This paper examines the development of the literary and historical persona of the poet Hassan ibn Thabit. By exploring how scholars of the ninth to twelfth centuries represented the life, poetry, and legacy of Hassan, I will explore the prevailing discourses of the ‘Abbasid era regarding the earlier pre-Islamic period (al-jahiliyya) and the rise of Islam. Specifically, I will argue that Hassan’s symbolic importance to these later Muslim scholars lies in his embodiment of the transition from the “ignorance” of the jahiliyya to the “wisdom” of the Islamic period. For example, ‘Abbasid authors often note that Hassan’s life was divided equally between the two historical periods in which he lived, sixty years in the jahiliyya and sixty in the Islamic period. These dates are best viewed as a symbolic demonstration of Hassan’s connection to each period. The most important fact to the narrators is Hassan’s identity as a transformational figure, one rooted in pre-Islamic Arabia but equally connected to the new world of Islam. When Hassan appears in ‘Abbasid texts it is often as an emblem of the transformational possibilities of Islam; thus, he is portrayed as a figure who demonstrates the legitimacy and superiority of Islam and Islamic civilization. To demonstrate this point, three diverse works from the ‘Abbasid period will be studied: Tabaqat fuhul al-shu‘ara’ by Ibn Sallam al-Jumahi (d. 846), al-Muwashshah by al-Marzubani (d. 994), and Tarikh madinat Dimashq by ‘Ali Ibn ‘Asakir (d. 1176). The texts represent a sampling of the breadth of the genres of scholarly writing produced in this period, from biographical dictionaries to works of literary criticism. Each text will be examined as a literary artifact imbued with unique ideological content. Additionally, the study will consider the various modes of discourse employed by the authors in each text.