ET looks back at Brad Pitt and Angelina Jolie's turbulent relationship journey since they first split in 2016.
Angelina Jolie, 49, and Brad Pitt, 60, shocked fans around the world when news broke on Sept. 20, 2016 that Jolie filed for divorce from Pitt after two years of marriage.
Jolie cited irreconcilable differences in her filing and also asked for physical custody of their kids -- 22-year-old Maddox, 20-year-old Pax, 19-year-old Zahara, 18-year-old Shiloh and 15-year-old twins Knox and Vivienne. In November of the same year, Pitt responded to Jolie's divorce petition, asking for both joint legal and physical custody of their six children in his filing.
Since then, it's been anything but conscious uncoupling between the two due to an intense custody battle and a long, protracted fight over the sale of their French vineyard, their demands over NDAs and new allegations of abuse and manipulation.
From their legal fight to their dating lives, let's take a look at where Pitt and Jolie stand now since their separation in 2016.
Their Court Battle Begins
Shortly after Jolie filed for divorce, reports surfaced that Pitt was being investigated for child abuse after Maddox allegedly inserted himself into a fight between his parents during a flight home from Europe.
However, a source told ET at the time that it was "totally a child-parent disagreement," and any reports of inappropriate physical conduct are "exaggerated or untrue."
By November 2016, Pitt had been cleared of child abuse allegations by the Department of Child and Family Services. “It wasn’t clearly founded that there was any abuse by Pitt,” a source told ET at the time.
In a statement to ET, Jolie's team expressed relief that the investigation had concluded. "The job of the DCFS is to make sure the children are in a safe and secure situation," the statement read. "As we said earlier this week, childcare professionals encouraged a legal agreement accepted and signed by both sides that was in the best interest of the children. Angelina said from the beginning that she felt she had to take action for the health of the family and is relieved that after their 8-week involvement, the DCFS is now satisfied the safeguards are put in place that will allow the children to heal.”
The Temporary Custody Arrangement
In late September 2016, the two agreed to a temporary custody arrangement. Jolie and Pitt each volunteered to participate in individual counseling, and Pitt also agreed to undergo drug and alcohol testing, though he was not required to, sources told ET.
One month later, a judge approved a custody agreement between the two, granting Jolie physical custody of all six children. According to documents, Pitt would continue to have agreed-upon therapeutic visitations with the kids, as determined by the family's therapist who "shall at all times consider the best interests of the minor children."
Still, the two continued to be at odds when it came to their children, later engaging in a more complicated custody battle, as Pitt continued to request more time with the children.
Pitt Tries to Seal the Docs
In December 2016, Pitt's request for an emergency hearing to seal all documents related to his custody case with Jolie was denied. A source told ET that Pitt filed the motion to seal the documents "because he wants to keep this custody battle out of the public eye to protect his children." Meanwhile, another source told ET that contrary to some reports, Jolie was not trying to make Pitt "look bad" in court.
"Angelina's team is not opposed to sealing the documents," a source told ET at the time. "There have been many reports that Angelina wants to keep these documents public to make Brad look bad, that is false. As the document states, their custody agreement was already legally binding. The only reason to formally file it with a court would be to enforce the agreement because one of the parties was trying to change it and that is what was happening."
"Brad was attempting to set up his own schedule with the children," the source further claimed. "He was not relying on the advice of the healthcare professionals [as to] what should be done. In order to keep everything in line with the custody agreement, it had to be reinforced in court. Therefore that forced Angelina's side to file it within the courts."
However, by January 2017, the situation between the two appeared to have improved, and they sent their first joint statement together agreeing to keep all of their court documents private.
Pitt Speaks Out in a Big Way
In May 2017, Pitt opened up like never before about his split from Jolie in a tell-all interview with GQ Style.
"I was really on my back and chained to a system when Child Services was called," Pitt said. "And you know, after that, we've [he and Jolie] 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."
"I just refuse," he continued. "And 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," he added.
Jolie Goes Public With Vanity Fair
In July 2017, Jolie opened up in her own interview with Vanity Fair, and addressed how she was described as "defensive" when addressing reports that Pitt wanting "a more stable, normal life for the whole family" was a catalyst for their breakup.
"[Our lifestyle] was not in any way a negative," Jolie replied. "That was not the problem. That is and will remain one of the wonderful opportunities we are able to give our children. ... They're six very strong-minded, thoughtful, worldly individuals. I'm very proud of them."
