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(From Jerusalem Post)
Byline: Jonathan Rosenblum
There is a mitzva of rejoicing on each of the three pilgrimage festivals of the Jewish calendar. We are encouraged to have festive meals, with meat and wine, and husbands are enjoined to buy their wives new clothing or jewelry for the holiday.
Yet of the three festivals only Succot is specifically known as zman simhateinu - the time of our rejoicing.
What exactly is the special connection between Succot and joy? A hint to the answer lies in a puzzling Midrash. The Midrash asks why we begin building our succah immediately after the sealing of our judgment for the coming year on Yom Kippur. The Midrash answers that perhaps the Jewish people received a judgment of exile, but in lieu of exile God accepts our leaving our homes and entering the succah.