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A-List To Bankrupt: The Most Expensive Toxic Celebrity Divorces Ever

Darren April 11, 2023
WNCT

Michael Jordan & Juanita Vanoy

Every self-respecting celebrity manager tells their client to place a prenup agreement in their marriage. It may seem like the most unromantic idea on the planet but the reality is that it’s pragmatic. Unfortunately, NBA icon Jordan didn’t read this memo and it cost him a massive fortune. We’re talking about $168 million because that’s what he paid his ex-wife Juanita.

Huffington Post

Vanoy correctly believed that Jordan was having affairs behind her back. She went as far as hiring a private eye to prove his shenanigans. This also meant that the court didn’t have much sympathy for the Bulls legend. They had three children together so Jordan lost custody of them in one of the messiest celebrity divorces ever (via The Sports Rush).

Marca

Megan Fox & Brian Austin Green

Fox is no stranger to a public breakup as her recent relationship with Machine Gun Kelly proves. But before she dated the Cleveland rapper she married her fellow actor. The pair remained together for 10 years with three children before it all came crashing down around them. Those two words appeared again: ‘irreconcilable differences.’

Vulture

Green resented the speed with which Fox moved on as she became engaged to Kelly before the divorce’s finalization. However, he may be the winner in this situation because she’s a bigger star. The pair didn’t have a prenup arrangement and this meant that they split their assets in another of the most expensive celebrity divorces (via Page Six).

Sky Sports

Tiger Woods & Elin Nordegren

It appeared that Woods had everything and that his life was perfect in 2009. He was one of the most popular athletes on the planet with never-ending wealth and a Swedish supermodel wife. Then he drunkenly smashed his vehicle and the world came crashing down. Dozens of women emerged from the woodwork and revealed their affairs with the superstar.

People

These included porn stars and exotic dancers who willingly divulged their stories. Needless to say, this humiliated Woods’ wife Nordegren and she obviously filed for divorce. Nordegren received an outrageous $750 million settlement in one of the most expensive celebrity divorces ever. Meanwhile, Woods lost custody of his children and went to rehab for his sex addiction (via Fox News).

People

Johnny Depp & Amber Heard

Depp and Heard had one of the most dysfunctional relationships on this list and also one of the messiest celebrity divorces that ended in a high-profile court case. Heard sued her former husband for defamation in 2022 as this toxic mess heated up. She alleged that Depp was violent toward her while he claimed psychological abuse.

Marca

He also alleged that Heard excreted on their bed during one argument. They agreed to a seven million divorce settlement but Heard directed some of that toward a children’s hospital. A judge ordered her to pay Depp $10 million in damages while Depp paid her two million. In the end, they broke even but suffered humiliation in front of the world (via The Guardian).

AP

Donald & Ivana Trump

It’s not difficult to feel sorry for Ivana Zelinickova after her strained marriage to the former U.S. President. She met the business tycoon in 1976 and bore three children. On paper, everything was fantastic because she was a beautiful socialite with a successful career. It felt like a match made in heaven but it turned into a disaster.

Insider

In the end, it became one of the most well-publicized celebrity divorces ever. Ivana discovered that Trump cheated on her. She also accused him of cruel treatment, including rape. Finally, they settled and she received $14 million as well as other tangible assets. Both Donald and Ivana remarried after they separated (via The Atlantic).

The Independent

Paul McCartney & Heather Mills

McCartney and Mills finally divorced after a two-year battle in 2008. The settlement cost the former Beatles member a ludicrous $50 million in one of the most expensive celebrity divorces in UK history. But the writing was on the wall for the couple after they claimed irreconcilable differences.

Daily Star

Allegedly, McCartney’s daughter Stella was a major issue as she didn’t have a good relationship with Mills. “Stella wasn’t interested in her dad’s happiness,” Mills said in one interview (via Extra). “I can’t protect her any longer. Unfortunately, this was too much of a bridge for them to cross together.

ABC News

Khloe Kardashian & Lamar Odom

Odom was a decent NBA player before he fell in with the Kardashians. He married Khloe and became a common feature on their TV shows. But Odom struggled to balance his newfound fame with living a normal life. He fell into substance abuse and cheated on Khloe more times than she will ever know.

Entertainment Tonight

Finally, he almost died after he fell into a coma in a Nevada brothel. Kardashian helped him to heal before she finally filed for divorce and the pair split. It’s understandable because she went through a lot of humiliation too. It was one of the most dramatic celebrity divorces because of its seedy details (via ET Online).

People

Ben Affleck & Jennifer Garner

Affleck met Garner on the set of ‘Pearl Harbor’ in 2000. Perhaps this should have served as a warning to the Hollywood star because it was a garbage movie. The pair eventually married and had children together. At the time, tthey were one of the cutest celebrity couples. Then they shocked everybody who cares by announcing their divorce.

