Brad Pitt and Angelina Jolie’s "Transsexual" Tween: Dynastic Planning in a Brave New World

“Open gender architecture” has always been the privilege of the elite, but as orientation choices move down the lifecycle and the asset scale ground-level advisors wrestle with the nuances.

Gossip around one of the now-estranged Brad Pitt and Angelina Jolie’s children as a boy born in a girl’s body has circulated since Shiloh was six years old. 

The family keeps brushing it off. As far as they’re concerned, she’s still a daughter and a sister who simply likes to wear boys’ clothes.

But affluent and alert kids are identifying across birth gender lines younger and younger, so even if Shiloh elects to stay a girl, it’s going to be a factor for a lot of high-net-worth households in the very near future.

Transsexual kids become transsexual heirs. The big picture doesn’t really change, but a few of the nuances need to remain flexible to support a dynastic agenda.

The Shiloh scenario

Today’s pre-teens were born into a world where someone who’s unhappy with what would have been genetic destiny can pay to have it changed.

They may get pushback from friends and family that don’t like the choice. That pushback may drive them away. Rifts happen.

But a lot of parents ultimately regret cutting a son who wanted to be a daughter (or the other way around) out of their lives and out of the will. Like any disinheritance scenario, it’s a cruel move that rarely reflects well on posterity.

On the other side of the estate plan, rich kids who do inherit have been blurring the gender line for centuries. Modern medical science only makes that transition legal. 

Among the Pitt-Jolies, Angelina in particular takes the expansive view. Her kids aren’t going to let any accident of birth get in their way and Shiloh is no exception. 

So far the family hasn’t signaled that their daughter would rather be a boy, which is probably all the proof we need that her disdain for frilly skirts is about comfortable clothes and not so much feeling like an alien in her own skin.

If that changes, I’m sure we’ll all hear about it. And in the meantime, kids’ identities are more fluid, which means the really binding decisions are off limits for minors.  

Someone Shiloh’s age could easily cycle back and forth for years before hormone therapy is even an option. In the meantime, kids are kids no matter what gender they are, so the parents are the ultimate arbiters.

When the parents aren’t okay with the prospect, the time to make that position clear is early on. Once the kids turn 18, it’s their call.

That’s probably why rumors about Will Smith’s occasionally smock-wearing son Jaden wanting to become a woman fizzled after his 18th birthday a year ago.

If he was that hot to have the surgery, it would have happened. It didn’t, so he’s not.

So if Angelina or Brad is willing to risk losing a daughter if it means gaining a son, they need to argue their case now instead of turning their backs if and when surgery becomes an option.

I doubt they’ll do that. They’d probably think it’s cool. But a lot of kids don’t have it so easy.

Details and dynastic grace notes

As long as the estate planning documents follow gender-neutral usage, a sex change really doesn’t have much more impact than a marriage.

A will generally won’t need to be redrafted. Even if a hypothetical “Shiloh” becomes a “Samuel” in the interim, that transition should be a matter of legal record, easy to verify that the heir’s personal identity hasn’t shifted.

If parents have any doubt at all, references to “sons” or “daughters” can become “children” — society can move fast in a lifetime, so leaving wiggle room can prevent awkwardness when the will is read as well as more serious challenges afterward.

On that note, it’s probably worth holding off on naming long-term legal entities after the kids until they’re adults who know who they are. 

Shiloh Jolie-Pitt, for example, already has an African wildlife preservation foundation named after her. Retitling and rebranding if she decides that name no longer applies will be a drag on its work — and the more serious it becomes in the meantime, the bigger the headaches will be.

The Shiloh Foundation is in it for the long haul. That means any work it’s already done to establish itself will be set back if and when she rejects that name.

Better to keep everything in a family trust until the kids reach maturity, then let them brand the entities as they like. After all, right now these are primarily Angelina’s causes anyway and it’s her money. If she wants to make a difference now, she doesn’t need to bring the kids into it.

If the kids want in, they can step up when they’re older. That’s the real dynastic lesson right there. 

Whatever changes happen to the bodies in the meantime, the relationship to the family ethos and the wealth that sustains it is essential.

As long as Shiloh and the other kids live up to Angelina’s philanthropic example and pursue her causes when mom is gone, that’s a win.

And from there, even if they marry the wrong people or never marry at all, they can still continue the dynasty.

Rich families have been adopting kids for ages to carry on the line. Transsexuals can do it too. 

Even if a parent thinks a particular heir will never reproduce, it’s good to leave room for those hypothetical grandkids in the estate just like those who enter the family via birth.

 

The future is a big place. Hollywood royalty two generations ago would be stunned at the possibilities that today’s stars wrestle with. Just about any wealthy family you work with is looking at a similar transition — if not now, then when the millennial generation takes the reins.

 

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