Brad Pitt and Angelina Jolie’s Ups and Downs Through the Years: Divorce Drama, Custody Battle and More

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Brad Pitt and Angelina Jolie’s Ups and Downs Through the Years: Divorce Drama, Custody Battle and More

Brad Pitt and Angelina Jolie have been locked in a messy court battle ever since she filed for divorce in September 2016, but the pair were not always at odds. The Oscar winners fell for each other while filming the 2005 action film Mr. & Mrs. Smith. The origination of their relationship instantly caused controversy since Pitt was married to Jennifer Aniston at the time. The Friends alum and the Once Upon a Time in Hollywood star announced their separation in January 2005. She filed for divorce the following March, and the proceedings were finalized in October 2005. “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,” Jolie told Vogue in January 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.” Pitt and the Salt star became serious rather quickly, with her confirming her pregnancy with their first child in January 2006. He formally adopted her son Maddox and daughter Zahara in 2006, and their children took on the surname Jolie-Pitt. [sendtonews type="float" key="X7741c8pmy-3115072-14453"] The couple welcomed Shiloh in May 2006. The Maleficent actress adopted son Pax in March 2007, while the actor followed suit in February 2008. Their twins, son Knox and daughter Vivienne, were born in July 2008. “One of the greatest, smartest things I ever did was give my kids Angie as their mom,” he gushed to Parade in September 2011. “She’s such a great mom. Oh, man, I’m so happy to have her. With a partner like Angie, I know that when I’m working, the kids are happy, safe and prospering. And when Angie’s working, she knows she has the same.” Jolie and Pitt announced their engagement in April 2012. They tied the knot in France in August 2014. However, Brangelina called it quits in September 2016. In addition to their lengthy custody battle, Jolie accused her ex of being “physically and emotionally abusive” toward her and their kids on a September 2016 flight from California to France, which Pitt denied. Pitt, for his part, filed a lawsuit against the By the Sea actress in February 2022, claiming she illegally sold her share of the French winery Château Miraval, after previously agreeing not to do so without each other’s permission. Scroll down to rediscover how Pitt and Jolie’s post-split relationship became so contentious.

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September 2016

The Lara Croft: Tomb Raider star filed for divorce after two years of marriage, citing irreconcilable differences. She requested sole physical custody of their six children. “This decision was made for the health of the family,” her rep told Us Weekly in a statement at the time.

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September 2016

An altercation on the duo’s private jet led to a child abuse investigation into Pitt. “He got drunk and was fighting with Angie,” a source claimed. “Maddox stepped in to defend Angie and got in Brad’s face.” 

The Fight Club actor was cleared of the allegations in November 2016.

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September 2016

The By the Sea costars reached a temporary custody agreement one week after their separation. She received full physical custody, while he was granted visitation rights. They were both ordered to undergo individual counseling as well as attend family counseling with their kids. He was subjected to random drug and alcohol testing at the time too.

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November 2016

Pitt sought joint physical and legal custody of the children in his response to Jolie’s divorce filing. While Maddox initially refused to see his father, they reunited in October 2016 as their relationship remained strained.

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February 2017

The Girl, Interrupted star opened up about the divorce in a BBC interview. “I don’t want to say very much about [the incident] except to say that it was a very difficult time and we are a family. And we’ll always be a family,” she said, growing emotional. “And we’ll get through this time and hopefully be a stronger family for it.”

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March 2017

Us confirmed that Jolie and Pitt were speaking again after their split. “They are in a place where they can put anger or hurt aside to focus on their children and how they plan to coparent,” a source revealed, while another insider added: “They are only speaking about the kids but have agreed that the kids’ best interest comes first and that they will be civil to one another.”

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May 2017

The Ad Astra actor got real about the aftermath of the split nearly one year later. “I was really on my back and chained to a system when Child Services was called,” he admitted to GQ Style. “And you know, after that, we’ve been able to work together to sort this out. We’re both doing our best. I heard one lawyer say, ‘No one wins in court — it’s just a matter of who gets hurt worse.’ And it seems to be true. You spend a year just focused on building a case to prove your point and why you’re right and why they’re wrong, and it’s just an investment in vitriolic hatred.” 