Popsugar

Unfortunately, it appears that Affleck was responsible for the change in their marital status. His well-documented drinking problem created tensions and toxicity in their relationship. Finally, it became too much for Garner to bear and she decided that it was time to move on. Now Affleck is with Jennifer Lopez after they rekindled their relationship (via People).

Page Six

Guy Ritchie & Madonna

Madonna and Ritchie remained married for eight years before they finally parted ways. This was the second time that the Queen of Pop ended her nuptials after a relationship with Sean Penn. But this was one of the most toxic celebrity divorces because everybody knew about it. There was no hiding away because of their massive public profiles.

Grazia Daily

Some reports speculated that Madonna paid Ritchie $75 million as part of a settlement. However, the reality was less than this but he still had a nice payday. Madonna said that their connection fizzled out as life moved on. It also left her questioning whether true love was something that existed (via Nicki Swift).

InStyle

Demi Moore & Ashton Kutcher

Kutcher revealed the emotional cost of his divorce from Moore. “Nothing makes you feel like a failure like divorce,” he said (via No To Love). “Divorce feels like a wholesale f***ing failure. You failed at marriage.” He also explained how uncomfortable it was when paparazzi waited for him outside their children’s school.

Harper’s Bazaar

The pair had a 10-year relationship before they ended their marriage. Then Kutcher married his former co-star, Mila Kunis. Moore allegedly demanded $20 million from her ex-husband because he cheated on her. Kutcher refused to pay support spousal support and walked away after his payout. Moore already made $80 million when she divorced Bruce Willis.

Insider

Miley Cyrus & Liam Hemsworth

Cyrus and Hemsworth waded through one of the most public celebrity divorces on this list. The former Disney star told Joe Rogan that the paparazzi made her life a living nightmare. She said: “What really sucked about it wasn’t the fact that me and someone that I loved realize that we don’t love each other the way that we used to anymore. That’s OK. I can accept that.”

ABC News

However, their divorce also went smoothly because they had a prenuptial agreement. Allegedly, Hemsworth initially resisted signing it but Cyrus forced his hand. It’s probably just as well because they were able to split amicably and move forward without financial pressures. That’s more than most of the people on this list can say (via Stylecaster).

Newsweek

Brad Pitt & Jennifer Aniston

It’s no surprise that Pitt and Aniston had one of the most notorious celebrity divorces ever. Pitt was a major Hollywood superstar and one of the biggest box-office draws in the U.S. Meanwhile, Aniston was one of America’s darlings after her starring role in “Friends” and a host of rom-coms. It looked like they were a match made in heaven but that wasn’t the case.

Hollywood Tonight

Their wedding was one of the biggest celebrity events of 2000 yet their marriage only lasted for five years. There was speculation that Pitt cheated on Aniston with Angelina Jolie because he moved on very quickly. In the end, Aniston retained their $29 million home after they settled (via Brides.com).

Vanity Fair

Jeff Bezos & MacKenzie Scott

Divorces can be very profitable for some people if they marry the right people. Ask Scott because she earned two fortunes from a pair of separations. She won $38 million in Amazon stock after her marriage to Jeff Bezos broke down. It was a blow to the billionaire but he kept control of 75 percent of the company.

Town & Country Magazine

Scott’s relationship with Bezos made her the third-richest woman in the U.S. Crucially, Bezos retained voting control over her shares but they’re worth a fortune. Scott allegedly found that Bezos sent explicit pictures to Lauren Sanchez. This enraged her and signaled the end of their happy life (via NDTV).

Us Weekly

Tom Cruise & Katie Holmes

The King of Scientology, Cruise actually appears a couple of times on this list. He married Holmes in 2006 and became one of the most iconic couples of their era. But it came to a miserable end and the pair divorced after five years. Cruise agreed to pay $400,000 per year in alimony but included some strict clauses (via Fandom Wire).

CNN

He blocked Holmes from talking about Scientology for five years and prevented her from publicly dating any man. Allegedly, Holmes resented the marriage so much that she accepted. But she also received five million dollars in child support and an extra five million for herself. It was one of the most notorious celebrity divorces ever and tarnished Cruise’s image.

Reuters

Arnold Schwarzenegger & Maria Shriver

The former Governor of California called his divorce from Shriver ‘the biggest failure’ of his life. It came after Schwarzenegger admitted that he fathered a child with a member of their household staff. Needless to say, this didn’t please Shriver and she filed for divorce. But it took the couple 10 years to finalize the end of their relationship.

Us Weekly

This immediately captured the media’s attention but there wasn’t a lot of drama to report. It’s unclear why it took so long for them to sign off but in the end, they legally separated. Shriver received 50 percent of her ex-husband’s SAG producer’s pension. It’s estimated that she may have walked away with about $200 million (via NBC News).

