Pele Yoetz (Chanufa): The great evil of chanifa (flattery) is explicitly expressed in the Talmud and medrashim. A pure man – Rav Chaim Vital – has collected the relevant material in his holy sefer Sha’arei Kedusha. A G-d fearing man who studies his sefer will strongly oppose chanifa and this will be firmly implanted in his mind. Nevertheless it is necessary to clarify precisely what chanifa is. That is because there are types of flattery which are not prohibited as chanifa but those who lack proper halachic understanding insist that they are prohibited. For example they mistakenly consider a person who honors a wealthy man as being a flatterer while someone who protests against and ridicules the rich takes pride in his disparagement and claims that he does not know how to flatter. However he greatly errs in what he says because it is in fact proper and fitting to show respect to the wealthy – as we see that Rabbi Yehuda HaNasi and Rabbi Akiva honored the rich (Eiruvin 86a). The reason is that because G-d desires that this man be valued and He therefore has bestowed upon him an abundance of blessings from Above – we are also obligated to honor him. This is especially true for any person who has been the beneficiary of the rich person that he is clearly obligated to honor him. Furthermore the rich person since he has more possessions he is more likely to increase the amount of mitzvos and good deed that he does – compared to the less wealthy and this in turn reverses the spiritual damage done by his sins. Therefore it is appropriate to show him some respect - even if he has done something inappropriate and has deviated slightly from the correct path - and consequently he shouldn't demean the rich man as much as a poor man. We learn this from Pesachim (53a) where the Sages say, "If it were not that you are Todus we would excommunicate you." It is explained that they moderated their criticism because he provide food for Torah scholars.
In fact the prohibition of chanifa (flattery) applies only in two situations – the first is difficult while the second is even more so. The first situation is when someone who looks friendly and acts in a very loving manner – and yet his mouth and his heart are not the same. With his mouth he speaks words of peace while inside himself he is plotting to trap the other person. And even if he in fact is not the enemy and has no interest in harming the other in anyway - nonetheless every instance in which he appears to have greater love and greater respect for the other person then he actually feels – he has transgressed the sin of chanifa.
Nevertheless there is an exception to the first type chanifa of prohibiting acting and speaking differently then you feel. Our Sages have permitted this type of hypocrisy in dealing with one's spouse in order to have shalom bayis, one's teacher in order to learn Torah, and even with evil men in order to have peace and minimize disputes (darchei shalom).
However the second type of chanifa is evil and bitter and involves saying to an evil person that he is good and not chastising him or protesting against his evil act - even when he is capable of doing so. Not only will he be held accountable for the sinful transgression of the evil person – as if he had done it himself - but in addition he will be surely be punished for the major sin of chanifa. A pure person who fears G d should not show favoritism to the poor nor the wealthy or powerful nor should he act out of concern that he will lose honor or benefit. His sole concern should be to trust in G d that He will not withhold good from those who conduct themselves with pure faith. In fact all those who increase the honor of Heaven will find that their own honor increases and he will not lack what he needs. In fact he should roar like a lion and raise his voice like a shofar to protest against those sinners who might listen to him...
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