I want to zero in on the meaning of Shmini Atzeret, but I want to start with a quotation:
It is designed to break your heart. The game begins in the spring, when everything else begins again, and it blossoms in the summer, filling the afternoons and evenings, and then as soon as the chill rains come, it stops and leaves you to face the fall all alone.
That is not a Torah scholar but Bart Giamatti, and he’s describing the baseball season in words you can find written on the bricks of the concourse at Oracle Park.
But he’s also describing the arc of the Chagim. It's basically a Spring and Summer religion. The Chagim begin in the spring, as everything blossoms, and end when the leaves are falling, or the chill rains come. There are, significantly, important holidays during the winter, but they are from the Rabbis. The Torah lays it out as a journey through the summer.
But there’s a big difference. Giamatti is writing as a life-long fan of the Boston Red Sox, whose gap between championships was much longer than his life. They had last won way before he was born and he passed away about 15 years before they won again. It would be the same for a Cub fan of course. These are teams and fan bases acutely aware of the fact that only one team is left as a winner in the end and all of the rest face the chill rains alone.
We, on the other hand, are that team left as a winner in the end. All of the nations have paraded through during Sukkot. Seventy offerings were made, corresponding to the nations of the world. Even today, Sukkot in Yerushalayim is a gathering time for non-Jews who are aware of this aspect of the Chag. But on Shmini Atzeret Hashem asks us to stay one more day, alone with Him. It is a day of intimacy, just us.
And how would we spend our time together? And where would we spend it together? Shmini Atzeret is a day of rejoicing with the Torah because that is what we share with Hashem. And it is also a day of celebrating Eretz Yisrael, which is the proper venue for our rendezvous with Hashem.
The Vilna Gaon says that the arc of the Chagim inevitably ends in Eretz Yisrael. He traces that arc in the first four verses of Shir Hashirim. First comes a verse that announces, “Shir Hashirim,” a song, and Pesach is a song of Hallel in the beginning and the song by the sea at the end. The next verse seeks the kisses of the beloved’s mouth, as we rendezvous with Hashem at Har Sinai and receive the Torah on Shavuot. The next verse is about the scent of the beloved, which invokes the Mishkan. Sukkot is a Chag that celebrates the clouds of glory. Not the original clouds as the Jews left Egypt but the clouds which were restored after Yom Kippur, when the Jews began to build the Mishkan. Har Sinai is made mobile as the Mishkan moves through the desert.
The fourth verse says that the beloved should follow the king into “his chambers.” Where is that? The Gaon says that that is Eretz Yisrael, and that is why Shmini Atzeret celebrates the entrance into the land.
A guest we had for dinner during the summer commented to me, “Shmini Atzeret must have been a forlorn day until the Gaonim put Simchat Torah there.” Even Talmidei Chachamim have asked how we can mix happy occasions together. We don’t have weddings during Chol Hamoed because we don’t mix Simchas. But Simchat Torah is not slapped on top of Shmini Atzeret. If we are celebrating with Hashem, there is nothing more appropriate with which to do it than the Torah, which binds us together. And the proper place to come together is Eretz Yisrael. Both belong with Shmini Atzeret, the triumphant end of the Chagim, which sends us into the Fall with a flourish.
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