Angelina Jolie & Brad Pitt’s Romance Timeline & Split Drama – Hollywood Life

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• Brad Pitt and Angelina Jolie sparked a relationship after filming Mr. & Mrs. Smith together in 2005.
• They had six children together — three adopted and three biological — and got married in 2014.
• Brad and Angelina split after an explosive argument in 2016 and have been battling over custody of their children and shared winery, Miraval, ever since.

Brad Pitt and Angelina Jolie have one of the most infamous Hollywood love stories. What started out as two of the most respected and beloved actors of their time working together laid the foundation for a love affair that would last over 10 years, include six children, and a number of collaborative projects. Unfortunately, since the two split in 2016, things have turned ugly between them, and it’s all been highly publicized.

Between a custody battle and a lawsuit over Chateau Miraval, a property they bought in France while together, Brad and Angelina have been warring for years. Catch up on everything to know about the pair’s history, as well as where they stand today, below.

When Did Brad Pitt & Angelina Jolie Meet?

Back in 2005, a little movie came out that would become the catalyst for Brad and Angie’s relationship. In 2005’s Mr. & Mrs. Smith, the future couple played husband and wife with a mission to try and assassinate the one another! Now, that wouldn’t instantly sound like a recipe for romance, but for Brad and Angie their time on set and working together really brought them closer.

At the time, Brad was still married to Friends star Jennifer Aniston. But by the time the filmed had wrapped and speculation swirled around Brad and Angie, the actor’s five-year marriage to Jen was all but over. Soon, Jennifer filed for divorce from Brad, giving him the freedom to pursue Angie. The love triangle made headlines for months, with the public dying to know whether Brad had cheated on Jen with his new love interest.

“I would be a robot if I said I didn’t feel moments of anger, hurt, of embarrassment,” Jen admitted in a 2006 Vanity Fair interview, which took place as Brad and Angie were flaunting their new romance publicly. “I just don’t know what happened. There’s a lot I don’t understand, a lot I don’t know, and probably never will know, really.”

Brad and Angelina denied being involved while he was still married to Jen, and Jen said she had no choice but to believe that. “I choose to believe my husband,” she said. “At this point, I wouldn’t be surprised by anything, but I would much rather choose to believe him.”

Brad Pitt & Angelina Jolie’s Family

Before Angelina and Brad got together, the actress adopted a son, Maddox, now 21, from Cambodia in 2002 when he was seven months old. Angelina was with Billy Bob Thornton at the time, but took Maddox in as a single mother (she and Billy Bob split just months after the adoption was finalized). In July 2005, Angelina adopted a daughter, Zahara, now 18, from Ethiopia. Brad was with her at the time she picked Zahara up, and he legally adopted both Maddox and Zahara in 2006.

Just one year into their romance, Brad and Angie were expecting their first biological child together. In May 2006, Shiloh Jolie-Pitt (now 17 years old) was born, making the clan a family of five. In March 2007, Angie adopted Pax, 19, from Vietnam and Brad became the young child’s legal, adoptive father in February 2008. The couple then went on to have twins, Vivienne and Knox, now 14, in July 2008. Angie famously announced her pregnancy with the twins by debuting her baby bump at the Cannes Film Festival in 2008.

Brad Pitt & Angelina Jolie’s Marriage

In 2014, the former couple wed at the Château Miraval estate in Correns, France, which was a property they purchased as a hideout from the media’s scrutiny. It was such a beautiful, intimate ceremony that heavily involved the couple’s children. Maddox and Pax walked their mom down the aisle, with Knox and Shiloh serving as ring bearers and Zahara and Vivienne as flower girls.

Angelina wore a custom Atelier Versace dress for the wedding, which was attended by just 20 guests. The kids all helped design the gown, which Brad didn’t see until the moment Angie walked down the aisle, she told PEOPLE. The kids also helped out by writing their parents’ vows. “It was very sweet what they came up with,” Angie gushed.

Unfortunately, the marriage was quite short-lived. After just two years as a married couple, Brad and Angelina announced that they would be getting divorced in Sept. 2016. What followed were explosive claims about what happened that led to the messy split (see below).

Brad Pitt & Angelina Jolie’s Custody Battle

Everything exploded between Brad and Angelina when they were on a private flight home from France back to the United States with the six kids. The aftermath was a years-long custody battle that remains to 2023, despite three of the pair’s children now being legal adults. Angelina was initially granted temporary full custody of the children, with Brad granted visitation. The agreement was put into place amidst claims that Brad had gotten physically violent with Maddox on the flight following an argument with Angelina. Specific details of the alleged altercation were not made public.

By November 2016, Brad was cleared of the abuse allegations by the Department of Child & Family Services and FBI. A temporary custody arrangement was put in place that allowed Brad unsupervised visits with the children, but only after approval from a court-appointed psychologist.

