Brad Pitt just handed Angelina Jolie two back-to-back courtroom losses. The price tag on their 2024 divorce keeps climbing higher and higher.
The Battle Continues
The news comes as Pitt’s estrangement from his children appears to have deepened after his eldest son, Maddox, reportedly filed legal documents in May seeking to remove the actor’s last name. According to court filings, the 24-year-old cited “personal” reasons for changing his name from Maddox Chivan Jolie-Pitt to Maddox Chivan Jolie. The move comes after Maddox informally used the name “Maddox Jolie” in the credits for Angelina Jolie’s film “Couture.”
In April, Zahara signed the official name-change petition. And in May, when she graduated from Spelman Collegenn she was introduced aloud as “Zahara Marley Jolie.” In June, The legal name-change documents were processed and officially filed in court.
Shiloh legally dropped Pitt from her surname shortly after turning 18 in 2024. Pitt and Jolie, split in 2016 and finalized their divorce in 2024. Jolie maintained primary custody of the six children they share: Maddox (24), Pax (22), Zahara (21), Shiloh (20), and 17-year-old twins Knox and Vivienne.
Now it seems that the Jolie may have dug her own grave when it comes to courtroom battles, and its going to cost her.
In a single week in June 2026, his legal team secured rulings that forced a billionaire Russian expatriate and his top executives into sworn testimony. The move cracked open the hidden mechanics of a $64 million winery deal Jolie allegedly made behind his back. The prize: Château Miraval, a 1,200-acre Provençal estate valued at $164 million and the subject of nearly $500 million in combined legal claims.
According to People, on June 17, a California Superior Court granted Pitt’s motion to compel depositions from high-level executives at the Stoli Group — the spirits giant that purchased Jolie’s 50 percent stake in 2021. Among those now ordered to testify is executive Alexey Oliynik, who had argued for months that his Swiss residency put him beyond the court’s reach. He has been ordered to give testimony in London by late September.
Seven days later, the California Court of Appeals reversed a prior ruling that had allowed Stoli Group owner Yuri Shefler to walk away from the lawsuit entirely.
The appeals court determined that because the transaction involved a California resident and a California-governed agreement, he must face the legal proceedings.
Writing in its opinion, the appellate panel stated, “It defies credulity that Shefler, a sophisticated businessman, would risk almost $40 million on a transaction about which he knew nothing and with which he had no involvement.” A hearing to compel his deposition is set for early July.
These rulings go to the heart of the original dispute.
Back in 2022, Pitt alleged his ex-wife violated a mutual verbal agreement — that neither would sell their respective shares of the estate without the other’s consent. By compelling these depositions, his legal team is now closer to forcing a full trial and uncovering exactly how the secret sale was arranged.
“This win is another step towards transparency over what took place,” a source close to Pitt told People exclusively.
To understand what’s truly at stake, the financial backstory is essential.
The former couple purchased Château Miraval in 2008 for €25 million — roughly $28.4 million at the time. The initial split wasn’t equal. Operating through their respective corporate structures, Mondo Bongo and Nouvel, Jolie covered 40 percent of the purchase price while Pitt paid 60 percent.
He later transferred a 10 percent stake to her for a symbolic €1, making them equal 50/50 partners. Today, the estate and its luxury rosé business are valued at $164 million in court filings. The total legal war has ballooned to nearly $500 million in combined damages claims.
What happened in 2021 is the core of the case.
Without Pitt’s knowledge or consent — or so he alleges — Jolie sold her holding company, Nouvel, to Stoli subsidiary Tenute del Mondo for $64 million, Courthouse News reported. Of that, $25 million went directly to her at closing. Shefler personally guaranteed the remaining $39 million using his own funds.
That guarantee is now the legal thread being pulled hardest. It ties the billionaire directly to a California-governed transaction and squarely into the jurisdiction of a California court.
The $250 million countersuit cuts the other way. Her team accuses Pitt of treating the estate as his personal fiefdom, freezing her out of profits, and burning winery earnings on vanity projects — including over $1 million on a pool renovation and four separate rebuilds of a chateau staircase. She also alleges he deliberately stripped the value of her stake during failed buyout negotiations to force a cheaper payout. Jolie’s attorney told People the recent rulings have “no impact on the merits of the case.”
A source close to her was blunter. “The truth is that Pitt’s ego and obsession for control got in the way,” the insider said. “Brad refused to work with Stoli simply because Angie chose them, not him.”
Not every ruling has gone Pitt’s way. In May 2026, a Los Angeles Superior Court judge shut down his attempt to obtain Jolie’s private emails related to the winery sale, finding them legally protected.
According to USA Today, the Los Angeles County Superior Court’s official website states that the former couple is expected to go to trial in August 2027. Mediation is scheduled for October 2026.