In this essay, dedicated to Mike [Rosenak]’s memory, I propose to bring him just such an issue of current concern in the philosophy of Jewish education and to consider the response that he might offer—or, rather, that he did offer, directly and indirectly, in his book, Tree of Life, Tree of Knowledge: Conversations with the Torah. The question I have pertains to Jewish leaders and teachers (for example, campus Hillel rabbis) who are committed (a) to the strengthening of Jewish life in their communities and beyond, and (b) to the strengthening of the Jewish lives of individual Jews (students, for example) but are committed no less (c) to a vision of Judaism and Jewish life that crosses ideological and denominational boundaries. How can such leaders and teachers, speak cogently and forcefully about Judaism to Jews and in particular to emerging Jewish adults, or varied conviction and direction?