He continued: “Fortunately my partner in this agrees. It’s just very, very jarring for the kids, to suddenly have their family ripped apart. If anyone can make sense of it, we have to with great care and delicacy, building everything around that. … Our focus is that everyone come out stronger and better people — there is no other outcome. I see it happen to friends — I see where the one spouse literally can’t tell their own part in it, and it’s still competing with the other in some way and wants to destroy them, and needs vindication by destruction, and just wasting years on that hatred. I don’t want to live that way.”

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June 2018

Pitt and Jolie reached a temporary custody agreement for summer 2018 after the court decided that “not having a relationship with their father” would be “harmful” to the children. The court determined the kids “are safe with their father” too. Maddox, due to his age, was free to stay with either parent.  

The Emmy winner had physical custody during portions of the summer and was required to spend time with the children with a psychologist present.

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August 2018

Jolie’s attorney claimed in a filing that Pitt had “paid no meaningful child support since separation” as of August 2018. In response, his lawyer noted that “[Pitt] adamantly disputes the contention that he has not paid significant child support. [Pitt] has previously loaned [Jolie] $8 million to assist her in purchasing her current residence and has paid over $1.3 million in bills for the benefit of [Jolie] and the minor children.”

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November 2018

The estranged duo avoided going to trial over custody by reaching a new agreement. “Brad and Angelina will have joint physical and legal custody of the children,” a source close to Pitt told Us at the time. “Over a period of the next six to eight weeks, the monitored visits will come to a conclusion. The children will immediately begin to have overnight visits with their father.”

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April 2019

Jolie and Pitt filed for a bifurcated judgment, which meant they were deemed legally single though their divorce continued.

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June 2019

“Brad is enjoying spending more time with the kids and things have been improving with the four younger kids,” an insider revealed in June 2019. “Brad and Angie have been coparenting, utilizing OurFamilyWizard, which has probably been one of the most beneficial tools for their family in terms of keeping things moving forward in the best amicable terms possible. … Once Brad and Angie began using the platform, it allowed them to coordinate the kids’ schedules. They have very busy lives.”

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October 2019

The French chateau where they wed caused more problems in the divorce settlement. “The sticking point is the value of Miraval,” a source said. “Angelina wants to be awarded the property as hers entirely because it was her idea to purchase the property to begin with.” However, Pitt believed he’d been “more than generous with other financial elements.”

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November 2019

Jolie admitted to Harper’s Bazaar in November 2019 that she “would love to live abroad and will do so as soon as my children are 18” because at the moment, she was “having to base where their father chooses to live.”  

According to an insider, Pitt “doesn’t want them living in another country where he’d never get to see them unless he flew there.” On the other hand, the director would “like to move around — Europe, Asia, Africa.”

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May 2020

The exes seemed to be on good terms as of May 2020. “Things between Brad and Angelina are better than they have been,” a source said. “They’re more cordial — they’re aiming toward resolutions that work for each of them.”

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July 2020

Us exclusively reported in July 2020 that their legal proceedings were “slowed down” by the COVID-19 pandemic. “They are continuing regular visits but there has not been a lot of progress in terms of resolving anything,” an insider told Us as Pitt was spotted visiting the children at Jolie’s home.

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August 2020

Jolie requested to disqualify the judge in their custody trial. “Unfortunately, the individuals hurt most by Jolie’s transparently tactical gambit are the parties’ own children, who continue to be deprived of a final resolution to these custody issues,” Pitt’s lawyers said in court documents obtained by Us.  

“Brad says Angelina has gone way too far this time,” a source revealed. “He’s left with no other option but to dig in and fight back — hard.”  

However, Jolie’s lawyer told Us, “All my client is asking for is a fair trial based on facts, with no special favors extended to either side.” Neama Rahmani, president of West Coast Trial Lawyers, added that the Tourist actress believed the judge handling the proceedings was “biased in Brad’s favor” due to their personal connections. 

In court documents obtained by Us, Jolie’s attorney went so far as to accuse Pitt’s legal team of going “behind her back” to cover up judicial bias.

