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- Estimated amount: $60 million
- Year married: 1977
- Year divorced: 1993
- Number of children: 1

Five-times married country star Kenny Rogers held no ill will toward ex-wife Marianne Gordon when their divorce ended in a $60 million settlement. The two met when Rogers was in the band First Edition and $60,000 in debt. Despite their financial struggles, Gordon stood by her man and supported him as he pursued a solo career. Soon enough, Rogers rocketed to wealth through hit singles and successful chicken franchises. He attributes the end of the marriage to the fact that Gordon stayed home to take care of their newborn son while he went on tour, causing their lifestyles to drift apart.

- Estimated amount: $80 million
- Year married: 1978
- Year divorced: 1994
- Number of children: 3

It was love at first sight when Kevin Costner and Cindy Silva met as college students at the Delta Chi fraternity house in 1975, marrying three years later. However, Costner's subsequent success as a film star put continuous friction on the marriage, . By 1994, it was all over. Costner walked away with his movie career. Cindy walked away with $80 million.

- Estimated amount: $80 million
- Year married: 1970
- Year divorced: 2012
- Number of children: 3

She was a former Malaysian beauty queen with an . He was a Chinese businessman who made a fortune on Laura Ashley and allegedly spent up to . Suffice it to say, the divorce between Dr. Khoo Kay Peng and Pauline Chai was epic, with a hefty price tag to show for it.

- Estimated amount: $76-$92 million
- Year married: 2000
- Year divorced: 2008
- Number of children: 2

Most of the high-profile divorce cases on this list end with the husbands paying settlements. This wasn't the outcome for Madonna, whose decadeslong career as a global pop star made her the breadwinner in her marriage to director Guy Ritchie. Given that both individuals had a penchant for absolute control, the marriage was seemingly doomed from the start. The , and whether they wanted blueberry or chocolate chip pancakes for breakfast. A widely publicized divorce inevitably followed, as did an intense, .

- Estimated amount: $100 million
- Year married: 2004
- Year divorced: 2010
- Number of children: 2

Few divorces are as legendary as that between pro golfer Tiger Woods and model Elin Nordegren. Their five-year marriage came crashing to a halt after a physical altercation in 2009, prompting Woods to flee the home and accidentally crash his SUV into a fire hydrant after Nordegren discovered he had been anything but faithful. The prenup was torn to shreds, and she walked away with $100 million, or .

- Estimated amount: $100 million
- Year married: 1985
- Year divorced: 1989
- Number of children: 1

Given his indisputable success as a director, producer, and businessman, one might never imagine Steven Spielberg signing a . Yet that's exactly what he did before marrying actress Amy Irving in 1985. Irving would later argue in court that she didn't have a lawyer present when signing the impromptu prenup, which ended up putting a whopping $100 million settlement in her hands, half of Spielberg's estate at the time.

- Estimated amount: $103 million
- Year married: 1981
- Year divorced: 2007
- Number of children: 2

Greg Norman was married to Laura Andrassy for 25 years until she caught him cheating with a woman named Kirsten Kutner. As a result, Norman and Andrassy divorced, with the Australian pro golfer coughing up $103 million in the settlement. However, that didn't mean an end to the drama. Years later, Norman ended up marrying Kutner, further .

- Estimated amount: $118 million
- Year married: 1983
- Year divorced: 2004
- Number of children: 2

What began as a mid-life crisis ended in a costly divorce for movie star Harrison Ford. Citing "irreconcilable differences," he and screenwriter Melissa Mathison ended their supposedly rock-solid marriage in 2004. Rumor has it Ford had gone on an epic .

- Estimated amount: $130 million
- Year married: 1979
- Year divorced: 2011
- Number of children: 4

Touted as the costliest divorce in California history, the split between Frank and Jamie McCourt was about far more than just money. As co-owners of the Los Angeles Dodgers, the McCourts engaged in a vicious battle over their individual stakes in the franchise. , and the press ate every word. Eventually, Jamie relinquished her claim to ownership for a cool $130 million. It's estimated that were racked up throughout the proceedings.