Brad requested to have all court documents relating to the custody case sealed in Jan. 2017. At first, Angelina argued this decision, and claimed that Brad was just “terrified that the public would learn the truth about him” if the documents weren’t kept private. They were able to reach an agreement to seal the documents by the end of that month.

In June 2018, Brad scored a big win in the custody case when a judge ruled that Angelina wasn’t doing enough to ensure that the kids had a relationship with their father. Brad was granted an increase in custody over those summer months in a new temporary agreement. That August, they had a disagreement about child support, with her accusing him of not paying a “meaningful” amount.

Brad and Angelina were expected to go to trial for the custody hearing in Dec. 2018, but by November, they were able to come to an agreement out of court. The agreement stated that Brad would still have less than 50 percent custody, but said that his time with the kids would increase.

By April 2020, a judge ruled that Angelina and Brad would be declared “legally single,” but their divorce was not finalized. That summer, they had a new disagreement when Angelina tried to have the judge in their divorce case, John W. Oudenkirk, removed and replaced because of his relationship with Brad’s attorney. Her request was denied in Nov. 2020.

In March 2021, Angelina filed new court documents, where she alleged that she had proof to support claims of domestic violence against Brad. Angelina also claimed that, if her children were able to testify in the custody hearing, their statements would support her allegations. At the time, a source close to Brad told HollywoodLife that Angelina was simply trying to “target and tarnish” her ex with these allegations.

The judge ruled that the kids would not be allowed to testify in May 2021. Angelina blamed Judge Oudenkirk, claiming that he was not giving her a fair trial. That same month, Brad was finally awarded joint custody of the remaining minor children, but Angelina appealed the decision in June, insisting that Judge Oudenkirk was not acting impartial in his decisions. Lawyers for the stars appeared in court in July 2021.

Following that hearing, Angelina was granted the request to remove Judge Oudenkirk from the case, voiding the joint custody decision that he had made the previous month. At the time, a rep for Brad told HollywoodLife, “The appeals court ruling was based on a technical procedural issue, but the facts haven’t changed. There is an extraordinary amount of factual evidence which led the judge – and the many experts who testified – to reach their clear conclusion about what is in the children’s best interests. We will continue to do what’s necessary legally based on those detailed findings of what’s best for the children.” Brad went to court in Oct. 2021 to try and reinstate the decision that Judge Oudenkirk had made, but was denied.

At the end of summer and beginning of fall 2022, Brad and Angelina’s custody case made headlines once again when she went public with shocking allegations against him amidst another legal issue they were having (more info on that below). In court documents, Angelina finally shared her story about what allegedly happened on that Sept. 2016 plane ride between herself, Brad and the kids.

Angelina’s statement alleged that Brad had a confrontation with one of the kids (believed to be Maddox) before even getting on the plane. Then, during the flight, he allegedly accused Angie of being “too deferential” with the kids. More than an hour into the trip, he allegedly “grabbed [Angelina] by the head and shook her” before “[grabbing] her by the shoulders and [shaking her again],” according to the complaint. One of the kids reportedly tried to step in and defend Angelina, and she said that Brad allegedly “lunged” at the minor child.

“The children rushed in and all bravely tried to protect each other,” Angelina’s statement alleged. “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.”

When the plane landed, Brad allegedly wouldn’t let Angelina and the kids off the aircraft. It wasn’t until he fell asleep that she was able to devise a plan to get the kids safely to a hotel, according to the documents. At the time, a source close to Brad confirmed that the actor had been drinking and said that he “acknowledged that he crossed a line,” but immediately worked towards making amends. After Angelina went public with her accusations in 2022, a rep for Brad added, ““(Jolie’s) story continues to evolve each time she tells it with new, unsubstantiated claims. Brad has accepted responsibility for what he did but will not for things he didn’t do. These new allegations are completely untrue.”

The War Over Miraval

The previously mentioned “other lawsuit” Brad and Angelina were dealing with had to do with their winery, Chateau Miraval. Brad and Angelina first visited Chateau Miraval in France in June 2007 when they were looking for private properties to bring their family. They bought the property from Tom Bove, who told Vanity Fair in a 2023 profile that Brad and Angie desperately wanted somewhere private to go before the birth of Vivienne and Knox. They purchased the property in May 2008 through individual holding companies, with Brad taking a 60 percent stake and Angelina taking 40 percent.

In addition to using the property as refuge, Brad also began to take an interest in making wine himself. He teamed up with wine producer Marc Perrin to create a rosé. Although Angelina was less involved with the wine production, the ‘Jolie-Pitt’ name was on all of the labels of the extremely successful wines. Brad and Angelina became equal partners in Miraval in 2013 when he transferred 10 percent of his stakes to Angelina for the price of one euro (which he later claimed that she never paid), according to the Vanity Fair article.