InStyle

Kim Kardashian & Kris Humphries

It’s easy to forget that Kardashian had another husband before she met Kanye West. However, her marriage to Humphries only lasted for 72 days before they decided to end things. Kim filed for divorce but her angry husband filed for an annulment because he thought she tricked him. He believed that the wedding was a sham for the Kardashian TV show (via USA Today).

Cosmopolitan

Unfortunately, he became the big loser in this situation. He wanted seven million dollars but didn’t get anything. But luckily, they had a prenup and this meant that he only lost his court fees. In the end, the pair separated in one of the messiest celebrity divorces of 2013. Kardashian admitted that she handled things the wrong way and tried to apologize to her former partner.

Glamours

Chris Pratt & Anna Faris

Pratt and Faris appeared to have one of the most perfect Hollywood relationships. But the pressures of fame affected the couple amid rumors of Pratt cheating. Finally, they rocked their fans’ worlds when they announced the end of their marriage. It came as a blow to people who love the idea of a perfect couple in love (via Who).

Axelle/Bauer Griffin

The pair had a prenup so it wasn’t one of the most expensive celebrity divorces. But there was one interesting condition in their settlement. They agreed to live within a five-mile radius of each other so that they could raise their son Jack. Pratt remarried and has a daughter with his new wife, Katherine Schwarzenegger. Nevertheless, he maintains a good relationship with Faris.

Independent

Mel Gibson & Robyn Moore

Even the longest Hollywood marriages occasionally end in tears. Gibson and Moore remained married for 30 years with seven children but even they didn’t stay together. The pair separated in 2009 after one of the most expensive celebrity divorces in history. Gibson had a $900 million fortune and there wasn’t a prenup agreement.

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Robyn walked away with about half of Gibson’s wealth. Meanwhile, she secured half of his film residual income for the rest of his life. Now she’s living the high life and has a $20 million house in Malibu. But Gibson remarried and has another child with his new partner, Oksana Grigorieva (via Daily Express).

Brides

King Charles & Princess Diana

This was one of the most notorious celebrity divorces ever but it wasn’t a shock. Remember, the future King of England cheated on Diana on the eve of their wedding. He spent the night with Camilla, the woman he married after Diana’s death. Both Charles and Diana had extramarital affairs throughout their relationship.

Vanity Fair

In the end, public sympathy rested with Diana because they saw that the Royal Family bullied her. Her death almost ruined their image completely and tarnished the Queen’s legacy. It was a relief to Diana when she finally quit the Windsors because they made her life a nightmare. Nonetheless, she maintained massive popularity (via Vanity Fair).

Glamour

Brad Pitt & Angelina Jolie

After Pitt left Jennifer Aniston, he fell into Jolie’s arms. They became one of Hollywood’s super couples as two of the biggest box office stars. Meanwhile, they adopted a brood of children from around the world. They also starred in a movie together: Mr. And Mrs. Smith. But their bliss didn’t last and they split up in 2016.

Elle

Jolie filed for divorce because of Pitt’s alleged substance abuse and anger issues. They also had differences in opinion over raising their children. However, it was a mark of Jolie’s respect for her husband and her financial success that she didn’t ask for marital support. They also had an ironclad prenup that succinctly divided their assets (via TMZ).

The Sun

Ashley Cole & Cheryl Tweedy

Cole and Tweedy became one of the most popular couples in the UK after their marriage. The soccer star was an elite fullback and represented England with pride. Meanwhile, Tweedy lit up stages with her group, Girls Aloud, before a successful solo career. However, their honeymoon bliss didn’t last for long.

Extra

That’s because Cole cheated on her multiple times. Their marriage survived the first public affair with a hairdresser. But he broke Tweedy’s heart when it emerged that he was with four more women. Remember, these are the ones that the media learned about so it’s possible that there were many more (via The Mirror).

Vanity Fair

Tom Brady & Gisele Bundchen

Brady and Bundchen had one of the most publically stable celebrity relationships before it came to an abrupt end. Bundchen filed for divorce after she lost patience with the quarterback in 2022. The writing was on the wall for Brady but he refused to retire from the NFL. He played another season with the Tampa Bay Buccaneers and left his family.

Marca

“Obviously, I have my concerns,” Bundchen told Elle before the divorce. ‘This is a very violent sport, and I have my children and I would like him to be more present. I have definitely had those conversations with him over and over again. But ultimately, I feel that everybody has to make a decision that works for them.” Brady didn’t take heed of her words and she had enough.

