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November 18, 202514 min read

Brangelina: The Fairytale Romance That Became Hollywood's Messiest Divorce

From the controversial Mr. & Mrs. Smith romance to the 2016 plane incident and $67 million winery war—the complete story of Hollywood's most explosive relationship and breakup.

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On December 30, 2024, after eight years of legal warfare, Brad Pitt and Angelina Jolie finally signed their divorce settlement.

Eight years. Tens of millions in legal fees. Six children caught in the crossfire. A $67 million winery lawsuit still raging. Children dropping their father's surname. Allegations of abuse, control, and bitter custody battles.

The couple that once represented Hollywood's ideal—beautiful, humanitarian, raising six kids across the globe—became a cautionary tale about how spectacular love can become spectacular hatred.

This is the complete story of Brangelina: from controversial beginning to bitter end.

The Mr. & Mrs. Smith Romance: When Sparks Flew (2004-2005)

The Meeting (2003-2004)

Filming began in 2003 for Mr. & Mrs. Smith, an action-comedy about married assassins who discover they've been hired to kill each other.

Brad Pitt: Married to Jennifer Aniston since July 2000 (married 5 years, together 7)

Angelina Jolie: Recently divorced from Billy Bob Thornton (filed July 2002)

Brad later admitted to Rolling Stone (December 2008): "I fell in love with Jolie on the Mr. & Mrs. Smith set."

Both initially denied an affair, but the chemistry was undeniable on screen.

The Aniston Divorce Announcement (January 7, 2005)

Brad and Jennifer released a joint statement:

"After seven years together we have decided to formally separate. For those who follow these sorts of things, we would like to explain that our separation is not the result of any of the speculation reported by the tabloid media."

March 2005: Jennifer files for divorce citing "irreconcilable differences" October 2005: Divorce finalized

The Kenya Photos (April 29, 2005)

Photographers captured Pitt vacationing with Jolie and her son Maddox at Diani Beach, Kenya.

Later revealed: Jolie provided the photographer with resort details and timing.

The photos were released while Mr. & Mrs. Smith was in post-production.

Film premiere: June 10, 2005 Box office: Success fueled by real-life romance speculation

The "Domestic Bliss" W Magazine Photoshoot (July 2005)

The most controversial moment: A 60-page spread shot in March 2005—the same month Aniston filed for divorce.

The concept: Brad and Angelina playing married suburban life, shot in Palm Springs by photographer Steven Klein.

The problem: The relationship was still unconfirmed publicly when the spread published. Pitt had conceptualized the shoot himself and retained international rights, profiting from it.

Jennifer Aniston's response (Vanity Fair): "There's a sensitivity chip that's missing."

Public Reaction: Team Aniston vs. Team Angelina

The media frenzy divided public opinion:

  • Jolie painted as "homewrecker"
  • Aniston portrayed as victim of Hollywood's most public betrayal
  • Timeline questions: Did affair happen during filming? (They maintained it didn't)

The coverage became a morality play about infidelity, motherhood, and fame.

Building the Brangelina Empire (2005-2012)

Going Public (2005-2006)

January 2006: Jolie confirms pregnancy with their first biological child

December 2006: First red carpet appearance together at The Good Shepherd premiere

They officially became "Brangelina"—Hollywood's most powerful couple.

Creating Their Global Family

Adopted Children:

  • Maddox Chivan (born August 5, 2001): Adopted by Jolie from Cambodia in 2002 at 7 months; Brad formally adopted ~2005-2006
  • Zahara Marley (born January 8, 2005): Adopted from Ethiopia July 6, 2005 at 6 months; Brad adopted in 2006
  • Pax Thien (born November 29, 2003): Adopted from Vietnam March 15, 2007 at 3 years; Brad adopted February 21, 2008

Biological Children:

  • Shiloh Nouvel (born May 27, 2006): Born in Swakopmund, Namibia
  • Knox Léon and Vivienne Marcheline (twins, born July 12, 2008): Born in Nice, France

Six children: Three adopted, three biological

Humanitarian Power Couple

  • Angelina continued work as UNHCR Goodwill Ambassador (since 2001)
  • September 2006: Established the Jolie-Pitt Foundation
  • Early 2007: Donated $1 million to UNHCR and agencies for Darfur crisis
  • April 2010: Surprise visit to Bosnia to meet civil war refugees
  • December 2010: Created Shiloh Jolie-Pitt Foundation for Naankuse Wildlife Sanctuary

Brad occasionally accompanied Jolie on humanitarian missions. Their combined philanthropy elevated them beyond celebrity status.

