Teaching Israel is a complex endeavor in today's world where the founding myths of Israel no longer appear to capture the hearts and minds of American Jews as they did a generation ago. As a result, a new way of speaking about and conceptualizing Israel education is evolving among researchers, program providers, policy makers, and many teachers. Through an in-depth case study, this paper explores whether and how this new way of thinking and speaking about Israel actually plays out in a community Jewish day high school that espouses a commitment to critical thinking and pluralistic education. The analysis is informed by a conceptual framework that argues that a meaningful and holistic approach to Israel education demands critical engagement with both the sacred vision and complex realities of Israel, past, present, and future as well as the literature on pluralism in Jewish educational settings. The key question threaded throughout the article is: How does a pluralistic Jewish curriculum navigate between fostering open inquiry and supporting a commitment to Israel and the Jewish people? (Contains 1 table and 6 footnotes.)