There’s Always Money in the Banana Stand

There is a very real chance that my entire existence today is only possible because my grandfather was exceptionally accurate with a rifle.

In 1942, he enlisted in the United States Marine Corps, joining hundreds of thousands of other young men answering the same call. Like many of them, he was sent to Camp Pendleton for basic training. And like most things in his life, he approached it with quiet seriousness.

It turned out he was an extraordinary marksman.

During training, he posted the highest marksmanship scores in his entire cohort—more than 1,000 Marines. As a result, the Corps made a decision that would alter the course of his life. Instead of shipping him overseas immediately, they kept him at Camp Pendleton for roughly six months, assigning him to train other Marines how to shoot effectively.

Eventually, he did go overseas. He served in the Pacific Theater for more than two years, like so many others who never came home.

But those six months mattered.

They may have made all the difference between surviving that conflict and not making it out at all.

After the war, he came home and built a life that felt almost improbably full.

He walked away from professional baseball to raise a family, choosing reliability over romance. He worked as a milkman—the kind who showed up before dawn and knew every customer by name. In his spare time, he became an award-winning iris gardener in Monroe, Washington, collecting ribbons year after year. He sang in a barbershop quartet. He collected fine china with a care that suggested appreciation rather than extravagance.

If you had to describe him in one word, “interesting” wouldn’t quite be enough. He lived broadly, but never loudly.

When he passed away, life went on the way it always does. A couple of years later, my grandmother decided to sell the house they had lived in for more than sixty years and move into a retirement community. As a family, we gathered to help prepare the house for sale, which meant sorting through decades of accumulated life—drawers, closets, boxes, and sheds that hadn’t been opened in years.

One afternoon, I was in the shed, surrounded by reminders of who he’d been. Gardening tools worn smooth from use. Ribbons from iris competitions. Old equipment from jobs long finished. I opened a drawer filled with gloves—work gloves, gardening gloves, odds and ends collected over time. Toward the back sat an especially old leather pair, cracked and stiff with age.

When I picked it up, it felt heavier than it should have.

Rolled tightly into the finger of one glove was a bundle of cash. No envelope. No note. Just bills, carefully hidden. When we counted it later, it totaled $10,000.

At first, it was baffling. This wasn’t secrecy born of mistrust. This wasn’t confusion. It was deliberate. Intentional. And then the explanation arrived almost immediately.

He was a product of the Great Depression.

For those who lived through it, the Depression wasn’t an economic concept—it was a rupture. Banks failed overnight. Savings disappeared. Institutions that were supposed to be permanent simply shut their doors. Money that existed on paper ceased to exist at all.

People learned, the hard way, that safety was fragile.

That lesson didn’t fade when prosperity returned. It hardened.

Decades later, families across the country uncovered similar discoveries. Elderly parents passed away, and children found cash hidden behind walls, tucked into mattresses, buried in backyards, or sealed inside jars and shoeboxes. Contractors renovating old homes occasionally discovered stacks of bills stuffed into insulation or floorboards, untouched for half a century. Newspapers periodically ran stories about people who lived modestly while quietly sitting on large sums of cash no one knew existed.

This wasn’t eccentric behavior. It was a pattern.

An entire generation had internalized the same conclusion: institutions can fail, but physical cash won’t vanish overnight. Keeping money close wasn’t about optimization. It was about control.

From a modern perspective, it’s easy to critique those choices. The money could have earned interest. It could have been safer in a bank. It could have been invested and put to work. All of that may be true.

But judging the decision misses the point.

Financial behavior doesn’t begin with math. It begins with memory.

My grandfather didn’t hide that money because he didn’t understand how banks worked later in life. He hid it because, at a formative moment, he learned that systems could collapse and that self-reliance mattered. That lesson stayed with him quietly, long after it stopped being necessary.

This dynamic shows up constantly today. One person insists on holding far more cash than seems reasonable. Another refuses to use debt, even when the numbers suggest it could help. Someone panics during market downturns while someone else sleeps just fine. These differences aren’t about intelligence or discipline. They’re about experience.

We all carry financial histories we didn’t choose. Some were shaped by inflation. Some by job loss. Some by watching parents struggle—or watching them lose everything. Those moments write rules, and those rules tend to persist.

That $10,000 rolled into the finger of an old leather glove wasn’t a strategy. It was a memory, preserved. A quiet reminder that what looks irrational in isolation often makes perfect sense once you understand the road that led there.

And the longer you work with people and money, the clearer this becomes: before judging someone’s financial decisions, it’s worth asking what they’ve lived through.

Because once you know the story, the behavior usually explains itself.