The Gates of Repentance

We touch now upon the third of the "four types" of egregious offenders, flatterers. The Hebrew term for "flatterers" can actually also be translated as "hypocrites" or the unwieldy but accurate "those who try to ingratiate themselves to others in order to curry favor with them". We’ll use the term most appropriate to the context from time to time. Once again, though, the astute reader will be embarrassed to find him- or herself so aptly singled out here!

There are nine sorts of "flatterers". The first kind (the "ingratiator") knows someone has done something wrong, or has been inconsiderate or even cruel to someone else and actually tells the perpetrator that he’s done nothing wrong (because he wants to get on his "good side"). This flatterer is considered an accomplice to a "crime", and could be said to be an enemy of truth.

The second kind goes out of his way to actually *praise* wrongdoers and to say things like, "You know, he’s actually a good fellow despite his flaws". While on one level that shows empathy for that side of each one of us that’s capable of wrongdoing, on the other hand it encourages wrongdoing per se. So while you might sympathize with the fact that they’d slipped and fallen, as Rabbeinu Yonah put’s it, "at least don’t bless them!"

The third kind at least knows to only praise wrongdoers to their face rather than to others. But still and all he validates the wrongdoer’s actions in his own eyes by complimenting him, and thus disallows him a chance to regret his ways and do teshuva (return to G-d).

The fourth kind not only doesn’t chastise wrongdoers-- they actually befriend them. But as Rabbeinu Yonah points out, quoting from the Talmud, "Birds dwell with their kind, and people dwell with others like themselves" (Babba Kama 92B); i.e., "Birds of a feather flock together". So a person’s having befriended a wrongdoer says something about him too.

The fifth kind of flatterer (or "hypocrite") is someone who’s trusted and depended upon by others who belies that trust, and recommends a friend or crony for an auspicious position (or for a partnership with someone, for example) that the friend isn’t qualified for. A world of damage often results from such situations.

The sixth kind is the sort of person who has a chance to gently point out another person’s faults and show how off the mark he is, but doesn’t. He doesn’t even look askance at what that other person does. What he does instead is "accept" it all passively (or with a wink of an eye). But as we’re taught, "Whoever can protest (against wrongdoing) in the world and doesn’t is held responsible for it" (Shabbat 54B), i.e., he’s a party to it on some level.

The seventh kind of flatterer sees people around him stubbornly doing harm and says to himself, "They’re not likely to listen to me anyway if I say anything about it, so why bother?" But the truth be known, he might very well be able to turn them around, and he’d miss the chance. Rabbeinu Yonah does point out, though, that certain wrongdoers are simply *known* to hate criticism, in which case nothing you’d say would do any good. It’s said in that instance that "Just as it’s a mitzvah to say something that will be listened to, so too is it a mitzvah to *not* say something that won’t be listened to" (Yevamot 65B).

The eighth kind would hear about people slandering others, speaking profanely, or demeaning Torah and would keep his mouth closed, because he too is convinced they wouldn’t listen to him (like the previous example). But this is one of those cases in which you’re obliged to stop associating with certain people-- people like this, in this instance. For otherwise you’d find yourself hearing what they had to say over and over again, to your spiritual detriment.

And the ninth kind show wrongdoers respect in order to be on good terms with them. And while this sort of flatterer doesn’t say anything good about those wrongdoers, and doesn’t show them the kind of respect that would lead others to think highly of them, what he’s doing is still ill-advised.

As we indicated above, the sensitive soul would take stock of just how often he finds himself telling wrongdoers they’re not doing anything wrong; going out of his way to praise or at least somehow endorse wrongdoers, to complement them, or to actually befriend them; recommending a friend for a position he or she isn’t really qualified for; not looking askance at but rather accepting wrongdoing on one level or another; saying to yourself about wrongdoers, "They’re not likely to listen to me anyway if I say anything, so why bother?"; keeping quiet in the face of slander and blasphemy; or showing wrongdoers respect in order to be on good terms with them.

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