It really is an insult for checkers as a game. It is a common misconception that it’s simple. The game has surprising amount of depth, and the saying “x is playing chess while y is playing checkers” should really die.

X is playing chess while Y is playing tictactoe would be a better analogy.

I usually take the chess/checkers idiom to be more like “the left hand didn’t know what the right hand was doing” Not that one is smart and one is dumb, but that they’re going in completely different directions and playing by different rules.