A single word in the Torah can make a great deal of difference. So is it with the introduction to the sin-offering brought by a nasi, the political leader of the nation or tribe (4:22). As opposed to the high priest, the nation (understood to mean the high court) or the individual – about all of which the Torah says “if (eem) they sin” – the Torah writes about the nasi, “when (asher) he sins.” 

Some commentators says that asher can also mean, if (Rabbenu Bachya) or that the reason the word appears with the nasi is an indication that he is a subset of the previous group, which is the nation (Ibn Ezra). While they may technically be right, that the Torah chose to express this in such an anomalous way makes it ripe material for interpretation.  

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The simplest interpretation is that this indicates that a political leader is more likely to sin than any of the other categories mentioned. Rabbenu Bachya also presents this as a possible understanding, explaining that a political leader is prone to haughtiness and lacks the intrinsic balances that generally keep religious leaders in check. It is true that Torah creates extrinsic balances – such as taking a Torah with him wherever he goes – for the highest type of nasi, the king. Nonetheless, it is understood that the power and prestige that comes with the office will still engender much temptation to sin. And so were even the greatest of Jewish kings challenged.  

And yet the Gemara turns this teaching around, relating to the fact that “when” is more often written as ki than as asher. If so, says Rabbi Yochanan ben Zakkai, the word, asher, could be understood to remind us of the word, ashrei, happy. Obviously, sin and happy are not words that go together well. But, says Rabbi Yochanan, when people admit to and atone for their sins, that is cause for happiness. And if that is generally true, it is even truer when the penitent is the nasi (Horayot 10a).  

What both interpretations have in common is the recognition that sin is an occupational hazard for a leader. But whereas the first understanding simply recognizes that fact, the second finds its redemptive value: We all know the great value the Jewish tradition puts on teshuva, repentance. As is well known, the penitent is viewed as someone who has accomplished what the totally righteous person cannot. This not only has a private side, but a public side to it as well. For when someone has sinned and then says that they he regrets it, it impacts on the popular evaluation of sin. This, because the temptation of sin is only as great as the benefit seen coming from it. When someone who has sinned sincerely says they wish they had not done it, it devaluates the sin’s perceived benefit.  

So while a political leader is not likely to be a paragon of virtue, it is exactly this shortcoming that allows him to teach the rest of us about the relative benefit of sin. And it is perhaps for this reason that we judge a Jewish leader by how quickly and whole-heartedly he is willing to repent. For it is known that more than anything else, what separated David from Shaul was David’s immediate acceptance of guilt. As even though it took very little time for Shaul to accept his guilt, the slightest moment of hesitation can make all of the difference. For as soon as there is hesitation, the ensuing repentance’s public impact is compromised. The hesitation means that there is a side to think that the sin was worthwhile, even if that is not the conclusion. Hence, even if sin may not be worth it, the penitent only reinforces our view that there is enough benefit to make it worth giving a second thought. 

A leader need not regret mistakes he has not made. But neither should he avoid seeking out the ones he has. Common wisdom may see a leader’s willingness to find his own faults as a political weakness. Yet the example of David and Shaul shows that a Jewish political leader can never be successful if he is not cognizant of his ethical responsibilities. And apparently among the most important of these responsibilities is to be enthusiastically self-critical.  

For it is only such a leader that the Jewish people can look up to with happiness.  

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Rabbi Francis Nataf (www.francisnataf.com) is a veteran Tanach educator who has written an acclaimed contemporary commentary on the Torah entitled “Redeeming Relevance.” He teaches Tanach at Midreshet Rachel v'Chaya and is Associate Editor of the Jewish Bible Quarterly. He is also Translations and Research Specialist at Sefaria, where he has authored most of Sefaria's in-house translations, including such classics as Sefer HaChinuch, Shaarei Teshuva, Derech Hashem, Chovat HaTalmidim and many others. He is a prolific writer and his articles on parsha, current events and Jewish thought appear regularly in many Jewish publications such as The Jewish Press, Tradition, Hakira, the Times of Israel, the Jerusalem Post, Jewish Action and Haaretz.