Chess boards and checker boards are common occult symbols because of the alternating grid of light and dark squares. The light and the dark represent the right hand and left hand of baphomet, a demonic idol of the occult. There are graven images of baphomet with breasts and a penis, and with hands pointed in different directions. The right hand path points up towards the light, and the left hand path points down towards the dark. This means that amoral occultists can do as they wilt to accomplish their goals such as using light magic or black magic, or masculine or feminine energy.

edit: the “check mate” part is interesting. Maybe from white hats?