This paper demonstrates that the production of knowledge in the Umayyad and early Abbasid diwan (ca. 60–183 AH/680–800 CE) involved questions of social order and political authority. It is well established that the diwan relied heavily on expert knowledge. This was particularly the case when the Arab conquests of the first/seventh century set out to lay the foundation for a vast empire. The Arabs adopted the administrative systems that were prevalent prior to the conquests throughout the Near East. As such, the Iraqi diwan was managed on the Sasanian model while the Byzantine administrative practices continued in Syria and Egypt. The Persian mawali played a crucial role in managing certain divisions of the Umayyad diwan in Iraq. In that regard, this paper calls attention to the efforts made by some diwan secretaries in constructing a discourse that incorporated elements of Persian ancient wisdom and Islamic/Arabian tradition. The paper highlights such elements in the writings, among others, of ‘Abd al-Hamid ibn Yahya and ‘Abdallah ibn al-Muqaffa‘. The “Mirror for Princes” (mir’at al-muluk) literature produced by these secretaries in the form of translation and/or original composition sought to introduce a political system which derived from both Persian/Greek political wisdom and Islamic/Arabian tradition. These exemplars of early adab promoted a model of government in which the secretary, in his advisory capacity, took the center stage. Viewed from this vantage point, the secretary’s professional interests seem to have taken precedence over the putative interests of the class (i.e., mawali) to which he belonged. This paper concludes that despite the crucial role of the Persian mawali in the Abbasid Revolution, this bourgeoning discourse fared poorly with the Abbasid caliphs. For the Abbasid caliphate appears to have preferred to draw its legitimacy from a rival discourse, which relied on the ‘ulama as the spokesmen of Islam and the interpreters of the Qur’an and Sunnah. This alternative discourse had a different vision for social and political order—a vision that, contrary to Ibn al-Muqaffa’s vision, had no interest in deferring the ‘ulama’s legal authority to that of the caliph’s.