for the 13 years that it did.
Ben Affleck and Jennifer Garner – $47 Million
The pair were separated for two years before officially getting divorced in 2021. While Jennifer got $47 million, Ben got a new and, also famous, Jennifer in his life, as he’s now with Jennifer Lopez.
64. Britney Spears and Kevin Federline – $13 Million
Britney Spears, like the rest of us, just wanted her marriage with Kevin Federline to be over. In fact, Britney was so eager to be out of that relationship that she paid far more than what the prenup required in order to finalize the divorce quicker.
Britney Spears and Kevin Federline – $13 Million
Instead of $250,000 for each year they were together, Britney gave Kevin $500,000 per year. In exchange, Kevin is not allowed to talk to the press about his experiences with the Princess of Pop.
65. Denise Richards and Charlie Sheen – $40 Million
Charlie Sheen and Denise Richards had a notoriously nasty divorce, which wasn’t helped by Charlie’s personal and professional hardships.
Denise Richards and Charlie Sheen – $40 Million
The controversial celebrity went from being the highest-paid actor on TV and a married man to being an often unemployed divorce. Denise, on the other hand, got $7 million in the divorce, $10 million in child support, and $25 million in royalties from Two and a Half Men. All she had to do was be married to Charlie Sheen for four years, so… she earned it.
66. Kenny & Marianne Rogers – $60 Million
Country crooner Kenny Rogers is no stranger to divorce—he’s been married five times—but his most expensive split was with his fourth wife, Marianne Gordon. In 1993, the couple divorced, and Rogers shelled out a cool $60 million to Gordon.
Kenny & Marianne Rogers – $60 Million
67. Neil Diamond & Marcia Murphey – $150 million
25 years and two children later, Murphey filed for divorce  and walked away with $150 million! Once rumors of Diamond’s unfaithfulness spread around Hollywood, the odds were in Marcia’s favor. He later said that “she’s worth every penny.”
Neil Diamond & Marcia Murphey – $150 million
68. Jennifer Lopez & Chris Judd – $14 Million
The Bronx-born singer-actress filed for divorce from Chris Judd less than a year after tying the knot, citing irreconcilable differences as the reason for the split. Although they settled for an undisclosed amount, there are numerous reports that J.Lo shelled out $14 million.
Jennifer Lopez & Chris Judd – $14 Million
69. Prince Charles & Princess Diana- $22 Million
Prince Charles and Princess Diana appeared to have a fairytale marriage. Affairs lead to the dissolution of the royal marriage, and Diana was paid a lump sum of around 17.5 million pounds, which at today’s exchange rate is about $22 million.
Prince Charles & Princess Diana- $22 Million
70. Craig McCaw & Wendy Petrak – $450 Million
Founder of McCaw Cellular, Craig McCaw, sold his company to AT& T for over $12 billion and was married to his wife Wendy Petrak for 21 years. By 1995, the  couple split when McCaw filed for divorce. Petrak received $450 million cash in the couple’s divorce settlement.
Craig McCaw & Wendy Petrak – $450 Million