A century after Israel Friedlaender's seminal essay on Judaism in America, his core questions about Jewish identity and survival remain startlingly relevant and largely unresolved. Four fundamental challenges he identified continue to shape American Jewish discourse today: defining Judaism itself, negotiating American Jewish identity, relating to Israel, and addressing God's role in Jewish life. Through close textual analysis of Friedlaender's original work and comparative examination of subsequent Jewish thinkers like Mordecai Kaplan and Abraham Joshua Heschel, alongside contemporary sociological data, persistent patterns emerge in American Jewish thought and practice. Despite transformative historical events—the Holocaust, Israeli statehood, and unprecedented American Jewish success—the community still grapples with tensions between particularist and universalist orientations, struggles with hyphenated identity formation, shows inadequate engagement with Israeli realities, and marginalizes theological discourse. While recent developments in Jewish education, spirituality, and intellectual discourse offer grounds for optimism, American Jewry has yet to develop coherent responses to the fundamental challenges of maintaining distinctive Jewish identity within pluralistic American society.