The following is a brief summary of some of thoughts said over by R' Frand on the parsha this evening. I have attempted to reproduce these vorts to the best of my ability. Any perceived inconsistency is the result of my efforts to transcribe the shiur and should not be attributed to R' Frand.
R' Frand began this week's parsha vort by making reference to the rules of Eved Ivri - the Jewish born slave. The Torah teaches that the Eved Ivri can be provided by his master with a Shifcha Canaanis who he may live with. However at the end of his tenure as a slave, the Shifcha and any resulting children stay with the master.
The Gemara in Kiddushin instructs that in regards to personal luxuries, the Eved Ivri must be treated identical to his master. If the master is eating meat for dinner, the Eved must be given the same food. If the master sleeps on a soft mattress, the Eved cannot be given a straw bed and he must be allowed the same kind of mattress as his master. Similar rules apply to the bread and wine consumed. In each instance, the Eved must be given an equal level of luxury as his master.
The Tosasfos on the daf in Kiddushin takes this one step further in discussing the rules of pillows. If there is only one pillow in the house, it must be given to the slave. It would not be right if the master had a pillow and the slave did not, so the pillow must go to the slave. Why? Because the slave has a feeling of inferiority which will only be reinforced if he sees the master receiving luxuries which he himself does not enjoy.
R' Frand then asked - if the purpose of giving these things to the Eved is to place on him on equal footing with the master, why does the Eved have to forfeit the Shifcha and children when he goes free?
R' Frand quoted R' Matisyahu Solomon who explained that the concept of Eved Ivri exists in order to rehabilitate the slave. This man became an Eved Ivri because he stole from someone and could not pay back what he stole. The thief did not think about how a person has an attachment to his possessions and that the act of stealing the items broke the personal connection between the victim and his heirlooms. In order to teach him not to steal in the future, we show him what it feels like to forfeit something for which he has a strong personal connection - the Shifcha and children. When he protests that he has a connection with them, we remind the Eved that his victims had a personal connection too. Should the Eved decide that he wants to stay for an additional period, he must go to the door post to have a peg drilled through his ear - because he forgot that he once had heard in the Ten Commandments - do not steal.
R' Frand closed the vort by asking - why do we wait until the end of the period of slavery in order to teach this lesson? He answered that the concept of slavery is meant to teach the Eved a lesson as to respecting other's property. But if he does not learn the lesson, then we drill his ear.
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