The Incredible Transformation Of Shiloh Jolie-Pitt No One Expected


Jolie to Jolie-Pitt

It might seem that celebrities have an easier time adopting children, but really their only advantage is having more funds available. Jolie and Pitt still had to physically travel to Ethiopia when they became Zahara’s caretakers. At the time, the children were only in Jolie’s custody, but Brad would soon change that. By 2006, Brad was also named as guardian to the children, and Angelina had their last names changed to Jolie-Pitt, signaling that they were one united family.

Brangelina Bunch

In 2002, Angeline Jolie soothed herself after her divorce from Billy Bob Thornton by adopting her first child, Maddox, who was a six month old orphan born in Cambodia. Angelina then adopted Zahara, an orphaned baby from Ethiopia in 2005, but nothing could compare to news that Brangelina were expecting.


The hype surrounding Brad and Angelina’s relationship never quite seemed to die down, no matter how long they were together. As the media formed a constant presence around their home, Angelina made the drastic decision to give birth in Namibia, away from the cameras of the paparazzi. The public was ravenous for a glimpse of their offspring, speculating whose good looks she would ultimately inherit, but it was important to the couple that they kept her away from the spotlight for as long as possible.

Expanding The Brood

Many families are content to stop with three children, but not Brad and Angelina. Both knew they wanted a large family, and were happy to continue adopting children in need of parents. A year after Shiloh was born, the couple adopted three year old Pax from Vietnam. It warmed Angelina’s heart to have such a diverse family, and it never made a difference to the parents if the children were theirs biologically, they loved them all the same.

Media Madness

If Brad and Angelina thought the public would soon shift their attention to someone else, they were mistaken. Shiloh Jolie-Pitt earned herself such a following, even as an infant, that a likeness of her was created out of wax for Madame Tussauds. Janine DiGioacchino, who managed the wax museum, said, “Even though she’s just a few months old, Shiloh is already an iconic figure in world of popular culture.” It’s clear that American priorities were out of order as they obsessed over an infant.

The Big Announcement

The Brangelina romance may have already seemed like it was sufficient tabloid fodder in and of itself, but the couple could hardly have prepared for just how crazy the public would go when they announced Angelina’s first pregnancy. Actors often understand that their line of work is inherently public, however, they recognize that it’s unfair for their children to be thrust into the spotlight just because they have famous parents. For all their efforts to keep their relationship between them, it was a hard balance to strike.

Back To The Beginning

The romance between Brad and Angelina didn’t begin under the most auspicious circumstances. The two became acquainted with one another while co-starring in Mr. & Mrs. Smith, however, at the time, Brad was married to Jennifer Aniston. As Pitt realized he was developing feelings for Jolie, he filed to divorce Aniston, an action which fans considered traitorous. Jolie claimed nothing happened before the divorce, saying, “To be intimate with a married man, when my own father cheated on my mother, is not something I could forgive.”

Brangelina Baby

Fans went crazy when they heard the happy news that Angelina and Brad were having a child of their own. Bringing children into the world is a serious commitment, one that can’t be broken by divorce or a break up. In an attempt to keep such an intimate moment private, the couple flew to the country of Namibia, and only verified that their baby girl was born on May 27, 2006. The pair kept their baby well hidden, inflating the price magazines were willing to pay for a photo.

Family Protection

In order to keep the photographers at bay, Brad and Angelina employed officials from the Namibian government in order to ensure their security, which even included closing down the entire hospital wing in which Angelina and the baby were located. Only those with a written waiver from Brangelina could enter, and an entire security staging area was erected around their accommodations. Even so, one photo got himself arrested for trying to sneak into the hotel without security clearance.

The Big Reveal

Brad and Angelina extended their stay in Namibia in order to let the American media relax before returning home with the infant Shiloh. Fans began to worry that the couple would keep the baby’s face hidden forever, though others expected them to have made a deal with a specific outlet. It was eventually discovered that the Jolie-Pitt family struck a deal with Getty images, who then sold them for a hefty price. For their part, the couple donated the payout.

