There is a family story that goes along with today's but of overthinking about the phrase playing chess not checkers.
Many summers we would go visit my grandparents in southeastern Connecticut. That stretch of Connecticut required fancy antennas and/or cable to get more than two TV stations unless the wind was blowing a certain way. One of the two channels that came in pretty well was PBS, which meant my grandparents were happy enough since they could watch their nightly news show.
For us children used to a larger diet of TV, this led to a lot of boredom. So, in an attempt to stave this off, there were a lot of evening games. We played Taboo, gun, gin rummy, double solitaire, crazy eights, and once or twice hearts. (One of my cousin's relatives tried to teach us bridge. I called it reverse hearts and she was not pleased. We did not play enough for me to have retained much.)
So one night we are playing crazy eights. And my mother lays all her cards down and yells, "Gin!"
We all stared stunned, hoping this was a not very funny joke. And then realizing our mother is basically sleepwalking at this point, so we just kept playing around her.
So when people say someone is playing chess not checkers, I understand that the point is chess requires generally more long term strategy than checkers. But I also wonder. It hardly matters what chess strategy you are using, if the game you are actually playing is checkers, you are going to lose.