How does one lead a life of law, love and freedom? This inquiry has very deep roots in the Judeo-Christian tradition. Indeed, the divergent answers to this inquiry mark the transition from Judeo to Christian. This dissertation returns to those roots to trace the routes that these ideas have taken as they move from the sacred to the secular. The argument of this dissertation is threefold. First, it argues that the concepts of law, love and freedom are each internally polarized. Each concept contains, within itself, conflicting values. Paul’s equivocation in his letters is a striking manifestation of this internal polarization. Second, it argues that, while values are many, my life is one. Hence, one needs to combine the plurality of values within a singular life. Values find their coherence within a form of life. There are, at least, two ways of leading a life of law, love and freedom: monastic versus antinomian. Third, it argues that the Reformation transformed these religious ideals into political ideologies. The monastic ideal is politically manifested as constitutionalism, and the antinomian ideal is politically manifested as anarchism. There are, at least, two ways of creating a polity of law, love and freedom: constitutional versus anarchic. To mount the threefold argument, the dissertation deploys a whole range of disciplinary tools. The dissertation draws on analytic jurisprudence in its analysis of law; ethics and aesthetics in its analysis of love; political philosophy in its analysis of freedom; biblical scholarship in its interpretation of Paul; the history of ideas in its study of the formation and transformation of these ideas; and moral philosophy in concluding how one could lead a life of law, love and freedom.