I was never much for gambling, but there were times when I wanted to be. The movies made it look like so much fun. A popular plot device in 80’s film and television was for the protagonist to win an improbable jackpot on a horse race or card game to usher in a happy ending, against all odds. Maverick comes to mind but there are countless other examples. I even watched a Highway to Heaven episode that featured this device – though it was framed as the power of God putting his thumb on the scales of probability.

As a child, I understood that television wasn’t real, but I still believed that it was a relatively accurate reflection of reality. I understood that there was no actual person named Brett Maverick who won a poker tournament by wishing real hard for an Ace of Spades. But I believed that there were people like Brett Maverick, and that, while pulling the exact card he needed at the climax of the final poker game was improbable, it was still possible.

With this as a backdrop I’d like to share a short story about the time I got hustled by my sister. I was probably 11 years old, which would make her 13. We weren’t avid card players. We would play games like 31 and crazy eights during camping trips, but we didn’t often play at home. And we didn’t often gamble. We were kids, after all, and didn’t have any money of our own to speak of. The few times that we did incorporate gambling into our card play, it would be in the form of buttons from our mom’s spare buttons bag. (E.g. I’ll see your button, and I’ll raise you two buttons).

For whatever reason, this one time, we started playing card games for real money. I must have had a few dollars that I earned from allowance or doing chores. I don’t remember exactly what the game was. It wasn’t poker. It was probably 31. We started out betting for small change. I lost. She offered “double or nothing”, and I agreed.

As the losses mounted, I started to feel the temperature in my ears and head rising, and I began to worry that I had lost more money than I could comfortably afford.

“Do you want me to loan you more money to bet?”, she asked, after I was out of money.

Of course! I needed to win my money back. So she loaned me more money. And I lost again.

At this point I was in way over my head. Not only had I lost all of my money, but I now was in dept to her for substantial amounts of money. I don’t recall dollar amounts, but I remember thinking that it was so much money that I would never be able to pay off the debt.

There had to be a way out. I wished I had never started this foolish game. If only I could return to the moment just before we started betting. I decided to take my case before the court of “Mom”.

“Mom”, I said, “We’re not supposed to be gambling at all. So Erin should have to give me my money back, right?”

“No”, she said. “If you agreed to it, you have to pay it. This will be a good lesson to you about gambling.”

I’m sure there was some back and forth on this – as I surely would have attempted all angles to get this debt cancelled. But effectively, my appeal was denied. My debts would not be cancelled – at least not by this judge.

It all seemed hopeless, until my merciful sister offered me a way out.

“Steven, I’ll give you another chance to win your money back, with one more bet”, she offered.

“What’s the bet”?, I asked, skeptical – but frankly full of naive hope that this could be the stroke of luck that changed my fortunes.

“I’ll bet you that Charlie Sheen and Emilio Estevez are brothers”, she replied.

Now, before I go on, please understand that in 1989/1990, Wikipedia wasn’t a thing. Also understand, that in my world, brothers always had the same last name. I mean, do the math. Brothers with the same dad (I clarified that they had the same dad before proceeding into the bet) should have the same last name, right? Right??

Having done the math in my head, I said “You’re on!”

And for about 2 seconds, I was sure that I had managed to climb out from under this mountain of debt. Then:

“You’re wrong. They’re brothers.”, she said.

“No they’re not!”, I said.

Eventually this went to the panel (my Dad), who confirmed that Emilio Estevez and Charlie Sheen were, in fact, brothers.

I’m sure that I accepted this decision with a Trumpian display of grace and class.

There’s a silver lining to this tragedy, however. The following year, “Men at Work”, starring Emilio Estevez and Charlie Sheen, was released, which gave me ample opportunity to share this fun piece of movie trivia.

“They’re brothers, you know”, I would say to anyone who would listen.