Hollywood's Most Expensive Divorce Settlements

Steve & Elaine Wynn – $741 million

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.

Steve Wynn managed to strike out twice, with the same woman!

Paul McCartney & Heather Mills – $48.6 Million

Wynn divorced Elaine Wynn, for the second time in 2010, costing the billionaire $741 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.

Neil Diamond & Marcia Murphey – $150 million

McCartney had to pay her $48.6 million settlement.

  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.

Robert & Sheila Johnson – $400 million

He later said that “she’s worth every penny.”

After 33 years of marriage to his partner, Sheila Johnson, co-founder of BET Robert Johnson separated in 2002.

Harrison Ford & Melissa Mathison – $118 Million

Two years before their divorce, in 2000, Johnson sold BET to Viacom for $3 billion; of which Sheila ended up getting $400 million.

17 years of marriage and having two children couldn’t save this doomed Hollywood couple.

Bernie & Slavica Ecclestone – $1 Billion

Ford and Mathison divorced in 2001, and with no prenuptial agreement, she ended up getting away with $118 million of the actor’s cash.

Bernie and Slavica Ecclestone made headlines for all the wrong reasons after having a divorce settlement worth an incredible $1 billion!

Heidi Klum & Seal – $70 Million

Not wasting any time, Slavica turned this money into $1.6 billion from investments.

Heidi claims that Seal’s temper got so out of control, it scared their children.

Michael & Diandra Douglas – $45 Million

Heidi left with a broken heart and bank account. Despite their prenup agreement, Klum ended up settling the divorce for $70 million.

Michael Douglas married Diandra in 1977 and had a son with her a year later. In 1995, Diane filed for divorce.

Demi Moore & Bruce Willis – $90 Million

By the end of their divorce, Diandra received a $45 million settlement, which was half of the actor’s net worth at the time.

Demi and Bruce were married for 11 years and have three daughters.

Steven Spielberg & Amy Irving – $100 Million

They divorced in 2000, and Bruce said that he felt like “he had failed as a father and husband.” Demi moved on to a younger man, Ashton Kutcher, as well as a $90 million settlement.

Three and a half years into their marriage, the couple agreed to divorce.

Craig McCaw & Wendy Petrak – $450 Million

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.

  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.

Donald & Ivana Trump – $25 Million

Petrak received $450 million cash in the couple’s divorce settlement.

  Donald Trump and Ivana were the “it” couple of NYC in the 80’s. When rumors of Donald’s reported affair with former beauty queen Marla Maples started, Ivana filed for divorce.

Madonna & Guy Ritchie – $92 Million

The heavily publicized break-up, settled in 1992, allowed Ivana to pocket around $25 million from her ex-husband.

  The marriage between the Madonna and Guy Ritchie lasted only seven years.

Lionel Richie & Diane Richie – $25 Million

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.

  After seven years, the singer and his second wife, Diane Alexander, called it quits.

Alec & Jocelyn Wildenstein – $2.5 Billion

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.

Jocelyn managed to get $2.5 billion out of her ex-husband Alec Wildenstein, French businessman and billionaire.

Dmitry & Elena Rybolovlevi – $4.5 Billion

Known for her plastic surgery, which cost her a total of $2 million, Jocelyn thought changing her look would keep her husband around.

After 26 years of marriage, Dmitry and Elena called it quits.

Rupert Murdoch & Wendi Deng – $1.8 Million

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.

The News Corporation CEO didn’t waste any time as he married Deng 17 days after his previous divorce was finalized.

Rupert Murdoch & Anna Maria Torv – $1.2 Billion

In June 2013, Murdoch decided Deng wasn’t doing it for him anymore and divorced her too, settling for $1.8 million.

This couple who lasted 32 years and have three children together split up in 1999.

Mel Gibson & Robyn Moore – $425 Million

Murdoch ended up amassing a net worth of $8 billion. Torv received $1.2 billion as part of the couple’s divorce settlement.

  After 26 years together, Robyn’s final decision to file for divorce was brought on by Mel’s DUI arrest in 2006.

Frank & Jamie McCourt – $130 Million

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.

  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.

Harold Hamm & Sue Ann Arnall – $974.8 Million

Since Frank is such a successful entrepreneur, the divorce ended up costing him a substantial $130 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.

Angelina Jolie & Brad Pitt – $400 Million

The legal battle ended when Sue accepted Mann’s settlement check of $974.8 million!

  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.

Jennifer Lopez & Chris Judd – $14 Million

It’s too soon to tell, but rumor has it that the divorce will end up costing $400 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.

