"At the highest levels, checkers is a game of mental attrition. Most games are draws. In serious matches, players don’t begin with the standard initial starting position. Instead, a three-move opening is drawn from a stack of approved beginnings, which give some tiny advantage to one or the other player. They play that out, then switch colors. The primary way to lose is to make a mistake that your opponent can jump on."
Champion checkers player Marion Tinsley died in 1995, having never lost a match to Jonathan Schaeffer's Chinook program, an early example of machine learning. Schaeffer spent the next decade trying to exorcise Tinsley's ghost by building the perfect checkers program.
This lovely story in The Atlantic lets the quaint but mathematically challenging game of checkers serve as a metaphor for the human condition.
Read: How Checkers Was Solved by Alexis Madrigal