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 the vort by noting that when Yehuda tried to convince Yosef to pardon Binyamin, Yehuda told him that if Binyamin would not return to Ya'akov it could cause Ya'akov's death. However, at this time Binyamin was already the father of ten children. Why didn't Yehuda try to appeal to Yosef's sense that these children could not live without their father?
R' Frand quoted the Sefer Pardes Yosef who linked this to a story involving the Kotsker Rebbi. A man came to him complaining that he was indigent, but had wealthy children who would not assist him. Meanwhile he had sacrificed to pay for their schooling and made sure that they had what they needed when they lived at home. Is there anything that can be done, he asked? The Kotsker responded that the mercy that a father has for his child is much greater than the mercy the child has for the father - as we see from Yehuda's plea to Yosef which invoked Ya'akov and not Binyamin's children.
He further noted that each Middah that a person has can be traced back to Adam HaRishon. Whether it is anger, or humility or jealousy, each Middah finds its genesis in Adam. However Adam lacked one Middah - he had no feeling of mercy towards his father, because Adam had no father. He had children and his feelings for them were implanted in the human DNA. But he had no concept of a father and as such we do not feel the way about our fathers as we do about our children.
R' Frand closed the vort by quoting the Shela who says that a mother can take care of 10 children, but 10 children cannot take care of one mother.
R' Frand said a second vort related to the children of Binyamin. He made reference to a Rashi in Mikeitz which provides the dialogue between Binyamin and Yosef in Bereishis 43:30. In so doing, Rashi relates that Yosef asked about Binyamin's children and he was told that each child was linked to Binyamin's feelings about his "lost" old brother. One of these children was Huppim - because Yosef did not see Binyamin's Chuppa and Binyamin did not see Yosef's.
R' Frand quoted the Pnei Menachem who cited the Mishna in Pirkei Avos 1:6 which states עֲשֵׂה לְךָ רַב, וּקְנֵה לְךָ חָבֵר. The Rambam explains that the friend who is referred to is someone that a person can share all of his experiences with - be it his triumphs or failures, with no fear that the person will think less of him because of these acts.
He further explained that we saw this in Parshas Vayeshev 38:20 in that Yehuda sent his "payment" with רֵעֵ֣הוּ הָֽעֲדֻלָּמִ֔י. The Pnei Menachem notes that this is the first time that the word רֵעֵ֣הוּ is used as friend in Chumash and we certainly see how much faith Yehuda had in his friend. This is the meaning of the Mishna in Pirkei Avos which prioritizes "buying" a friend vs "acquiring" a rav. Because a friend can be there for you throughout your life.
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