One element of Ya’akov’s prayer - before Yaakov confronts his nemesis Eisav - reads as follows: “I have been diminished by all the kindnesses and by all the truth that You have done for your servant [Yaakov]” (B’reishit 32:11).
Our rabbis teach that the kindnesses are benefits conferred by G-d with- out Hashem having first promised them, whereas truth is the fulfillment of earlier promises. But either way, the humble Yaakov feels unworthy to have received them. Perhaps, according to Ramban, because he never felt worthy in the first place or, maybe, having been the recipient of these kindnesses, he felt he now no longer deserved Hashem’s intervention - his merits were now diminished (Rashi).
The Talmud discusses the question of pride vs. humility: A plethora of rabbinic statements denigrate pride. As for modesty, we recall that as the Almighty appeared to us mortals on a lowly mount and in a desert bush, so it behooves us, too, to tread humbly (cf. Sota 5a).
However, R. Hiyya b. Ashi said in the name of Rav, “A Talmid Chacham should possess an eighth [measure of pride]” - for there is a time when humility must bend to the honor due to Torah, especially when the learned need to exercise their authority. The challenge, it seems, is to know how to maintain that “eighth” portion of pride at the appropriate time and place.
Shabbat Shalom, Menachem Persoff
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