Celebrities Who Spent Millions On Divorces

25. Brad Pitt and Jennifer Aniston

When Brad Pitt and Jennifer Aniston divorced in 2005, it wasn’t a blockbuster payout, but it still ranked pricey for Hollywood. Jennifer got to keep their Beverly Hills mansion, estimated at $29 million at the time of the settlement. Meanwhile, Brad walked away with complete control of their production company, Plan B Entertainment, valued at over $50 million, leaving Jennifer with only a minor share. As the duo had no prenuptial agreement, California’s community property laws applied, and the blow only felt harder.

24. Madonna and Guy Ritchie

Madonna’s divorce from British filmmaker Guy Ritchie in 2008 was one of the most expensive splits in U.K. celebrity history. Reports at the time confirmed that Ritchie received between $76 million and $92 million as part of the settlement. The deal wasn’t just cash, though, and Ritchie also took ownership of the couple’s Wiltshire estate, Ashcombe House, valued at nearly £20 million, along with their London pub. Unlike many high-profile breakups, the financial aspects were resolved relatively quickly, which allowed both parties to move on without prolonged legal battles. Madonna kept control of her recording empire and touring revenues, while Ritchie walked away with a substantial payout and property holdings.

23. Donald Trump and Ivana Trump

In 1991–92, Donald and Ivana Trump’s divorce made headlines for the jaw‑dropping settlement. Ivana walked away with around $14 million in cash, their lavish mansion in Greenwich, Connecticut, a Trump Plaza apartment, and the exclusive right to use Mar-a-Lago for one month each year. Prior attempts at a prenup had capped her payout at $25 million, which her side claimed was unfair; however, the final deal balanced the empire-building contributions with Trump’s financial pressure at the time.

22. Tiger Woods and Elin Nordegren

Following the scandal that halted sports coverage, the couple finalized their Florida divorce in August 2010. Multiple reputable outlets reported that Nordegren received approximately $100 million, a considerable sum for a six-year marriage, but understandable given that Woods' peak-of-power endorsements and tournament winnings significantly inflated the marital estate. While specific line items remained sealed, Nordegren soon purchased (and subsequently rebuilt) a sprawling oceanfront property on Jupiter Island; Woods retained the yacht, jet, and primary sports/business entities.

21. Steven Spielberg and Amy Irving

When Steven Spielberg and Amy Irving split after just four years of marriage, the price tag made as many headlines as his films. The pair had signed what became known as the infamous “napkin prenup”, an informal agreement scribbled without legal oversight. A California judge quickly dismissed it, ruling it invalid under state law. With no prenup to protect Spielberg’s fortune, Irving secured a reported $100 million settlement.

20. Rupert Murdoch and Anna Murdoch

Rupert Murdoch’s split from Anna Murdoch in 1999 is still remembered as one of the costliest divorces in history. Reports at the time stated that Anna walked away with approximately $1.7 billion, including $110 million in cash. While the exact figure was never confirmed and some analysts later questioned the number, it is clear that this settlement involved one of the biggest transfers of personal wealth ever linked to a marriage breakup. The couple had been together for more than 30 years, during which Murdoch built News Corp into a media empire. That long partnership meant Anna had strong claims on the fortune.

19. Mick Jagger and Jerry Hall

Mick Jagger and supermodel Jerry Hall didn’t divorce because their Bali wedding wasn’t legally valid; the High Court granted an annulment in 1999. That meant the marriage was treated as if it never existed under English law. Yet, behind the scenes, the financial settlement was low-key. While both parties kept the details sealed, reports revealed that Hall had sought up to £30 million and a five‑million‑pound mansion on Richmond Hill, part of Jagger’s estimated £150 million fortune.

18. Michael And Diandra Douglas

Married in 1977, they split as Douglas’s movie fortune began to take off. Reports say the payout is around $45 million, a product of a long marriage, community-property principles, and the lion’s share of the actor’s peak earnings arriving during that span. Years later, Diandra litigated for a slice of the profits from “Wall Street: Money Never Sleeps,” arguing that the sequel exploited characters from the original created during their marriage; that bid also failed.