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August 2020

As the legal battle between the Mr. and Mrs. Smith costars continued, Jolie asked for their judge, John W. Ouderkirk, to be disqualified from overseeing their case after failing to disclose "ongoing business and professional relationships" with Pitt and his team. In a response filed to the court in August, Ouderkirk asserted that he "can and will remain impartial" in the actors' case and that Jolie had "clearly failed" to prove that he had shown any sort of special treatment in Pitt's favor.

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August 2020

As the custody battle continued, news broke that Pitt had a new love in his life. He was spotted with German model Nicole Poturalski in August 2020.

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September 2020

A source revealed that tensions had significantly "escalated between Brad and Angelina, with family therapy no longer taking place" as they prepared for their October 2020 custody trial. While the Fight Club actor was hoping to negotiate "50/50 joint physical and legal custody of the kids," the insider told Us that Jolie had been "unagreeable to those terms."

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February 2021

The Girl, Interrupted actress reflected on her tumultuous divorce during an interview with British Vogue, admitting that it's "been pretty hard" to navigate. "I've been focusing on healing our family. It's slowly coming back, like the ice melting and the blood returning to my body," she said at the time.

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March 2021

Court documents obtained by Us amid the duo's messy divorce alleged incidents of domestic violence. In her filing, Jolie claimed that her children were willing to share "proof and authority in support" of the accusations against Pitt, which a source viewed as nothing more than an attempt to "hurt" the Troy actor. "Over the past four and a half years there have been a number of claims made by Angelina that have been reviewed and not substantiated," the insider said. "The children have been used by Angelina to hurt Brad before and this is more of that behavior."

A separate source later revealed that Maddox, the pair's eldest son, had already provided his testimony to the court. "It wasn't very flattering toward Brad," the source added.

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May 2021

The Those Who Wish Me Dead actress claimed in court documents that the judge presiding over her divorce case refused to hear evidence from her children regarding Pitt's alleged history of domestic violence, claiming that awarding joint custody would not be in the kids' best interests. Despite her testimony, a judge ruled in favor of Pitt and issued a tentative ruling for the exes to share time with their children.

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June 2021

After a judge issued a temporary ruling that would allow the former couple to share custody of their kids, a source told Us that Jolie was "bitterly disappointed" by the decision. "Angelina’s testimony lacked credibility,” the source added. “The decision was based on extensive testimonies from people who spent time with the kids and by highly respected professionals.” Pitt, for his part, was "delighted" by the judge's ruling, but the insider said Jolie was already planning her next move. “She will never forgive him,” the source explained, adding that the actress will use “everything she’s got” to appeal the arrangement. “She maintains it’s far from over and still believes that justice will prevail.”

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August 2021

Jolie was successful in disqualifying the judge in her custody case in July 2021 after alleging that Judge John W. Ouderkirk failed to disclose his prior relationship with Pitt. The next month, the actor fought back, filing court documents asking the decision from the Second District Court of Appeal in California be reviewed by the state’s highest court.

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September 2021

The pair fought over their joint ownership of Château Miraval, with Pitt alleging that Jolie's attempted sale of her shares cuts him out of the chance to make a profit. The lawsuit was filed in Luxembourg. A September 22 order stated that the Miraval dispute does not belong in the L.A. court. 

Jolie later responded to her ex-husband's request to review the removal of Judge Ouderkirk, arguing in court docs obtained by Us that it was a "last-ditch effort by a celebrity litigant seeking special treatment."

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October 2021

After the back-and-forth over Château Miraval, Jolie sold her share of the $164 million estate and company to Tenute del Mondo, a subsidiary of the Stoli Group. According to a press release announcing the news, Pitt will remain a part of the business.

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December 2021

Pitt "would dearly love to date again," a source exclusively revealed to Us, but the actor wasn't quite ready to have his love life "scrutinized" in the public eye again. "[He wants to] find that special someone to be with long-term," the insider added, noting that Pitt had "trouble" with the constant speculation — even when he's simply "out for a friendly coffee."

