Teaching my Son to Lose

I played chess growing up. Not a lot, really. I would never say I’m good at chess. I just know how to play, I guess.

I played checkers first, with my grandmother. Grandma Buono was kind of ruthless when it came to checkers with a six-year-old. Within minutes of each match, she levied an onslaught of double- and triple-jumps, clearing the board and demanding “King Me!” again and again while I grappled with reality. Grandma taught me how to lose in that way. I had no choice — if I wanted to play again, I had to swallow my defeat and ask for a rematch before she returned to her place by the stove or in front of her pictures.

Chess replaced checkers when we set up our family computer sometime around 1993 or 1994. We had a top-of-the-line Packard Bell, complete with a textured gray finish that would yellow from cigarette smoke over the years it spent in our spare bedroom.

The machine ran Windows 3.1, and that OS had Windows Chess preinstalled. If you weren’t alive before the internet was as ubiquitous as it is today, you’ll never really understand the initial thrill and immediate disappointment that arrives with a new computer. Without access to the internet as a kid, you either tooled around with the software that came bundled with the computer or you hoped your parents needed to run to Office Max so you could peruse the $0.99 clip art and encyclopedia CD-ROMs while they checked out.

Windows Chess became my obsession. I had no idea what I was doing, so I learned through trial and error. I sunk hours and hours into the experience, trying new approaches and strategies. I don’t think I ever won a single game. I came close. I remember whittling the computer player down to only a handful of pieces and, at best, forcing a stalemate.

I had to look up stalemate in our family dictionary back then. It was just a fancy way to say “tie.” I was bummed.

It’s hard to pinpoint when I stopped playing chess as a kid. My parents didn’t really play the game, though I could push my dad into a few rounds of it when he was home from work. Windows…

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