My great-great-grandfather, Frederick H. Prince, built a fortune on stockyards, railroads, and meatpacking. By the early 1900s, he controlled hundreds of miles of rail lines and nearly a million acres of land.

He had two sons: Norman and Frederick Jr.

He expected them to carry on his empire.

Both refused.

The son who died free

Norman, the eldest, loved flying and learned from the Wright Brothers. In 1911, he became the 55th American to be licensed to fly an airplane. He trained under an alias name “George Manor” to hide his flight training from his controlling father, who disapproved.

In 1915, Norman sailed to France to help found the Lafayette Escadrille, one of the first American volunteer fighter squadrons in World War I. He flew 122 combat missions before crashing on October 12, 1916, 109 years ago today.

Meanwhile, his brother Frederick Jr. trained as a pilot and was preparing to join his brother in the squadron.

Norman died three days later at age 29.

His father had his body removed from the official tomb, The Lafayette Escadrille Memorial Cemetery, in France which was built to honor Americans who flew with French squadrons during World War I. Sixty-eight aviators who died are memorialized there, forty-nine entombed in the crypt with their French commanding officers.

Norman’s body was flown to America and buried at the National Cathedral in Washington, D.C. He should have remained with his brothers-in-arms.

Even in death, the old man had to control where his son would rest.

The son who had to stay

After Norman’s death, the patriarch turned his attention to his surviving son, Frederick Jr. He couldn’t bear to lose another son, so he pulled him home.

Frederick Jr. obeyed, but refused to take part in the empire. He had just lost his brother, his best friend. Now he was alone with a controlling father.

His brother had died escaping their father’s control. Frederick Jr. had to find another way out. His rebellion came through polo, excess, and quiet defiance.

When the old man couldn’t force him into line, he adopted a distant cousin to run the business instead.

The next generation

Frederick Jr.’s son, Frederick III, wanted no part of it either.

It was his daughter—my mother—who finally wanted to work for the business. By then, the patriarch was gone, but the culture of control lived on. The adopted cousin refused to hire her.

Eventually, my mother’s brother—my uncle—forced his way citing the patriarch’s will, which declared that a “liberal employment policy” be extended to his descendants. When I applied decades later, I was denied, too. This, despite having worked in finance after graduating from college.

The patriarch had designed a trust that was to have survived until 2019 - sixty-six years after his death, still commanding us from the grave. Four generations later, a fight was brewing to control his empire.

The end of the empire

In 2006, fourteen family members gathered to decide the company’s fate.

We voted to liquidate it. The process took three years. By 2009, it was done—ten years before the trust was supposed to end.

The empire that caused Norman to flee to war, that Frederick Jr. refused, that divided our family for generations—was over.

We chose to let it go.

What I learned

The wealth remained. But the control finally died.

And that’s when our family could breathe again.

Here’s what I learned from living this story:

It wasn’t the money that hurt us. It was the control that came with it.

My great-great-grandfather built something extraordinary—but he couldn’t let go. He couldn’t trust his sons to make their own choices. He tried to command them in life and in death.

Norman chose freedom and paid with his life.

Frederick Jr. chose rebellion and paid in other ways.

And four generations later, we chose peace.

Why this matters

When people hear “pressures of privilege,” they often think about stress, isolation, or purpose. Those are real.

But there’s another, quieter pressure that doesn’t get talked about enough: the pressure to accept control disguised as legacy.

The expectation that you’ll be grateful. That you’ll take your place. That you’ll carry on what was built for you, even if it’s destroying you.

Sometimes the most powerful thing you can do is to choose what to let go of.

The money can stay.

The control must die.