Jolie answered with a simple "no" when asked if she was surprised by Pitt's emotional GQ profile, and Vanity Fair describes her as looking "unmoved." Still, she said at the time that the two are keeping it amicable for the children.
“We care for each other and care about our family, and we are both working towards the same goal," she said.
She also suggested that their children were dealing with more than a divorce between their parents.
"They've been very brave. They were very brave. In times they needed to be," she said cryptically. "We're all just healing from the events that led to the filing. ... They're not healing from divorce. They’re healing from some ... from life, from things in life."
Jolie Opens up About Balancing Responsibilities
In February 2018, Jolie talked about balancing her work with priorities as a mother.
"You have your creative, and you have your work, and every day of your life is going to be about somehow growing as a person," she told Deadline Hollywood. "Somehow feeling you can contribute to the extent that you can get tribute."
"We’re all trying to find balance, as people," she continued. "I think to be a balanced person, you have to find those things that you just purely enjoy. But, of course, if you aren’t participating in the bigger picture of life, and in being somehow useful, and you aren’t doing something and growing, then really, you’ll find you’re not very happy. Really, you’ll have quite an empty life."
Legal Tensions Rise Once More
Jolie and Pitt's legal battle flared up again in June 2018. The court drama came after Jolie was ordered by a judge in June to help repair her children's relationship with Pitt. According to the court documents obtained by ET, the actor was given more time with five of his children over the summer, while Maddox, "because of his age and maturity," was able to determine how much time he wanted to spend with his father.
In August 2018, Jolie accused Pitt of not paying any "meaningful" child support for a year and a half in a court filing, and said she is planning to get a court order mandating that he pay it. Pitt's lawyers filed their response one day later, and in court papers obtained by ET, Pitt denied that he hasn't paid any significant child support and claimed that he'd paid Jolie over $9 million since their September 2016 split.
Trying to Take Steps Forward
On the eve of the two-year anniversary of their split, in September 2018, a source told ET that the actress had reached out to Pitt to improve their co-parenting relationship.
"Brad and Angelina actually set up a secret meeting at her house," the source said. "It’s the first time they have truly gotten together to make things work since their group therapy with the children. Brad and Angie’s meeting was a success. They are going to stay with the plan set forth through the courts."
"Angelina decided it was time to try to make things work and Brad was relieved and very ready for the offer," the source continued. "Brad has been dedicated to making peace throughout the process and now it finally seems like they are at a point where they can create a calmer situation for the kids."
The source noted that the meeting between Jolie and Pitt was a "huge step" for the two, and "they both hope to continue to work together for the kids."
Pitt Gets Back on Set
In October 2018, Pitt was photographed on the set of his 2019 sci-fi film, Ad Astra -- in which he played an astronaut -- and a source told ET at the time that the actor was the consummate professional on set.
"When he’s not on set filming, he hangs out in his trailer,” the source told ET. "He’s never late and he always arrives to set ready to work."
"Physically, he looks fantastic," the source added. "Brad is very friendly and genuine with everyone on set."
Legally Single
On April 12, 2019, a court ruled that both Jolie and Pitt were legally single, despite their divorce not yet being settled. A judge ruled that the former couple's marriage was officially over after Pitt and Jolie requested a bifurcated judgment, which would allow their single status to be restored while they continue to finalize their divorce.
Days later, a source told ET that the former couple's relationship was "the best it's been since their split."
"Brad and Angelina have come a long way," the source said at the time. "To the surprise of many of their closest friends, their communication has improved tremendously and they're both dedicated to co-parenting. Their kids have a custody schedule and that's made a huge difference for the whole family. The schedule has alleviated any of the planning pressures Brad and Angelina have faced in the past. Now the kids spend time with both their parents and are happy and thriving."
The source added that "While they don't agree about everything, they rarely argue now. Brad and Angelina are now at a point where they can discuss their children's plans calmly."
Pitt Thanks His Kids in His Oscars Speech
Pitt's biggest professional accomplishment after his split from Jolie came in February 2020 when he took home his first-ever acting Oscar for his role in Quentin Tarantino's Once Upon a Time in Hollywood.
During his emotional acceptance speech, Pitt sweetly thanked his children, sharing, "This is for my kids. You color everything I do. I adore you."
Jolie Dishes on Divorce Once Again
In an interview with Vogue India in June 2020, the actress said that her decision to divorce was largely for the sake of her and Pitt's six children.
"I separated for the well-being of my family. It was the right decision," Jolie told the magazine. "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."