Château Miraval Purchase (2008)

Purchased 1,200-acre estate in Correns, France for reportedly $60 million.

They developed an award-winning rosé wine business.

The estate became their family retreat and later, their wedding venue.

It would eventually become the center of a bitter $67 million legal battle.

Financial Empire

Combined earnings 2004-2016: $555 million (Forbes)

  • Brad earned $315 million
  • Angelina earned $235 million

Combined net worth: Estimated $400 million during relationship

2016:

  • Brad: #94 on Forbes highest-paid celebrities ($31.5M)
  • Angelina: Forbes highest-paid actresses list ($15M)

They commanded $20 million+ per film each at peak.

The 12 Years Together (2005-2016)

Family Life

  • Raised six children across Los Angeles mansion and Château Miraval
  • Relatively private despite massive media attention
  • Children traveled with parents on film sets and humanitarian missions
  • Homeschooled for flexibility and privacy

The Wedding at Château Miraval (August 23, 2014)

After 9 years together, they married in a secret ceremony at their French estate.

Details:

  • 20 close friends and family attended
  • Non-denominational civil ceremony in small chapel
  • Officiated by Judge John Ouderkirk (who later presided over custody battle)
  • Children deeply involved in planning:
    • Maddox and Pax walked Angelina down the aisle
    • Zahara and Vivienne threw petals
    • Shiloh and Knox served as ring bearers
  • Handwritten vows, emotional throughout
  • Reception: local foods, Miraval rosé, three cakes chosen by children

By the Sea – The Final Collaboration (2015)

Written and directed by Angelina Jolie. Shot August 2014 during their honeymoon in Malta.

The premise: A 1960s France setting about a troubled marriage.

Jolie later revealed it was an attempt to save their relationship:

"I wanted us to do some serious work together... I thought it would be a good way for us to communicate. In some ways it was, and in some ways we learned some things. Whatever it was maybe it didn't solve certain things, but we did communicate something that needed to be communicated."

Box office: $3.3 million on $10 million budget (major flop)

Reviews: Mixed

Irony: A film about a failing marriage released one year before their actual marriage collapsed.

The 2016 Plane Incident: When It All Fell Apart

September 14, 2016: The Private Jet Altercation

The family was returning from a two-week trip in France. Their private jet departed France, stopped in Minnesota, and landed in Los Angeles.

An altercation occurred approximately 90 minutes into the flight.

FBI Investigation Details (Revealed in 2022 Documents)

In 2022, FBI documents obtained through FOIA revealed Jolie's account:

Jolie's allegations to FBI:

  • Pitt allegedly "grabbed her by her head," shook her, "pushed her into the bathroom wall"
  • Repeatedly punched the ceiling of the plane during an outburst
  • When one child allegedly called Pitt a "prick," he "bolted at the minor like he was going to attack"
  • Jolie got Pitt in a chokehold; he tried to break free by throwing himself back, pushing her into chairs
  • Pitt allegedly "poured beer on Jolie and the blanket she was under"
  • Jolie suffered injuries to back and elbow (photo shared with FBI)
  • Plane sustained $25,000 damage from spilled red wine

Investigation Outcome

November 22, 2016: FBI case agent reported charges would not be pursued "due to several factors"

November 2016: Both FBI and LA County Department of Children and Family Services closed investigations

No arrest or criminal charges filed against Pitt.

September 19, 2016: Jolie Files for Divorce

Just five days after the plane incident, Jolie filed for divorce.

Reasons cited: "Irreconcilable differences"

Requests:

  • Physical custody of children with visitation rights for Pitt
  • Court terminate spousal support to both parties

Brad's Statement

"I am very saddened by this, but what matters most now is the wellbeing of our kids. I kindly ask the press to give them the space they deserve during this challenging time."

