The way of tzaddikim; the way of the Torah
Once Yitzchak approached the age that his mother was when she passed, he felt it was time to settle his affairs. He decided to give incredibly powerful berachos, blessings, to his favorite son Eisav. However, to get into the proper state of mind to give these blessings, Yitzchak wanted to have a meal made up of his favorite delicacies. Eisav was an expert trapper. So before receiving these blessings, Yitzchak sent him on a hunting mission. He told Eisav to take his instruments with him and go. Rashi is bothered that one doesn’t need to tell an expert hunter to take along his weapons, just like a plumber doesn’t need to be told to bring his wrench. Therefore, he interprets the command שא-נא, literally please carry, as השחזה, sharpen. Yitzchak was telling Eisav to sharpen his knives. Why? Yitzchak was worried that when Eisav did shechitah, ritual slaughter on the animals he catches, the knife might have a blemish which would go unnoticed. Slaughtering with this knife would render the food forbidden to eat.
On the surface, it would appear that Yitzchak was concerned that Eisav wasn’t careful with the laws of kashrus. This is why he had to instruct him to take great care with the food he was about to prepare. The problem is, earlier we are taught that Eisav was איש יודע ציד, a man that knows how to trap. Read literally it is self-understood, but figuratively it is also teaching us that Eisav was a master con artist. He would ask his father questions that would make him appear to be scrupulous with the observance of mitzvos. The verse continues and says that Yitzchak loved Eisav (more than Yaakov), because ציד בפיו, trappings were in his mouth. On the literal level it means that Yitzchak enjoyed the food Eisav hunted. Figuratively however, it means that Eisav fooled his father into loving him. Eisav had successfully manipulated his father into thinking he was an extremely righteous individual. How then could Yitzchak ever suspect that his beloved, favorite son would feed him something that wasn’t kosher?
Rav Yerucham Levovitz, the former mashgiach of Mir, gives a very terse answer, which makes it difficult to understand what he means. Yitzchak’s concern wasn’t coming from doubts to the sincerity of his son. He would have asked the very same thing if it was Yaakov who was going to hunt for him; he would have asked it of any righteous individual. Why then did he make this request? He writes: כי כן דרכן של צדיקים, this is the way of tzaddikim, righteous individuals, וכן הוא סדר התורה, and this is the way of the Torah. What does Rav Yerucham mean? The way of tzaddikim is to constantly remind others to follow Jewish law? Definitely not. To bring out the point, there’s a mitzvah of בצדק תשפט עמיתך. There is a religious requirement to judge others favorably, and not to assume they’re doing something improper. The halacha is, if a person is deemed to be a tzaddik, and they appear to be doing something improper, the mitzvah obligates one to assume that they are doing the right thing; there must be some misunderstanding. How then could Yitzchak suspecting Eisav, who was at this stage a presumed tzaddik, be the way of the Torah? It seems against the Torah!
Cleary then, it must not be an issue of judging favorably or not judging favorably. There must be some other reason Yitzchak is warning his son about the laws of kashrus. It’s based off a profound principle in relationships. When something or someone is very, very important to a person, they stay very, very far away from anything that can hurt it. Not just because they’re concerned that something might hurt it, but that is the way that human beings convey value. The way we express that something is important to us is we keep it very far from anything that could damage it. An illustration that demonstrates this: Let’s say, somebody gave you a $5000 glass plate as a gift, and you want to now transfer it to your home. Would you hold it with one hand? Would you continue a phone conversation with the other hand? Would you use this opportunity to go for a run? For sure not. The way you would treat a $5000 plate, is that you would wrap it twice in newspaper, once in cotton, hold it with both hands, walk very slow. Not because you actually think anything will happen to it. Rather, because that’s part of the honor that you give to something that’s so precious. The same is not only true with objects, but the same is with relationships. If someone is very dear to you, you don’t only avoid things that cause them pain. You show your love, by creating a distance between you and those things that cause them pain. Every inch that you add between you and the things that cause them pain, is your way of saying: “I love you”. It’s your way of expressing how precious they are to you.
In Jewish thought, the relationship between G-d and the Jews is akin to that of a husband and wife. There are certain things, that for whatever reason, He does not want us to do. If the relationship really means something to us, then we won’t casually play with the $5000 plate. Not because we’re afraid we’re going to drop it. When Yitzchak requested his son Eisav be careful with the shechitah, he didn’t really think anything would go wrong. He was merely demonstrating how dear his relationship with Hashem was. He was expressing this dearness by creating a distance between himself and anything that could have damaged that relationship. That’s the way of tzaddikim. That’s the way of the Torah.
 Based on a shiur by Rabbi Leib Keleman, which can be heard here: http://simpletoremember.com/media/a/landofintimacy/
 Based off Rashi ad. loc. Literally, your hanging things. It’s not clear to me why Rashi makes it singular when the original word is plural
 Genesis 27:3
 verse 2 with Rashi
 See note 11
 to Genesis 27:3
 Be’er BaSadeh ad. loc.; cf. Maskil LeDavid ad. loc.
 Quoting Bereishis Rabbah 65:13
 Since it would have the status of a neveilah, whose consumption is prohibited from Leviticus 17:15, 22:8
 Genesis 25:27
 Rashi ad. loc.; Minchas Yehudah ad. loc., based on the explanation of the Mizrachi, explains that if it was only to be understood literally, the verse should have simply said that Eisav was a איש ציד. The phrase יודע ציד is superfluous. Also, the verse is contrasting Eisav with Yaakov, who was known as a איש תם. Rashi ad. loc. says that means that due to his innocence he doesn’t know how to scam others. According to this explanation then, Eisav being a con artist teaches us that he was the exact opposite of his brother Yaakov.
 ibid verse 28
 Rashi ad. loc, quoting Midrash Tanchuma Toldos § 8.
 Gur Aryeh to Rashi on Genesis 27:3. See there for his approach to this question. Cf. Mizrachi ad. loc.
 Da’as Torah ad. loc.
 Leviticus 19:15 with Rashi
 See Chofetz Chaim Pesichah – Asin § 3 with Be’er Mayim Chaim
 For example, Song of Songs with the commentary of Rashi
 I’m confident that Rabbi Keleman got this explanation for the words of Rav Yerucham from his rebbe Rav Shlomo Wolbe, who heard them live from Rav Yerucham