Ron Perelman & Ellen Barkin – $20 Million

Although they settled for an undisclosed amount, there are numerous reports that J.Lo shelled out $14 million.

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.

Greg Norman & Laura Andrassy – $103 Million

Ellen reportedly received a settlement of more than $20 million after she sold off jewelry Ron had given her.

  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!

Kenny & Marianne Rogers – $60 Million

You’d think those big payouts would make couples work harder to keep their relationships together.

  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.

Johnny Carson & Joanna Holland – $20 Million

In 1993, the couple divorced, and Rogers shelled out a cool $60 million to Gordon.

  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.

Ted Danson & Casey Coates – $30 Million

When they divorced, Carson was the highest paid TV personality, raking in $15 million a year.

  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.

Adnan Khashoggi & Soraya Khashoggi – $874 Million

In one of Hollywood’s most expensive divorce settlements at the time, Danson paid Coates $30 million.

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.

Kelsey & Camille Grammer – $30 Million

Soraya was awarded $874 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.

Tiger Woods & Elin Nordegren – $750 Million

Camille ended up on the Real Housewives of Beverly Hills and $30 million of Grammer’s money.

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.

John & Beverly Charman -$95 Million

Tiger was reportedly forced to hand over $750 million in their divorce.

  When Charman married his high school sweetheart Beverley, he had no money, but during their 29 years of marriage, he became the eighth richest businessman in London.

Samathur Li-kan & Florence Tsang-Chiu-wing -$154 Million

Beverly gave up her job to raise their children, so when the couple separated, Beverly received $95 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.

Michael & Juanita Jordan – $168 Million

A Hong Kong judge ordered the wealthy real estate mogul to pay his ex-wife $154 million.

After years of trying to make the marriage work, Michael and Juanita Jordan mutually agreed to a divorce.

Arnold Schwarzenegger & Maria Shriver – $375 Million

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.

  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.

Reba McEntire & Narvel Blackstock – $47.5 Million

Because they never had a prenup agreement, Shriver ended up getting $375 million and custody of their children.

  Reba McEntire and Narvel Blackstock shocked fans when they announced their split in 2015. Despite this, the two remain friends and support each other.

Roman & Irina Malandina – $300 Million

Given that there was no prenuptial agreement was in place, we can assume that the couple divided their assets evenly.

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.

Michael Strahan & Jean Muggli – $15 Million

When the couple divorced, Irina ended up getting $300 million which included cash as well as lavish homes in Moscow and London.

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.

Jesse Williams & Aryn Drake-Lee – Approx. $4 Million

After filing for divorce, Muggli was awarded $15 million in a settlement and $18,000 in child support each month.

  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.

Eddie Murphy & Nicole Mitchell Murphy

No settlement amount was disclosed but is estimated that it will cost around $4 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.

Kevin Costner & Cindy Silva – $80 Million

Nicole went on to date Michael Strahan. Currently, Eddie is dating Paige Butcher and the couple has a child together.

  16 years of marriage and three children later, the Hollywood couple decided to call it quits as a result of Costner’s alleged infidelity.

James Cameron & Linda Hamilton – $50 Million

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.

  This relationship came to an end after Cameron was unfaithful while on the set of Titanic.

Johnny Depp & Amber Heard – $6.8 Million

Within days of Cameron winning an Oscar for the movie, the couple announced their separation and Linda’s $50 million settlement.

  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.

Prince Charles & Princess Diana- $22 Million

Although the couple never had children together, Depp has two, including model Lily-Rose Depp.

  Prince Charles and Princess Diana appeared to have a fairytale marriage.

Alex Baldwin & Kim Basinger – Approx. $3 Million

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.

  Kim Basinger 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.

Vladimir Potanin & Natalia Potanina – $7 Billion

It is reported that they settled for around $3 million.

  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.

Michael Polsky & Maya Polsky – $184 Million

The divorce was extremely complicated, and Natalia received around $7 billion.

  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!

Charles Fipke & Marlene Fipke – $200 Million

He split from his wife Maya in 2003 and it cost him an astonishing $184 million.

  Charles Fipke discovered the first diamonds in Canada’s Northwest Territories, which in turn made him a very rich man.

Gwen Stefani & Gavin Rossdale – $2.5 Million

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.

  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.

Hilary Duff & Mike Comrie – $2.5 Million

Since the split, Gwen has gone on to date Blake Shelton.

  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.

Teddy Landau & Michelle Branch – Approx. $300,000

What followed was a messy divorce and a settlement which cost around $2.5 million.

  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.

Dr. Phil McGraw & Debbie Higgins – Approx. $1 Million

The settlement cost close to $300,000.

  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.”