The Mishnah (Sotah 41a) states that once every years during the Sukkot holiday following the conclusion of the Shemitta year, the Mitzvah of Hak’hel was performed. This Mitzvah entailed all Jewish men, women, and children traveling to Jerusalem to hear the king read the Torah. With Hashem’s help, if we merit Mashiach’s arrival this year, this Mitzvah will be fulfilled on the first day of Chol Ha’Moed Sukkot 5783. The Mishnah describes the observance of this Mitzvah:
“The Chazzan of the synagogue takes the Sefer Torah and passes it to the head of the synagogue (the individual decides who receives the Aliyot).He then passes it to the deputy Kohen Gadol who then passes it to the Kohen Gadol. The Kohen Gadol then passes it to the king. The king receives the Sefer Torah standing and then sits down and begins reading. King Agripas received the Sefer Torah standing and remained standing for the reading and was praised by the Sages. When he reached the verse, ‘You shall not appoint a foreign man upon you,’ his eyes began to tear. They told him, ‘Do not fear, Agripas. You are our brother!’”
Agripas was the son of a Jewish woman, but his father was a descendant of Herod, a slave who forcefully claimed the kingdom over the Jewish people. When Agripas reached the verse in the Torah prohibiting appointment of a non-Jew as king of Israel, he began to cry, for he knew that he was unworthy of the kingdom since his father was a slave. The nation comforted him by telling him not to worry and that he was their brother, for his mother was a Jew.
Nevertheless, it was actually forbidden to have appointed Agripas as king, for only an individual whose both parents were Jewish was worthy of this position. Thus, the Jewish nation having told him that he was their brother was an act of flattery, for this was not the will of Hashem.
Indeed, the Gemara states: “Rabbi Natan said: When the Jewish nation told Agripas that he was their brother, a terrible decree was pronounced upon them, for they had flattered Agripas.”
Our Sages speak lengthily about the prohibition to flatter someone who is acting against Torah law. The Gemara states, “Rabbi Elazar said: Anyone who acts with flattery brings anger to the world. Additionally, his prayers are not answered. Furthermore, such an individual falls to Gehinnom.” The Sages support these ideas based on verses.
The Rishonim wonder there was such great anger towards the Jewish nation for only having flattered Agripas. The Tosafot explain that the severity of flattering people who are acting in contrast with the will of Hashem is because “when one flatters an individual regarding a sin, one is doing so out of fear of the person, and this indicates a lack of fear of Hashem. One acts in a way that shows that, G-d-forbid, Hashem does not see what is happening.”
Based on the above, the primary prohibition of flattery applies to one who flatters a sinner, for instance, when one flatters a friend who is a successful businessman even though one is aware that he participates in forbidden matters. Similarly, if one flatters a well-known public figure even though one is aware that he is a wicked man, this constitutes the sin of flattery, for one is ignoring the honor of Hashem and showing respect to those who anger Him.
Nevertheless, there are some limitations to this prohibition, for Maran zt”l (in his Anaf Etz Avot, page 192) quotes Rabbeinu Shlomo Elgazi in his Sefer Me’ulefet Sappirim who writes that there is no prohibition to flatter the wicked when one is doing so to bring them closer to Torah (See Yabia Omer, Volume 2, Chapter 15). Even in this manner though, one must be sure not to praise him for his forbidden actions.
Summary: It is forbidden to flatter the wicked. When one flatters the wicked regarding actions that are contrary to the will of Hashem, this constitutes a grave sin for which the Gemara states that one does not merit greeting Hashem’s presence.
