Why does the Torah place the mitzvah of lulav before sukkah (in Emor) if sukkah applies at day and night?
The Emre Emes (5667) says that the Torah places luluv before sukkah because luluv is something one holds and draws toward himself. ולקחת לכם, the taking of the lulav is for yourself, it has an affect on the individual. On the other hand, sukkah is above a person's head, it is something that one can not comprehend. It is only be first having luluv that one can merit to sukkah. The Sfas Emes (5643) brings from the Chiddushay HaRim that's why the midrash has longer explanations about the lulav and not much about the sukkah because the sukkah's meaning is hidden from us. It is above our heads.
Why do we beseech Hashem so much on Hoshana Rabbah and why is the specific service of the day with the aravot? The Sfas Emes (5660) says להו"ר קבעו הרבה בקשות על המים. דאיתא ערבה רומז לאותן שאין בהם תורה ומצות לא טעם ולא ריח. א"כ מה השבח שלהם. רק מה שמצפים לישועת ה'. ערבי נ"חל ר"ת "נפשינו "חכתה "לה'. ומזה נפתח פי הבאר. והנחל נעשה מזה התשוקה שיש נטבע בנפשות בנ"י. The barren aravah represents those that have no maalot, nothing special to show off, all they have is to yearn and look to Hashem. That is what we are doing on Hoshana Rabbah. We are asking Hashem to open our souls, to fill them with the מי הדעת. The Midrash equates the aravah with the possuk in Tehillim (102:18) פָּ֭נָה אֶל־תְּפִלַּ֣ת הָעַרְעָ֑ר, Hashem listens to the desolate cry (the meforshim bring Yermiyahu 17:6 which says כְּעַרְעָ֣ר בָּעֲרָבָ֔ה.) It the cry of yearning that is symbolized by the aravah (that is why it is shaped liked lips as noted in the Tanchuma Emor 19) which we seek to evoke on Hoshana Rabbah. Despite our lack of merits we ask Hashem to expand our horizons.
What is the great happiness of the שחמת בית השואבה? The Sfas Emes (5643) says במשנה ובחג נדונין על המים. לכן מתפללין על הגשם. ומסתמא עיקר הכוונה על התורה שנאמ' כל צמא לכו למים. וכמו שהמים הם מזון וקיום העולם לפתוח הקרקע ולעשות פירות. כן התורה בלב האדם. The possuk in Yeshayahu (12:3) וּשְׁאַבְתֶּם־מַ֖יִם בְּשָׂשׂ֑וֹן מִמַּעַיְנֵ֖י הַיְשׁוּעָֽה the Targum and Rashi explain is about learning Torah. The great simcha is about opening our hearts to be ready to accept Torah. Although understanding the depths of Torah maybe beyond our comprehension we celebrate that we can ask Hashem to give us that which is beyond our capabilities. As the Yerushalmi says it is called בית השואבה because שמשם שואבין רוח הקודש. We can reach beyond our normal capacities and see that which we ordinarily are not privy too. That is the great שמחה of the בית השואבה and of Sukkot in its entirety. We are given a glimpse of that which is above our head. For one week we are able to look up at the schach and ask Hashem to reveal that which is hidden.
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