Brad Pitt, Angelina Jolie to Olivia Wilde, Jason Sudeikis: A look at Hollywood’s messiest splits

Hollywood has seen their fair share of messy splits.

Earlier this week, reality star Erika Jayne won a $5 million fraud lawsuit after two former colleagues of her estranged husband, Tom Girardi, accused her of “aiding and abetting” her former husband. Meanwhile, Olivia Wilde recently opened up for the first time about being served custody papers from her ex-fiancé, Jason Sudeikis, while onstage at CinemaCon in April. 

Plus in uncovered FBI documents earlier this month, Angelina Jolie said her ex-husband Brad Pitt was “becoming a monster” when he allegedly flew into a drunken rage during a 2016 fight on a plane that left their children scared.

Fox News Digital spoke to lawyer Steve Baric, who has been involved with high-end divorce cases, and he explained that splits are a “highly emotional” time in a person’s life where “good people do terrible things.”

However, he noted that “when you add the celebrity status – it adds to the craziness.”

Here’s a look at some of Hollywood’s recent messiest break-ups.

Erika Jayne, Tom Girardi

“Real Housewives of Beverly Hills” star Erika Jayne filed for divorce from the disgraced lawyer, Tom Girardi, in November 2020 after 21 years of marriage. The couple has since been sued by two of his estranged colleagues for fraud. 

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In court this week, Jayne, 51, won the $5 million fraud suit filed against her and took to Instagram to celebrate. “Thank you to my friends that have stood beside me. All I asked for was time and understanding,” she wrote.

The reality star also shared on Wednesday a screenshot of a Los Angeles Time article where Girardi, 81, was accused of buying his mistress a beachfront condo and a wire transfer from his law firm of $300,000.

“Wow. I knew about jewelry, shopping sprees, and plastic surgery but this really threw me for a loop,” she wrote.

Jayne and Girardi’s divorce has not been finalized. 

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Olivia Wilde, Jason Sudeikis 

Olivia Wilde was served custody papers from her ex-fiancé, Jason Sudeikis, while onstage at CinemaCon in April. 

The notorious incident occurred when the 38-year-old director and actress was introducing her upcoming psychological drama, “Don’t Worry Darling,” in front of an audience at the largest annual gathering for movie theater owners.

“It was my workplace,” Wilde told Variety, speaking out for the first time on the headline-making moment. “In any other workplace, it would be seen as an attack.”

At the time of the incident, a representative for Sudeikis asserted that he “had no prior knowledge” of how Wilde would be served the papers pertaining to custody arrangements for their son, Otis, 8, and daughter Daisy, 5.

“Papers were drawn up to establish jurisdiction relating to the children of Ms. Wilde and Mr. Sudeikis,” the 46-year-old actor’s spokesperson told Fox News Digital. 

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“Mr. Sudeikis had no prior knowledge of the time or place that the envelope would have been delivered as this would solely be up to the process service company involved and he would never condone her being served in such an inappropriate manner.”

After a seven-year engagement, the pair announced that they had separated in November 2020. The “Ted Lasso” star and the “The Lazarus Effect” actress have been engaged in a bitter custody battle over the past few months.

Wilde scored her first court win earlier this month when a judge ruled that their children’s home state was California, where she resides. Sudeikis had filed a petition against Wilde since he wanted to establish New York as the children’s home state.

Baric shared with Fox News Digital that ego and public perception get in the way when celebrities split. “I always advise clients to maintain a consistent public presence and to maintain a professional calm outlook and if there are children always put their interests first,” he said. 

“A great example of this is Jennifer Garner. She has come through that divorce with her reputation in tact.” Jennifer Garner was previously married to Ben Affleck from 2005 to 2018.

Wilde is currently dating “Don’t Worry Darling” star Harry Styles. The two went public with their romance in January 2021.

Angelina Jolie, Brad Pitt

Angelina Jolie filed for divorce from Brad Pitt in 2016 after just two years of marriage. During the filing, Jolie asked for physical custody of their kids — Maddox, 21, Pax, 18, Zahara, 17, Shiloh, 16 and 14-year-old twins Knox and Vivienne.

According to explosive FBI documents recently obtained by People magazine, Jolie told authorities that Pitt “ranted” on a 2016 private flight from France to Los Angeles in front of their six children and “mimicked the behavior of a monster,” screaming at them.

The kids were “shell-shocked” during the Sept. 14 blowup, said Jolie, who added that she was “frozen, scared and didn’t know what to do” in the moment, according to the documents. 

Pitt allegedly pounded the jet’s ceiling, shook her and shoved her into a wall. She said she felt “like a hostage.”

When it looked “like he was going to attack” one of their children, who had called him a “prick,” she admitted that she put her arm around his neck and squeezed. 

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The “Girl, Interrupted” star told officials that Pitt poured beer on her, spilled wine on the floor and caused approximately $25,000 in damage to the jet. Both parties reported injuries. Days later Jolie filed for divorce in 2016.

In November of the same year, Pitt responded to Jolie’s divorce petition and requested both joint and physical custody of their children. Since then, the couple have been battling it out in court.

In 2017, Pitt opened up about his split from Jolie in an interview with GQ.

“I was really on my back and chained to a system when Child Services was called,” he told the outlet. “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.”

Following Pitt’s tell-all interview, Jolie spoke with Vanity Fair in 2017 to get her side of the story out. “[Our lifestyle] was not in any way a negative,” Jolie said. “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.”

She answered “no” when Vanity Fair asked her if she was surprised Pitt spoke out in the GQ interview.

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In April 2019, a court ruled that both Jolie and Pitt were legally single despite their divorce not being finalized. In May 2021, Pitt was granted joint custody with Jolie.

Tensions flared-up again in February when the actor sued Jolie for selling Chateau Miraval Winery, which he is a part owner of. Their legal battles are still ongoing.

According to Baric, “Things get out of hand for two reasons. First ego…. One spouse still has feelings and when the other person starts dating or seen in public with another partner. Things get out of hand,” he shared. “Second with celebrities there is public perception for career reasons no one wants to be perceived as the bad spouse or parent.”

Kristin Cavallari, Jay Cutler

Kristin Cavallari and Jay Cutler got engaged in 2011, only to briefly separate, reunite, have their first child and get married all within two years. Since their split in 2020, Cavallari has openly discussed her marriage and even called it “toxic.”

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“I called off the engagement the same reason I got a divorce… If there’s any takeaway from that: You can’t ignore red flags. People don’t change. And, you gotta trust your gut,” she said on an episode of “Call Her Daddy” in early August.

On the podcast, Cavallari revealed, “Because I have three kids with him, I’m very careful about what I say… My oldest googles us now.”

Cavallari had one thing to say, though. “It was toxic. I think period, end of story.”

Cutler responded to Cavallari’s allegations of a “toxic” marriage on his own podcast appearance on “Sofia With an F.”

“If she wants to say stuff, she can say stuff,” Cutler said during the podcast. “I’m not going to go down that road about her. I mean, she’s still the mother of my kids.”

He accepts Cavallari has feelings about their relationship and why it ended. He’s just confused why she is speaking about it so long after it all played out.

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“It’s been two and a half years. Why are we having these conversations in public? Why are we doing this?” Cutler, who shares three children with Cavallari, asked. “Now we have to have this conversation now. It’s like, come on. We’re done here.”

Cavallari filed for divorce from her husband of seven years in April 2020. The couple share three children: Camden, 9, Jaxon, 8 and Saylor, 6. 

Fox News’ Ashley Hume and Rebecca Rosenberg contributed to this report.