Our parashah details the epic meeting of Yaakov and Eisav, the older brother who never forgave his twin for taking the blessings of their father Yitzchak. Due to the danger that hovered over him, the Torah describes how Yaakov took a number of preventative measures: Prayer, military tactics, and the preparation of a gift to appease the threatening Eisav.

Not only did Yaakov give his brother a generous gift. In convincing Eisav to receive the tribute, he also found it appropriate to offer the following words of praise (Bereishis 33:10): “No, I beg of you! If I have now found favor in your eyes, accept my tribute from me, inasmuch as I have seen your face, which is like seeing the face of a Divine being, and you were appeased by me.” This comes after Yaakov, together with his wives and his children, bowed before Eisav upon first encountering him.

The form of appeasement offered by Yaakov to Eisav raises an interesting halachic question. As we will see below, it is forbidden to flatter the wicked; according to some, this involves a full Torah prohibition. How, in this case, did Yaakov see it right to flatter Eisav, referring to his countenance as that of a Divine being, and prostrating himself before him? Is this not a case of forbidden flattery?

The Prohibition of Flattery

The Gemara uses the most severe language to illustrate the prohibition of flattering the wicked: Once, when King Agrippas, (who was disqualified by maternal lineage from being king over Israel) read in the Torah: “You shall not appoint over yourselves a foreign man,” his eyes flowed with tears, for he knew that he was a slave (and therefore unfit to rule). The wise of Israel told him: “Do not fear, Agrippas—you are our brother!” The Gemara writes that on account of this forbidden flattery, Israel’s destruction was decreed, Heaven forbid.

Tosfos explain that the elders of Israel sinned in flattering Aggripas: Although he was unfit to rule over Israel, they affirmed his position as king. Tosfos write further; even if the wise were unable to protest his appointment, they ought not to have affirmed his position. Rather, they should have remained silent: “This is the punishment for flattering a sinner’s sins, out of fear of the sinner, while disregarding the fear of God, and making the Divine eye as though it does not see.”

Chazal continue to denigrate the “band of flatterers,” to the extent that it is considered one of the groups that “does not receive the face of the Shechinah“. On the other hand, we also find a statement of Chazal that seems to lessen the severity of the prohibition: “It is permitted to flatter the wicked in this world.” Indeed, Reish Lakish learns this from the flattering words that Yaakov used in speaking to his brother Eisav: “I have seen your face, which is like seeing the face of a Divine being.”

On the one hand, we find that the Chafetz Chaim, in his introduction to Sefer Chafetz Chaim (la’vin, 16), treats flattery as a full Torah prohibition, as based on its inclusion in Yere’im’s list of mitzvos (mitzvah 248). On the other hand, there are instances in which it is permitted to flatter the wicked, as we find concerning Yaakov Avinu.

To understand this matter fully, we need to study the concept of forbidden flattery. How is the prohibition of flattery defined, and what are the details involved?

Flattery When in Danger

There is a statement of the Gemara: (Sotah, loc. cit.) “One who flatters his fellow, will eventually fall into his hands”. (One who flatters the wicked will ultimately fall victim to his wickedness) Tosfos writes that the above mentioned prohibitive statement is limited to ordinary circumstances. In times of danger, however, the prohibition does not apply.

Tosfos bring proof to this principle from the following anecdote, which is recorded by the Gemara in Nedarim (22a)

Ula was travelling to the land of Israel, accompanied by two people from Chozai. On the way, one of them rose up, and killed the other. He [the murderer] said to Ula, “Did I act properly?” Ula replied: “Yes, and cut his throat!” When he came to Rabbi Yochanan (in the land of Israel), he asked him, “Perhaps, Heaven forbid, I strengthened the hands of sinners?” He replied: “You saved your own life.”

According to Tosfos, it thus emerges that the prohibition of flattering the wicked applies in circumstances of fear, but not in conditions of danger. This explains why Yaakov Avinu flattered his brother Eisav: He was not troubled by the prohibition of flattering the wicked, because the flattery was required to save him from danger.

However, we find that Rabbeinu Yonah, who lists nine categories in the “band of flatterers,” writes that the most heinous of them is one that justifies a sinful act. This form of flattery, according to Rabbeinu Yonah, is forbidden even in dangerous situations (Shaarei Teshuva, part 3, no. 187-188). This stringent ruling is quoted by the Chafetz Chaim (op. cit.)

This ruling appears to be difficult to comprehend. Beyond the three cardinal sins, we do not find an obligation of sacrificing one’s life for any mitzvah or aveira. Why, then, should one be obligated to endanger himself for the sake of avoiding the prohibition of flattery? Even the above statement of Tosfos, which permits flattery when in danger, requires scrutiny: Obviously one may flatter the wicked in places of danger; all mitzvos are waived in place of danger! What chiddush is there in the words of Tosfos?

A number of commentaries (see Yad Ketanah, De’os 10:13; He’aros of Rav Elyashiv, Nedarim) suggest a distinction between an imminent danger, and a distant, remote danger. Rabbeinu Yonah agrees that there the prohibition of flattery would not apply in circumstances of immediate danger. However, he maintains that the prohibition does apply when the danger is remote. According to Tosfos, the prohibition does not apply even in cases of remote danger. ((Be’er Sheva))

Loss and Damage

The explanation above is sufficient to explain the action of Yaakov Avinu‘s flattering his brother Eisav. Because the situation involved no slight danger, it was permitted for him to flatter his wicked brother.

Does the same apply to a concern for physical harm or financial loss? According to Yere’im (mitzvah 248) who lists the prohibition of flattery as one of the 613 mitzvos, the prohibition does not apply when there is danger of loss. The prohibition of “telling the wicked, ‘you have done no wrong,'” applies only for one who flatters out of wickedness, or out of concern for losing love or respect, but not when there is concern for physical harm or for material possessions.