A High-Profile Home Visit
In late July 2020, Pitt was photographed leaving Jolie's Los Angeles mansion on his motorcycle in pictures published by The Daily Mail, marking the first time he'd been spotted at her home since their breakup.
"Brad and Angelina have come a very long way and they're finally in a place where they both want to work together to raise their kids," a source told ET. "They have no plans to reconcile and any communication between them is regarding their children's needs and future."
"They chose to live close to one another so they could easily go back and forth with the kids," the source adds. "This week wasn't the first time Brad and Angelina have spent time together at her home. They are in a much more amicable relationship."
Jolie Claims to Have Proof of Domestic Violence
In new court documents that were filed under seal on March 12, 2021, the actress alleged that she was prepared to offer "proof and authority" against Pitt regarding her claim of domestic violence during their then-pending divorce hearing.
A source familiar with the case told ET at the time that Jolie's claims were "another case of Angelina changing the narrative when it suits her." The source added, "Aside from the one accusation that she made in 2016 that was investigated and dismissed, there have never been any other records, police reports or even accusations until it suited her case."
Another source, close to Pitt, told ET that the actor was "heartbroken" over the claims.
"Brad is anxious to get custody worked out so that the family can finally move on," the source said. "He just wants to spend time with his children and move in a positive direction. His priority has always been his relationship with his children... Brad is heartbroken it has come to this."
Pitt Custody Granted but Met With Pushback
In May 2021, Pitt was granted joint custody of his kids, while Jolie challenged the tentative ruling. Judge John Ouderkirk issued a "detailed" ruling which found that Jolie's testimony lacked credibility in many important areas and that the existing custody order must be modified in the best interest of the children
Jolie, who sought divorce from Pitt in 2016, initially wanted primary custody, while Pitt requested joint custody. Peter Harvey, a lawyer for Jolie who is close to the case but not directly involved, told the Associated Press that the actress "supports joint custody," but added that the situation is complicated and he can’t go into detail because the court proceedings are under seal.
Jolie Scores a Legal Victory
After months of trying, unsuccessfully, to get Judge John Ouderkirk dismissed from their divorce case, Jolie finally scored a victory in July 2021, when a California appeals court ruled in Jolie's favor and disqualified the private judge and had all of his decisions vacated. According to court documents obtained by ET, the court agreed that Judge Ouderkirk didn't sufficiently disclose his business relationship with Pitt's attorneys, resulting in an "ethical breach."
The docs state that "the information disclosed concerning his recent professional relationships with Pitt’s counsel, might cause an objective person, aware of all the facts, reasonably to entertain a doubt as to the judge’s ability to be impartial. Disqualification is required." Pitt and/or Judge Ouderkirk could still appeal this decision.
This decision called back into question the joint custody granted to Pitt two months earlier.
The Winery Sale Leads to a Blow-Up
Tensions flared once more in February 2022 when Pitt sued Jolie for selling Chateau Miraval Winery, which he is part owner of, to Russian oligarch, Yuri Shefler. The actor stated he was seeking monetary damages, legal fees and for Jolie's sale of Miraval to Shefler to be voided.
In June, Pitt filed additional court documents accusing his ex of intentionally trying to "inflict harm" on him and his interests in their winery. Pitt's lawyers claimed Jolie sold her stake in their winery to Shefler in an effort to damage Pitt's involvement in the company.
"Pitt -- through significant financial investment and years of sweat equity—has built a highly successful family-owned business. Miraval has correspondingly grown massively in value since 2008 and is now worth hundreds of millions of dollars," the docs claimed. "Meanwhile, Jolie has not returned to Miraval since filing for divorce in 2016."
"Jolie pursued and then consummated the purported sale in secret, purposely keeping Pitt in the dark, and knowingly violating Pitt's contractual rights," the lawsuit further alleged.
The Details of the Fateful Flight Emerge
On Aug. 17, 2022, new details emerged regarding the alleged plane incident that led to their split in September 2016.
According to FBI investigative records, Jolie alleged in an interview with FBI officials that the actor “grabbed her by her head,” yelled at her, shook her, and “pushed her into the bathroom wall” during an outburst on the private jet, in which their six children were present.
In the records, Jolie claims Pitt's outburst scared the kids, prompting one of them to call their dad a "prick," to which he responded by approaching the minor "like he was going to attack." The actress says in the docs that she reacted by jumping up and grabbing Pitt around the neck as if to put him "in a choke hold," and that it was then when Pitt purportedly threw himself back, leading Jolie to be pushed into seats on the plane which caused injury to her back and elbow.
