Musar for Proverbs 9:8
אַל־תּ֣וֹכַח לֵ֭ץ פֶּן־יִשְׂנָאֶ֑ךָּ הוֹכַ֥ח לְ֝חָכָ֗ם וְיֶאֱהָבֶֽךָּ׃
Reprove not a scorner, lest he hate thee; reprove a wise man, and he will love thee.
Shaarei Teshuvah
The third section: One who always mocks things and actions, but he does not intend to disgrace those associated with them. Rather he pushes off things that should not be pushed off and pushes off the [possibility of] results from actions that have hope for results. And about this is it stated (Proverbs 13:13), “He who disdains a thing will be injured thereby.” And they said (Avot 4:3), “Do not disdain any man, and do not discriminate against anything; for there is no man that has not his hour, and there is no thing that has not its place.” And what brought this scoffer to this bad trait is his being wise in his [own] eyes. And sometimes this trait brings a person to heresy, to mock the commandments - like the matter that is stated (Psalms 119:51), “Though the arrogant have cruelly mocked me, I have not swerved from Your teaching.” And this third section is a group that does not accept reprimand, as it is stated (Proverbs 9:8), “Do not reprimand a scoffer, for he will hate you.” And it is [also] stated (Proverbs 9:7), “To rebuke a scoffer is to call down abuse on oneself.” And it is [further] stated (Proverbs 19:25), “Beat the scoffer and the simple will become clever.” And that which causes this group not to listen to reproof is that the trait that leads to this [type of scoffing] is that a person is wise in his [own] eyes. And this trait controls him so much until he scorns the intellect of anyone besides himself. And it is a trait that has no hope, as it is stated (Proverbs 26:12), “If you see a man who thinks himself wise, there is more hope for a dullard than for him.”
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Shaarei Teshuvah
The seventh section: One who sees the people of his place [being] a stiff-necked people, and says in his heart, “Perhaps they will not listen if I speak [words of] integrity with them and fill my mouth with reprimands.” Hence he saves his mouth [from speaking]. Yet he surely bears his sin, for he did not try to reprimand and warn [them] - (indeed) [maybe] if the city is pitied, they will awake from the slumber of their stupidity and their error will not [continue to] lay with them. And our Rabbis, may their memory be blessed, said (Shabbat 55a) about that which is written (Ezekiel 9:4), “and set a mark (tav) upon the foreheads of the men that sigh and that cry, etc.”: The attribute of justice said, “[Even though these are full-fledged righteous people and keep the Torah,] it was in their hands to protest, and they did not protest. [The Holy One, blessed be He,] said, “It is revealed and known before Me that had they protested, they would not have accepted [it] from them.” [The attribute of justice] said, “Master of the Universe, if it is revealed before You, [they did not know if the people would listen to their voice or ignore them].” So afterwards God, may He be blessed, commanded (Ezekiel 9:4), “and begin from My Temple (Mikdash)” - and that is the dedicated (mekudash) righteous ones. And it is stated (Leviticus 19:17), “you shall surely reprimand your countryman and not bear sin because of him.” But if the matter is revealed to all, known, tested and analyzed that the sinner hates rebuke and will not listen to the voice of his teachers and will not bend his ear to his instructors - about this is it stated (Proverbs 9:8), “Do not rebuke a scoffer, for he will hate you.” And they said (Yevamot 55b), “Just as it is a commandment to say something that will be heard, so is it a commandment to not say something that will not be heard.” And they said (Beitzah 30a), “It is better that they be inadvertent, and not be intentional.”
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Shenei Luchot HaBerit
When Moses commenced to admonish the people, he spoke of their virtues and their accomplishments, that they were to present him with distinguished men who were to serve as judges, etc. (1,13). He did so because we know already from Solomon in Proverbs 9,8: אל תוכח לץ פן ישנאך, הוכח לחכם ויאהבך, "Do not rebuke the scoffer for he will hate you; rebuke a wise man and he will love you." You need to impress the person whom you wish to rebuke with the fact that you esteem him highly; otherwise he will not accept your rebuke. You must convince such a person that it is shameful for a person of his niveau to act in a manner that ruins his image.
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