However, along with the divorce came big-time disagreements over what to do with the estate. Angelina wanted out of her business partnership with Brad, and she sent an email to him in Jan. 2021 to let him know, the Vanity Fair profile reveals. “I have tried to stay open to the business, to see it as something that could be positive for our family, and have therefore not walked away,” she reportedly wrote. “I see now how you have really wanted me out and will most likely be pleased to receive this email.”

At the time, Brad agreed to buy out Angelina’s portion of the winery, but the deal did not go through. Angelina later claimed that Brad would not agree to the deal because she wouldn’t sign an NDA that he had asked for. The alleged NDA “prohibited Jolie from discussing, outside of court, any of Pitt’s personal conduct toward her or the family,” according to Vanity Fair. However, a source close to Brad insisted that the NDA was strictly about Miraval.

In July 2021, Angie filed legal paperwork, accusing her ex of blocking her from selling her share of the winery to a third party. In Sept. 2021, Brad fired back with paperwork of his own, accusing Angelina of trying to cut him out of the potential sale.

He claimed that her decision to try and sell her stake in the winery went against an alleged previous deal that the two had made. “[Brad insisted] that he and Jolie made a pact agreeing never to “sell their respective interests in Miraval without the other’s consent.” It was a promise Jolie would deny, claiming “no such agreement ever existed,”” according to Vanity Fair. A source close to Brad also deemed Angelina’s behavior as “vindictive” at the time.

In October 2021, Angelina officially sold her 50 percent stake in Chateau Miraval to a company controlled by Russian oligarch Yuri Shefler. Then, in Feb. 2022, Brad sued her for not seeking his permission first. In his legal paperwork, he asked for damages, and said that he wanted to undo the deal with Shefler because he was making it difficult for Brad to run the winery in the way he wanted.

By June 2022, Brad amended his filing and accused Angelina of attempting to “inflict harm” on him by secretly making the sale to Shefler. He claimed that Shefler had “malicious intentions” for the winery. “Jolie knew and intended that Shefler and his affiliates would try to control the business Pitt had built and to undermine Pitt’s investment in Miraval,” Brad’s court docs stated. “And just as Jolie envisioned, that is exactly what Shefler has done.” Brad also claimed that Angelina purposely sold the winery to an “adversarial party” because he was granted 50/50 custody of the kids in a separate lawsuit. The actor’s lawsuit noted that he did not find out about the sale of the winery until it was in the press, as well.

That July, a judge granted Angelina and her lawyers the rights to subpoena documents from Brad’s team amidst the ongoing battle over Miraval. Once the team had the documents they needed, Angelina and her holding company, Nouvel, filed their countersuit in Sept. 2022. In the documents, Angelina accused Brad of “acting in a hostile, destructive and illegal manner.” Nouvel accused Brad of freezing them out of discussions about Miraval and sought financial damages based on claims that he “wasted its assets” with his projects at the Chateau over the years.  “Sadly, this is yet another rehash and repackaging of old material to try and distract from [Angelina]’s own behavior,” a source close to Brad told HollywoodLife at the time.

Things really blew up in October 2022, though, when Angelina filed another cross complaint that featured bombshell allegations about her ex-husband. In the suit, Angie publicly came forward with her allegations about Brad being “violent” towards her and their children during the 2016 airplane incident, which preceded Angie’s divorce filing (remember, Brad was previously cleared by the Department of Children and Family Services).  Angie had never openly discussed her allegations before, but claimed that Brad “forced” her to do so when he attempted to “reassert control over [her] financial life” by asking her to undo the Miraval sale and re-join him as a business partner.

The lawsuit featured Angelina’s allegations of Brad’s abuse (which we hashed out in the ‘custody battle’ section of this article). A rep for Brad denied the story, and pointed out that Brad previously “accepted responsibility” for what he did do on the plane. “These new allegations are completely untrue, [though],” the rep insisted. Angelina also claimed that she and Brad never had an agreement not to sell the winery without each other’s permission.

Where Angelina & Brad Stand Today

Unfortunately, as of June 2023, things are still messy between Brad and Angelina. Brad filed a new complaint against Angelina in the Miraval battle on June 1. In the newest suit, Brad said that Angelina “intentionally” tried to damage him with the sale of Miraval to Shefler. He reiterated his claim that the two had an agreement about not selling the winery without each other’s consent before their split. Brad also continues to claim that Angelina only wanted to sell her share of the winery as retribution for him getting a win in their custody case.

Since splitting from Angelina, Brad has not been photographed publicly with any of his six children. He has opted to keep his relationship with the kids out of the public eye. However, Angelina is often seen with the kids, both out and about and on red carpets.

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