Rashi comments on the verse (Devarim 20:8):
“‘The fearful and fainthearted’: Rabbi Akiva says: It is to be understood literally—one who is unable to stand in the ranks of battle and see a drawn sword. Rabbi Yosi HaGelili says: One who is afraid because of the sins in his hand. Therefore, the Torah provided him with the possibility of returning because of a house, a vineyard, or a wife, in order to conceal those who return because of sins in their hands, so that people should not realize that they are sinners. When someone sees him returning, he will say: Perhaps he built a house, planted a vineyard, or betrothed a woman.”
We must understand why Rashi brings two interpretations. Seemingly, the meaning of “the fearful and fainthearted” is straightforward.
The explanation is that a question arises in this verse. The “fearful and fainthearted” person can cause the hearts of his fellow soldiers to melt. If so, why is this category not mentioned at the very beginning of the passage, before the cases of one who “built a house,” and so forth, immediately following the warning, “Let your heart not be faint”?
To answer this, Rashi brings two interpretations.
According to the first interpretation, it is specifically immediately before the battle, when the sword is drawn, that fear is aroused in the heart of the fearful person. Therefore, “the fearful” is mentioned after the other categories, in direct proximity to the actual engagement in battle.
There is, however, a difficulty with this explanation: between the discussion of one who “built a house” and the statement concerning “the fearful and fainthearted,” nothing occurred that should suddenly cause the fearful person to become frightened.
Rashi therefore brings a second interpretation: “one who is afraid because of the sins in his hand.” According to this interpretation, the reason this category is mentioned at the end is in order to conceal those who are returning because of their sins. However, this is only Rashi’s second interpretation, because it does not follow the simple meaning of the words.
Rabbi Yosi HaGelili and Rabbi Akiva are consistent here with their general approaches elsewhere.
Rabbi Yosi HaGelili interprets verses in a number of places as referring specifically to one particular detail. Similarly here, he explains that “the fearful” refers specifically to one who is afraid because of the sins in his hand.
Rabbi Akiva, by contrast, interprets verses more broadly, in a manner that includes several possibilities. Here too, he explains that “the fearful” includes all forms of fear, not only fear caused by one’s sins.
There is also another reason for Rabbi Akiva’s view. Rabbi Akiva was accustomed to finding merit for the Jewish people. He therefore maintains that if a person is afraid because of sins in his hand, that very fear demonstrates that he regrets the sin. If so, he has already done teshuvah, and there is therefore no longer reason for him to fear because of those sins.
Regarding the awakening to teshuvah brought about by the shofar blasts during Elul, there is first a general awakening. This is alluded to by the tekiah, corresponding to Malchiyos. Afterwards, on Rosh Hashanah, one reaches higher levels of teshuvah, corresponding to Zichronos and Shofros.
Rashi alludes to this by bringing both interpretations.
He first brings Rabbi Akiva’s interpretation. According to Rabbi Akiva, it cannot be said that the person is afraid because of his sins, because he has already experienced a general awakening to teshuvah.
Yet this level alone is not sufficient. Rashi therefore afterwards brings the interpretation of Rabbi Yosi HaGelili, according to whom a general awakening to teshuvah alone does not suffice.