On Chess :
In his younger days when trading lumber Reb Simh.ah Bunim of Peshish.a used to play chess with people of dubious reputation, and he would jest sometimes at a fitting moment when making a move, e.g. "Be careful when you move at chess, or you'll end up with one pawn less," and his tone made people listen. Over time, they realized that the "jests" actually applied to their lives as well as the game. Eventually he turned their hearts.
Once he played chess with a man whom he wanted to turn from his evil ways. He made a bad move, and when his opponent took advantage of it, he begged to replay it. The man consented. A while later, the same thing happened again, but this time his opponent refused to let him replay it, "I let it pass once, but this time it must count." The tsaddiq replied, "Woe to the man who has crept so deep into evil that prayer can no longer help him turn." The man stared at him, silent, motionless, with his soul on fire.
On Checkers:
Rabbi Nah.um of Stepinesht, the son of the Ruzhiner, once walked into the studyhouse on H.anukkah and saw his disciples playing checkers. Embarrassed, they stopped. He asked them about the rules. They still remained silent. So he answered, "The first rule is that you cannot make two moves at once. The second rule is that you can only move forward, never backward. The third rule is that once you reach the last row, you may move wherever you like."
-Rabbi Michael Rascoe
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