This paper will place R. Kalonymous Kalman Shapira’s sermons in dialogue with Emil Fackenheim, arguably the most prominent philosopher/theologian of the Holocaust and his own single encounter with them at a mature juncture of his thinking about the Shoah, some four decades after the end of the war. The sermons consciously anticipate, even demand, such posthumous dialogues by the very fact of their composition and burial. As Fackenheim asserts in a work published in 1986, without exposure to the “subtleties” of R. Shapira’s thought, “I would not have known how to complete the last, crucial chapter of this book.” If we take Fackenheim at his own word then, in a very real sense, his entire Holocaust oeuvre would have remained fragmentary absent engagement with R. Shapira.Placing R. Shapira in dialogue with Fackenheim deepens our appreciation of both the Hasidic Rebbe and the Reform Rabbi/ professional philosopher. We can better appreciate how R. Shapira wrested ultimate meaning from the “useless suffering” that a philosopher such as Levinas considered devoid of meaning.