How did Angelina Jolie and Brad Pitt’s divorce get so messy?

·10-min read

When it comes to messy Hollywood divorces, Brad Pitt and Angelina Jolie’s parting of ways is surely up there amongst the most toxic. But where did it all go so wrong?

Let’s start at the beginning. The pair met on the set of Mr & Mrs Smith in 2004. Chemistry between the pair - playing a married couple who both turned out to be assassins hired to kill the other - was said to be palpable. At the time, Brad was married to Jennifer Aniston, making him one half of the most adored celebrity couple in a generation. Brad and Jen’s Malibu wedding in 2000 reportedly cost $1 million and was attended by the entire cast of Friends, including David Schwimmer, Lisa Kudrow, Courtney Cox, Matthew Perry, and Matt Leblanc.

He was the biggest movie star in the world and she was Rachel Green with the good hair. Hollywood was obsessed and ate up every available detail. Like their wedding vows: he promised to split the thermostat bill and Jen pledged to always make Brad his favourite banana milkshake.

Their approach to marriage was charmingly liberal. “Neither of us wants to be the spokesman for a happy marriage, for coupledom,” said Brad to Vanity Fair. “I’ll tell you what I despise: this two-becomes-one thing where you lose your individuality. We don’t cage each other with this pressure of happily ever after. You figure it out as you go along. We feel it out, rather than setting policies and rules.”

Adding: “Jen and I always made a pact; that we’ll see where this thing is going. I’m not sure it really is in our nature to be with someone for the rest of our lives, just because you made this pact. You keep going as long as you keep growing. When that dies, we do. We still have that friendship; we still have a good laugh, which can go in and out depending on the dynamics and outside influences. It’s complicated, but that’s what keeps it interesting.”

Brad Pitt and Jennifer Aniston (Getty Images)
Brad Pitt and Jennifer Aniston (Getty Images)

Enter Angelina who came with a wild image and described herself as having had a ‘dark and dangerous’ youth. She was twice divorced when she met Brad - having been hitched first to British actor Jonny Lee Miller and then Billy Bob Thornton. During her marriage to Billy Bob, the couple adopted a child, Maddox, from Cambodia in March 2002, but abruptly separated three months later.

Speaking about her divorce, she told Vogue at the time: “It took me by surprise, too, because overnight, we totally changed. I think one day we had just nothing in common. And it's scary but... I think it can happen when you get involved and you don't know yourself yet."

Dramatic beginnings

After seven years together, in 2005 Brad and Jennifer announced their separation and a tidal wave speculation was unleashed. Both the media and internet whipped up a frenzied Team Jen and Team Angelina rivalry, with brands even selling t-shirts for people wanting to pledge their allegiance.

Angelina was pitched as the mistress, but both have always strenuously denied their relationship started as an affair. "To be intimate with a married man, when my own father cheated on my mother, is not something I could forgive,” Angelina said. “I could not look at myself in the morning if I did that. I wouldn't be attracted to a man who would cheat on his wife."

Not long after their divorce, Jen gave a candid interview to Vanity Fair, saying “I’m not interested in taking public potshots. It’s not my concern anymore. What happened to him after the separation—it’s his life now. I’ve made a conscious effort not to add to the toxicity of this situation. I haven’t retaliated. I don’t want to be a part of it. I don’t have a halo that I’m polishing here; everyone has their personal thoughts. But I would much rather everyone move on. I am not defined by this relationship. I am not defined by the part they’re making me play in the triangle. It’s maddening to me...”

