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Why does the Midrash suggest Erev Rosh Hashanah has equal power to Yom Kippur for forgiveness? Erev Rosh Hashanah serves as both the final day of the year being judged and preparation for coronating Hashem (ה׳). Proper cheshbon hanefesh on this day can transform how the entire previous year is viewed, since 'hakol halach achar hagmar' - everything follows the conclusion.
Rabbi Yeshaya Greenberg ZT"L begins by examining a Midrash that questions why the Torah (תורה) refers to the first day of Sukkos (סוכות) as 'the first day' rather than simply stating the 15th of Tishrei. The Midrash explains this through a parable of a province owing taxes to a king, where forgiveness comes in thirds as the king approaches: the great people secure forgiveness of one-third, the average people another third, and when everyone comes out, complete forgiveness is granted. Applied spiritually, this means that when the gedolim fast on Erev Rosh Hashanah, Hashem (ה׳) forgives one-third of Klal Yisrael's sins; during the period from Rosh Hashanah through Yom Kippur, another third is forgiven; and on Yom Kippur itself, the final third is forgiven. The first day of Sukkos is called 'first' because it begins a new accounting of sins, as people are too busy preparing for the holiday to transgress. The Beis Yosef raises a troubling question about this Midrash: it seems to suggest that Erev Rosh Hashanah is as powerful as Yom Kippur in terms of forgiveness, and more powerful than Rosh Hashanah itself, since Rosh Hashanah is merely grouped with the other days of the Aseret Yemei Teshuvah. He resolves this by explaining that the forgiveness operates qualitatively rather than quantitatively - Erev Rosh Hashanah forgives the easiest sins to forgive, the middle period forgives more difficult sins, and Yom Kippur forgives the most challenging transgressions.
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Parashat Nitzavim - preparation for Rosh Hashanah
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