We are a chutzpadik people. I say this not merely as an experienced rabbi but as a student of the midrash. On Parashat Ki Tisa, Midrash Shemot Rabbah 42:9 [a nearly 2000 year old text] describes the Jewish people having chutzpa as a way of explaining this week’s repeated references to us being a “stiff-necked people.” We are called stiff-necked twice in the parasha. The first time [Exodus 33:3], God proclaims he will not be found among us because we are stiff-necked, whereas later [in Exodus 34:9] Moses asks God to remain amongst us precisely because we are characterized by this trait. In the first instance, being stiff-necked is clearly regarded as a problem, but in the second instance it seems that it is a positive. This is the way it is with chutzpa. It all depends upon context. When we are brazenly stubborn in resisting the right path, chutzpa only makes a bad situation worse. However when the situation calls for uncompromising and courageous steadfastness, chutzpa becomes a key virtue. We live in challenging times for the Jewish people. (Which generation of Jews has not?). When those challenges call for a chutzpadik response, we know that we can count on ourselves to meet the expectation.
Rabbi Mitch Levine