A person who is in a position of power, whether it be a judge, employer, parent, or teacher should be careful about allowing his natural instinct to make unconscious judgments about others. Before he has had a chance to make a considered evaluation he may be inclined to favor some people and disfavor others.
The tendency to show favoritism may be so subtle that he doesn’t even realize it. He may fool himself into believing that he is justifiably rewarding good behavior and discouraging bad behavior by means of his body language, his smile, and his choice of words.
However, those who look to his favor will be watching him very carefully for any sign of prejudice, whether it is justified or not. If he is not careful, he will be achieving an effect that is the opposite of what he was hoping for.
Anyone in a position of authority is advised to cultivate a carefully managed neutral attitude so that those dependent upon his fairness will feel that justice is being done and their honest efforts to earn his goodwill have been rewarded.
ה = שְׂאֵת פְּנֵי רָשָׁע לֹא טוֹב לְהַטּוֹת צַדִּיק בַּמִּשְׁפָּט
To show favor to a Rasha is not good,
it distorts justice for the Tzadik.
The proverb compares the effect of favoritism on both worthy and unworthy people. For this purpose, the one that is worthy is referred to as a Tzadik (righteous person) and the one that is unworthy is referred to as a Rasha (evildoer). However, these are merely labels of convenience and in practice they refer to people who deserve an unfavorable judgement (Rasha) and those who deserve a positive judgement
The proverb first considers the Rasha for whom the misguided judge has unconsciously decided to show favoritism. In his mind, the judge thinks of the Rasha who has come before him as having good qualities. But because the verdict is guilty, Mishlei describes the net effect as not good. Besides the failure to treat the Rasha as he should be treated, the other party will resent the unfairness and it will distort his trust in the fairness of the judicial system. That lack of confidence in being properly treated may even negatively influence the future behavior of the Tzadik.
(5) Favoring the Rasha — שְׂאֵת פְּנֵי רָשָׁע
is not good — לֹא טוֹב
even if the Rasha has good qualities.
Because of the distorting effect —לְהַטּוֹת
upon the Tzadik in relation to justice — צַדִּיק בַּמִּשְׁפָּט
 When a Rasha has good fortune in this world, he should not feel vindicated. On the contrary, he will have to face the bitterness of a harsh judgment in the next world. (רש”י, מצודות)
 The phrase “not good” applies to both parts of the proverb. (מצודות)
 If one party to a dispute sees that the other party is being favored, he is likely to become discouraged and he may fail to prepare his case properly. (רלב”ג)
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