Jolie says in the report that Pitt told her, "'You’re f**king up this family,'" and when the kids asked if she was OK, Pitt allegedly responded to them by saying, "No, she’s not OK, she’s ruining this family, she’s crazy."
Jolie claims Pitt had consumed alcoholic beverages during the flight, and poured beer on her. She described feeling "scared” and “like a hostage," during the alleged altercation. When describing her injuries, Jolie said she had a "rug-burn type wound on her right hand.” She also said a “scratch” on Pitt could have been caused by her.
This information comes months after ET obtained court documents that showed a woman identified as Jane Doe was suing the FBI for information regarding an investigation into an alleged domestic violence incident which took place on a private jet.
The Vanity Fair Exposé
In June 2023, Vanity Fair writer Mark Seal penned an in-depth feature on the couple's legal battle over Miraval. The couple were 50-50 partners in the property and winemaking ventures until 2021, when Jolie made the decision to sell her share.
As their relationship soured beyond repair in the last few years, the battle over Miraval has gotten personal and ugly. Vanity Fair's article notes that, prior to the couple's purchase of the property in May 2008, Jolie's business manager suggested a doomsday clause stipulating that, in the event that the pair ever split, each would have the right to buy the other’s share of Miraval.
In love as they were at the time, the couple rejected the idea. According to a cross-complaint by Jolie in the ongoing legal battle, Pitt said it "wasn’t necessary for two reasonable people." He would later state that he and Jolie promised each other to never sell their respective stakes in Miraval without the other's consent, a claim Jolie now denies.
Jolie emailed Pitt "with a heavy heart" on Jan. 21, 2021, to tell him of her decision to sell her stake in Miraval, in part because it was "a business that is centered around alcohol" -- likely a reference to the 2016 plane incident.
"Even now impossible to write this without crying," Jolie wrote. "Above all, it is the place we brought the twins home to, and where we were married over a plaque in my mother’s memory. A place…where I thought I would grow old…. But it is also the place that marks the beginning of the end of our family."
"Miraval for me died September 2016," she continued, referring to the date of the alleged plane confrontation, "and everything I have seen in the years since has sadly confirmed that."
Vanity Fair reports that Pitt was prepared to buy Jolie out of her shares, but when she refused to sign an NDA regarding her allegations of domestic abuse, Pitt reportedly walked away from the negotiation. On Oct. 5, 2021, the actress sold Nouvel -- the holding company in control of her Miraval shares -- to Tenute del Mondo, the wine division of the Stoli group controlled by Russian billionaire Yuri Shefler, for $67 million.
Pitt felt betrayed, Seal wrote, seeing the sale as retaliation related to their custody battle.
The couple's legal battle continues today. On June 1, 2023, Pitt filed an amended complaint, still seeking to have Jolie’s sale of Nouvel reversed. That led to a statement from Jolie’s attorney, saying that Pitt "has never publicly denied" the events of the 2016 plane incident.
Pitt’s attorney, Anne Kiley, replied, "Brad has owned everything he’s responsible for from day one, but he’s not going to own anything he didn’t do."
For sources familiar with the former couple and their family, the drawn-out legal battle is nothing short of a tragedy.
"This case has been covered as a celebrity divorce; it is really a story about abuse," said one source familiar with the matter, per Vanity Fair.
"I hope you’ll give some grace to somebody who had a breakdown," said another person who knew the family. "Everybody was shocked by the eruption on the plane, because Brad is not an abusive person. But even more devastating was what came afterwards: Brad being alienated from those he loves most—his children."
Jolie Alleges Pitt Was Abusive for Years
In April 2024, Jolie's lawyers filed a motion that largely revolved around the former flames' acrimonious legal dispute over their shares of ownership of their French winery. In the docs, obtained by ET, Jolie's lawyers claimed Pitt was "physically abusive" toward her before the alleged 2016 incident on a plane.
In the docs, Jolie's lawyers argued that Pitt was refusing to buy Jolie's shares in the winery unless she agreed to sign a more expansive non-disclosure agreement (NDA). Jolie's lawyers filed the motion asking a court to compel Pitt and his legal team to provide "responses" and "documents" explaining why the Oscar-winning actor "suddenly conditioned his purchase of Jolie's share of Miraval on her agreeing to a greatly expanded NDA now covering Pitt's personal misconduct, whether related to Miraval or not."
