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's first vort was based on the writings of R' Immanuel Bernstein and related to the last of the Aseres Hadibros - Lo Sachmod. R' Frand quoted the Ibn Ezra who writes that many people have trouble with this mitzva. How can they be told not to be jealous when they see that someone else has something? The Ibn Ezra used a parable - there was a poor villager who sees the princess. He does not desire her, because he knows that it is impossible for a villager to marry the princess. Similarly, a man is not jealous of birds that they can fly. So too, a person who thinks, should realize that everything that he does not have is because Hashem does not want him to have it.
R' Frand said that this mitzva is about Emunah - what you have is what Hashem wants you to have and what you don't - it is because He does not want you to have it.
R' Frand also quoted the Medrash Rabbah on Parshas Kedoshim which provides a different view of this mitzva. The Medrash writes that Kedoshim was said at Hakhel, because the Aseres HaDibros are all contained or referenced in Parshas Kedoshim. But while the first 9 Dibros are easily found in Kedoshim, where do we see Lo Sachmod? וְאָֽהַבְתָּ֥ לְרֵֽעֲךָ֖ כָּמ֑וֹךָ - because if you really love someone, you are not jealous of what they have.
R' Frand compared it to the way that a person feels about their child - a parent is not jealous of what his child has, because he loves the child. And if you really love the other person, you won't be jealous of what they have.
R' Frand next quoted the Kotsker Rebbi who analyzes the Mishna in Pirkei Avos which asks - who is wealthy - one who is happy "B'Chelko." The Kotsker Rebbi reads the word B'Chelko as not referring to a person being happy with his own lot. Instead he reads it as being happy that his friend has his own lot.
R' Frand said a second vort also from R' Bernstein in connection with the miztvos that come after the Aseres Hadibros in Shemos 20:20-23 in which the Jews are told not to use metal to build their Mizbeach, not to make other gods and not to walk on steps to the Mizbeach.
These mitzvos are preceded by the statement אַתֶּ֣ם רְאִיתֶ֔ם כִּ֚י מִן־הַשָּׁמַ֔יִם דִּבַּ֖רְתִּי עִמָּכֶֽם - Hashem reminds them that He spoke directly to them, unlike any other religion where their "prophet" was the only one to speak with the "god" of that religion. And then the Torah references these three mitzvos, but why these three?
R' Bernstein explains that the Aseres Hadibros could be viewed as something that people deem logical or known. I understand that I should not kill, or worship another deity or commit adultery. But these three mitzvos show the sensitivity that a person should have. Yes - you may know not to kill, but you need to be so sensitive to this, that you don't use metal when cutting the stones that will be used in the Mizbeach.. You may know not to worship other "gods" but Hashem is proscribing making images of other "gods." Similarly, you understand not to commit adultery, but the Torah is saying don't walk on steps up to a Mizbeach so that covered areas are not revealed.
R' Frand quoted Rashi on the last pasuk in which Rashi states that opening up ones steps is being insensitive to the stones. And this is an a fortiori argument - stones don't feel disgrace, but still don't act with them in a disrespectful manner and how much more so with another person.
R' Bernstein asks why Rashi uses this Derush explanation? He answers that the take away from the Aseres Hadibros is not just the actual commandments - its that a person should act in a manner that there is not even a glimmer of this in your daily life.
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