The thoughts of Mordecai Kaplan and Michael Rosenak present surprising commonalities as well as illuminating differences. Similarities include the perception that Judaism and Jewish education are in crisis, the belief that Jewish peoplehood must include commitment to meaningful content, the need for teachers to teach from a position of authenticity, and the importance of developing the inner life. The differences lie primarily in their divergent understandings of what in Judaism obligates, of the importance of reckoning with the Schwabian “milieu” when educating, of the acceptable boundaries of textual interpretation, and of the need to engage with families when educating children.