The Most Expensive Divorce Settlements of All-Time
Brad Pitt and Jennifer Aniston — $60 Million
Kicking it off with one of the most popular couples of the early 2000s. Brad Pitt (Fight Club) and Jennifer Aniston (Friends) met in 1994 and instantly sparked a connection. They began dating in 1998. From then on, every move the pair made was under a microscope as the tabloids couldn’t get enough of the high-profile couple. Pitt — who had recently ended a relationship with Seven co-star Gwyneth Paltrow — wed Aniston two years after the couple began dating in a private wedding in Malibu. Amidst rumors of Pitt getting romantically involved with a co-star (more on that in a bit), the pair announced their divorce in 2005. The paperwork was finalized later that year, and the couple reportedly remained cordial with each other even after the split.
Alex Rodriguez and Cynthia Scurtis — $12 Million
Former three-time MLB MVP Alex Rodriguez has built a catalog of ex-flings and high-profile relationships which would put the 1920s New York Yankees to shame. Perhaps his messiest union is the one with his first wife, psychology graduate Cynthia Scurtis. The pair were married in 2002, and had two children together (both daughters). In 2008, the marriage fell apart after Scurtis accused Rodriguez of having extramarital affairs. The divorce settlement reportedly cost A-Rod — the No. 1 career earner in MLB history — around $12 million.
Demi Moore and Bruce Willis — $90 Million
Shortly after meeting at a film premiere, Demi Moore married her second husband — Bruce Willis — in 1987. Moore was previously married to musician Freddy Moore — who’s surname she adopted as a stage name early in her career — and was engaged to actor Emilio Estevez (though they were never wed). Willis and Moore were married for 11 years and had three children together before announcing their split. The divorce was finalized in 2000. Willis stated that “he had failed as a father and husband.” Hate to break it to you, Bruce, but you also failed as a money-saver. Moore was paid $90 million in the settlement.
Madonna and Guy Ritchie — $92 Million
The Madonna and Guy Ritchie marriage just couldn’t work itself out. The pair met in 1998, and Madonna gave birth to their son, Rocco, two years later. In 2006, the Snatch director and the Queen of Pop adopted their second child, David, from Malawi. Just a couple of years later, Madonna had decided she had enough. The iconic singer said that the couple had irreconcilable difference and filed for divorce. The details of the settlement unveiled that Ritchie received the value of the couple’s London pub and 1,100-acre estate. In total, Ritchie — who is now married to model Jacqui Ainsley — received over $90 million in the split.
Michael Douglas and Diandra Luker — $45 Million
Two-time Academy Award winner Michael Douglas married Diandra Luker when he was 32 and she was 19. The teen was the daughter of an Austrian diplomat. Douglas had just helped produce One Flew Over the Cuckoo’s Nest. Their son, Cameron, was born a year later. Though their relationship seemed perfectly fine from the outside, that wasn’t necessarily the case. Luker filed for divorce in 1995 after nearly 18 years of marriage. As part of the settlement, Luker was awarded $45 million in her favor.
Tom Cruise and Nicole Kidman — $214 Million
None of Tom Cruise’s three marriages have ended in his favor. Cruise was introduced to Scientology from his first wife, Gung Ho and Someone to Watch Over Me actress Mimi Rogers. The couple split after two years together. Cruise’s most recent wife, Katie Holmes, reportedly received over $10 million in the couple’s divorce settlement. Holmes is said to have initiated the split due to Cruise’s intensifying religious beliefs. However, the biggest monetary loss Cruise faced was his divorce with Days of Thunder co-star Nicole Kidman. The pair were wed for ten years and adopted two children together. Cruise and Kidman settled on a 50-50 split (which cost the Mission Impossible star around $214 million).
Heidi Klum and Seal — $70 Million
Heidi Klum and Seal tied the knot in 2005. Seal is a British singer who sold over 20 million records worldwide. Klum was born in West Germany, and began working as a model before landing gigs as a television host and producer. During their marriage, the couple established a yearly tradition of exchanging vows in front of family and friends. They have three children together, and Seal even adopted Klum’s daughter from her previous marriage. Unfortunately, the couple called it quits after seven years of marriage — with the divorce finalized in 2014.
Tiger Woods and Elin Nordegren — $750 Million
The highly publicized split of golf legend Tiger Woods and Swedish model Elin Nordegren cost the former No. 1 paid athlete of all-time a hefty sum of cash in addition to the damage to his public persona. The shocking news of Woods’ infidelity went viral across all major news networks. It led, of course, to the Stockholm-born Nordegren filing for a divorce which was finalized in 2010. Though Woods earned nearly $1.7 billion over his career in winnings and endorsement deals, his net worth was around $500 million at the time. Nordegren was awarded $100 million (or, 20-percent) of Woods’ net worth in addition to monthly child support payments for their two children.
