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The Talmud records a story about how Moses could not understand even laws expounded in his name:

Rav Yehuda says that Rav says: When Moses ascended on High, he found the Holy One, Blessed be He, sitting and tying crowns on the letters [of the Torah]. … [God] said to him: There is a man who is destined to be born after several generations, and Akiva ben Yosef is his name. He is destined to derive from each and every thorn [of these crowns] mounds and mounds of laws. It is for his sake that the crowns must be added to the letters of the Torah. Moses said before God: Master of the Universe, show him to me. God said to him: Return behind you. Moses went and sat at the end of the eighth row in Rabbi Akiva’s study hall and did not understand what they were saying. Moses’ strength waned. [He thought his Torah knowledge was deficient]… [Rabbi Akiva’s] students said: My teacher, from where do you derive this? Rabbi Akiva said to them: It is a law transmitted to Moses from Sinai. When Moses heard this, his mind was put at ease. [Menachot 29b]

Why was Moses uncomfortable at first, then his mind was "put at ease" when he heard that?

(1) Because he realized he must have known it all along, but had forgotten it? (If so, what is the point of the story? That we all get old? Suggested in Parshat Vayelech, Deut 31:1-2.)

(2) Because he was happy to see that what he started would continue and evolve, even past his own ability to understand? (Perhaps Moses thought at first that Akiva was making things up, which made him uneasy, then realized Akiva was deriving it from what Moses himself taught, at which point he relaxed?)

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I think Rb Mordechai Shlesinger explains this as follows:

Rb Akiva explained piles of halachos on each thorn, this is because Rb Akiva experienced the thorns (hardships) of life which pierced his flesh, and from this he derived halachos and a deeper understanding of Hashem, life and the Torah. Moshe could not understand this mode of extrapolation and thinking because he was the king of the benei yisrael in their glory and had not experienced such vicissitude as Rb Akiva.

He was comforted when the halacha was stated to be a halachah le'moshe mi'sinai, this may be understood according to that which is evident from Rashi in Bava Basra, 12b

ולאו טעמא קאמר - במילתיה וכיון דאמר טעמא אין זה כסומא שמכוון לירד בארובה במקרה בעלמא אלא סברת הלב היא הבאה לו בנבואה וזכה להסכים להלכה למשה מסיני:

That a halachah le'moshe mi'sinai represents Moshe's level of havanah, and is not just something told to him by Hashem.

If so, it comes out that the gemara quoted above means that whether you start at the starting point of Rb Akiva's life experiences and type of exegesis or you start with Moshe's life experiences and type of exegesis, you will ultimately meet at the level of highest havanah.

Therefore Moshe was comforted because he knew the Torah would incorporate the full gamut of Jewish life experience.

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