Dear Jack

Dear Jack,

Grandpa never let me win, either. 

When you are older, you will read this letter. I hope you understand why I never let you win. See, last night, you almost got me. We were playing H-O-R-S-E, and you almost pulled it off. Luckily, I found my range and came back. The look on your face when your last shot bounced off the back of the rim was one I remember well. The look of disappointment, anger, sadness, and frustration. That look is why I can't let you win either, because when you do, it will be one of the best feelings of your life. 

Grandpa didn't let me win at golf; hell, he didn't let me win at anything. Rummy? Nope. Basketball? Not that, either. Fishing? He let me get the first cast at the best holes, but when I got it snagged, I was expected to hold my rod and wait patiently while he fished it.

But golf, he did everything he could to not let me win. And I hated it. I wanted to beat him so bad I could taste it. Almost my entire existence in sports from the ages of 11-15 was wrapped up in trying to beat my Dad at golf. I hated that I couldn't beat him. Hated it. Countless rounds ended with me so pissed I wouldn't talk to him. 

We'd come home, and Grandpa would finish the sundae I paid for with my allowance. Grandma would say, "Just let him win, Howard." 

"Never." 

We used to play for a sundae from McDonald's. If I agreed to play and lost, he made me pay, even though it was a good portion of my $7 weekly allowance. Everything was a lesson. I didn't know it then. 

I remember after one of the losses, I didn't have enough money for two sundaes. So he ordered one when we got to the drive-thru. I thought for sure it was for me. It wasn't. 

I won't let you win because of the best sundae I ever had. It came on the night I finally beat Grandpa. I can't remember what I shot or what he did, but it didn't matter. I remember the hug after, even though I didn’t understand the emotions in the moment. That was until last night after HORSE. 

I'm proud of you, kid. You have worked your ass off to become a better basketball player. Luckily, you were blessed with your Mom's smarts. Unfortunately, you were also saddled with her athletic skills. Which makes your improvement that much better. 

That hug from Grandpa was filled with pride because he knew I had earned it, and he didn't give me anything. But it also meant that Father Time was catching up with him. There was a bit of sadness in that hug, knowing that I was growing older, and so was he, but in many different ways. 

Let me be clear: it will be a few years before you beat me. And when you beat me at HORSE, I am going to make you play me one-on-one because HORSE doesn't really count as a true win. I've got some old tricks I can use on you, the same ones Grandpa used on me. 

I didn't realize it then, but whenever I was close with a few holes left, he would ask me about our scores to mess with me. After he asked me, I'd grip that club so tight my hands practically bled. You don't realize how quickly that hole shrinks when your Dad is playing mental games with you. I promise the hoop will feel smaller. 

But that day will come when you finally win. And I'll hug you just like Grandpa did me, and I will be so proud of you, but also there will be sadness. Father Time is undefeated.

And I'll take you out for a sundae, and it will be the best sundae you have ever had. 

I love you. 

Dad. 

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