Needless to say, this is a nickname for a very specific kind of dude, not specifically one who plays chess.
This is the kind of guy who always makes all the right plays, and receives an ungodly amount of rizz.
The "right plays" is originally based off the terminology used in the game, Chess.
Person 1: Hey! Did you see that sick guy at the party?
Person 2: How could I miss him?! He was a total Chessman!
slip of the tongue perhaps,
Those idiots who drive around in a ridiculously raised pick up truck, making a top heavy vehicle even more top heavy and unstable
A:*gah*
B: "Whats the matter"
A: This dam prickup is blinding me.
B: Stupid thing's, as if there lights weren't blinding enough as it is.