The Torah records two occasions when the Jewish people entered into a covenant (brit) with G-d regarding observance of the mitzvot. The first covenant was at Har Sinai and the second was in the Plains of Moav, just before the passing of Moshe Rabbeinu. Parshat Bechukotai describes the covenant made at Har Sinai; the covenant that occurred right before the Jews entered Israel is found in our parsha, Ki Tavo.
Why was there a need for a second covenant? If the covenant at Sinai was legally binding, what dimension was added with the brit of Ki Tavo?
Rav Herschel Schachter explains that this second covenant is not only binding on the individuals present at that time, but on all future generations as well. The covenant at Sinai was only binding on those individuals who were present. (This could be the impetus for the Midrashic caveat that ‘all souls were present at Sinai.’)
The concept of "Am Yisrael" only emerged in its fullest sense once the Jewish people entered Eretz Yisrael and acquired their own national homeland. For a covenant to be binding on future generations, it must be entered into by a nation; a nation to which future generations will still belong. The covenant of Ki Tavo was only begun by Moshe Rabbeinu, and was really completed by Yehoshua bin Nun at Har Grizim and Har Eival. The principle of arvut (that all Jews are held responsible for each other because they all constitute one entity) only started after the declaration of the blessings and curses at Har Grizim.
The verses in Bechukotai are written in the plural, as opposed to the text here in Ki Tavo, where all of the pesukim appear in the singular. The Vilna Gaon notes that when a parsha appears twice, once in the singular and once in the plural, the parsha in the singular is addressing all of the nation as one entity, while the one in the plural is addressing each and every individual. In our case as well, Parshat Bechukotai has the text of the covenant made with each individual Jew, while in Ki Tavo the text of the covenant made with Klal Yisrael is as one entity - one nation.
Ezra HaSofer instituted that we read Ki Tavo close to Rosh Hashanah. Perhaps this is because an important way to prepare for the High Holidays is by deepening our connection to community, to Klal Yisrael. On Rosh Hashanah and Yom Kippur we are judged as individuals. But the nation as a whole is also judged. Tradition teaches that the nation as a whole is guaranteed forgiveness from Hashem. This was indicated in the times of the Temple by the red string turning white on Yom Kippur. Individuals cannot be assured of atonement. We need to earn it through teshuva, tefilah, tzedaka, etc. At the same time the more we connect, identify and support the community, the more we can benefit from the Divine guarantee of national atonement.
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