The More The Merrier

The couple lingered in Namibia with the new baby, but when they finally brought Shiloh home, they soon became aware that there had been a shift in the family. Angelina felt that bringing another adopted child into the mix would fill a void in the house. Because the couple hadn’t yet married, Angelina had to adopt Vietnamese born Pax on her own, since Vietnam wouldn’t allow Brad to co-sign before tying the knot. Regardless, Pax was his too.

The Jolie-Pitts

Once Pax was back in the United States, Brangelina changed his legal guardianships to include Brad. The family wasn’t done growing, however, and they added another boy to the brood in 2008. The young family was amused that even with six people in the family, no one really looked similar to another, except Shiloh. Angelina would laugh, “Shiloh looks like Brad. It’s funny because she’s almost going to be the outcast in the family because she’s blonde and blue-eyed.”

Changing Looks

Once Shiloh’s face had made its public debut, the media couldn’t stop trying to snap pictures of her with her parents. Even as a toddler, people had to comment on just how much she had hit the genetic lottery, assuming that she would be just as attractive as her parents. Jolie always said that Shiloh resembled Brad more than her, though their likenesses weren’t dissimilar to when Jolie was a child. It’s important to remember that looks frequently change with age.

Six Strong

Four children still weren’t enough for the Jolie-Pitt family, nor for the fans who loved keeping track of their family updates. When Angelina made a public announcement about her second pregnancy, the frenzied chatter was renewed, especially when she divulged that there would be two new additions to the family. She gave birth to twins, Knox Léon and Vivienne Marcheline on July 12, 2008. After the experience of the high demand for Shiloh’s photos, the Jolie-Pitt’s cashed out to the tune of $14 million for their first photos.

Brad Or Shiloh?

The couple managed to successfully keep their kids away from cameras, which only meant that attention was still often focused on Shiloh. With her sunny locks and deep blue eyes, Shiloh looked more like her father every day. Even the shape of her face was similar, and when compared to photos of him in his youth, it could be difficult to tell who was who. Shiloh took after Brad in every way, even choosing to dress more like him than like her mother.

Suited Shiloh

Shiloh didn’t often accompany her parents to public events, but when she would walk down the red carpet with them, she was dressed in a suit like her dad’s. Her sisters, on the other hand, would follow their mother’s footsteps, getting dolled up in pint sized dresses. Even Shiloh took cues from Brad when it came to how she wanted to style her hair. Unsurprisingly, tongues started wagging about her more masculine appearance, even at such a young age.

Raised Eyebrows

Tabloids knew they’d make bank printing headlines about Shiloh’s looks, especially when they could link it to Angelina’s abilities as a parent. One Life & Style headline, released in 2010, read, “Why Is Angelina Turning Shiloh Into A Boy?” The magazine chose to quote statements from Focus on Family, who warned that unchecked androgyny in children could do more damage in the future. For Shiloh’s sake, the public began to push back at the insinuations that a child shouldn’t dress as they’d like.

Defending The Defenseless

The National Center for Transgender Equality in particular took issue with the misinformation being spouted by the Focus on Family organization. Their response stated, “Our society needs healthy, well-rounded children whose interests and tastes are as diverse as the children themselves and are not limited by outdated stereotypes of gender.” Angelina would not be cowed into taking the least controversial opinion, and her Vanity Fair interview defending her daughter just increased the scrutiny that young Shiloh was facing.

Blurred Lines

Angelina confessed in the 2010 interview, “[Shiloh] likes to dress like a boy.” The actress continued, “She wants to be a boy. So we had to cut her hair. She likes to wear boys’ everything. She thinks she’s one of the brothers.” Speculation that Shiloh could be transgender continued to increase following the statement. Armchair commentators seemed to forget, however, that Shiloh was still so young that it was possible she was just a tomboy, a phase she still could outgrow.

Support For Shiloh


When the issue hit the stand, other celebrities were quick to offer their support, as were those with powerful voices in the LGBTQ community. Chaz Bono, Cher’s son who is also transgender said, “I would love to talk to them at some point, [And] at least let them know we have this resource for them if they ever need it. For a child who had grown up in the spotlight, under the watchful eye of the media, it can be too much to handle.”