He later denied all allegations of abuse.

Media Firestorm

Initially, the plane incident details were sealed. Speculation ran rampant.

The FBI documents weren't revealed until 2022—six years later—after Jolie filed a FOIA request.

The Messy Custody Battle (2016-2021)

Initial Arrangements (2016-2017)

Temporary agreement:

  • Jolie had physical custody
  • Pitt granted therapeutic visitation rights
  • All six children initially part of custody considerations
  • Maddox aged out (turned 18 in 2019)

Judge John Ouderkirk Appointed

The same judge who married them in 2014 was appointed as a private judge by both parties.

He would become the center of controversy.

The Custody Trial (2020-2021)

Jolie believed the judge "denied her a fair trial."

Her claims:

  • Judge "improperly excluded her evidence relevant to the children's health, safety, and welfare"
  • Evidence "critical to making her case" was excluded
  • Judge "failed to adequately consider" California code section on domestic violence

May 2021: Pitt Wins Joint Custody

Judge Ouderkirk temporarily awarded Pitt joint custody (excluding Maddox, no longer a minor).

Applied to five remaining children. Major victory for Pitt.

Jolie's Appeal and Judge Disqualification (July 2021)

Jolie's legal team appealed.

California appeals court ruled in Jolie's favor:

  • Judge Ouderkirk disqualified for failing to disclose conflicts of interest
  • He had "multiple professional, business and financial relationships, ongoing during the course of the matter, with Pitt's counsel and their law firms"

Result: All of Ouderkirk's decisions vacated. Custody battle essentially reset.

Current Custody Arrangement

Details of final arrangement not publicly disclosed.

Settlement signed: December 30, 2024

Only minors remaining: Knox and Vivienne (16 at time of settlement)

Jolie's attorney: "Frankly, Angelina is exhausted, but she is relieved this one part is over."

The Château Miraval Winery War (2021-2025)

The Winery's Success

Award-winning rosé production Value: Reportedly $164 million Initial ownership: 50/50 split Development: Both parties invested

Became one of Provence's premier estates.

Jolie's Sale to Stoli (2021)

Jolie sold her 50% stake to Tenute del Mondo (Stoli Group wine division)—a company owned by Russian vodka magnate Yuri Shefler.

Pitt's claim: She violated an understanding that neither would sell without the other's approval.

Jolie's claim: No binding agreement existed.

Pitt's $67 Million Lawsuit (Filed 2022)

Initially sought $35 million, later increased to $67 million.

Claims:

  • Jolie sold to spite him and harm the business
  • She owed him right of first refusal
  • Stoli purchase meant to take control and damage brand

Jolie's Counterarguments (2024)

Jolie's claims:

  • Pitt demanded "expansive" NDA covering his alleged abuse
  • She couldn't sell to him because of NDA requirement
  • Pitt is "stripping Château Miraval of its assets"
  • He spent millions on a swimming pool "that only he uses"

November 25, 2024: Judge ruled Pitt must disclose documents.

Jolie's lawyer alleges documents will "prove communications concerning abuse, lies to authorities, and years of cover up."

November 8, 2024: LA Superior Court Judge Lia Martin dismissed three of Jolie's motions to dismiss—clear win for Pitt.

December 17, 2025: Hearing scheduled on discovery dispute—judge to rule if Jolie must release remaining documents.

February 2027: Full trial scheduled over Miraval and $35M damages claim.

What's at stake:

  • $164 million winery empire
  • Award-winning brand reputation
  • Years of shared investment
  • Ongoing business operations during litigation
  • Children's inheritance potentially affected

The Children's Estrangement (2024-Present)

Dropping the "Pitt" Surname (2024)

Shiloh (18):

  • Filed on 18th birthday (May 27, 2024) to become "Shiloh Jolie"
  • Legally approved August 2024
  • Hired and paid for own lawyer
  • Described as response to "painful events"
  • Pitt reportedly "aware and upset"

Zahara (19):

  • Introduced herself as "Zahara Marley Jolie" at Spelman College sorority

Vivienne (16):

  • Credited as "Vivienne Jolie" in The Outsiders Broadway playbill (producer's assistant)

Pax's Scathing Father's Day Post (2020)

From Pax's private Instagram (age 16), posted over photo of Pitt at 2020 Oscars:

"You have no consideration or empathy toward your four youngest children who tremble in fear when in your presence. You have made the lives of those closest to me a constant hell. Happy Father's Day, you f**ing awful human being!"*

Called Brad "world class a**hole."