According to the distinction we made above (between an imminent and remote danger), even Tosfos can agree with the ruling stated by Yere’im. According to Tosfos, not only is it permitted to flatter the wicked in circumstances of imminent danger, but even in cases of remote danger, such as the anecdote of Ula, it is permitted to flatter the wicked. Hence the prohibition of flattery does not apply when threatened by physical harm or material loss.

We can thus understand the statement many by Chazal that “it is permitted to flatter the wicked in this world,” which seems difficult, for surely it is forbidden to do so? According the ruling of Yere’im, there is no difficulty, for it is permitted to flatter the wicked in circumstances of potential loss and danger.

Defining the Prohibition of Flattery

Iggros Moshe (vol. 2, Orach Chaim, no. 51) explains the basic definition of the prohibition of flattery:

A renowned American doctor was also a philanthropist who made large contributions to Jewish causes. He was married to a non-Jewish woman. Because of his marital status, he was not called up for Torah readings, a matter which deeply offended him. He thereby threatened the shul and community with significant financial loss. The question addressed to Rav Moshe was whether it would be permitted to call up the doctor to open the Aron Ha-Kodesh.

Rav Moshe opens his response by quoting the above mentioned words of Tosfos, who entertain the possibility that one would be obligated to endanger himself for the sake of avoiding the prohibition of flattery. The reason for this, Rav Moshe explains, is the stringent ruling of Maharshal, who writes (Yam Shel Shlomo, Bava Kama 4:9) that the prohibition against warping Torah teachings (megaleh panim ba-Torah) applies even in cases when a person’s life is threatened. The reason for this is that one who warps and misquotes Torah teachings is considered to be contradicting the Torah of Moshe.

Tosfos conclude that flattery is permitted in circumstances of danger, because flattery does not involve changing the Torah, similar to the case of Ula who said “you have acted properly,” yet did not change any Torah teaching. However, Rav Moshe extracts from here that the fundamental prohibition of flattery only applies to instances in which a person voices his agreement to a wrong or sinful act:

The entire prohibition of flattery is only in a situation where agreement is given to a prohibition or to a false law, such as the case of Aggripas, in which they told him, “you are our brother,” thereby proclaiming his worthiness for ruling as king. They were not obligated to give up their lives, therefore they were punished, for they had no reason to fear for their lives… but concerning flattery in matters that do not involve agreement to prohibitions and wicked deeds, it is possible that there is no prohibition at all. For instance, praising a person for his beauty and his wisdom in worldly matters, or for his positive character traits, even if one exaggerates; it is possible that there is no prohibition involved here, because this is not found in the Gemara.

Based on this premise, Rav Moshe rules that it is permitted to call up the intermarried doctor to open the Aron, which is only a matter of honor, and in which there is no declaration of agreement to his misdeeds. Everybody knows why he is being honored, and therefore calling him up does not involve the prohibition of flattery. Rav Elyashiv (quoted in Moriah, vol. 22, p. 65) has also written his basic agreement with this principle. ((However, Rav Elyashiv added that although there might be no prohibition of flattery, there would remain a problem of denigration of the Torah, in using the Torah for matters of fundraising.))

Flattery in Daily Living

It should be noted that the prohibition of flattery is pertinent to daily living, and is more common that we might think.

Chafetz Chaim gives an example: “For instance, somebody who intends, while speaking lashon hara, to flatter those who hear him because he knows that they already hate the object of his scorn, and wishes through this to find favor in their eyes.” As Rabbeinu Yonah writes (fourth section), even joining the wicked, without explicitly praising or affirming his wicked deeds, is considered a transgression of the prohibition of flattery.

The following example is given in Lere’acha Kamocha (1:2): “While undergoing dental treatment from a famous specialist, who was also well-known for his wickedness in all matters concerning Torah and mitzvos, the patient commented: ‘You are very humane and considerate… there should be many like you in Israel!'” The final statement, which praises the wicked in a religious context (“there should be many like you in Israel!”), transgresses the prohibition of flattery (third section of Rabbeinu Yonah).

Another example is (similar to the case of Rav Moshe) of a Jew married to a non-Jewish woman, with whom he bears a child. Rav Chaim Pinchas Scheinberg ruled that it would be prohibited to offer such a Jew the traditional greeting of mazal tov, because this would be considered a transgression of the prohibition of flattery.

Commenting on the prohibition, Chafetz Chaim thus writes (Mishnah Berurah 239:9) that one must be very careful concerning this severe prohibition, stating that before one retires for the night, one should make sure to scrutinize the deeds of the day, and repent for any sin: “In particular, common sins such as flattery, falsehood, mockery, lashon hara, and the sin of bitul Torah, require special scrutiny.”

Positive Flattery

It is important to add that not all flattery is prohibited or negative; there is even a form of flattery that is considered a mitzvah. This is stated by Yalkut Shimoni (Kuntress Acharon, no. 28): “A person must flatter his wife, for the sake of marital harmony, and his creditor, so that he shouldn’t press him, and his rabbi so that he should teach him Torah.” Orchos Chaim (Gate of Chanifus) quotes the instruction, adding that anyone who believes that another will be drawn to him, and to the fulfillment of mitzvos; yet if he will approach him with anger he will not heed him, and will only accept his rebuke by means of flattery—it is a great mitzvah to flatter him, in order to ‘bring out the precious from the lowly’.

Like many Torah precepts, in particular those that are pertinent to character traits and to everyday actions, the division line that separates between permitted and forbidden, between a mitzvah and an aveirah, can be extremely thin. It is our duty to be wary of staying on the right side of the line, and to act with due caution and consideration.

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