Mike Tyson and Robin Givens — $10 Million
A rapid marriage which ended with a hefty settlement payment. This relationship was tumultuous, to say the least.. “Iron” Mike Tyson was on top of the boxing world when he met actress and model Robin Givens. Tyson had recently become the youngest heavyweight champion in history, while Givens was gaining notoriety for her role as Darlene on ABC’s Head of the Class. Givens has said that Tyson was abusive and she feared for her safety, leading to her decision to divorce the famed athlete. The couple were married for just 10 months, and Givens received $10 million in the eventual settlement.
Johnny Depp and Amber Heard — $7 Million
In one of the more unfortunate breakups featured on this list, Johnny Depp and Amber Heard’s messy divorce drew the ire of the media landscape. The pair met on a film in 2011, and were officially wed four years later. Heard filed for divorce a little over a year following the wedding, though it wouldn’t be made official until months later. She also requested a restraining order against Depp, claiming that the Pirates of the Caribbean and Edward Scissorhands star was both physically and verbally abusive during their relationship.
Depp has since sued his ex-wife for defamation and the pair are in the midst of a grueling court battle. Heard claimed she was donating her settlement money ($7 million) to charity — though the fulfillment of that donation remains unconfirmed.
Michael Jordan and Juanita Vanoy — $168 Million
The likelihood of the No. 1 paid athlete ever paying a large sum of money in a divorce is excruciatingly high. This was the case with Michael Jordan’s split from ex-wife Juanita Vanoy in 2006. Jordan and Vanoy tied the knot at A Little White Wedding Chapel in Las Vegas while the couple were awaiting the birth of their first son, Marcus. Though the couple never agreed to a prenup, Vanoy was awarded $168 million (equivalent to nearly $240 million in 2022). Today, Jordan is worth over $1.7 billion and is the principal owner and chairman of the Charlotte Hornets.
Britney Spears and Kevin Federline — $1.3 Million
Pop sensation Britney Spears has been in the limelight ever since she dropped two of the best-selling albums of all-time — Baby One More Time (1999) and Oops!…I Did It Again (2000). Seemingly every relationship she’s ever had gained enormous media attention. Spears’ first marriage to childhood friend Jason Alexander lasted a mere 55 hours before it was annulled. Her second marriage lasted a bit longer as Spears tied the knot with backup dancer Kevin Federline. The couple were together for three years and the relationship was highly publicized. In 2007, they agreed to call it quits with Spears forking over $1.3 million to her ex-husband in addition to on-going child support payments for their two sons.
Sean Penn and Robin Wright — $60 Million
Actors Sean Penn and Robin Wright originally met when the pair were filming the 1990 Phil Joanou crime film State of Grace. They began dating shortly after and had two kids together, a daughter named Dylan Frances and a son named Hopper Jack. Following the birth of their children, Penn and Wright separated and began dating other people. However, the pair got back together and finally tied the knot in 1996. Though they seemed to destined to spend the rest of their lives together, Penn and Wright announced their divorce which was eventually made official in 2010. Though they no longer stay in touch, it seems like the divorce paid off for both parties — thought it certainly made a dent in Penn’s wallet. The two-time Academy Award winner (Mystic River, Milk) reportedly lost $61 million in the settlement.
Brad Pitt and Angelina Jolie — $400 Million
The Mr. and Mrs. Smith co-stars developed a close, high-profile relationship shortly after filming the 2005 summer blockbuster. “Brangelina” became one of the most popular celebrity couples in Hollywood, though it did not come without plenty of controversy. Reportedly, the couple began dating while Pitt was still in the midst of his divorce with Jennifer Aniston — and some have implied that Jolie drove the split. Nevertheless, Pitt and Jolie were hitched in 2014, but the happy couple didn’t stay happy for long. Jolie filed for divorce in 2016 — citing irreconcilable differences — and they were officially divorced in a legal sense in 2019. The highly publicized split is rumored to have cost the two mega-stars over $400 million.
Harrison Ford and Mellisa Mathison — $118 Million
Harrison Ford is one of the highest paid actors in the history of Hollywood. In total, movies featuring Ford have amassed over $9.3 billion worldwide combined. This is thanks in large part to his roles in iconic film series like Star Wars and Indiana Jones. All of those earnings eventually came at a price. When it came time to settling a divorce with his second wife, screenwriter Melissa Mathison, Ford was handed a considerable tab. The couple had been together for 17 years and had two children together prior to splitting up. In the original settlement, Ford was ordered to pay $85 million to Mathison. However, there was an added stipulation which granted a percentage of Ford’s future earnings to Mathison, as well. In total, Mathison received $118 million in the split.
Steve and Elaine Wynn — $741 Million
Steve and Elaine Wynn tied the knot in 1963 when the couple were each just 21 years old. While married, the couple co-founded both Mirage Resorts and Wynn Resorts. The two companies are said to have played a large part in the revitalization of the Las Vegas Strip. However, the couple’s relationship wasn’t always on the best of terms. The pair divorced (for the first time) in 1986 but opted to remarry just five years later. During this time, Elaine gave birth to the couple’s children — daughters named Kevyn and Gillian. The second try at marriage didn’t work out, as the couple divorced for a final time in 2010. That same year, Wynn was ordered to transfer $741 million worth of stock in Wynn Resorts to his newly ex-wife.
