Losing the Raffle

The gambling lesson I learned at the tender age of 9

What was the most disappointing moment of your childhood? Think about it for a moment.

I’m sure many of you have actual, serious moments that come to mind — things involving your parents, family, or stuff at school. But if you also remember a disappointing moment that involved something downright dumb, welcome to the club.

Maybe you were like me and took things way too seriously as a kid. I had my fair share of interests back then that really did not matter in the grand scheme of things, as I imagine most kids do. And when those interests did not live up to the hype or go the way I planned, I would sink into a deep, deep state of disappointment that I’d hold dear to me like the nastiest grudge.

For most of my young life, I spent my free time making up fantastical worlds with my toys — a mishmash of Littlest Pet Shop figurines, Hot Wheels cars, generic stuffed animals, and special stuffed animals, like Beanie Babies. But nothing captured my attention quite like Webkinz, the novel (at the time) plush friends that came with a digital code so you could “adopt” them online in the Webkinz virtual world.

From the ages of 8 to 11(ish), I was obsessed with Webkinz. There was a store downtown that would sell them for about $10 or $15 a pop, and I’d save up my chore money and buy one whenever I could. I’d ask my friends and family to get me new Webkinz as a gift for every birthday and holiday. And I even went so far as to ask my orthodontist to emblazon the Webkinz logo on my rainbow-colored retainer, which they did.

I think I collected some 50 or 60 Webkinz by the end of my childhood. Yes, I’m aware that’s excessive. I definitely did not need that many, and I feel a twinge of guilt thinking about how most of them are rotting in a storage locker right now.

Anyway, let’s get back to disappointing childhood moments.

Imagine this: it’s the beginning of 5th grade, mid-August, and my school is putting on its annual fun fair. There are bouncy castles and field games on the playground. Kids and their parents are all over the place.

Indoors, they’re doing face paint and balloon animals, and there are more games where you can win prizes. Then, in the gymnasium, there are the raffle baskets. The huge, decadent raffle baskets with the absolute best prizes.

There was something for everyone at my elementary school’s annual fun fair raffle. Even if just one basket caught your eye, it was enough to make you buy a ticket and try your luck.

That year, 5th grade, the fun fair organizers made the best possible raffle basket for yours truly: a Webkinz basket that contained nothing but 10, maybe 20, Webkinz. I felt like it was my destiny to win the raffle basket. I was so obsessed that I spent almost all the money I had in the world (which was probably like, $40 or $50) on raffle tickets.

I diligently wrote my name down on every single one, and hoped and prayed as I put my tickets in the box that the universe would hear my plea. The Webkinz basket had to be mine. I liked Webkinz more than anybody at my school; I was sure of it. It would be an act of, dare I say, justice for me to win the raffle.

But of course, I was not the only kid putting my name in the hat. My best friend at the time was also a fan of Webkinz, and I saw her put just one or two tickets in the raffle box.

We were both super excited about the prospect of winning. But I was sure I was more excited, and the many, many tickets I entered would also up my chances of winning. Sorry, buddy.

I spent the rest of the fun fair playing games indoors and anxiously anticipating the raffle drawing. I remember being in the middle of some musical chairs-like carnival game when I heard they were about to announce the winners in the gym.

So, I bolted down there and waited for them to draw the Webkinz basket. My heart was beating out of my chest. Please, please, please, I begged God, or the universe, or whatever supernatural entity decides the winners of elementary school raffles.

When they called the winner’s name, I froze.

It wasn’t mine — it was my best friend’s. I looked over at her, and she was bouncing up and down with glee. Glee that should have been mine!

How could she have won with just a ticket or two? This was unbelievable to 5th-grade me. Completely outrageous! I spent my life’s savings on raffle tickets, putting dozens in the box, and now I was empty-handed.

I learned a hard lesson about gambling that night, which is funny when you consider I was, like, 9 years old at the time. Increasing my chances of winning didn’t really matter in the long run. All that mattered was if my name was on the single, winning ticket — which it was not.

Losing the Webkinz basket totally crushed me, and I still feel bitter about it in a weird way. I literally could not care less about owning a bunch of brand new Webkinz at age 26. But the disappointment I felt after losing still feels strangely vivid even though so much time has passed. I think that’s just because it was such a powerful, emotional moment — one where I allowed myself to take a big chance and lose (what felt like) everything. I’m sure I cried a lot on the way home.

So, there you have it: one of the most disappointing moments of my childhood. And I have no one but myself to blame.

It’s funny because that experience has made me sour on raffles, even to this day.

This past weekend, I was at an event where they had a raffle, and I had five free tickets that I could enter for various prizes. Instead of going all-in on the one I really wanted, I put just one ticket in five different boxes (for five different prizes). That way, I wasn’t too invested in any of them.

And guess what — I didn’t win! But my partner Ryan did, and he got a gift card to a sandwich shop in town that we like. I learned that he also put only a ticket or two in the jar, which made the surprise of winning even more exciting.

I guess we’d both rather be pleasantly surprised than sorely disappointed, hence why neither of us will ever work that hard at winning a raffle. And frankly, neither should you.

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