When Rabbi Nahman b. Yitzhak declared that "a sin done for God's sake is greater than a commandment done for ulterior motives," he posed a profound challenge to Jewish legal thought: can religious intention trump formal law? Through textual analysis of Babylonian Talmud sources and examination of responsa literature, two competing interpretations emerge. The teleological reading permits suspension of legal rules in extraordinary circumstances to serve higher divine purposes, while the kavvanah interpretation prioritizes inner religious intention over formal compliance. Drawing upon Robert Cover's theoretical framework of legal civilizations and the concept of nomos, this principle both challenges pan-halakhic assumptions while preserving Jewish legal stability. Medieval and modern halakhic decisors—including Rashba, R. Moshe Isserles, the Netziv, and R. Yosef Hayyim of Baghdad—have grappled with applying this teaching in practical jurisprudence. Their responsa reveal that while halakhah maintains strong normative authority, certain transcendent religious values—including peace, inner devotion, and exceptional ethical circumstances—exist beyond the boundaries of the legal universe. This analysis illuminates the delicate balance between religious law and transcendent religious experience, demonstrating how Jewish legal civilization acknowledges inherent limits to normative authority without compromising systematic legal stability.