Robert Cover's pioneering vision of law as both a redemptive and potentially anarchic force offers critical insights for contemporary Jewish legal thought. Through analysis of his major works, particularly "Nomos and Narrative," two central tensions emerge: law's capacity to bridge present reality with envisioned alternatives, and the inherent destabilizing potential within legal systems. Cover's concept of "redemptive constitutionalism" demonstrates how legal interpretation must incorporate narrative and moral vision alongside formal rules, rejecting purely positivist approaches that separate law from ethics. His framework of "polycentric norm articulation" emphasizes the necessity of both textual authority and human participation in ongoing legal conversations. Drawing on historical cases from antislavery jurisprudence to sixteenth-century attempts to renew rabbinical ordination in Safed, Cover illustrates how legal systems must navigate between formal constraints and moral imperatives. This retrospective analysis reveals three primary lessons for contemporary Jewish law: addressing the moral-formal dilemma inherent in legal decision-making, recognizing the role of human autonomy in legal development, and confronting the relationship between law and violence. Cover's jurisprudential vision ultimately advocates for law as a creative, redemptive force while acknowledging its potential for both liberation and oppression.