Unconfirmed Reports

Whispers about Shiloh’s identity were unrelenting, especially when other celebrities began publicizing her appearance of their own accord. Amber Rose, a model who has been embroiled in more than one controversy, shared a photo of Shiloh at one red carpet, writing, “How gorgeous is John Jolie Pitt?! Born into the perfect family for him. #TransKids #LoveUrKidsNoMatterWhat#Support.” Amber caught flack for the post, with critics railing against her for offering an opinion on a situation that she wasn’t personally involved in.

Standing Out

Some began to wonder if perhaps Shiloh’s fashion choices were the result of a need for extra attention. Even Jolie admitted, “I felt so much more for Madd, Zahara and Pax because they were survivors. Shiloh seemed so privileged from the moment she was born. But I’m conscious that I have to make sure I don’t ignore her needs, just because I think the others are more vulnerable.” This is not to say that Angelina was neglectful of Shiloh, but that she needed to distinguish herself somehow.


While some were quick to say Shiloh was suffering from gender dysphoria, others fired back that her more masculine fashion choices were just a way of demanding attention from her busy parents. Complicating matters even further than routine sibling rivalry was the unexpected announcement that Brad and Angelina had decided to separate. The revelation came to light in 2016, and it couldn’t have been easy for any of their children to manage. The trauma of a family splitting apart can do lasting damage to a child’s well being.

Brad vs. Maddox

The world was watching the family more closely than ever and were dismayed to hear that the family was undergoing strain in all arenas. Most worrying were the reports that Brad and Maddox, who was then 15, had gotten into an argument that allegedly became physical. Supposedly, Brad “attacked” his son, who was trying to protect Angelina while the couple was fighting. Brad vehemently denied the allegations, a claim which was supported by several sources who knew him personally.


As with any other major event in the life and times of Brangelina, their break up would be just as public as their celebrations were. Talk proliferated that Brad often turned to alcohol and other substances, resulting in some less than acceptable behavior. Others whispered that Brad had cheated on Angelina with Marion Cotillard, the French actress who starred in Allied alongside him. Right or wrong, fans wanted answers with regards to what had caused such a toxic situation to arise.


The downward spiral continued, even as the photographs of Brad moving out were published across a variety of publications. To make matters worse, someone caught wind of a joint investigation being conducted by the FBI and LA Department of Child and Family Services about Brad’s conduct towards his children. Fans could hardly believe what they were hearing about the highly regarded actor, despite realizing that a discrepancy between his public and private lives was expected. In the end, the investigation cleared all possible charges against Pitt.

Taking Its Toll

Any significant change like a divorce can be extremely difficult for children to bear as they see their entire worlds upended, but it seemed that out of all of their children, the split proved to affect Shiloh the most. A friend of the family’s said to Radar Online, “Shiloh’s not the same bubbly kid she was before Brad and Angie split, she doesn’t understand why Brad can’t be there on their family trips to Disneyland.” It was the last thing an 11 year old needed. 

Taking Sides

Angelina filed to take sole custody of the six children, a decision in which the children had no say, given their young ages. The update was particularly hard on Shiloh, who had always been especially close to Pitt. Taking any child away from a parent can be a traumatic experience. Shiloh in particular had relied on Brad’s presence. As a minor, Shiloh’s wishes don’t hold much weight, so for the time being, she is stuck being under Angelina’s sole care.

Protecting The Kids

Angelina hasn’t been afraid to get candid about the separation in recent interviews. In 2017, she said, “[I] think it’s very important to cry in the shower and not in front of the children. They need to know that everything’s going to be all right even when you’re not sure it is.” Jolie recognizes that this is not just a rough time for her children, however, she’s committed to making the transition as smooth as possible, even if it means swallowing her own sadness for their sake.

Staying Strong

While the early reports that Angelina had taken sole custody of the children seemed at first to mean keep Pitt away from Shiloh, it turns out that both parents will still be key figures in the children’s lives. So long as Brad takes adequate care of his progeny, there’s no reason that Shiloh can’t still be daddy’s little girl. Moreover, both parents have continued to support Shiloh following in her father’s footsteps, as she resembles him more with each passing day.

