In the Torah section of Mas’ei, we read (Bamidbar 35:31-33): “You shall not accept ransom for the life of a killer who is worthy of death, for he shall surely be put to death. You shall not accept ransom for one who fled to this city of refuge to return to dwell in the land, before the death of the priest. You shall not bring guilt upon the land in which you are.” In discussing cities of refuge to which those who accidentally commit murder should flee, the Torah warns that neither they nor intentional murderers should be allowed to pay money in order to be absolved from punishment, nor should anyone seek to flatter a distinguished or influential murderer by treating him leniently.
In commenting on the above verses, Nachmanides quotes the Sifre that states that the aforementioned verse is the source for the prohibition of flattering the wicked in order to ingratiate oneself.
We find a related comment on the verse (Bereshit 32:8), “Jacob became frightened and it distressed him” when preparing to meet his brother Esav despite being promised by G-d, “I am with you; I will guard you wherever you go” (Bereshit 28:15) and being reassured after leaving Lavan (see Bereshit 31:3). Our sages explain that Jacob was afraid that he may have sinned, thereby forfeiting G-d’s protection (Babylonian Talmud, Berakhot 4a). R. Shlomo Efraim of Lunchitz (1550-1619) wonders in his Kli Yakar on this verse what sin Jacob could have been afraid of doing in the eight days between having left Lavan and meeting Esav. The author of Kli Yakar suggests that Jacob was afraid that he was guilty of improperly flattering his wicked brother Esav when he sent messengers to him saying, “To my lord, to Esav, so said your servant Jacob” (Bereshit 32:5). Our Sages warn that one who flatters a wicked person will ultimately fall into his hands (Babylonian Talmud, Sotah 41b). This was Jacob’s fear, the author of Kli Yakar tells us.
It is related that R. Yisrael Meir Kagan, known as the Chafetz Chaim, once needed to write a letter to an anti-religious Jew to intercede in an important communal matter. Although he would normally act quickly and efficiently, the salutation of the letter took him days to write. The Chafetz Chaim feared flattering a wicked person just because his intervention was needed with the czarist officials on behalf of the Jewish community. Consequently, he grappled with writing a few lines of complimentary greetings to this man (Sholom Smith, A Vort from Rav Pam, p. 200).
As noted in the Sifre and confirmed by the great medieval scholar Nachmanides and later re-confirmed by the author of Kli Yakar and in modern times by the Chafetz Chaim, the Torah warns us: Do not flatter the wicked. We are to maintain our honesty towards ourselves and others. All too often, we are tempted to do otherwise in order to achieve a short-term gain. However, doing otherwise can skew people’s perception which in the long term will serve to be harmful rather than helpful. We are to maintain our honesty and the proper perspective on the world at large. This is the message of the Torah. This is the message of G-d. It is left for us to heed it.