Why is Rosh Hashana before Yom Kippur, it should be reverse, one should repent before being judged?
A couple of years ago we cited Rabbenu Yonah explains the avodah of Rosh Hashana is to give oneself a clean slate, a fresh start to be able to reconnect to Hashem. That is why Rosh Hashana precedes Yom Kippur for one can only do teshuva and make a real change if they don't bring their old baggage with themselves going forward. Why is that that the avodah connected to Rosh Hashana specifically?
Rosh Hashana is היום הרת עולם, the beginning of the world. Every Rosh Hashana the world goes back to a state of newness, a fresh beginning, and the shefa for the next year is provided for the world. The avodah of the day parallels that which is going on in the entire world.
The Midrash (Vayikra Rabbah 29:12) says אָמַר רַבִּי תַּחְלִיפָא קֵיסָרָא, בְּכָל מוּסָפִין כְּתִיב: וְהִקְרַבְתֶּם וְכָאן כְּתִיב: וַעֲשִׂיתֶם אִשֶּׁה, הָא כֵיצַד, אָמַר לָהֶן הַקָּדוֹשׁ בָּרוּךְ הוּא לְיִשְׂרָאֵל, בָּנַי מַעֲלֶה אֲנִי עֲלֵיכֶם כְּאִלּוּ הַיּוֹם נַעֲשֵׂיתֶם לְפָנַי, כְּאִלּוּ הַיּוֹם בָּרָאתִי אֶתְכֶם בְּרִיָּה חֲדָשָׁה, הֲדָא הוּא דִכְתִיב (ישעיה סו, כב): כִּי כַאֲשֶׁר הַשָּׁמַיִם הַחֲדָשִׁים וְהָאָרֶץ הַחֲדָשָׁה. The Midrash is conveying the above lesson. On Rosh Hashana, it's a day of renewal and you are viewed as a fresh, new person free from the errors of the past.
Chazal say אורי refers to Rosh Hashana. Why is Rosh Hashana known as אורי? In Nussach Ashkenaz it says אור חדש על ציון תאיר, where there is אור, there is a clarity of the truth. On Rosh Hashana things go back to their source, a person goes back to their beginning before sin led them off the straight path. It is on Rosh Hashana that we are given a new beginning to be able to move forward.
The Yalkut Shimoni on Tehillim (831:6) says ד"א בשופר אני מכסה עונותיכם תקעו בחדש שופר. When the shofar is blown, the sins are covered over, hidden from sight. It doesn't say they are forgiven, but they are not looked at. How does blowing the shofar accomplish this? The Gemarah says the blowing of the shofar is the means to convey acceptance of the malchut of Hashem, אמרו לפני בראש השנה מלכיות זכרונות ושופרות מלכיות כדי שתמליכוני עליכם זכרונות כדי שיעלה זכרוניכם לפני לטובה ובמה בשופר. The shofar is the method used to express kabblat malchut. When one is mekabal the malchut, as we said before, one is given a fresh start and the sins are not examined. The possuk in Balak (23:21) says לֹֽא־הִבִּ֥יט אָ֙וֶן֙ בְּיַעֲקֹ֔ב וְלֹא־רָאָ֥ה עָמָ֖ל בְּיִשְׂרָאֵ֑ל י״י֤ אֱלֹקיו עִמּ֔וֹ וּתְרוּעַ֥ת מֶ֖לֶךְ בּֽו. Rashi says G-d doesn't look at the sins of Klal Yisrael because of the great love He has for them. When we blow the תרועה it is an expression of our love for Hashem. When there is this reciprocal relationship, the sins are inconsequential and are covered over. (Based upon Yarech L'moadim simanim 31, 32.)
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