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I remember once learning that the Vilna Gaon said that Maseches Sukkah (Bavli, Yerushalmi, Tosefta) talks about 85 non-kosher sukkot and 91 kosher sukkot.

The Gra said the way to remember this is that:
סכה (with no "ו") has a gematria of 85 - which represents the number of non-kosher sukkot.
סוכה (with a "ו") has a gematria of 91 - which represents the number of kosher sukkot.

A couple questions:

  • 1) Does anyone know the source/ link where this teaching can be found?
  • 2) Has anyone scoured the Bavli, Yerushalmi, Tosefta and compiled a list of these 85 non-kosher and 91 kosher sukkot?
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It's apparently an oral tradition relating to one of the students of the Vilna Gaon, Rabbi Yisrael of Shklov. The more complete story is recounted here in Hebrew. It begins like this:

הגאון רבי ישראל משקלוב מספר, על תלמיד מתלמידי הגר"א, שבא לקבל פני רבו בחול המועד סוכות, וביקש מרבו כי יעמידו במבחן על כל מסכתא דסוכה על פה. היה זה אחר שקודם החג עורר הגאון את תלמידיו, על החובה להיות בקי בעל-פה לכל הפחות במסכת אחת, לבל יתבטל מתלמודו בלכתו בדרך או בשבתו בחושך. אחד השומעים קיבל על עצמו ללמוד מסכת סוכה, ואחר שלמדה פעמים הרבה, וגם הקדים להבחן על-ידי חבריו, שמצאו כי היא שגורה על פיו, אז בא להבחן אצל רבו.

The story is also recounted in Sefer Shalmei Yosef by Rabbi Shlomo Yosef Levin of Nishovitz, Bulgaria. This quotation appears at the bottom of page 6 in the PDF.

And thanks to JoelK for the asset in finding the source as recounted by Rabbi Yisrael of Shklov himself in Pe'at HaShulchan.

I know of no listing, but I'm sure someone has done it somewhere.

  • 1
    The story appears in the introduction R. Yisrael Shklover wrote to his Pe'at HaShulchan hebrewbooks.org/pdfpager.aspx?req=37666&st=&pgnum=7 – Joel K Sep 24 at 13:45
  • The quotation from Shalmei Yosef on p6 of the linked pdf is not this story. The story is on p7, quoting from the introduction to Peat Hashulchan – Joel K Sep 26 at 11:30

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