Jolie cited irreconcilable differences in her filing, and an attorney for the actress, Robert Offer, told the Associated Press at the time that the decision was made "for the health of the family." She also asked for physical custody of their kids -- 21-year-old Maddox, 18-year-old Pax, 17-year-old Zahara, 16-year-old Shiloh and 14-year-old twins Knox and Vivienne.
Since then, it's been anything but conscious uncoupling between the two, due to an intense custody battle, though things seemed to have cooled in recent months. From their legal fight to their dating lives, let's take a look at where 58-year-old Pitt and 47-year-old 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, 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."
"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."
"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.
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."
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.
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."
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."
"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 push-back
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.
"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.
For more on the years-long divorce and as-yet-unsettled custody battle, see the video below.