Daf Yomi: Kiddush Rabba and הֶחָכָם עֵינָיו בְּרֹאשׁוֹ

I came up with an interesting insight into the meaning of a particular derasha. Perhaps others have said it before, but I want to write it down before I forget it. The specific incident, from Pesachim 106a:

Rav Ashi visited Mechoza. They told him: Master should make kiddush for us the Great Kiddush. He said {to himself}: What is the Great Kiddush? Let us see. Whenever there is a blessing, Borei Peri HaGafen is at the head. He said Borei Peri HaGafen, drawing it out. He saw an elderly man bend down and drink {and realized that that was the entirety of it}. He applied to himself the verse {Kohelet 2:14}:

יד הֶחָכָם עֵינָיו בְּרֹאשׁוֹ, וְהַכְּסִיל בַּחֹשֶׁךְ הוֹלֵךְ; וְיָדַעְתִּי גַם-אָנִי, שֶׁמִּקְרֶה אֶחָד יִקְרֶה אֶת-כֻּלָּם.

14 The wise man, his eyes are in his head; but the fool walketh in darkness. And I also perceived that one event happeneth to them all.

Rashi does not comment here explaining why Rav Ashi applied this particular verse to himself. The "Point By Point Summary" on Daf Yomi from shemayisrael explains:

he applied to himself "Ha'Chacham Einav b'Rosho" (a Chachamim plans in advance. 'Kedusha Rabah'

But this is not really planning ahead, now is it? He came unprepared, and started, then stalled a bit for time.

Rather, with an eye to how these derashot typically work, I would put forth the following explanation which is obvious in retrospect.

Rav Ashi does not intend the simple meaning of the verse that a wise man plans in advance, but rather I would say he interprets this as follows: The wise man looks towards its head. It in this case is kiddush, and at its head is Borei Peri HaGafen. Thus, he was the wise man who looks towards the head and intuited that he should start with Borei Peri HaGafen.

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