The Troy star was "focused on his family, charities and work," and hoped "he and Angelina find a way to forgive each other and move forward, for the kids' sakes if nothing else," the source said.

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February 2022

Pitt filed a lawsuit against the Eternals star, alleging in docs obtained by Us that Jolie sold her stake in Château Miraval to a third party without his knowledge. According to Pitt, his former spouse breached their initial agreement to only sell their stakes with mutual consent and attempted to gain profits she didn't earn. The actor wanted the sale of Jolie's shares to be voided and to receive damages.

"Unfortunately, this is another example of the same person disregarding her legal and ethical obligations," a source told Us at the time, claiming that Jolie "violated" Pitt's rights through her sale.

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February 2022

Pitt allegedly tried to purchase Jolie’s stake in the company, a source exclusively told Us after news broke that he was suing his ex-wife for selling her shares in the Château Miraval winery without notifying him. “[Angelina] made the negotiations difficult and was not being fair,” the insider said, claiming that Pitt was “blindsided” when he learned in October 2021 that Jolie sold her share in the winery amid their talks of him buying her out.

“He assumed they’d work it out because she knows how important the winery is to him,” the source told Us, adding that when the Kung Fu Panda actress sold it “out from under him” allegedly “out of the blue,” Pitt was “devastated.”

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April 2022

A source exclusively told Us that Pitt wasn't ready to "give up the fight" for custody — despite Jolie's apparent hopes that the kids "will want nothing to do with" him. The Golden Globe winner was "lamenting to pals" that his ex-wife would "never agree to joint custody," claiming that the actress was "going to run out the clock until the kids are 18," the insider said.

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June 2022

An insider exclusively told Us that Pitt has been "holed up in his place" in Los Angeles while dealing with the ongoing custody battle with Jolie. "It’s very clear to him that Angie has gone out of her way to delay and stall the process," the source claimed. "All he can do is work with his legal team and file the paperwork whilst responding to her claims. Month after month goes by with one piece of red tape after another, endless jumping through hoops and bickering between their lawyers with no resolution."

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June 2022

In an amended filing in their Miraval lawsuit, Pitt's lawyers called for a trial by jury and claimed the Eternals star "sought to inflict harm on Pitt."

The court documents, obtained by Us, allege that since the actress' share of Miraval was sold, the buyer has "launched a hostile takeover," destabilizing the business and tarnishing the brand's reputation.

"All of this is the direct result of Jolie’s unlawful and tortious conduct," the Thelma and Louise actor's lawyers wrote. "In violation of the parties’ agreement, Jolie has sought to force Pitt into partnership with a stranger, and worse yet, a stranger with poisonous associations and intentions."

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June 2022

In an amended filing in their Miraval lawsuit, Pitt's lawyers called for a trial by jury and claimed the Eternals star "sought to inflict harm on Pitt."

The court documents, obtained by Us, allege that since the actress' share of Miraval was sold, the buyer has "launched a hostile takeover," destabilizing the business and tarnishing the brand's reputation.

"All of this is the direct result of Jolie’s unlawful and tortious conduct," the Thelma and Louise actor's lawyers wrote. "In violation of the parties’ agreement, Jolie has sought to force Pitt into partnership with a stranger, and worse yet, a stranger with poisonous associations and intentions."

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August 2022

As Pitt and Jolie continued battling it out over the winery, an insider exclusively told Us that the Meet Joe Black actor is trying to keep the drama from affecting his relationship with his kids. “[He] pushes to see them as often as possible wherever they all are in the world,” the source explained. “He flew to Italy for the twins’ birthday and that meant a lot to them, plus he made a big fuss of Shiloh on her 16th. Brad cherishes every moment he gets with the kids. He loves being a parent and has tried to make the best of a tricky situation given how hostile it’s been with Angelina.”

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August 2022

According to Puck, Jolie was revealed as the anonymous plaintiff in a lawsuit filed against the FBI over their handling of the investigation into the 2016 plane incident. In her complaint, the actress alleged that the agency withheld certain documents when she and Maddox filed a Freedom of Information Act (FOIA) request. In court docs obtained by Us, "Jane Doe" claimed that she has been "seeking the withheld information for ... years in an effort to ensure that her children receive" the "care" and "counseling" they need to "address harm suffered."

