Rav Moshe Feinstein, zt”l, dismissed the notion of “holy arrogance” (Mesores Moshe, vol. 3, p. 383), but is there a place for “holy chutzpah?”
Rav Elchonon Wasserman, zt”l Hy”d, asserted that when the pre-Messianic era Jews declare, “And for us what can we rely on but our Father in Heaven” (Sotah 49b), it’s not a form of encouragement but a symptom of misfortune. Many of us picture piety as passively throwing up our hands and allowing G-d to do the fighting on our behalf. The truth is that we are experiencing a deficiency of the chutzpah required to proudly advocate authentic Jewish values to the world (Kovetz Ma’amarim, vol. 1, p. 262).
I interviewed a local Catholic community leader on my show As I Walk Through the Valley, who shared that many in his faith had reached the same realization. But instead of invoking “chutzpah” he advocated for moral “courage.” So perhaps there is no “holy chutzpah,” but I know that I can personally use some more holy courage in unabashedly declaring the values of Hashem, even when – especially when – they are regrettably not in vogue.