17. Mel Gibson and Robyn Moore

Three decades of marriage, no prenup, and California community property law; mix those, and you get one of Hollywood’s priciest splits. Moore, who was a dental nurse when they married, reportedly received up to half of Gibson’s fortune because it was accumulated during their marriage. It’s a textbook example of how long marriages without prenups can reset even an A-lister’s net worth.

16. Lionel and Diane Richie

Lionel Richie’s divorce from Diane Alexander in 2004 became infamous because of the staggering lifestyle costs laid out in her court filings. She asked for $300,000 every month in spousal and child support, breaking it down to include $15,000 for clothes, $20,000 a year for cosmetic surgery, plus private school, staff salaries, and six-figure property expenses. Although the final settlement figure was never officially released, multiple outlets later reported it to be around $20 million.

15. Paul McCartney & Heather Mills

In 2008, Paul McCartney and Heather Mills’ marriage came to an end and the High Court laid out the details of the settlement in black and white. Mills walked away with a total of £24.3 million; £16.5 million awarded as a lump sum, plus another £7.8 million in assets already in her name. On top of that, she was granted £35,000 a year in child maintenance for their daughter Beatrice, while McCartney agreed to cover her school fees and the cost of a nanny.

14. James Cameron and Linda Hamilton

When James Cameron and Linda Hamilton divorced in 1999, the settlement became almost as famous as his films. Their marriage had been brief, but Cameron’s record-breaking success 'Titanic', became a controversial point during settlement negotiations. Ultimately, Hamilton walked away with a reported $50 million in a lump-sum settlement. However, no detailed breakdown of homes, cars, or other physical property was ever released.

13. Ron Perelman and Ellen Barkin

When billionaire investor Ron Perelman and actress Ellen Barkin divorced in 2006, the split came with a price tag that raised eyebrows even in New York’s wealthiest circles. Barkin reportedly walked away with $20 million that was considered hefty even by billionaire standards. Yet the drama didn’t stop there. Later, she also demanded $4.3 million for not fulfilling the contract rules.

12. Hulk Hogan and Linda

When Hulk Hogan and his wife Linda finally settled their divorce in 2009, it turned out to be one of the most expensive splits in pro-wrestling history. Linda walked away with a massive 70% of the couple’s liquid assets, about $7.44 million out of $10.41 million, plus a $3 million property settlement on top. That's not all but she also secured 40% ownership of his Gawker settlement.

11. Arnold Schwarzenegger and Maria Shriver

Arnold Schwarzenegger and Maria Shriver’s love story ended long before their divorce papers were signed, but it took a full decade for the split to become official. The long legal limbo, finally closed in December 2021. The settlement itself remains largely confidential, owing to the sheer complexity of dividing their enormous fortune and property without a prenup in place. But what we do know is neither owes the other spousal support, though both retain the right to petition for it down the road. With their four children now all adults, there were no child custody or support arrangements involved.

10. Kenny and Marianne Rogers

Country legend Kenny Rogers’ fourth divorce was a wallet-opener, about $60 million, according to long-standing coverage and Rogers’ own recounting in interviews at the time. The price tag was the result of a 16-year marriage that spanned Rogers’ peak chart and touring years, i.e., the period when “The Gambler” brand became a cross-media juggernaut. Rogers later called it an expensive lesson in love and business colliding.

9. Jeff Bezos and MacKenzie Scott

The Bezos–Scott divorce was the most expensive split in celebrity history because of the sheer scale of Amazon’s market value. Unlike cash payouts, MacKenzie Scott walked away with 25% of the couple’s Amazon holdings, equal to about 4% of the company’s outstanding stock. That single transaction instantly made her one of the wealthiest women in the world. In comparison, most Hollywood divorces involve real estate, royalties, or lump-sum checks; this one was tied to Wall Street.

