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 said multiple vorts this evening on the topic of Eved Ivri. He began by quoting the Gemara in Kiddushin which states that a master must treat his Eved Ivri as an equal. If the master eats refined bread he cannot give his Eved coarse bread. And if the master sleeps on a mattress he must give the same to the Eved and not have him sleep on straw. The Gemara then remarks that a person who acquires an Eved Ivri has acquired a master of himself.
Tosafos asks the obvious question - why has he acquired a master, his obligation is only to treat him as an equal! Tosafos answers by quoting the Yerushalmi which explains that the Eved is the "master" in a situation where there is only one object. If there is only one pillow he cannot keep it for himself as that will put the Eved on a lower level. Nor can he say that no one will use it as that is Midas S'dom.
R' Frand then quoted the Abir Ya'akov who asked why the law of Chayecha Kodmin (the rule that when two people are in equal need, your life takes precedence) does not apply? He answers that the rule cannot apply when the result will cause someone to be on a lower level. If the master does without a pillow he will be uncomfortable. But if the Eved does not have it and the master does, it will be demeaning to the Eved.
R' Frand also discussed the concept that an Eved Ivri is given a Shifcha to live with, but when he leaves, the Shifcha and children stay with the master. Why? R' Frand quoted R' Matisyahu Solomon [who should have a refuah sheleima] who explains that it is meant to teach the Eved about the personal value of objects. A man becomes an Eved Ivri when he has stolen and can't repay. Often the thief has no concept of the emotional attachment that his victim has to the possession. When he now has to leave the master but cannot take the Shifcha and children with him, he feels a loss of something he was connected with.
R' Frand said a cute vort from the Chizkuni on the pasuk in Shemos 21:6 - וְהִגִּישׁ֤וֹ אֲדֹנָיו֙ אֶל־הָ֣אֱלֹהִ֔ים וְהִגִּישׁוֹ֙ אֶל־הַדֶּ֔לֶת א֖וֹ אֶל־הַמְּזוּזָ֑ה וְרָצַ֨ע אֲדֹנָ֤יו אֶת־אָזְנוֹ֙ בַּמַּרְצֵ֔עַ וַֽעֲבָד֖וֹ לְעֹלָֽם. The Gemara teaches that his ear is pierced because the Eved had heard the First Commandment but chose to be a slave to a mortal. Hashem is saying to him - I took the Jews out of Egypt from being slaves and in so doing I even shortened the length of the Shibud from 400 years. You chose to stay a slave - so we will use a מַּרְצֵ֔עַ which has a gematria of 400.
The final vort that R' Frand said was a thoughtful take on why the master is the one who does the piercing. He quoted R' Shach who explained that the Eved stays with the master because he claims that he loves him. The best person to give mussar to someone is a person who he loves as it will be most likely to be well received.
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