The Opening I Keep Losing To

Morgan Boss

The Opening I Keep Losing To

30 April 2026

Every player has an opening they lose to. Mine is the Sicilian, and I have been losing to it in roughly the same way for six years, which is a fairly useless sentence but an honest one.

The pattern is this. We reach the position where the pawns are half open, the knight is on its usual square, and my opponent does the sensible aggressive thing. And I play my sensible reply, the one I have played a hundred times, the one I was taught when I was young and slightly frightened and wanted the position to close. Then twenty moves later I am sitting there with a bad bishop and a vague sense that the game went wrong somewhere I did not look.

The way you find out is written records, not memory. I went back through my old score books and found the same game, more or less, four times in two years: my own pawn move in the sixth, a familiar trade, and then the same slow slide. There is a particular position, which I will not insult anyone by naming since somebody can look it up, that used to make my stomach drop when I saw it on the board. Now it makes my stomach drop and I can write down the next three moves of my own disaster.

That is the second thing I learned, and it is the less convenient one. The move I repeat is a memory, not a decision. It was the move that felt safe at fifteen, when safety was the whole ambition, and I have been playing it ever since without ever asking whether it is any good. Most of my worst chess is this: a nine-year-old's plan, executed with a thirty-year-old's vocabulary.

So I have stopped trying to beat people at the opening. I play the same thing. What I have added is one extra moment before the sixth move, a moment in which I try to state, in words, what my opponent wants. It has not fixed anything. But the games are shorter, my losses are less mysterious, and I no longer blame the opening for what happens twelve moves after it.