Current Status

"Permanent estrangement" from Maddox (23) and Pax (21)

Sources: Pitt "devastated" but realizes "bond can never be repaired"

Relationship with youngest children: Reportedly "desperate" to reconnect with Knox and Vivienne before 17th birthday. "Virtually no contact" according to sources.

Brad's grief: "The reminders that he's lost his children is of course not easy for Brad. He loves his children and misses them."

Brad's New Life (2024-2025)

Dating: Jewelry designer Ines de Ramon (32) since late 2022 Relationship status: "Going really strong"—moved in together Sources: Pitt doesn't want to remarry after "tumultuous divorce"

Net worth: Approximately $400 million Career: Continues acting and producing; won Oscar for Once Upon a Time in Hollywood (2020)

Relationship with Ines and the children:

  • Reports: Jolie won't allow de Ramon to meet children
  • Sources claim Jolie "still exerts control over Brad"

Angelina's Current Life (2024-2025)

Focus: Raising children Net worth: Approximately $120 million Career: Continues acting and directing

  • 2024: Appeared in Maria (Pablo Larraín biopic)

Priorities: Children remain first, humanitarian work continues

The Legacy of Hollywood's Biggest Breakup

From Fairytale to Cautionary Tale

  • 12 years together (2005-2016) + 2 years married
  • Started as controversial affair, ended in acrimonious divorce
  • Represented idealized modern blended family
  • Reality proved far more complicated

The Cost

  • 8-year legal battle over custody
  • Ongoing $67 million winery lawsuit
  • Children estranged from father
  • Careers impacted by personal turmoil
  • Privacy shattered by legal disclosures

What Made This Different

  • Not just celebrity divorce—involved child welfare allegations
  • FBI investigation unprecedented for celebrity couple
  • Children's voices and choices (dropping surname) made public
  • Legal battles continue years after separation
  • Multiple layers: custody, property, business interests

The Children as Victims

Six children caught in crossfire:

  • Forced to choose sides
  • Private pain made public
  • Long-term psychological impact unknown
  • Estrangement from father ongoing

Cultural Impact

  • Defined modern celebrity romance and its dissolution
  • Showed reality behind Hollywood glamour
  • Raised questions about privacy, power, parenting
  • Media coverage evolved from gossip to serious abuse allegations
  • Demonstrated no wealth or fame prevents family dysfunction

The Unfinished Story

Divorce finalized: December 30, 2024 Miraval war continues: Trial set for February 2027 Reconciliation with children: Seems unlikely Both moving forward separately: Building new lives

Brangelina's legacy: Epic rise, bitter fall, lasting impact on how we view celebrity relationships.

The Lesson

The Brangelina story teaches:

  1. Controversial beginnings cast long shadows: The way it started (affair, Aniston heartbreak) foreshadowed how it ended

  2. Public image ≠ private reality: The humanitarian power couple facade masked deep dysfunction

  3. Fame amplifies family pain: Their children's suffering became global entertainment

  4. Money can't fix broken relationships: $400 million combined couldn't save their marriage

  5. Children pay the price: Six kids caught in an 8-year war, estranged from their father

  6. Legal warfare destroys families: What should've been settled in months took 8 years

From the controversial Mr. & Mrs. Smith romance to the 2016 plane incident to children dropping their father's name—Brangelina went from Hollywood's golden couple to one of its most bitter divorces.

The fairytale became a nightmare. The love story became a cautionary tale.

And the six children, who once represented their blended family ideal, became collateral damage in one of the messiest celebrity divorces in history.

The divorce is finalized. The winery war rages on. The children have chosen their mother. And Brad and Angelina, who once loved each other enough to build a global family, can barely stand to be in the same room.

This is Brangelina: from the highest highs to the lowest lows—a story of love, betrayal, and the devastating cost of fame.