Milton Steinberg's theological journey challenges our understanding of true discipleship, revealing how intellectual inheritance demands creative transformation rather than mere repetition of a master's teachings. Through biographical analysis and close examination of Steinberg's writings in *Anatomy of Faith*, a complex portrait emerges of a thinker whose relationship with Reconstructionist doctrine evolved dramatically over a decade. While beginning as a skilled synthesizer and publicist of Jewish values, Steinberg's later work engaged deeply with Protestant theology, process philosophy, and non-absolutist conceptions of God's nature. His theological position shifted significantly in his final years, moving beyond strict Reconstructionist orthodoxy toward a nuanced reengagement with classical theistic concepts. Though critics have disputed this interpretation, evidence shows that despite maintaining personal loyalty to Reconstructionist leadership, Steinberg's theological investigations increasingly departed from Kaplan's naturalistic conception of God. As a transitional figure bridging rationalist and devotional traditions within Judaism, Steinberg's premature death cut short a promising theological development that might have reshaped contemporary Jewish thought.