2

Rashi comments on שמות כא,ו, quoting the מכילתא and קידושין דף כב עמוד ב, that an עבד עברי who was sold into slavery due to stealing has a hole put in his ear for not listening to לא תגנוב and one in slavery due to selling himself must experience the same as he didn't listen to כי לי בני ישראל עבדים. Two questions:

  1. Why do you get this punishment for specifically these עבירות? This logic would seem to apply to all עבירות!
  2. Why do you only get this when choosing to stay after six years of slavery? You did this עבירה at the beginning of the six years!

I'm sure these questions are really famous...

2

Rav Hirsch points out that the punishment of being a slave is not for the purpose of punishment (as in a modern prison sentence), but is a method of repayment. In addition, it is to teach the transgressor of the necessity of proper behavior. This means that the six years of service and the seventh year of freedom are analogous to the six days of creation and the seventh day of shabbat or the six years of working the land and the seventh year of shmittah or the year of the Yovel.

The Jew who attempts to avoid being freed

belittles the dignity of being "doorposts", independently to bear on his own shoulders the burden of a home, and sells his freedom for the ease of "belonging" to some one and who has no ear for the call of Hashem to freedom and independence, his ear is bored to a door, in the presence of a "doorpost" and therebye the stamp of "belonging to a home" impressed on him. (cf. kiddushin 22b).

Thus, it is not that he refused to listen at the time of the original sale, but that he refused to learn the lesson of Yetzias Mitzraim and Matan Torah at the time when he refuses to go free. This punishment is midah keneged midah.

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