This paper deals with how the practice of the Abbasid Caliphs (ca.750-945) and the projection of their power generated antinomian opposition to the caliphate itself and the emerging ideals of legitimate government, known as the imamate in medieval Islamic political discourse. Literature in the field has so far been largely concerned with the "Sunni" (e.g. Umayyad and Abbasid) and "Shii" (e.g. Fatimid) caliphates as well as the normative expositions of the caliphate by Sunni jurists and theologians. Lost in the debate are the marginal yet significant voices articulating alternative views emanating from a particular stand against the caliphate and against the proto-Sunni and Sunni political and legal discourse. In this paper I intend to address a) the identity of the ninth century Sufi and Mu'tazili antinomians as proponents of an emerging alternative discourse about religious law, society, and government, and b) the Abbasid political and legal discourse responding to such antinomians. Disillusioned by the political trajectory of the Abbasids, certain antinomian individuals and groups (sufis and zahids) not only equated the caliphate with illegitimate kingship, but also criticized the views of proto-Sunni and Sunni scholars who legitimized it on the basis of religious law, reason, or necessity. Actual manifestations of this antinomian attitude included a total renunciation of political and economic life to avoid operating under illegitimate government as well as a serious criticism of Abbasid political practice and its legitimizing discourse without disengaging society. By looking into the social and political contexts of Muslim antinomianism and anarchism in the ninth century as they transpire in medieval literature I hope to contribute to a more nuanced understanding of the notions of legitimacy in Abbasid society. My sources will include works in different genres, such as Masa'il al-Imama, Muhasibi, al-Makasib, Shaybani, Kitab al-Kasb, Baghdadi, Usul al-Din, and historiographical literature.