Chess Against Your Dad

A Parable

Last weekend I went on a mini-retreat with my father to a beautiful, very old hotel in the mountains of Virginia. He had been wanting to do something like this for years. I, with four young children, had finally managed simply to say, “Yes.” He planned everything. We played golf and tennis during the day and chess at night over bourbon. 

As you might imagine, the Shenandoah in October does not disappoint. Blue skies. Trees aflame with autumn colors falling over green valleys and stony streams. Jackets in the morning. Short sleeves in the midday sun. No internet. Just two grown men wondering if they still have enough in common to keep the conversation going for a whole weekend after two decades in separate households. In fact, we did. I don’t think we stopped talking, except to marvel at the scenery here and there. I brought two books on the trip, which I never cracked. It’s a startling thing to rediscover—and be rediscovered by—someone you’ve known since the day your were born, someone who has lived inside of you your whole life, but who also, mysteriously, has his own existence apart from you, hidden from you in ways that may never be revealed to you, except perhaps…in you. 

It has been something of a tradition of ours to play golf together once or twice a year. It’s usually the only time I play, and I always look forward to it. He drives the cart, keeps score, and introduces each hole to me as though we’re both setting eyes on some new, uncharted corner of the world. He’s seen it before, but he’s still enthralled about me experiencing all the beauty and treachery of the course for the first time. “This one’s a dog-leg left. Straight uphill. You don’t want to be too far right. Just wait til you see the view of the mountains from the green.” In between shots, I talk his ear off about whatever random philosophical thing I’ve been thinking about that day. He listens intently and interjects cool thoughts here and there. 

Though I don’t play a ton of golf, I’m not as bad as I should be. This is almost certainly due to the fact that my father taught me how to swing a golf club before I can even remember. It’s one of a thousand subtle gems dropped in the bucket of my invisible inheritance, which I did nothing to earn. He’s still the better golfer. Yet somehow he always finds a way to massage the scoring so we are inevitably neck-and-neck going into 18. (By the way, if you ask him, he will tell you he does not do this, and I’m sure he believes he’s telling the truth.) Anyway, it’s always a good competition. I want to beat him, and I play better when there’s something at stake. Occasionally, I hit it really well too. It’s a good feeling when you strike a golf ball right, and it flies straight. My father praises my good shots as though they were far better than his best shots. And I know he means it. But even his massaged scoring in my favor does not often prove this to be true. At the end of day one, at least, I found myself undeniably in second place. No matter, I thought. I would get him back on the chess table that night. 

About this, I was mistaken.

First, a word about my chess abilities. I won’t lie. I’ve become something of a chess nerd in the past year or two. One of our surf camp employees is a brilliant chess player, and he was patient enough to show me a bit of strategy last summer. Prior to that, I basically just knew how the pieces moved and had some basic intuitions about how not to lose too quickly. This basic knowledge, in fact, came from my father, who patiently taught me how to play just about every game and sport under the sun when I was a kid. No special emphasis was given to chess then—we were more into sports—and I hadn’t paid much attention to the game until recently. My father and I had never played each other as adults, that I recall. But over the past year I had trained with YouTube videos and practiced on chess apps. I was getting pretty good, I thought. So when I saw the chess board in the hotel lobby, I had visions of showing my dad a thing or two. 

Now a word about my father: He’s a wise man, a gifted salesman, and a natural athlete. He’s very down to earth. Much more so than I. He grew up humble and hard-working. Went to military school. When I was a kid, he worked in the beer business, as did his father before him. Eventually, he started his own company with a friend and became very successful. He’s very sharp. But he’s not the professorial type. Sometimes I’ll give him a book to read, and he’ll say, “The words were too big. I couldn’t keep up. I’m not as smart as you.” But this, as you will see, is not so.

Over the course of the weekend, we must have played chess eight or nine times. I won only once, and that was the very first game we played. Of course, in light of my recent chess training, I was unsurprised by my opening victory. 

I was very surprised by what followed. 

