Mama's Boy! Angelina Jolie & 'Golden Child' Son Maddox's Tight Bond Exposed
Apr. 25 2019, Updated 1:01 p.m. ET
Angelina Jolie has cultivated a closer bond with her oldest child, son Maddox, than any person in her life.
The Tomb Raider star adopted the Cambodian orphan in 2002, when she was still married to second husband Billy Bob Thornton, and they have been inseparable ever since.
Jolie went on to hook up with Brad Pitt when Maddox was still just a boy.
Jolie and Brad Pitt married in 2014 and ruled Hollywood's A List with Maddox and their five other kids, but have been going through a nasty divorce since 2016, after the actor and Maddox got involved in a fight on a private plane.
Since then, Maddox has been Jolie's man of the house.
While he's turned his back on his father Pitt, Maddox, 17, has helped his mom take care of the other kids and been her shoulder to lean on.
Maddox, who has looked at colleges with Jolie by his side, is now set to take over her movie empire, a source exclusively told RadarOnline.com
Amid Jolie's fragile health, she's decided to cut five of her six children out of her $116 million fortune, and leave everything to her eldest son, an insider told RadarOnline.com.
Scroll through RadarOnline.com's gallery for more on how Jolie and Maddox have shared years together.
Love At First Sight
In late 2001, Jolie visited Cambodia with her then-husband, Billy Bob Thornton. They met Maddox in an orphanage there and Jolie said she "cried and cried" due to their strong connection. The actress and Thornton applied to adopt him and in March 2002, Jolie picked up 7-month-old Maddox. However, her marriage to Thornton fell apart and she wound up adopting the boy on her own.
Adoption Struggle
The star's international adoption of Maddox wasn't easy. The boy's adoption process was reportedly initially halted when the U.S. government had stopped all adoptions from Cambodia over concern over child trafficking. But Jolie was cleared to adopt Maddox and she's said, "I prefer to stay on the right side of the law. I would never take a child away from a place where adoption is illegal."
Family Forshadowing
The world first saw that Jolie and Pitt, who had left his wife Jennifer Aniston, were a couple when they were spotted together with little Maddox on a beach in Kenya. The three looked like the perfect family.
New Dad
After Jolie and Pitt began dating, he applied to adopt both Maddox and her second adopted child, daughter Zahara. They went on to have biological daughter Shiloh and twins Knox and Vivienne and another adopted son Pax. Jolie and Pitt eventually married in 2014, but there were cracks in their relationship.
Father/Son Fight
Jolie suddenly filed for divorce in September 2016, shortly after an alleged altercation took place between Pitt and Maddox on a private plane returning from Europe. The FBI and child welfare authorities investigated and Pitt was cleared of any child abuse allegations. However, the incident had wrecked the famous marriage.
Bitter Battle
Jolie and Pitt's divorce has been nasty and Maddox has taken his mom's side, sources say.
Star Shunned
Maddox has refused to see Pitt during his divorce from Jolie, and the court ruled he didn't have to.
Single Mom
Maddox has reportedly gotten even closer to his mother after her split from Pitt.
Beloved Babysitter
Maddox has helped Angelina care for his siblings as they've all been devastated by their parents' divorce.
On To College
As RadarOnline.com readers know, Jolie recently went with Maddox to visit universities in Seoul, South Korea as he contemplates going to college. "The trip to Seoul with Maddox was totally orchestrated by Angelina," a source said.
Favorite Child?
While Jolie is close to all her children, she appears to have a special bond with her oldest.
Young Mogul
RadarOnline.com exclusively learned that Jolie plans to put Maddox in charge of her movie empire. Maddox was just 15 when he was credited as an executive producer on Jolie's movie, First They Killed My Father, and she's continuing to groom him a big mogul role.
Fragile Mom
Scary skinny Jolie is increasingly relying on Maddox amid health concerns, RadarOnline.com has reported. Besides undergoing successful cancer-related surgery in 2015, she's admitted to suffering from Bell's Palsy, which affects facial muscles. Friends also fear anorexia.
Screening Her Dates
A source told RadarOnline.com that Jolie is dating a mystery hunk and Maddox is all in favor of it.
Friendly Skies
Maddox followed in his mom's wings by flying! While Jolie got her pilot's license in 2005, in 2011, The Daily Mail reported that her then-10-year old son had already started taking flying lessons.
Kindred Spirits
Super chill Maddox is leery of the trappings of Hollywood and, like his mom, enjoys philanthropic causes, according to reports.
Galpal Hunt
Maddox recently hit the dating scene, and mom Jolie has given him her blessing.
Moving On?
Maddox might go to college and is gearing up to leave the family nest. Jolie will be devastated to lose her boy, sources say.
Shopping Pals!
Jolie was seen taking Maddox on a Beverly Hills shopping spree after Pitt attended Jennifer Aniston's 50th birthday party.
Mama’s Boy
The movie star and Maddox's closeness has culminated in Jolie deciding to give Maddox her whopping $116 million fortune, a source told RadarOnline.com. "He's her golden boy."