Brad Pitt's relationships - In pictures

Angelina Jolie: Pitt and Jolie hit the headlines when they began dating after meeting on the set of Mr and Mrs Smith in 2005 and denied they had hooked up while Pitt was still married to Jennifer Aniston. The pair became one of the biggest power couples in Hollywood and had three adopted children, Maddox, Zahara and Pax and three biological children Shiloh and twins Vivienna and Knox. Jolie filed for divorce in September 2015 with her lawyer revealing the decision had been made
Angelina Jolie: Pitt and Jolie hit the headlines when they began dating after meeting on the set of Mr and Mrs Smith in 2005 and denied they had hooked up while Pitt was still married to Jennifer Aniston. The pair became one of the biggest power couples in Hollywood and had three adopted children, Maddox, Zahara and Pax and three biological children Shiloh and twins Vivienna and Knox. Jolie filed for divorce in September 2015 with her lawyer revealing the decision had been made
April Florio: Florio was rumoured to have had a brief fling with Pitt before he hooked up with Jolie – but a representative for the actor denied the claim. (Rex)
April Florio: Florio was rumoured to have had a brief fling with Pitt before he hooked up with Jolie – but a representative for the actor denied the claim. (Rex)
Jennifer Aniston: Pitt met Aniston in 1998 and the couple tied the knot at a private Malibu ceremony in 2000. They were seen as one of the most solid relationships in Hollywood but Aniston filed for divorce in 2005 citing irreconcilable differences. Pitt hit the headlines at the time for his relationship with co-star Angelina Jolie who he went on to marry. Despite the divorce and alleged affair with Jolie, Pitt said he has remained friends with Aniston. Speaking to W Magazine in 2009 he said: “We still check in with each other. She was a big part of my life, and me hers. I don’t see how there cannot be [that]. That’s life, man. That’s life.” (AFP/Getty Images)
Jennifer Aniston: Pitt met Aniston in 1998 and the couple tied the knot at a private Malibu ceremony in 2000. They were seen as one of the most solid relationships in Hollywood but Aniston filed for divorce in 2005 citing irreconcilable differences. Pitt hit the headlines at the time for his relationship with co-star Angelina Jolie who he went on to marry. Despite the divorce and alleged affair with Jolie, Pitt said he has remained friends with Aniston. Speaking to W Magazine in 2009 he said: “We still check in with each other. She was a big part of my life, and me hers. I don’t see how there cannot be [that]. That’s life, man. That’s life.” (AFP/Getty Images)
Demi Moore: Pitt is rumoured to have hooked up with Demi Moore in 1998. (Rex)
Demi Moore: Pitt is rumoured to have hooked up with Demi Moore in 1998. (Rex)
Claire Forlani: There were reports that Pitt had a fling with his Meet Joe Black co-star Forlani. (Getty Images)
Claire Forlani: There were reports that Pitt had a fling with his Meet Joe Black co-star Forlani. (Getty Images)
Gwyneth Paltrow: Pitt and Paltrow got together in 1994 and it became one of Pitt’s most high profile relationships. But the pair called time on the union in 1999 with Paltrow recently admitting that she “wasn't ready” and that Pitt was “too good for me”. (AFP/Getty Images)
Gwyneth Paltrow: Pitt and Paltrow got together in 1994 and it became one of Pitt’s most high profile relationships. But the pair called time on the union in 1999 with Paltrow recently admitting that she “wasn't ready” and that Pitt was “too good for me”. (AFP/Getty Images)
Thandie Newton: Pitt was linked to his Interview With the Vampire costar for a short time in 1994. (Getty Images)
Thandie Newton: Pitt was linked to his Interview With the Vampire costar for a short time in 1994. (Getty Images)
Julia Ormond: Ormond enjoyed a kiss... or two with Pitt in Legends Of The Fall and it was rumoured that they had briefly taken the romance off screen. (Columbia Tristar)
Julia Ormond: Ormond enjoyed a kiss... or two with Pitt in Legends Of The Fall and it was rumoured that they had briefly taken the romance off screen. (Columbia Tristar)
Jitka Valkova: Brad Pitt reportedly had a fling with Jitka Válková in 1993. (Getty Images)
Jitka Valkova: Brad Pitt reportedly had a fling with Jitka Válková in 1993. (Getty Images)
Genna Davis: Genna Davis and Brad Pitt (MGM)
Genna Davis: Genna Davis and Brad Pitt (MGM)
Juliette Lewis: Lewis and Pitt briefly dated in 1989. She was 16-years-old at the time - which was a decade younger than Pitt. (Rex)
Juliette Lewis: Lewis and Pitt briefly dated in 1989. She was 16-years-old at the time - which was a decade younger than Pitt. (Rex)

Rainbow family

In January 2006, Angelina confirmed to People that she was pregnant with the couple’s first child. It was the first time she’d publicly acknowledged their relationship. The pair then started assembling their ‘rainbow’ family, as she called it, at pace. That year, Brad became the adoptive father of Maddox and Angelina’s second child, Zahara. Both of the children's surnames were changed from "Jolie" to "Jolie-Pitt". Angelina gave birth to daughter Shiloh Nouvel in Namibia, in May 2006. In the spring of the next year, Angelina adopted three-year-old Pax Thien from an orphanage in Vietnam and Brad adopted Pax in the United States about a year later.

“We spent a lot of time contemplating and thinking and talking about what we both wanted in life and realized that we wanted very, very similar things,” Angelina said to Vogue in 2007. “And then we just continued to take time. We remained very, very good friends—with this realization—for a long time. And then life developed in a way where we could be together, where it felt like something we would do, we should do." At the Cannes Film Festival in 2008, Angelina confirmed that she was expecting twins, and Knox Léon and daughter Vivienne Marcheline were born in July that year.

 (Masatoshi Okauchi/Rex)
(Masatoshi Okauchi/Rex)

A few years later, speaking to The Telegraph, Ange said: "I am very lucky with Brad. He is a real gentleman, but he is also a real man's man. He's got the wonderful balance of being an extraordinary, great, loving father, a very, very intelligent man and physically he's a real man." Meanwhile, Brad told Esquire in mid 2013: “I have very few friends. I have a handful of close friends and I have my family and I haven't known life to be any happier. I'm making things. I just haven't known life to be any happier."