Insider

Sandra Bullock & Jesse James

It looked like James struck gold when he married Bullock. He was a reality TV star while she was an A-Lister. But he proved that some men will cheat on anybody because he had affairs with at least four women. This reasonably enraged Bullock and she filed for divorce, taking their son with her.

Entertainment Tonight

According to James, this was the hardest part of their breakup. “I think losing my son that I adopted, for sure — not being able to see him and see him grow up and all that stuff,” James explained. “Whether that’s fair, whether I should’ve lost a kid due to infidelity – which I don’t think anybody ever does – but I think with ‘Hollywood law,’ that’s totally fair (via ET Online).”

InStyle

Jennifer Lopez & Marc Anthony

Lopez is no stranger to wedding cakes because she had five marriages. Anthony was one of the most interesting because they wedded in a secret ceremony. It appeared that he would be the man to help her settle down because they had children together. In the end, it didn’t matter and they divorced with strict co-parenting conditions.

Hollywood Reporter

Jenny from the block explained that she wasn’t sure if she would marry again after this. You know, I’ve always believed in that institution,” she said (via Women’s Health). I believe in it, but it is difficult. I’ve had my challenges but at the same time I believe in love, and I think that is the main thing.” Spoiler alert: she married again twice.

Hello!

Christie Brinkley & Peter Cook

Brinkley was one of the preeminent supermodels of her era. She married Hamptons-based architect Peter Cook in a lavish ceremony but scandal arose. He cheated on her after years of marriage with his 19-year-old assistant. Then they had one of the nastiest divorce battles on this list with rude emails and court battles (via CBS News).

Page Six

The supermodel made this statement after they finally settled. She said: “I had a prenup, a confidentiality agreement, and a ‘civility clause’ that all cost a lot of money, but were ignored and useless against the extended character assignation and extortion attempts I have endured.

Vogue

Channing Tatum & Jenna Dewan

Tatum and Dewan had a 10-year relationship but that came crashing down around them. This shocked many people because it seemed that everything was perfect in their world. In the end, one of Hollywood’s most beautiful couples didn’t last. They quickly agreed on a custody settlement but the financial side was more difficult.

AP News

Tatum told Entertainment Tonight that their marriage changed after they became parents. He said: “Relationships are hard for me. Even though I am a bit of a monogamist. In business, I have no real fear of anything being destroyed. But heart things, when it comes to people I love, I have a really hard time. I end up trying too hard, you know?”

Us Weekly

Tom Cruise & Nicole Kidman

A former Scientologist claimed that the controversial church influenced Cruise to divorce Kidman. They were one of the most popular couples of the ’90s and even starred in a movie together. But this story had a sad ending and became one of the most highly publicized celebrity divorces ever (via Us Magazine).

She Knows

However, it was a joyous moment for Kidman when they finally signed terms. She raised her arms to the heavens in relief after she stepped out of the attorney’s office. Later, Kidman said that it was a mistake to marry when she was so young. She said that she was looking for protection in a vicious industry.

Women’s Health

Charlie Sheen & Denise Richards

It looked like Sheen met his match when he married Richards. The Wild Things star was one of the most popular actresses in the U.S. as well as a major sex symbol. But she couldn’t handle his drug abuse and cheating. In the end, she divorced him when she was six months pregnant and accepted $80,000 monthly in support.

Page Six

Despite everything, Richards wants their children to respect him “Even though he’s Charlie Sheen, that is still, to them, their dad,” Richards explained. “I never talk badly about him and I want him to be part of their lives because I met a lot of the women that Charlie entertained and a lot of them had father-daughter issues. And I do not want that to be our girls (via Page Six).”

Architectural Digest

Kim Kardashian & Kanye West

Kardashian’s third marriage came to a brutal end in 2022 after a well-publicized spat with her husband. Once again, she was canny enough to include a prenuptial agreement in their nuptials. This meant that the pair retained the bulk of their fortunes. However, the court ruling forced West to pay $200,000 per month in child support.

CNN

The hip hop icon resented Kardashian because she allegedly prevented him from attending their children’s birthday parties. They agreed to co-parent but the children stayed with her. Nonetheless, it brought an end to one of the most dramatic celebrity divorces ever. This one was always going to end in tears but it came crashing down quickly (via The Guardian).

US Weekly

Bill Gates & Melinda French

There’s no denying that Gates and French had one of the most complicated celebrity divorces ever. That’s because the pair shared personal fortunes of almost $150 billion. It’s a staggering amount of money that’s beyond the comprehension of most ordinary people. In the end, French walked away with about $76 billion.

AP News

However, Gates won’t pay spousal support to his ex-wife unlike many of the former husbands on this list. Despite the breakdown in their relationship they vowed to maintain the Bill & Melinda Gates Foundation. They’ve donated billions of dollars in charitable funds and feel that is still important (via Forbes).

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