Milton Steinberg's profound insight that authentic religious experience thrives in the tension between faith and reason stands as both his greatest contribution and an unfinished theological project. His posthumously published "Anatomy of Faith" presents religion not as a rejection of intellectual inquiry, but as a dynamic oscillation between rational thought and spiritual conviction. Through comparative analysis of Steinberg's work against broader Jewish theological traditions, this examination reveals both the power and limitations of his religious philosophy. While Steinberg masterfully articulated the bi-polar nature of religious experience, his rigid conception of "normative Judaism" overlooked crucial mystical traditions and ultimately hindered his ability to fully engage with Christian theological perspectives. The analysis employs detailed textual examination and theological comparison to demonstrate how Steinberg's recognition of spiritual ambivalence positioned him to potentially transform interfaith dialogue - an opportunity cut short by his untimely death. Though preliminary, his essays offer valuable contributions to Jewish religious philosophy, even as they hint at deeper insights left unexplored.