Playing Chess in Prison

September 27th, 2026

Yesterday we took the little boy to visit his mama. She is doing time at the Milwaukee Women’s Correctional Center. It’s a minimum-security facility, and the guards are actually quite friendly toward visitors, but it’s still a prison. The visiting area is in the cafeteria. There are two vending machines available. They do not consistently cough up snacks. Trying to buy some junk food is a little like playing on a slot machine. There is a table in the visiting area that has a pile of old board games. Those games are all there is for entertainment. They get a lot of use.

The visits can last up to three hours on a Saturday afternoon. The time goes by quickly during the first hour. After that, we run out of things to say, and that is when the board games become necessary. The five-year-old is learning a number of new ways to play. He has become adept at checkers (he beat his mama once without any help from me or my wife). He knows how to play Sorry. The boy has not yet learned how to lose gracefully. He is not shy about flipping the board over and scattering the pieces. He likes to win and he is easily frustrated when he can’t. He takes it all too seriously.

Yesterday he got bored with the usual games and we brought a chess set to our table. My wife and his mama do not know how to play the game. I attempted to teach the lad. I hadn’t played chess in years, maybe decades. I still knew the basic rules. The boy and I played a game. We were at it for at least 45 minutes. He caught on quickly. He understood the need to protect his king, and he figured out how to use the other pieces. He did quite well for his first game ever.

A long time ago, I was fascinated with chess. I don’t know why. When I took metal shop in high school, I made my own chess set on a lathe. Half the pieces were made of brass. The others were aluminum. It took me nearly the entire semester to make all the pieces. I don’t have them anymore. Like most things in my life, the pieces have been lost and forgotten. Every once in a while, I find a stray pawn, but I will never get the whole set together again.

I was never very good at chess. I liked to play, but I couldn’t plan my moves far enough ahead. It’s odd that I have spent most of my work life planning and organizing operations, but the game was beyond me. I guess I just lost interest during a chess match. It stopped being fun.

I lost interest in most games and sports once I got into my late twenties. Part of that was due to the fact that I went to West Point for four years. At the military academy we had to participate in sports almost the entire year, every year. We had to attend (and stand at) every home football game. Mandatory fun is an oxymoron, and it was part of the culture at the school. Also, the sports, along with everything else at West Point, were relentlessly competitive. We fought every match like it was the only thing that mattered in life. We hardly ever just played a game. It was never just for fun.

As I got older, I forgot how to play. I was busy with work and family. I became a boss, a husband, and a father. Life became serious, and I forgot what it was like to just screw around. I lost part of myself, perhaps the best part.

Being with the little boy has helped me to bring back that part of me that went dormant. The kid likes to play. It pains me to see him get intensely competitive so soon in life. We have to remember that chess or checkers are just a game. Maybe all of life is a game. Maybe we should just play at it.

Leave a comment