Jolie claims in the documents that Pitt's demand for this NDA was his attempt to "cover up" his abuse of her and their children. Jolie's lawyers allege in the motion that "Pitt's history of physical abuse of Jolie started well before the family's September 2016 plane trip from France to Los Angeles." However, the docs claim that "this flight marked the first time he turned his physical abuse on the children as well" and that "Jolie then immediately left him."
"The conduct is egregious and caused significant and ongoing post-traumatic stress," the documents allege. "At trial, Jolie will prove through testimony, emails, photographs, and other evidence why Pitt was so concerned about his own misconduct that he blew up his own deal to purchase Jolie’s interest in Miraval because she refused to agree to his new, expansive NDA. Some of that evidence is currently under Pitt's control. This is the evidence Jolie seeks by this motion."
In contrast, Jolie's lawyers, docs filed by Pitt's legal team in June 2023 claim that it was actually Jolie's team who requested a "broader" NDA, not him.
Additionally, a close friend of Pitt -- who is familiar with the litigation over the years -- told ET at the time that the latest claims of abuse are part of "a pattern of behavior" for Jolie and her legal team. The source claimed, "Whenever there is a decision that goes against the other side they consistently choose to introduce misleading, inaccurate and/or irrelevant information as a distraction."
With regard to why Jolie opted to never press criminal charges against Pitt, the docs claim, "Jolie never pressed charges as she believed the best course was for Pitt to accept responsibility and help the family recover from the post-traumatic stress he caused."
Family's Former Bodyguard Makes New Claims
In court documents filed in May 2024, a former security guard for Pitt and Jolie alleged that the actress attempted to drive a wedge between the actor and their children.
According to the documents, obtained by ET, lawyers for Pitt claim that a former security guard, Tony Webb, was told that Jolie had instructed her children not to speak to Pitt during custody visits. The documents also claim that Jolie attempted to threaten the security guards into silence through the use of non-disclosure agreements (NDAs).
During their custody battle, Webb claims to have "received multiple calls from Jolie's representative, who told Mr. Webb to remind his staff that they had entered into NDAs with Jolie and that if they testified in a custody proceeding, Jolie would sue them."
Webb states that he conveyed this message to his contractors, and that both contractors "confirmed that they had planned to testify if subpoenaed." Furthermore, the docs claim that "one of them told Webb that 'he would testify about statements he overheard that Ms. Jolie made to the children, encouraging them to avoid spending time with Mr. Pitt during custody visits.'"
The docs claim that "the two security contractors both testified" despite the alleged threat of being sued, and "shortly thereafter Jolie fired Mr. Webb's company." It appears that Webb himself -- who now works for Pitt -- does not claim to have personally heard Jolie's alleged comments to her kids.
Shiloh Files for a Name Change
On May 27, the day she turned 18, Shiloh filed a request with the court to allow her to drop her father's surname from her own hyphenated surname, a source familiar with the matter told ET. The source added that the teen is requesting a new legal name, hoping to go by simply, "Shiloh Jolie."
A source told ET in June, "Brad has always loved being a father and loves his children. This situation is upsetting to him, and he recognizes that things have been difficult for him and the whole family."
"Brad has made a tremendous effort to grow and learn from all of his experiences," the source continued. "He would love to find a way to continue to do this, repair things with his kids, and for everyone to get to a better place."
Shiloh is not alone when it comes to dropping her father's last name. Her younger sister, Vivienne, recently co-produced the Broadway production of The Outsiders, alongside her famous mom, and was credited as "Vivienne Jolie."
Vivienne also joined her mom at the 77th Tony Awards in New York City on June 16, where The Outsiders was nominated for 12 awards -- and took home four, including Best Musical. The mother-daughter duo took the stage with the rest of the cast and crew and basked in the glory of the big win.
Additionally, Zahara recently joined the Alpha Kappa Alpha sorority at Spelman College in Atlanta, Georgia, and during an introduction ceremony event, she introduced herself as "Zahara Marley Jolie." However, it appears that Shiloh is the first of their children to file paperwork to legally change their last name.
Notably, the Eternals actress -- who is the daughter of Jon Voight and Marcheline Bertrand -- was originally born Angelina Jolie Voight. However, following a long estrangement from her father, Jolie petitioned the court to legally drop Voight from her name. That request was granted in 2002.
For more on the years-long divorce and as-yet-unsettled custody battle, see the video below.
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