- Estimated amount: $150 million
- Year married: 1969
- Year divorced: 1995
- Number of children: 2

Neil Diamond might have been singing about "Sweet Caroline," but it was a girl named Marcia Murphey who stole his heart in 1969. Their marriage lasted 26 years and yielded two sons before the couple called it quits in 1995. Thanks to an impressive catalog of popular songs, Diamond was wealthy enough to pay out $150 million in the divorce, an exceptionally high sum for its time. Why was the singer feeling so generous? He would later claim that .

- Estimated amount: $160 million
- Year married: 1991
- Year divorced: 2010
- Number of children: 2

Russian oligarch Boris Berezovsky and his ex-wife Galina Besharova were separated for 16 years before making it official in 2010. The reason? Besharova had grown too annoyed with everyone referring to Berezovsky's girlfriend as his wife. The divorce , though the settlement details took much longer to hash out. Ultimately, Besharova walked away with $160 million, possibly the largest settlement in Britain's history.

- Estimated amount: $168 million
- Year married: 1989
- Year divorced: 2006
- Number of children: 3

Basketball legend Michael Jordan and Juanita Vanoy had been married for 13 years and had three children when they first decided to divorce in 2002. However, the couple reconciled soon after, with the marriage lasting another four years before officially falling apart in 2006. The decision was reportedly mutual, and Jordan's estimated payout of $168 million was the .

- Estimated amount: $184 million
- Year married: 1975
- Year divorced: 2007
- Number of children: 2

According to court records, Ukrainian couple Michael and Maya Polsky arrived in the United States in 1976 with . A few years later, Michael achieved massive wealth in the energy industry, making him a multimillionaire. During their divorce proceedings, which lasted years, Maya argued that as someone who provided Michael with she was integral to his accumulated wealth. The court eventually agreed, awarding her $184 million for her troubles.

- Estimated amount: $200 million
- Year married: 1966
- Year divorced: 2000
- Number of children: 5

They say diamonds last forever. Marriages? Not so much. Famed Canadian diamond prospector Charles "Chuck" Fipke, who discovered one of the world's biggest diamond mines and reaped a subsequent fortune, split from his wife, Marlene, after over 30 years of marriage. Marlene—who'd accompanied Chuck on expeditions, dried core samples in the kitchen, and even handled the accounting—was granted a .

- Estimated amount: $300 million
- Year married: 1991
- Year divorced: 2007
- Number of children: 5

The rule goes that in the case of a divorce with no prenuptial agreement, the spouse is entitled to half of the breadwinner's earnings. That turned out to be bad news for Roman Abramovich, who'd amassed his entire $10.2 billion fortune virtually during his 16-year marriage to former stewardess Irina Malandina. Thankfully for him, Malandina wasn't feeling particularly aggressive. She  of $300 million to get the whole thing over with.

- Estimated amount: $400 million
- Year married: 1969
- Year divorced: 2002
- Number of children: 2

They say people in relationships should never work together, but Robert Johnson and Sheila Crump would probably be much less wealthy had they heeded such advice. The married couple co-founded BET in 1980 and took in a collective fortune. However, time-tested adages prevailed and things turned ugly in the '90s when . Meanwhile, rumors of Robert's infidelity persisted. He would end up selling BET for $3 billion to Viacom in 2001 and divorcing his wife soon after.

- Estimated amount: $425 million
- Year married: 1980
- Year divorced: 2011
- Number of children: 7

He might be a devout Catholic with a self-produced film to show for it, but even Mel Gibson struggled to maintain his marital vows. After seven children and 26 years of marriage, Gibson and his wife, Robyn Moore, separated in 2006 on the heels of Gibson's .

Three years later, Moore came across and officially filed for divorce. Gibson would eventually settle for an estimated $425 million, considered the largest payout in Hollywood history.