The complaint also alleged that the FBI agent in charge of the investigation actually "prepared a statement of probable cause" for an arrest of "Mr. Doe," believed to be Pitt, and presented it to the assistant U.S. attorney and the chief of the criminal division at the U.S. attorney's office in L.A. The U.S. attorney's office did not press charges after seeing the statement, but the complaint states she and her children should be allowed to see the statement as well as other documents related to the FBI's investigation.

"The consistent, years-long denial of access to records" has "subjected the children to harm in the family law system," added the complaint. "The records that [Jolie] is seeking the FBI to release in unredacted or far less heavily redacted form in compliance with FOIA are critical to her efforts to obtain medical and care for her children and protect the children in the family law system, and should be released to her without further delay."

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August 2022

Pitt wants Jolie to be “happy” amid their winery battle, a source exclusively told Us. “He’s not rooting against her, not personally, not professionally, not romantically,” the insider said. “If she’s happy, he’s happy. Brad loved Angelina and he still cares about her.”

The Oklahoma native has been “consistent” about the fact that he wants the Original Sin actress to be “happy and healthy and the best mother she can be for their children,” the source added.

Jolie, for her part, is “angry that the public adores Brad so much when she feels he was very unkind to her,” the insider told Us.

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October 2022

In court documents obtained by Us, Jolie accused Pitt of being "physically and emotionally abusive" toward her and their children during the September 2016 flight that led to her filing for divorce. "When one of the children verbally defended Jolie, Pitt lunged at his own child and Jolie grabbed him from behind to stop him," Jolie's legal team alleged in the court docs. "To get Jolie off his back, Pitt threw himself backwards into the airplane’s seats injuring Jolie’s back and elbow. The children rushed in and all bravely tried to protect each other. Before it was over, Pitt choked one of the children and struck another in the face. Some of the children pleaded with Pitt to stop. They were all frightened. Many were crying." The Come Away star also claimed that her ex "poured beer" on her during the flight and "poured beer and red wine on the children."

The documents were filed as part of the former couple's ongoing battle over the French winery they owned together during their marriage. In the filing, Jolie's team alleged that she actually did give Pitt the opportunity to buy her share of the business, but he wanted her to sign an NDA "that would have contractually prohibited her from speaking outside of court about Pitt’s physical and emotional abuse of her and their children." When she refused to agree to that provision, her ex allegedly "walked away from the deal."

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October 2022

Pitt reacted to Jolie's abuse allegations in a statement shared via his lawyer, Anne Kiley. “Brad has owned everything he’s responsible for from day one — unlike the other side — but he’s not going to own anything he didn't do," the attorney told Us. "He has been on the receiving end of every type of personal attack and misrepresentation. Thankfully, the various public authorities the other side has tried to use against him over the past six years have made their own independent decisions. Brad will continue to respond in court as he has consistently done."

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October 2022

Following Jolie's abuse accusations, a source exclusively told Us that Pitt felt "sick to his stomach" about the claims. "He maintains [that] it’s lies and that Angelina will stop at nothing to ruin his name,” the insider said. "At the end of the day, he and Angelina seem destined to fight each other for the rest of their lives, or at least until the kids are grown up and there’s nothing left for them to contest."

That same month, the actor reflected on how art helped him amid his personal issues. "Out of this misery came a flame of joy in my life," he told the Financial Times. "I was looking at my own life and really concentrating on owning my own s--t. Where was I complicit in failures in my relationships, where have I misstepped."

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June 2023

In court documents obtained by Us, Pitt claimed that Jolie sold her Château Miraval shares in secret as payback amid their ongoing custody battle. Though the two previously began negotiations for Pitt to buy out his ex-wife’s stake in the French property in 2019, she went on to sell them to Yuri Shefler, who owns the Russia-affiliated spirits conglomerate Tenute del Mondo. Pitt claimed he was not given the opportunity to match or outbid Shefler’s offer, despite having a “contractual right to do so.”