There was a time when my Rolex meant something.

Not to me, of course. I’m not shallow.

It just happened to be a luxury timepiece worth more than my first three cars combined.

And yes, when I bought it, I wore it proudly. Not because I wanted attention. I simply wanted every person I encountered to immediately understand that I was doing well financially.

There’s a difference.

I worked hard for that watch. Years of long hours, stress, meetings, spreadsheets, and pretending to understand what accountants were talking about. When I finally bought it, I felt I had earned the right to occasionally adjust my sleeve in a way that exposed exactly the correct amount of stainless steel and prestige.

The Rolex wasn’t just a watch.

It was emotional support.

Whenever I had a rough day, I would glance at my wrist.

Client yelling at me?

Rolex.

Mortgage payment due?

Rolex.

Kid’s rebbi requesting a meeting?

Rolex.

I could be feeling like a complete failure, but then I’d look down and think, “A loser? Really? Have you seen what’s on your wrist?”

Was this healthy?

Probably not.

Was it effective?

Absolutely.

Even my 11-year-old son looked up to me.

He’d stare at the watch with admiration.

“Tatty, that’s a Rolex, right?”

“Yes.”

“Wow.”

That “wow” carried weight.

To him, I wasn’t just Tatty. I was a successful businessman. A man of accomplishment. A man who apparently understood investing, taxes, and how not to accidentally overdraft a checking account.

The watch helped tell that story.

Then came the raffles.

At first it was one organization.

“Grand Prize: A Rolex!”

Cute idea.

Then another yeshiva raffle offered a Rolex.

Then another.

Then another.

At this point, I’m convinced there are more Rolexes being given away in fundraising campaigns than are being sold by Rolex itself.

Every month there’s a new campaign.

Support Torah!

Win a Rolex!

Help build a mikvah!

Win a Rolex!

Sponsor a (Women’s) breakfast!

Win a Rolex!

At this point, if a shul announces a raffle and the prize isn’t a Rolex, people assume the organizers aren’t trying.

And just like that, years of carefully curated wrist-based status vanished.

Now when people see my watch, they don’t think, “This man has achieved financial success.”

They think, “Five dollars a ticket.”

The other day I was standing at a vort and someone noticed it.

“Nice Rolex.”

“Thank you.”

“What organization was it?”

“What?”

“The raffle. Which raffle did you win it from?”

I almost choked on the Mike’s Chicken. (You cannot reheat Mike’s, it gets too dry.)

Win it?

WIN IT?

Sir, I spent an amount of money on this watch that I am still hiding from my wife.

But the damage was done.

The Rolex had been democratized.

It used to be a symbol of success.

Now it’s a symbol of knowing somebody who sold enough raffle tickets.

Even my son has changed.

A few months ago he told a friend, “My father has a Rolex.”

The friend shrugged.

“My uncle won two.”

Two.

Do you know what that does to a child?

My son used to think he came from a family of achievers.

Now he thinks we’re underperforming.

Last week he asked why I only have one.

I’ve even noticed people looking at my watch differently.

Not impressed.

Curious.

They’re trying to figure out which fundraiser I supported.

Nobody assumes I bought it anymore.

If anything, buying one outright now seems suspicious.

Why would you spend thousands of dollars when you could just purchase 400 raffle tickets and convince yourself you’re helping tzedakah?

The economics have completely shifted.

So these days, the Rolex mostly sits in a drawer.

Occasionally I take it out, wind it, and remember the glory days.

Back when it meant something.

Back when a Rolex told the world you had money.

Back before every yeshiva dinner journal, Chinese auction, scholarship campaign, and building fund turned it into the Jewish community’s equivalent of a participation trophy.

I’ve had to find new ways to feel successful.

It’s been difficult.

Sometimes when I’m feeling down, I open the drawer and look at the Rolex.

Then I remember everyone assumes I won it.

And somehow I feel worse than before.

Maybe next year some organization will raffle off a private jet.

Then the Rolex might become exclusive again.

Until then, if you see me wearing an ordinary watch, understand that it’s not because I can’t afford a Rolex.

It’s because I can no longer afford the misunderstanding.

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