8. Harrison Ford and Melissa Mathison

The Harrison Ford and Melissa Mathison divorce was so expensive because it mixed two things Hollywood knows well: no prenup and big box office money. The couple was married for over 20 years, and with no agreement in place, Mathison was entitled to a large share of what Ford earned during that time. Reports put her payout at around $85 million, already huge. However, what made it even more valuable was how the deal was made. But Mathison didn’t stop with the cash, though; she also secured a share of Ford’s movie residuals and back-end profits from classics like Indiana Jones and The Fugitive.

7. Dr. Dre Young and Nicole Young

Dr. Dre’s divorce from Nicole Young ended with a jaw‑dropping $100 million property settlement, split into $50 million upfront and $50 million a year later. This happened after a prolonged court battle over a contested prenuptial agreement. Despite that huge payout, Dre retained most of the major assets. He owned seven properties (including a Brentwood estate reportedly valued at nearly $100 million), six vehicles, and full ownership of his master recordings, trademarks, Apple stock (from the Beats sale), and all his business interests. Nicole, however, walked away with cash, vehicles, jewelry, and her own bank accounts.

6. Cindy Silva and Kevin Costner

Kevin Costner’s first divorce came just as he was becoming one of Hollywood’s biggest stars. After 16 years of marriage, his split from college sweetheart Cindy Silva cost him around $80 million, one of the largest settlements of the decade. The massive payout reflected Costner’s peak-era earnings from hits like Dances with Wolves and Robin Hood: Prince of Thieves. As there was no ironclad prenup in place, Silva’s settlement included a major share of the wealth he had built during the marriage. At the time, the number turned heads in Hollywood and cemented their split as one of the most expensive in entertainment history.

5. Britney Spears and Kevin Federline

Britney Spears and Kevin Federline finalized their divorce in 2007, and the financial aftermath was huge. Although details of a lump-sum settlement weren’t public, the real eye-opener was the massive child support payments. Initially, Britney paid $20,000 a month, but after the court reassessed when their kids lived primarily with their father, it jumped to $40,000 per month, a whopping $480,000 yearly burden.

4. Bill Gates and Melinda Gates

The Bill and Melinda Gates divorce was so expensive because it involved billions of dollars in company shares being moved almost immediately after they announced their split in May 2021. Since they had no prenup, the couple relied on a separation contract to divide assets. Within days, Bill transferred about $1.5 billion in Canadian National Railway stock and $300 million in AutoNation shares to Melinda. More followed, including $850 million in Deere & Co. stock, plus stakes in Coca-Cola FEMSA and Televisa, and by mid-2021, the transfers added up to around $6 billion.

3. Michael Jordan and Juanita Vanoy

When basketball royalty calls it quits, the numbers are as jaw-dropping as a slam dunk from the free-throw line. Michael Jordan’s split from Juanita Vanoy in 2006 resulted in a record-setting payout that made headlines worldwide. After 17 years of marriage, Juanita walked away with a staggering $168 million, plus their sprawling Chicago mansion and custody arrangements for their three kids. For starters, there was no prenup. That meant Juanita had a claim on the fortune Jordan racked up during his Bulls glory years.

2. Johnny Depp and Amber Heard

Johnny Depp and Amber Heard’s 2016 divorce may have carried a $7 million settlement, but the real cost stretched far beyond the check. Heard pledged to donate the money to the ACLU and Children’s Hospital Los Angeles, turning the payout into a high-profile statement about image as much as money. The settlement also included strict confidentiality and non-disparagement clauses. But in Hollywood, reputation is currency, and here’s where the true expense came in. Both stars were already fighting to protect their careers, and the split unleashed years of negative headlines, legal fees, and damage to their brands.

1. Kanye West and Kim Kardashian

When Kim Kardashian and Kanye West officially ended their marriage in November 2022, it was largely due to the ongoing costs that scream 'Hollywood expensive'. The court granted them joint custody of their four children, but Kanye was ordered to pay a whopping $200,000 every month in child support, plus half the cost of security, school, and healthcare. Neither side will pay spousal support, but the Kardashian lifestyle doesn’t come cheap, and those monthly bills add up to millions every year. With sprawling mansions, private schools, and round-the-clock protection, the cost of raising North, Saint, Chicago, and Psalm is Hollywood-scale high.