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When the Sadducees tried to argue that Shavuot comes on the Sunday after the first Shabbat in Pessah (because the Torah says "the day after Shabbat") Rabban Yoḥanan ben Zakkai countered them sharply as follows:

"Fools! From where have you derived this?" And there was no man who answered him, except for one elderly man who was prattling [mefatpet] at him, and he said: "Moses, our teacher, was a lover of the Jewish people and he knew that Shavuot is only one day. Therefore, he arose and established it after Shabbat, in order that the Jewish people would enjoy themselves for two days." Rabban Yoḥanan ben Zakkai recited this verse in response: “It is eleven days’ journey from Horeb to Kadesh Barnea by the way of Mount Seir” (Deuteronomy 1:2)" He added: "And if Moses, our teacher, was a lover of the Jewish people, why did he delay them in the wilderness forty years?" The elderly man said to him: "My teacher, you dismiss me with this retort?" Rabbi Yoḥanan ben Zakkai replied: "Fool! And will our perfect Torah not be as worthy as your frivolous speech? [Your claim can easily be refuted.]" [Menachot 65a-b]

Rabbi Yoḥanan ben Zakkai's retort, "And if Moses, our teacher, was a lover of the Jewish people, why did he delay them in the wilderness forty years?", seems strange and appears to denies God's love for Israel. What did he mean? Is this discussed anywhere?

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    Isn't he just making the rhetorical point that one cannot measure "love" by the timing? Since the 40 years is not a show of a lack of love, having a holiday of only one day is not a show of lack of love.
    – rosends
    May 18 at 17:16
  • There is no need to use the Sadducee's line "Moses, our teacher, was a lover of the Jewish people" against him to make the point. May 18 at 17:29
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    But that was the point of this as a retort and not an answer -- the Boethusians's logic was predicated on that claim. Using it against him shows the fallacy.
    – rosends
    May 18 at 18:28
  • @rosends -- I still think the Sadducee's line "Moses, our teacher, was a lover of the Jewish people" should not have been used to heap scorn on him, since there is no disagreement there. We are just witnessing sectarian feuding. May 19 at 2:36
  • The point is that Moses's love for the Jewish people has nothing to do with when holidays occur just like it has nothing to do with how long the Jews were in the desert.
    – Esther
    May 23 at 20:08

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Mishlei 26 states, עֲנֵה כְסִיל, כְּאִוַּלְתּוֹ: פֶּן-יִהְיֶה חָכָם בְּעֵינָיו. "Answer a fool according to his folly."

Rabbi Yochanan ben Zakkai was confronted with someone "prattling", and had two purposes. First, to push him off instead of answering seriously. (Look up לזה דחית בקנה in terms of fights with sectarians.)

Second, to demonstrate that the Sadducee's original premise was flawed. If we are to assume X, then see how Y (the 40 year wilderness delay) doesn't work. Therefore, X is not true. That is called proof by contradiction. Rather than decisions of ritual and events being guided by what would give the Jews the most comfort, they are guided by Divine considerations.

(Also, Moshe's love, meaning results of a human being constructing something convenient in a legal system, is not the same as God's love. So he wasn't denying anything about God's love even in his retort.)

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