Mel Gibson and Robyn Moore — $425 Million
Far before Mel Gibson became a household name for his acting prowess, the Braveheart star fell in love with a dental assistant named Robyn Moore. The couple met soon after Gibson finished filming for Mad Max. The couple seemed to be living the ideal life together as Moore was right beside Gibson as his fame ballooned to grand heights. They parented seven children (six sons and one daughter). In an unfortunate turn of events, Gibson’s poor decision-making ultimately led to the couple’s split. The pair decided to separate in 2006. Gibson cites his drunk driving arrest as playing a major role in the eventual divorce which came three years later. The settlement was finalized in 2011, ordering Gibson to surrender half of his net worth ($850 million) at the time.
Adnan and Soraya Khashoggi — $874 Million
Harold Hamm and Sue Ann Arnall — $974 Million
Harold Hamm is a rather important figure in the oil and gas industry. The founder of Continental Resources — a gas production company based in Oklahoma City — Hamm is worth over $16 billion and was pegged as the energy advisor for presidential candidate Mitt Romney during the 2012 election. Hamm had three children with his first wife before getting divorced in 1987. A year later, Hamm tied the knot with his second wife — lawyer Sue Ann Arnall. Arnall was made an executive of Continental Resources and the couple had two children together. The pair split in 2012, though they had allegedly been separated for seven years before that. Originally, some thought nearly half of Hamm’s fortune could be sent to Arnall in a settlement. However, in 2015 a judge ruled that $1 billion would be paid to Hamm. Later that year, a check worth $974 million was deposited into Arnall’s back account.
Bernie Ecclestone and Slavica Radic — $100m
Chief executive Bernie Ecclestone and Croatian model Slavica Radic had one of the most expensive splits in history. However, the ensuing settlement may not have played like some expected. Ecclestone is one of the richest people in the United Kingdom. Despite having been replaced in his role with Formula One in 2017, the 91-year-old has amassed a net worth of $3 billion. However, this billionaire didn’t end up with the proverbial short end of the stick as it pertains to the divorce. Court documents revealed that Ecclestone has been receiving yearly payments of $100 million from Radic’s trust fund since 2009. Don’t feel too bad for the model. As of 2022, Radic’s net worth is reportedly over $1 billion.
Rupert Murdoch and Anna Torv — $1.7 Billion
An amicable divorce which results in $1.7 billion isn’t the worst way to exit a 31-year marriage. That was the payout in favor of Anna Torv, the ex-wife of Australian-born businessman and media tycoon Rupert Murdoch. The couple had been together for over three decades before deciding to call it quits. Murdoch and Torv had decided they were headed in different directions in life and opted for a clean breakup. They had three children together. Just 17 days after the split, Murdoch would marry his third wife — Wendi Deng. Torv tied the knot with financier William Mann six months later.
Alec Wildenstein and Jocelyne Perisset — $3.8 Billion
All the way back in 1977, the famed Wildenstein family purchased a 49-percent stake in the 60,000-acre wildlife conservatory known as Ol Jogi Ranch in Kenya. Heir to the family’s art dealing business, Alec Wildenstein likely wishes his family never decided to make such a purchase. The Ol Jogi Ranch is where Wildenstein would meet his first wife, socialite Jocelyne Perisset. The couple were married a year later and had two children together. Twenty years later, the couple were involved in the costliest divorce in world history. The pair called it quits in 1999, with Wildenstein ordered to pay Perisset $2.5 billion up-front in addition to $100 million more for each of the following 13 years.
Jeff and Mackenzie Bezos — $35 Billion
Dmitry and Elena Rybolovleva — $600 Million
Note to all billionaire businessmen: don’t get caught being unfaithful on a yacht. It might just cost you a private island. Russian mogul Dmitry Rybolovlev did not heed this advice. The majority owner of AS Monaco found himself in a unenvious situation when his wife, Elena Rybolovleva, caught him with his mistress aboard the family yacht. Elena filed for divorce in 2008 which spawned a near six-year struggle between both parties. The courts originally ruled in favor of Elena for the sum of a whopping $4.8 billion. However, Rybolovlev’s attorney successfully appealed the charge and the Russian billionaire was instead ordered to pay his ex-wife $600 million.
Bill and Melinda Gates — $76 Billion
A decade after helping co-found Microsoft, Bill Gates began dating his eventual wife, Melinda Ann French. The pair met 1987 at a trade fair in New York, and were wed seven years later at a luxurious private ceremony on an island of Hawaii. Together, the Gates’ accomplished several impressive feats. In 2006, Time magazine recognized the pair as Persons of the Year (alongside U2 front-man Bono). Additionally, they co-founded the Bill and Melinda Gates Foundation, which pledged over $2 billion to aid in COVID-19 vaccine efforts. Seeing as the couple had one of the most influential marriages in history, it’s no surprise that the divorce came with a hefty price tag. In total, Melinda reportedly received $76 billion — dropping Bill all the way down to No. 4 on the list of the richest people in the world.