The subsequent games we played shared a pattern that I now see as nothing short of poetic. It went like this. He would make the first move. I would ignore it and confidently begin to unleash some early-game strategy of my own. My father revealed nothing of the kind. He just seemed to respond rather aimlessly to my devastating advance down the middle of the board. A third of the way through the game, I would smile at my optimal–and his sub-optimal–positioning. By the time we were two thirds of the way through, I would basically have the game in hand. It would go like this. Early on, I take a pawn or two, nothing sacrificed on my end. I trap one of his bishops. He acts—and, I think, truthfully is—disappointed he didn’t see the trap. I give up the pieces I want to give up when I want to give them up. Then, at some climactic moment, I pull out one of my signature moves, e.g. forking his rook and queen—or even his king and queen—with my knight. Game over, I think. I’m up a substantial amount of points. Nothing left to do but force checkmate. 

Now, all this time, you must understand, my dad is having the best time. He is genuinely impressed with his son’s acumen. “Wow, I did not see that coming.” “Where did you learn that?” “Oh no, I’m in trouble. I should have seen that.” “You are too clever.” I cannot expect you to believe this without knowing my father, so you’ll just have to take my word for it: Every one of these remarks was 100% sincere. He was not just messing with me. He really thought I was good. He really loved to see my skill and intelligence on display. He really thought I would probably win. And he was going to enjoy me beating him, just like he would have on the golf course, because I am his son. 

But then, each time, the games would take a curious turn. And, I kid you not, I never saw it coming. Sometimes he would hesitate for a moment at one of my moves. He’d kindly say, “Oh, are you sure you want to do that?” And I would scour the board for any hint at how my move could be interpreted as anything other than textbook. “Yes, I’m sure.” The game would continue, and my move would be more or less justified in my eyes by the four or five moves that followed. But then it would happen. Every time, it would happen. He would make one move, and everything would change. It might be…his only remaining rook, which I swore had been paralyzed by an unmoved pawn, would suddenly be free and slide directly to my back line, putting me in a costly check. Or else, perhaps a lone bishop which had sat still for half the game would find itself perfectly aimed, not even because of his move, but because of mine. It was different each time. He would use whatever was at his disposal. No clean, predictable strategy. It was almost like he hadn’t even been playing until that move, just waiting, letting my own moves work against themselves. It was the tortoise versus the hare. And the tortoise kept finding checkmate.

“Play again?” he would say. And he’d order us another round of drinks. “Yes,” I said each time. And each time it would happen. And each time I would commence with just as much confidence as the time before. I’m still not exactly sure how I never saw the pattern. Perhaps it was my early win that led me to double down repeatedly on a losing strategy. Perhaps I simply couldn’t conceive of any other strategy. But even as his victories began to stack on each other, I remained not the slightest bit tempted to become more like a tortoise and less like a hare. In retrospect I can see the problem a bit more clearly. But even now, if we played again, in the heat of the game, I’m not sure I would avoid falling into a similar trap.

On the last night, we played until very late. The pattern—at least, who was winning and who was losing—was becoming more and more obvious to the both of us. We were drinking only water and coffee now. He was looking very tired. But each time a game ended and I expected him to say, “Let’s go to bed,” he would say instead, “One more game.” And I would agree, because I was the one who wanted one more game. He was exhausted. But he kept granting me one more game, because he knew how determined I was to win one. His own fun—inasmuch as it had to do with the game of chess—had ended a couple of hours before. He wanted to keep playing for my sake. He wanted to see me win. 

At one point, in our last game of the night, he stopped me and said, “Ross, do not make that move.” This frustrated me. I knew then that he was right. And I knew he wanted me to win. But I didn’t want to win like that. So I said, “No, I insist.” In that moment, I imagine, my father fully realized his predicament. He wanted me to win, but he couldn’t entirely do the winning for me. Rather, I had to become the kind of man who was worthy enough to beat him. And that, of course, was all he really wanted anyway. In a way, that’s what he had been celebrating all weekend long. That was the whole reason he was there. That was his “fun.” Not to beat me in golf or chess. But to soak up each and every little glimpse he could get of me becoming all I was meant to be—all he dreamed I would be when I was just a baby being held in his arms.  

You cannot beat your father in chess. It is impossible. And not merely because he is more patient and wise. You cannot beat your father in chess, because he is not playing the same game as you. In his game, he wins even if you win, because he is in you, and your perfection is his glory.

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P.S. If you’d like to get a bit more of a taste of who I am and what the Patient Kingdom writing project is all about, please check out the About Page.

P.P.S. If you’d like to know why I used the word “perfection” in the last line of this story, check out “Be Perfect” on the Mere Sanity podcast. It’s a short listen, and it’ll provide a few more hints as to what I’m up to with this project.