Fraying Nerves

If Brad and Angelina had once thought there was a chance they’d easily manage to divide up their lives, they would be sorely mistaken. While there are plenty of couples willing to get contentious about material possessions, bringing children into the mix often complicates things further. Shiloh would discover this first hand as her mother’s efforts to gain full-time custody of the children became ever more extreme. Despite agreeing to keep things in the family, Angelina would soon take her battle public.

Pulling The Rug

As 2018 wore on, it became clear that Brad and Angelina still hadn’t come to an agreement with regards to their kids. Angelina’s behavior became increasingly more aggressive in her attempts to keep Brad away from them, whether it was in their best interests or not. Though her legal team brought out new allegations that Brad wasn’t pulling his weight, he fired back with all of the money he’d spent on them, pleading that he just wanted to see his children. Shiloh was taking it harshly.

London Hideaway

When Angelina began filming for a new role in Maleficent 2, it seemed that the situation was coming to a head. Her work would be taking place in London, while Brad was busy filming a movie of his own in Los Angeles. Without considering Brad, Angelina decided to pull the kids even further away by taking them to London. Shots were fired, whether the kids agreed or not, and Brad was finally ready to begin fighting back, begging for more open communication.

Striking Back

In most cases of divorce, keeping children away from one parent or the other is almost always detrimental. One judge finally recognized that even if Angelina had been trying to act in her children’s best interests, she was, in fact, exacerbating the situation by keeping them apart from Brad. He finally ordered that Angelina had to let Brad see them regularly, as well as allowing him to have unmonitored communication. Even so, the separation was taking its toll.

Making A Statement

According to many of the sources keeping the public abreast of the ongoing custody battle, Shiloh has been one of the hardest hit of the entire clan. Star reported that she has even gone so far as to tell her mother that she’d rather live with her father. For Brad, it must come as a relief after the continued allegations of wrongdoing. In fact, Angelina’s continued attempts at sowing discord seem to be backfiring, as the judge suggested she might lose custody of the kids all together.

Spirited Celebrations

The pending divorce hasn’t kept Shiloh from enjoying plenty of celebratory activities for her last few birthdays, even as her parents’ relationship has become even more contentious. Her previous jet-setting included trips to her birth country of Namibia, Disneyland, and Utah. It seemed the only thing getting her down was her forced exile to London, which was recently ended by a court order. Not even a broken collarbone in a snowboarding accident could hurt as much as the separation from her dad.

Daddy’s Little Girl

There are other reports that Angelina’s machinations have been somewhat successful in turning her sons against their father, which may come entirely as a surprise, given that the split seemed to be sparked by a disagreement that Pitt had with their eldest son Maddox two years ago. Although she’s tried her best, the girls aren’t so easily swayed by whatever Angelina has been telling them. Despite the reported tension between the boys, Pitt’s relationship with his daughters has stood firm.

Ready To Blab

In August, several reports revealed that Shiloh was fed up with her mother’s actions towards her father. A source shared, “She’s been biting her tongue for a long time and has been longing to speak out for the last few months. But after Angelina’s recent stunt to try to paint her dad in a bad light last week, something snapped in her and she really wants to tell everyone just how much she and her siblings miss Brad and want him back in their lives.”

Toeing The Finish Line

By late November, it seemed that Brad and Angelina had turned over a new leaf with regards to their divorce negotiations. Though they had been fighting bitterly since they announced their separation, suddenly it seemed like the two superstars would reach a deal before they’d have to bring their case to a drawn-out trial. As hard as Angelina tried to keep Brad away from the kids, it looks like there’s nothing she can do to separate her family further.

Leveling Up

With her preferences supposedly expressed, the 12-year-old Shiloh is clearly on the brink of her adolescence, which hopefully means that her opinions with regards to her parents hold more weight. Although Brad seems to finally be making headway, Angelina’s dissatisfaction with the results has led her to hire yet another legal team. For Shiloh’s sake, however, it would be prudent to do whatever it takes to allow her, and her siblings, to spend as much time with their father as possible.