They got married after ten years together with an intimate ceremony at their winery Château Miraval in France. Angelina wore Versace with a veil that the couples’ children had doodles all over. "It does feel different. It feels nice to be husband and wife,” Angelina told Vanity Fair at the time.

The beginning of the end

Two years later and it was over.

In September 2016, Angelina filed for divorce, citing irreconcilable differences. The FBI and the Los Angeles Department of Children and Family Services confirmed they were investigating Brad for alleged child abuse following an incident on the family’s private jet. The actor was accused by an anonymous person of getting physical with one of his children. According to TMZ at the time, “the details of precisely what happened” were “murky.” But it was reported that Maddox had stepped in to verbally stand up for his mother during a fight with Brad - and that the latter lost his temper. A source close to Brad told People he was “was drunk, and there was an argument between him and Angelina,” said the source. “There was a parent-child argument which was not handled in the right way and escalated more than it should have.” Brad has since been cleared of all allegations.

 (Justin Tallis/PA)
(Justin Tallis/PA)

The actor hasn’t made any comment about the allegations but has been open about his drinking and drug use. In a May 2017 GQ interview, Brad revealed he had quit drinking and smoking cannabis. “I can't remember a day since I got out of college when I wasn't boozing or had a spliff, or something. And I'm running from feelings. I stopped everything except boozing when I started my family. But even this last year [...] I was boozing too much,” Brad told the magazine. “It's just become a problem. You either deny them all of your life or you answer them and evolve.”

Divorce drama

Brangelina have been wrangling over the split through legal proceedings in California privately and quietly, but in February 2017, Angelina spoke out about the divorce for the first time saying "we will get through this time and hopefully be a stronger family for it”.

 (Charley Gallay/Getty Images)
(Charley Gallay/Getty Images)

According to court documents, Brad had been failing to give her “meaningful support” financially since the split. Brad countered that he had actually loaned her $8 million plus $1.3 million for bills. The next year it was revealed that Angelina had given Brad access to the children - but they were still working towards a full settlement.

In an interview with Vogue last year, Angelina said she split from Brad for the “wellbeing” of her family. “It was the right decision,” she said. “I continue to focus on their healing. Some have taken advantage of my silence, and the children see lies about themselves in the media, but I remind them that they know their own truth and their own minds. In fact, they are six very brave, very strong young people.”

In December 2020, court proceedings began in Los Angeles over child custody for the five youngest children, as Maddox is now 19 and therefore an adult in the eyes of the law. Pax is now 17, while Zahara is 16, Shiloh, 15 and twins Vivienne and Knox are 12. Brad was granted joint custody of his children with Angelina in a tentative ruling.

A source close to the case told PA the judge’s ruling would “significantly increase” Oscar-winner Brad’s time with the children. The decision is said to have been based on “extensive testimony” from those involved with the case, including professionals who had spent time with the children.

It marked a major breakthrough for the couple - but there is still a long way to go.

 (Pascal Le Segretain/Getty Images)
(Pascal Le Segretain/Getty Images)

What next?

It’s taken nearly six years and $1 million each to get to this point and the pair haven’t yet even begun to divvy up their combined assets, including the French vineyard and estate, Chateau Miraval, they bought together for $60 million. In an extra twist, Brad is now suing his ex-wife for, according to the lawsuit, selling her stake in their co-owned vineyard to a Luxembourg-based spirits manufacturer controlled by Russian oligarch Yuri Shefler without his knowledge.

Court papers submitted by Brad say Angelina intentionally “sought to inflict harm on” him by selling her stake in the business. He says they had agreed to never sell their respective interests without the other’s consent. He also claims the wine company grew “into a multimillion-dollar global business and one of the world’s most highly regarded producers of rosé wine” through his work and that Jolie had contributed “nothing to Miraval’s success.”

In August 2022, details of Angelina’s 2016 FBI complaint against her then-husband leaked. She told the authorities that Brad had become violent on a private jet flight to Los Angeles from southern France. The actress claimed to police that Brad had yelled at her, “grabbed her by her head”, shook her, “pushed her into the bathroom wall” and punched the ceiling of the plane. According to the documents, he also poured beer over her shouted: “You’ve f***** up this family.” Angelina also claimed Brad became physically abusive to their eldest son Maddox. He denied the allegations at the time and the Los Angeles County Department of Children and Family Services concluded that he did not physically abuse any of his children. He was also cleared by the FBI.

For now Angelina is based in Los Angeles (at the former home of Hollywood legend Cecil B DeMille which she bought for $25 million), but appears keen to eventually move away. “I would love to live abroad and will do so as soon as my children are 18,” She told Harper's Bazaar. “Right now I'm having to base where their father chooses to live.”

As for Brad, he will continue to forever be linked back to ex-wife Jen. The pair most recently made headlines when the actress said he was one of her favourite Friends guest stars. “And Mr Pitt was wonderful. He was fantastic,” she said.

Some commentators are speculating Brangelina’s divorce could be fought for six more years and rack up millions more in legal fees. Let’s hope both parties get what they want in the end.