DEUT1222 The ninth category [of flattery] consists of one who honors the wicked by way of courtesy. He does not speak well of the wicked man and he does not honor him in such a way as to lead others to believe that he respects him, or he will apportion him honor only in the manner that men honor the rich, by way of "preening" and expectation of gain because their ways have prospered and not because of their intrinsic worth. But herein, too, lies sin and wrongdoing, for though it is permitted to honor the rich, it is not so with the wicked. It is permitted to honor the wicked only on the grounds of fear, fear that they will cause injury or loss at a time when they have the upper hand. It was thus permitted to honor them as men honor the powerful, out of fear and fright by standing, deferring, and the like, but it was not permitted to praise them or speak well of them to others. And thus have our Rabbis of blessed memory said (Sotah 41b): "It is permitted to flatter the wicked in this world." And there are some wicked men whom it is not permitted to flatter, as we find in the case of Mordecai, who is told: "Flatter Haman," and who replied [this verse]: "Do not seek their peace or their good." And even when he was told: "Our Rabbis taught that it is permitted to flatter the wicked to keep the peace," he refused to accept it, as it is written (Esther 5:9): "And he did not stand or stir for him." A man should flatter his wife to preserve household harmony; his creditor, that he not press him; and his teacher, that he teach him Torah. And it is a great mitzvah to flatter one's students and friends so that they learn and listen to his words, to accept his rebuke toward the fulfillment of the mitzvos. Similarly, any man that one thinks he can draw to himself to listen to him to fulfill the mitzvos, who will not respond to severity, but who will accept his chastisement if flattered – – it is a great mitzvah to flatter such a man, to extract what is precious from what is base. There are some men who accept chastisement not through rebuke but through gentle speech, as it is written (Koheles 9:17): "The words of the wise, spoken gently, are heard." And there are some who must be rebuked, as it is written (Mishlei 17:10): "A rebuke enters more deeply into an understanding man." And there are some who require stripes, as it is written (ibid. 19:29): "And stripes to the back of fools." And there are some who even blows will not help, as it is written (ibid.17:10): "Than 100 blows to the fool." If so, what can be done with him? There is no remedy for him but banishment.
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