- Estimated amount: $460 million
- Year married: 1974
- Year divorced: 1997
- Number of children: 0

The divorce proceedings were so vast in scope between entrepreneurs Craig McCaw and Wendy Petrak that the law firm she hired , coming right behind the Exxon Valdez oil spill. Apparently, there were enough documents uncovered during litigation to fill a warehouse. Ultimately, Wendy walked with $460 million () and the private jet.

- Estimated amount: $604 million
- Year married: 1985
- Year divorced: 2015
- Number of children: 2

Dmitry Rybolovlev made a fortune in potassium, among other things, and began to enjoy his newfound lifestyle by reportedly attending opulent . Rybolovlev's wife, Elena, wasn't amused; she petitioned for divorce in 2008. Her actions kicked off a prolonged series of litigations, which resulted in a spectacular $4.5 billion settlement in 2014. However, that amount was quickly and successfully appealed by Dmitry and .

- Estimated amount: $874 million
- Year married: 1961
- Year divorced: 1982
- Number of children: 5

Before she was the wife of a Saudi Arabian arms-dealing billionaire, her name was Sandra Daly. The illegitimate daughter of a British waitress, Daly married Adnan Khashoggi, converted to Islam, changed her name to Soraya, and began living a life of which she could have only dreamed. Both her beauty and spending habits were the stuff of legend, and she counts . Despite winning $874 million in a 1984 settlement (reportedly the biggest payout of its time), Soraya Khashoggi was living the modest life of a .

- Estimated amount: $974.8 million
- Year married: 1988
- Year divorced: 2015
- Number of children: 2

After a long separation and contentious divorce battle, Continental Resources CEO Harold Hamm handed his wife, Sue Ann, a personal check for $975 million. Worried it would interfere with her current appeal, Arnall's initial response was a firm rejection. After giving it some more thought, however, she ended up depositing the check and settling the divorce. As for Hamm, he was probably relieved, given his (a figure that's only increased since).

- Estimated amount: $1 billion
- Year married: 1963
- Year divorced: 2010
- Number of children: 2

Vegas casino magnate Steve Wynn and wife Elaine first divorced in the mid-'80s, only to remarry in 1991 and then divorce again in 2010. The second time around was far more brutal, with the couple battling fiercely over shares of Wynn Resorts Ltd. Pascal eventually secured a 9.4% stake in the company but later sued her husband because he was .

- Estimated amount: $1.2 billion
- Year married: 1985
- Year divorced: 2009
- Number of children: 2

The divorce between Formula One tycoon Bernie Ecclestone and his discernibly tall, model wife, Slavica Radić, was a tricky one. It seemed that Ecclestone was initially ordered to pay over $1 billion to Radić per the settlement agreement. However, as it turned out, much of the wealth was in trust funds under Radić's name, so it was .

- Estimated amount: $1.7 billion
- Year married: 1967
- Year divorced: 1999
- Number of children: 3

While frequently pointed to as the second-costliest divorce of all time, at least one between media tycoon Rupert Murdoch and his second wife, Anna Torv, was far less outlandish than reports suggest. However, to this day, the legacy of the $1.7 billion payout persists.

Regardless of specifics, it's safe to say she was handsomely rewarded for her time with Murdoch, whom she described as "." In keeping with his reputation, Murdoch allegedly walked out on the marriage in 1999.

- Estimated amount: $3.8 billion
- Year married: 1978
- Year divorced: 1999
- Number of children: 2

If one ever wonders how the rich and famous spend all their money, look no further than the lifestyle of Jocelyn Périsset Wildenstein. That was just one of the many aspects that made her 1999 divorce from billionaire Alec Wildenstein pure catnip for the media. The reported tales of were equally compelling. One other huge thing the press latched on to? That gargantuan $3.8 billion settlement, of course, considered the largest in world history.

Additional writing by Cu Fleshman.